SUBSTITUTED STEROIDS FOR THE TREATMENT OF CANCER

Abstract

A compound and pharmaceutically acceptable salts thereof for treating cancer, having a structure represented by the following formula (I) or formula (II):

##STR00001##

in which X and Y each individually represent:

##STR00002## R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 individually represents hydrogen atom, acyl having 20 or less carbon atoms, alkyl having 20 or less carbon atoms, alkanoyl having 20 or less carbon atoms, aroyl having 20 or less carbon atoms, aryl having 20 or less carbon atoms, aralkyl having 20 or less carbon atoms, sulfonyl having 20 or less carbon atoms, phosphonyl having 20 or less carbon atoms, or haloacyl having 20 or less carbon atoms.

Claims

1. A method for inhibiting cancer cell proliferation in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of a compound, wherein the cancer cell is at least one or more selected from the group consisting of a human leukemia cell, a human lung cancer cell, a human glioblastoma cell, a human liver cancer cell, a human colorectal cancer cell, and a human breast cancer cell; the compound has an improved IC50 against the cancer cell; and the compound is extracted from Momordica charantia and has a structure represented by the following formula: ##STR00028## ##STR00029##

2. The method according to claim 1, wherein the human leukemia cell is a U937 cell, the human lung cancer cell is a A549 cell, the human glioblastoma cell is a U87-MG cell, the human liver cancer cell is an Mahlavu cell, the human colorectal cancer cell is a SW-480 cell, and the human breast cancer cell is an MDA-MB-231 cell or an MDA-MB-468 cell.

3. The method according to claim 2, wherein the compound has an IC50 value of 11.15 M or less against the human leukemia cell U937 in vitro.

4. The method according to claim 2, wherein the compound has an IC50 value of 24.41 M or less against the human lung cancer cell A549 in vitro.

5. The method according to claim 2, wherein the compound has an IC50 value of 15.55 M or less against the human glioblastoma cell U87-MG in vitro.

6. The method according to claim 2, wherein the compound has an IC50 value of 29.42 M or less against the human liver cancer cell Mahlavu in vitro.

7. The method according to claim 2, wherein the compound has an IC50 value of 31.82 M or less against the human colorectal cancer cell SW-480 in vitro.

8. The method according to claim 2, wherein the compound has an IC50 value of 18.33 M or less against the human breast cancer cell MDA-MB-231 in vitro.

9. The method according to claim 2, wherein the compound has an IC50 value of 26.77 M or less against the human breast cancer cell MDA-MB-468 in vitro.

Description

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF DRAWING

[0027] FIG. 1 is a flow diagram illustrating separation of compounds 1, 2, and 11 to 14 in preparative example 1 according to the present invention.

[0028] FIG. 2 is a flow diagram illustrating separation of compounds 3 to 10 in preparative example 1 according to the present invention.

[0029] FIG. 3 is a flow diagram illustrating separation of compounds 15 to 23 in preparative example 1 according to the present invention.

[0030] FIG. 4 is a diagram illustrating results of cell viability tests for compound 1 in example 1 according to the present invention.

[0031] FIG. 5 is a diagram illustrating results of cell viability tests for compound 2 in example 2 according to the present invention.

[0032] FIG. 6 is a diagram illustrating results of cell viability tests for compound 3 in example 3 according to the present invention.

[0033] FIG. 7 is a diagram illustrating results of cell viability tests for compound 4 in example 4 according to the present invention.

[0034] FIG. 8 is a diagram illustrating results of cell viability tests for compound 5 in example 5 according to the present invention.

[0035] FIG. 9 is a diagram illustrating results of cell viability tests for compound 6 in example 6 according to the present invention.

[0036] FIG. 10 is a diagram illustrating results of cell viability tests for compound 7 in example 7 according to the present invention.

[0037] FIG. 11 is a diagram illustrating results of cell viability tests for compound 8 in example 8 according to the present invention.

[0038] FIG. 12 is a diagram illustrating results of cell viability tests for compound 9 in example 9 according to the present invention.

[0039] FIG. 13 is a diagram illustrating results of cell viability tests for compound 10 in example 10 according to the present invention.

[0040] FIG. 14 is a diagram illustrating results of cell viability tests for compound 11 in example 11 according to the present invention.

[0041] FIG. 15 is a diagram illustrating results of cell viability tests for compound 12 in example 12 according to the present invention.

[0042] FIG. 16 is a diagram illustrating results of cell viability tests for compound 13 in example 13 according to the present invention.

[0043] FIG. 17 is a diagram illustrating results of cell viability tests for compound 14 in example 14 according to the present invention.

[0044] FIG. 18 is a diagram illustrating results of cell viability tests for compound 15 in example 15 according to the present invention.

[0045] FIG. 19 is a diagram illustrating results of cell viability tests for compound 16 in example 16 according to the present invention.

[0046] FIG. 20 is a diagram illustrating results of cell viability tests for compound 17 in example 17 according to the present invention.

[0047] FIG. 21 is a diagram illustrating results of cell viability tests for compound 18 in example 18 according to the present invention.

[0048] FIG. 22 is a diagram illustrating results of cell viability tests for compound 19 in example 19 according to the present invention.

[0049] FIG. 23 is a diagram illustrating results of cell viability tests for compound 20 in example 20 according to the present invention.

[0050] FIG. 24 is a diagram illustrating results of cell viability tests for compound 21 in example 21 according to the present invention.

[0051] FIG. 25 is a diagram illustrating results of cell viability tests for compound 22 in example 22 according to the present invention.

[0052] FIG. 26 is a diagram illustrating results of cell viability tests for compound 23 in example 23 according to the present invention.

DETAILED DESCRIPTION OF THE INVENTION

[0053] Herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Further, unless otherwise clearly contradicted by context, singular terms used herein shall include pluralities and plural terms shall include the singular.

[0054] Herein, the term alkyl means a hydrocarbyl group which has 1 to 20 carbon atoms and is straight, branched, and/or cyclic (cycloalkyl) (i.e., 1-10, 1-9, 1-8, 1-7, 1-6, 1-5, 1-4, 1-3, 1-2, or 1 carbon atom). An alkyl structure containing 1 to 4 carbon atoms is referred to as lower alkyl. For example, the alkyl group includes methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, 2-isopropyl-3-methylbutyl, pentyl, pent-2-yl, hexyl, isohexyl, heptyl, hept-2-yl, 4,4-dimethylpentyl, octyl, 2,2,4-trimethylpentyl, nonyl, decyl, undecyl, and dodecyl. The cycloalkyl structure may be monocyclic or polycyclic, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Unless otherwise defined, an alkyl group in each example individually contains an optional substituent, i.e. unsubstituted alkyl or substituted alkyl. In a particular embodiment, the alkyl group is substituted C2-10 alkyl.

[0055] Herein, the term acyl means a moiety remaining after the removal of hydroxyl (OH) from the molecule of an inorganic or organic oxoacid. Examples of the acyl group include, but not limited to, formyl, acetyl, propionyl, butyryl, i-butyryl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, tert-butylsulfonyl), and the like.

[0056] Herein, the term alkoxy means O alkyl group. Examples of the alkyl group include, but not limited to OCH3, OCH2CH3, O(CH2) 2CH3, O(CH2) 3CH3, O(CH2)4CH3, O(CH2)5CH3. The term lower alkoxy means O-(lower alkyl), such as OCH3 and OCH2CH3.

[0057] Herein, the term aryl means an aromatic ring or a partially aromatic ring system consisting of C and H atoms. An aryl group may contain a plurality of rings bonded or fused to each other. Examples of the aryl group include naphthyl and phenyl. Unless otherwise indicated, an aryl group in each example individually contains an optional substituent, i.e. unsubstituted aryl or substituted aryl. In a particular embodiment, the aryl group is substituted phenyl. In another embodiment, the aryl group is substituted naphthyl.

[0058] Herein, the heteroaryl means that at least one carbon atom in an aryl group carries a heteroatom (e.g., N, O, or S). Examples thereof include benzofuranyl, benzothienyl, quinolyl, benzodioxolyl, furyl, and thienyl.

[0059] Herein, the term aralkyl means that an alkyl group is bound to an aryl group.

[0060] Unless otherwise defined herein, the term halogen (halo) includes F, Cl, Br, and I.

[0061] Unless otherwise defined herein, the term substituted, when used to describe a chemical structure or chemical group, means that one or more hydrogen are substituted with an atom, chemical group, or functional group, i.e., but not limited to, OH, CHO, alkoxy, acyl (e.g., OAc), alkenyl, alkyl (e.g., methyl, ethyl, propyl, t-butyl), aryl, aryloxy, halo, or haloalkyl (e.g., CCl3, CF3, C(CF3)3).

[0062] In a particular embodiment, the term substituted, when used to describe a chemical structure or chemical group, means that one or more hydrogen atoms in the structure or group of a derivative are substituted with one or more of alkoxy, acyl, alkyl, aryl, halo, haloalkyl, or hydroxyl.

[0063] Unless otherwise defined herein, a therapeutically effective amount of a compound means the amount of a compound that, when used in treating or managing a disease or condition, is sufficient to provide a therapeutic effect or to delay or reduce a symptom related to the disease or condition. A therapeutically effective amount of a compound means an amount, alone or in combination with other agents, sufficient to provide a therapeutic effect of treating or managing a disease or disorder. The term therapeutically effective amount can encompass an amount that improves overall therapeutic effect, reduces or avoids symptoms of a disease or condition, or enhances the efficacy of another therapeutic agent.

[0064] Unless otherwise defined herein, the term treat, treating or treatment means an action of administration to a patient with a particular disease or disorder, where the action can reduce the disease or disorder of the patient, or the severity of one or more symptoms, or slow or delay the progress of the disease or disorder.

[0065] It should be noted that if the stereochemistry of a structure or a portion of a structure is not indicated with, for example, bold or dashed lines, the structure or portion of the structure is to be interpreted as encompassing all stereoisomers of it. Similarly, where a compound contains one or more asymmetric centers and its name does not specifically define the stereochemistry encompassed by these asymmetric centers, the compound should be interpreted as encompassing its pure optical isomers and mixtures thereof. Furthermore, any atom with unsatisfied valences shown in the figures is assumed to have the sufficient hydrogen atoms to satisfy the valences.

[0066] Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values set forth in the specific examples are presented herein as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in its respective testing measurement. Herein, the term about generally means that an actual value is within 10%, 5%, 1%, or 0.5% above and below a particular value or range. Alternatively, the term about indicates that the actual value falls within an acceptable standard error of the mean when considered by one of ordinary skill in the art. Except in the Examples, or where otherwise explicitly indicated, all ranges, amounts, values, and percentages used herein (for example, for describing amounts of materials, time, temperature, operation conditions, amount ratio, and the like) are understood to be modified by the word about. Thus, unless expressly stated to the contrary, the numerical parameters disclosed in this specification and the appended claims are all approximations and, if required, may vary. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0067] The compounds of this invention are momordicin I derivatives which may contain one or more stereogenic centers; and therefore, the compounds are present as different isomers, for example, a racemic mixture of enantiomers and/or mixture of diastereomers. The present invention encompasses enantiomers of these compounds, and a mixture of these enantiomers and/or diastereomers. Enantiomers may be prepared by asymmetric synthesis, or separated using conventional techniques, e.g., crystallization, chromatography, and separation with a resolving agent. High-performance liquid chromatography (HPLC) is a preferred method for separating enantiomers from a racemic mixture. Additionally, two enantiomers may also be separated from each other from racemic isomers through a reaction with the optically active form of a resolving agent in a solvent. Depending on the optical form of the resolving agent used, one isomer of two enantiomers may be separated as an insoluble salt, and compared to the isomer remaining in the solution, the separated isomer has high yield and high optical purity.

[0068] The present invention further includes a mixture of stereoisomers of the compounds. Furthermore, the present invention also encompasses conformational isomers (i.e., cis and trans isomers, with or without double bonds) of the compounds, including a mixture of the isomers, pure isomers, or substantially pure form.

[0069] The pharmaceutical composition disclosed in this invention is suitable for treating various cancers, for example, such as, but not limited to, liver cancer, colorectal cancer, esophageal cancer, gastric cancer, leukemia, malignant lymphoma, nasopharyngeal cancer, malignant glial brain tumor, lung cancer, breast cancer, cervical cancer, bone cancer, rectal cancer, liver cancer, breast cancer, or hematologic cancer, and preferably, liver cancer, colorectal cancer, esophageal cancer, gastric cancer, leukemia, malignant lymphoma, nasopharyngeal cancer, malignant glial brain tumor, lung cancer, breast cancer, cervical cancer, hematologic cancer, or bone cancer.

[0070] The pharmaceutical composition disclosed in this invention may be prepared by well-known pharmaceutical processes. In one implementation aspect of this invention, the pharmaceutical composition disclosed in this invention may be administered by way of any appropriate dosing route, for example, systemic administration modes by oral administration as capsules, suspensions, or dragees, or by parenteral administration, for example, as intramuscular injection, intravenous injection, subcutaneous injection, or intraperitoneal injection. In addition, in some embodiments, the pharmaceutical composition disclosed in this invention may also be administered through transmucosal or transdermal means, for example, topical dermal application, or bronchial, nasal, or oral inhalation, or instillation as nasal drops; and may also be administered rectally.

[0071] For oral administration, the pharmaceutical composition disclosed in this invention may be administered with excipients or may be administered without excipients. Also, the pharmaceutical composition of this invention may also be formulated into dragees as a solid dosage form containing various auxiliaries, disintegrants, granular binders, or lubricants therein. Additionally, in an example, lactose or high molecular weight polyethylene glycols may also be used. In addition, optionally, the rate of release of any pharmaceutically active ingredient may be further improved with a coating or cladding, for example, enteric coating. In other examples, the pharmaceutical composition of this invention may also be formulated into a liposome structure or biomimetic extracellular matrix system structure, or may be filled into hard and soft gelatin capsules, or may be encapsulated into biodegradable granules in kits.

[0072] Also, in the present invention, a pharmaceutically acceptable excipient means one that is compatible with other ingredients of the pharmaceutical formulation and compatible with organisms, for example, encapsulating materials, or various additives such as absorption enhancer, antioxidant, binder, buffer, coating agent, coloring agent, diluent, disintegrant, emulsifier, supplement, filler, flavoring agent, humectant, lubricant, perfume, preservative, propellant, release agent, sterilization agent, sweating agent, solubilizing agent, wetting agent, and mixtures thereof.

[0073] Examples of auxiliaries suitable for use in the present invention may be, for example, microcrystalline cellulose, calcium carbonate, dicalcium phosphate, or glycine. Examples of disintegrants suitable for use in the present invention may be, for example, starch, alginic acids, or certain silicates. Examples of granular binders suitable for use in the present invention may be, for example, polyvinylpyrrolidone, sucrose, gelatin, or acacia. Examples of granular binders suitable for use in the present invention may be, for example, magnesium stearate, sodium lauryl sulfate, or talc. Examples of excipients suitable for use in the present invention may be, for example, lactose, sucrose, mannitol, sorbitol, maize starch, wheat starch, rice starch, potato starch, gelatin, or gum tragacanth.

[0074] In some embodiments, the pharmaceutical composition of this invention is formulated into a liquid dosage form suitable for oral administration, for example, oral suspensions, emulsions, microemulsions, and/or elixirs. For such a liquid dosage form, the active ingredients of the pharmaceutical composition of this invention may be further formulated with various sweating agents or flavoring agents, coloring agents or dyes, if desired, with addition of emulsifiers and/or suspending agents, or diluents such as water, alcohol, propylene glycol, or glycerine, or buffers used to maintain the pH.

[0075] Also, in other embodiments, the liquid formulation containing the pharmaceutical composition of this invention is made into sterile injectable solutions or suspensions; for example, made into solutions suitable for administration by intravenous, intramuscular, subcutaneous, or intraperitoneal injection.

[0076] Examples of diluents suitable for use in the sterile injectable solutions or suspensions may be, for example, but not limited to, 1,3-butanediol, mannitol, water, Ringer's solution, or isotonic sodium chloride solution; fatty acids such as oleic acid, glyceride derivatives, or natural pharmaceutically acceptable oils such as olive oil or rapeseed oil.

[0077] Furthermore, in some embodiments, alcohol or carboxymethyl cellulose dispersants, surfactants, emulsifiers, or the like may also be further added.

[0078] In addition, in some embodiments, the liquid formulation containing the pharmaceutical composition of this invention may also be filled into soft capsules for use.

[0079] In addition, in one embodiment, the mendicant or pharmaceutical composition of this invention may also be prepared with pharmaceutically acceptable polymeric auxiliaries into many dosage forms suitable for mucosal application, for example, buccal and/or sublingual dosage form. Generally, the polymeric auxiliaries include hydrophilic polymers, for example, including, but not limited to, acrylic acid polymers, hydrolyzed polyvinylalcohol, polyethylene oxides, polyacrylates, vinyl polymers, polyvinylpyrrolidones, dextran, guar gum, pectins, starches, or cellulosic polymers.

[0080] In some embodiments, the pharmaceutical composition disclosed in this invention may be used as an additional adjunctive therapeutic agent, so as to improve the therapeutic effect of a primary treatment method of cancers such as surgery, radiotherapy, or chemotherapy. The pharmaceutical composition disclosed in this invention may be applied alone or in combination with conventional pharmaceutically acceptable auxiliaries, and, for example, may be administered orally or with a food to an individual.

[0081] In some embodiments, the method of this invention further includes before, during or after administering the pharmaceutical composition of this invention to the individual, additionally applying another primary treatment means of cancers such as surgery, radiotherapy, or chemotherapy to the individual, so as to improve the therapeutic effect of cancers in the individual.

[0082] For a more thorough and complete description of this disclosure, illustrative description for implementation aspects and specific examples of this invention is provided below; however, this is not intended to represent the only form of specific examples in which the present invention may be practiced or utilized. Features of a number of specific examples and process steps and sequences to construct and operate these specific examples are covered in the embodiments. However, the same or equivalent functions and step sequences may also be accomplished by other examples.

[0083] Firstly, standard operation processes of the tests in examples of this invention are described.

[0084] <Cell Viability Tests>

[0085] Cells used the tests were human leukemia cells U937, human lung cancer cells A549, African green monkey kidney cells Vero, human Glioblastoma cells U87-MG, human liver cancer cells Mahlavu, human colorectal cancer cells SW-480, human breast cancer cells MDA-MB-231, and human breast cancer cells MDA-MB-468.

[0086] U937 and A549 cells were cultured in RPMI 1640 medium, supplemented with 10% fetal calf serum (FCS), 100 U/ml penicillin, and 10 g/ml streptomycin.

[0087] Vero, U87-MG, MDA-MB-231, MDA-MB-468, Mahlavu, and SW480 were cultured in DMEM medium containing 10% fetal calf serum (FCS), 100 U/ml penicillin, and 10 g/ml streptomycin.

[0088] Vero, U87-MG, MDA-MB-231, MDA-MB-468, A549, and Mahlavu cells were seeded at 1104 cells/well in 96-well plates in cell culture medium containing 10% fetal calf serum (FCS), incubated for 16 hours in an incubator for complete cell adhesion, washed twice with phosphate-buffered saline (PBS), added with cell culture medium containing 10% fetal calf serum (FCS), incubated for 24 hours in the incubator, washed once with phosphate-buffered saline (PBS), added with cell culture medium containing the agent and 0.1% fetal calf serum (FCS) (at final concentrations of the agent of 200, 100, 50, 25, 12.5, 6.25, 3.125, 1.5625, 0.78125, 0 M), and incubated for 48 hours in the incubator. Cell viability was determined with Resazurin (at a final concentration of 25 g/mL).

[0089] SW480 cells were seeded at 1104 cells/well in 96-well plates in cell culture medium containing 10% fetal calf serum (FCS), incubated for 36 hours in an incubator for complete cell adhesion, washed twice with phosphate-buffered saline (PBS), added with cell culture medium containing the agent and 0.1% fetal calf serum (FCS) (at final concentrations of the agent of 200, 100, 50, 25, 12.5, 6.25, 3.125, 1.5625, 0.78125, 0 M), and incubated for 48 hours in the incubator. Cell viability was determined with Resazurin (at a final concentration of 25 g/mL).

[0090] U937 cells were incubated for 24 hours in the incubator in cell culture medium containing 0.1% fetal calf serum (FCS), washed twice with phosphate-buffered saline (PBS), again added with cell culture medium containing 0.1% fetal calf serum (FCS), seeded at 1104 cells/well in 96-well plates, added with cell culture medium containing the agent and 0.1% fetal calf serum (FCS) (at final concentrations of the agent of 200, 100, 50, 25, 12.5, 6.25, 3.125, 1.5625, 0.78125, 0 M), and incubated for 48 hours in the incubator. Cell viability was determined with Resazurin (at a final concentration of 25 g/mL).

[0091] Hereafter, the present invention will be described in detail by explaining preferred embodiments of the invention with reference to the attached drawings.

Preparative Example 1

[0092] Referring to FIGS. 1 to 3, flow diagrams illustrating separation of compounds 1 to 23 are shown. Firstly, air-dried balsam pear stem (at a dry weight of 1.0 kg) was ground by a grinder, and extracted with 10 L MeOH3. The extracts were combined, filtered, and concentrated under reduced pressure. Liquid/liquid layer separation was performed with EtOAc/H2O. The upper EtOAc layer was concentrated under reduced pressure to give 35 g of a dark green crude extract.

[0093] The crude extract was subjected to preliminary separation by column chromatography using Silica gel 60, 70-230 mesh in combination with organic solvents n-hexane/EtOAc/MeOH at different ratios for gradient elution. Firstly, n-hexane was used as initial elution solvent, and the proportion of EtOAc was gradually increased to enhance the polarity of the eluent till the proportion of EtOAc reached 100%. Then, EtOAc was used as eluent, and the proportion of MeOH was gradually increased to enhance the polarity of the eluent till the proportion of MeOH reached 100%. Fractions were combined by 1H-NMR and TLC sheet to give 29 fractions in total, MC-1 to MC-29, respectively. The separation process diagram is shown in FIG. 1.

[0094] 1. Purification and Separation of Compounds 1 and 2

[0095] Referring to FIG. 1, MC-19 (5 g) obtained using n-hexane/EtOAc (1:8) as eluent was subjected to reverse-phase column chromatography over silica gel (RP-18, 230 to 400 mesh) with MeOH/water (80:20) as eluent, and divided into two fractions, MC-19-R1 and MC-19-R2, respectively. Then, MC-19-R1 (4 g) was subjected to reverse-phase column chromatography over silica gel (RP-18, 230 to 400 mesh) with MeOH/water (60:40 to 100:0) as eluent, and divided into five fractions, MC-19-R1-R1 to MC-19-R1-R5, respectively. Then, MC-19-R1-R4 (3.3 g) was subjected to reverse-phase HPLC (RP-18, 5 m, 25025 mm, Merck, UV-vis detector), and separated and purified with MeOH/water (80:20) as eluent, to give 30 mg compound 1 and 40 mg compound 2.

[0096] 2. Purification and Separation of Compounds 3 to 10

[0097] Referring to FIG. 2, 270 mg of MC-19-R1-R4 (3.3 g) was dissolved into pyridine (2 ml), and the reaction lasted for 3 h with addition of 4 drops of acetic anhydride and then was stopped with water. Liquid/liquid layer separation was performed with EtOAc. The upper EtOAc layer was concentrated under reduced pressure, and separated and purified using normal-phase column chromatography over silica gel and reverse-phase HPLC to give compounds 3 (7 mg), 4 (3.2 mg), 5 (5.2 mg), 6 (9 mg), 7 (26.2 mg), 8 (3.5 mg), 9 (10.6 mg), and 10 (24 mg).

[0098] 3. Purification and Separation of Compound 11

[0099] Referring to FIG. 1, MC-18 (2 g) obtained using n-hexane/EtOAc (1:6) as eluent was subjected to normal-phase column chromatography over silica gel (Silica gel 60, 230-400 mesh) with n-hexane/EtOAc (1:1-0:1) as eluent, and divided into 11 fractions, MC-18-N1 to MC-18-N11, respectively. Then, MC-18-N4 (750 mg) obtained using n-hexane/EtOAc (1:3) as eluent was subjected to reverse-phase column chromatography over silica gel (RP-18, 230 to 400 mesh) with MeOH/water (70:30 to 100:0) as eluent, and divided into 11 fractions, MC-18-N4-R1 to MC-18-N4-R11, respectively. Then, MC-18-N4-R3 (119.3 mg) was subjected to reverse-phase HPLC (RP-18, 5 m, 25025 nm, Merck, UV-vis detector), and separated and purified with MeOH/water (75:25) as eluent, to give compound 11 (26 mg).

[0100] 4. Purification and Separation of Compounds 12 to 14

[0101] Referring to FIG. 1, MC-27 (6.3 g) obtained using EtOAc/MeOH (2:1) as eluent was subjected to reverse-phase column chromatography (MCI) with MeOH/water (60:40-100:0) as eluent, and divided into 10 fractions, MC-27-M1 to MC-27-M10, respectively. MC-27-M2 (1 g) obtained using MeOH/water (80:20) as eluent was subjected to reverse-phase column chromatography over silica gel (RP-18, 230 to 400 mesh) with MeOH/water (60:40-100:0) as eluent, and divided into 8 fractions, MC-27-M2-R1 to MC-27-M2-R8, respectively.

[0102] MC-27-M2-R5 (568.3 mg) was subjected to reverse-phase HPLC (RP-18, 5 m, 25025 mm, Merck, UV-vis detector), and separated and purified with MeOH/water (77:23) as eluent, to give compound 12 (32 mg), compound 13 (30 mg), and compound 14 (5 mg).

[0103] 5. Purification and Separation of Compounds 15 to 23

[0104] Referring to FIG. 3, 300 mg of MC-19-R1-R4 (3.3 g) was dissolved into MeOH (10 ml), and reacted with HCl (0.1 M, 1 ml) for 3.5 at RT, and then the reaction was stopped with water. Liquid/liquid layer separation was performed with EtOAc and water. The upper EtOAc layer was concentrated under reduced pressure, and separated and purified using reverse-phase column chromatography over silica gel and reverse-phase HPLC to give compounds 15 (14 mg), 16 (6 mg), 17 (14 mg), 18 (3 mg), 19 (3 mg), 20 (3 mg), 21 (2.9 mg), 22 (2 mg), 23 (12.2 mg).

[0105] Then, the obtained compounds 1 to 23 were further subjected to nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry, so as to identify or measure their chemical structural characteristics, functionality, molecular weight, and spectral data, etc. The results of identification or measurement of compounds 1 to 23 are shown in Table 1.

TABLE-US-00001 TABLE 1 Compound Chemical structure Spectral data Compound 1 [00005] Molecular formula C.sub.30H.sub.48O.sub.4; amorphous white powder; optical activity [].sup.26.sub.D + 58.0 (c = 0.48, MeOH); IR(KBr) v.sub.max 3400 (br), 1715, 1660, 1470, 1460, 1385, 1155, 1090, 1050, 1020, 980 cm.sup.1; .sup.1H-NMR (C.sub.5D.sub.5N, 400 MHz) .sub.H 1.76 (1H, m, H-1), 2.09 (2H, m, H-2), 3.84 (1H, m, H-3), 6.28 (1H, br d, J = 4.1 Hz, H-6), 4.38 (1H, br d, J = 5.5 Hz, H-7), 2.39 (1H, br s, H-8), 2.69 (1H, m, H-10), 1.24 (1H, m, H-16), 0.88 (3H, s, H-18), 10.66 (1H, s, H-19), 0.99 (3H, d, J = 6.3 Hz, H-21), 1.85 (1H, m, H-22), 2.24 (1 H, m, H-22), 5.93 (1 H, m, H-23), 5.91 (1H, d, J = 15.4 Hz, H-24), 1.54, (3H, br s, H-26), 1.55 (3H, br s, H-27), 1.49 (3H, s, H-28), 1.19 (3H, s, H-29), 0.85 (3H, s, H-30); .sup.13C-NMR (C.sub.5D.sub.5N, 100 MHz) .sub.C 21.8 (t, C-1), 29.9 (t, C-2), 75.7 (d, C-3), 41.8 (s, C-4), 145.3 (s, C-5), 124.3 (d, C-6), 65.7 (d, C-7), 50.7 (d, C-8), 50.6 (s, C-9), 36.9 (d, C-10), 22.7 (t, C-11), 29.4 (t, C-12), 45.8 (s, C-13), 48.3 (s, C-14), 35.0 (t, C-15), 27.8 (t, C-16), 50.2 (d, C-17), 15.1 (q, C-18), 207.8 (d, C-19), 36.6 (d, C-20), 19.0 (q, C-21), 39.6 (t, C-22), 124.2 (d, C-23), 141.7 (d, C-24), 69.7 (s, C-25), 30.9 (q, C-26), 30.9 (q, C-27), 26.2 (q, C-28), 27.4 (q, C-29), 18.2 (q, C-30); EIMS m/z 472.3519 [M].sup.+ (calcd for C.sub.30H.sub.48O.sub.4, 472.3552); FABMS m/z 495 [M + Na].sup.+, 511 [M + K].sup.+. A d. found C 73.89%, H 10.52%; calcd for C.sub.30H.sub.48O.sub.4H.sub.2O, C 73.43%, H 10.27%. Compound 2 [00006] Molecular formula C.sub.30H.sub.48O.sub.4; amorphous white powder; optical activity [].sub.D + 73.1 (c = 0.160, CHCI.sub.3); IR v.sub.max 3418, 2945, 2871, 1708, 1663, 1467, 1382 cm.sup.1; .sup.1H-NMR (MeOD, 400 MHz) .sub.H 1.25, 1.08, 0.93, 0.82 (each 3 H, s), 3.55 (1H, br s, H-3), 5.91 (1H, d, J = 4.0 Hz, H-6), 4.00 (1H, d, J = 5.2 Hz, H-7), 2.40 (1H, m, H-8), 2.58 (1H, m, H-10), 9.88 (1H, s, H-19), 1.98 (1H, m, H-20), 1.00 (3H, d, J = 6.4 Hz, H-21), 4.41 (1H, dt, J.sub.1 = 8.8 Hz, J.sub.2 = 3.2 Hz, H-23), 5.16 (1H, d, J = 8.8 Hz, H-24), 1.70 (3H, s, H-26), 1.67 (3H, s, H-27); .sup.13C-NMR (MeOD, 100 MHz) .sub.C 22.2 (t, C-1), 30.3 (t, C-2), 77.1 (d, C-3), 42.3 (s, C-4), 147.3 (s, C-5), 124.0 (d, C-6), 66.9 (d, C-7), 50.8 (d, C-8), 52.1 (s, C-9), 37.7 (d, C-10), 23.3 (t, C-11), 29.8 (t, C-12), 46.8 (s, C-13), 49.0 (s, C-14), 35.6 (t, C-15), 28.6 (t, C-16), 51.3 (d, C-17), 15.3 (q, C-18), 209.7 (d, C-19), 33.7 (d, C-20), 19.3 (q, C-21), 45.6 (t, C-22), 66.6 (d, C-23), 133.4 (d, C-24), 130.5 (s, C-25), 18.8 (q, C-26), 26.0 (q, C-27), 25.9 (q, C-28), 27.8 (q, C-29), 18.1 (q, C-30); HRMS m/z 472.3551 [M].sup.+ (calcd for C.sub.30H.sub.48O.sub.4, 472.3552). Compound 3 [00007] Molecular formula C.sub.36H.sub.54O.sub.7; amorphous white powder; optical activity [].sup.26.sub.D 24.7 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,430 (br), 2,948, 2,357, 1,726, 1,451, 1,376, 1,236, 1,025, 969, 754 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.66 (1H, m, H-1), 1.34 (1H, m, H-1), 1.24 (1H, m, H-2), 1.85 (1H, m, H-2), 4.82 (1H, br s, H-3), 5.86 (1H, d, J = 4.8 Hz, H-6), 5.21 (1H, d, J = 5.6 Hz, H-7), 1.89 (1H, s, H-8), 2.56 (1H, m, H-10), 1.45 (2H, m, H-11), 2.38 (2H, m, H-11), 1.60 (2H, m, H-12), 1.65 (2H, m, H-12), 1.42 (2H, m, H-15), 1.36 (1H, m, H-16), 1.92 (1H, m, H-16), 1.47 (1H, m, H-17), 0.86 (3H, s, H-18), 9.83 (1H, s, H-19), 1.46 (1H, m, H-20), 0.95 (3H, d, J = 6.4 Hz, H-21), 1.78 (1H, m, H-22a), 1.06 (1H, m, H-22b), 5.60 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.09 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.70 (3H, d, J = 1.2 Hz, H-26), 1.73 (3H, d, J = 1.2 Hz, H-27), 1.16 (3H, s, H-28), 1.13 (3H, s, H-29), 0.81 (3H, s, H-30), 2.04 (s, 3-OAc), 2.03 (s, 7-OAc), 2.02 (s, 23-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 21.5 (t, C-1), 26.1 (t, C-2), 77.9 (d, C-3), 40.1 (s, C-4), 148.1 (s, C-5), 119.5 (d, C-6), 68.7 (d, C-7), 46.4 (d, C-8), 49.7 (s, C-9), 35.9 (d, C-10), 21.9 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.9 (s, C-14), 34.5 (t, C-15), 27.5 (t, C-16), 50.3 (d, C-17), 14.7 (q, C-18), 207.0 (d, C-19), 32.7 (d, C-20), 18.9 (q, C-21), 41.8 (t, C-22), 69.3 (d, C-23), 124.6 (d, C-24), 135.8 (s, C-25), 18.3 (q, C-26), 25.6 (q, C-27), 24.8 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.6 (s, 3-OAc), 21.9 (q, 3-OAc), 170.2 (s, 7-OAc), 21.3 (q, 7-OAc), 170.6 (q, 23-OAc), 21.5 (s, 23-OAc); ESIMS m/z 621 [M + Na].sup.+; HRESIMS m/z 621.3763 [M + Na].sup.+. Compound 4 [00008] Molecular formula C.sub.34H.sub.52O.sub.6; amorphous white powder; melt point 101-104 C.; IR (KBr) v.sub.max 3,450 (br), 1,735, 1,720, 1,610, 1,470, 1,380, 1,260, 1,220, 1,190, 1,020, 990, 940, 920 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.62 (1H, m, H-1), 1.56 (1H, m, H-1), 1.93 (1H, m, H-2), 1.77 (1H, m, H-2), 4.82 (1H, br s, H-3), 5.88 (1H, d, J = 5.2 Hz, H-6), 5.19 (1H, d, J = 5.6 Hz, H-7), 1.91 (1H, s, H-8), 2.55 (1H, m, H-10), 1.42 (2H, m, H-11), 2.38 (2H, m, H-11), 1.56 (2H, m, H-12), 1.64 (2H, m, H-12), 1.43 (2H, m, H-15), 1.35 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.87 (3H, s, H-18), 9.80 (1H, s, H-19), 1.52 (1H, m, H-20), 0.91 (3H, d, J = 5.5 Hz, H-21), 1.72 (1H, m, H-22a), 2.15 (1H, m, H-22b), 5 (1H, ddd, J.sub.1 = 15.6 Hz, J.sub.2 = 8.4 Hz, J.sub.3 = 5.6 Hz, H-23), 5.59 (1H, d, J = 5.6 Hz, J, H-24), 1.31 (3H, d, J = 1.2 Hz, H-26), 1.31 (3H, d, J = 1.2 Hz, H-27), 1.26 (3H, s, H-28), 1.09 (3H, s, H-29), 0.81 (3H, s, H-30), 2.04 (s, 3-OAc), 2.01 (s, 7-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 20.9 (t, C-1), 28.5 (t, C-2), 76.2 (d, C-3), 41.6 (s, C-4), 149.5 (s, C-5), 120.2 (d, C-6), 68.7 (d, C-7), 46.1 (d, C-8), 49.9 (s, C-9), 35.8 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.6 (t, C-15), 27.3 (t, C-16), 49.8 (d, C-17), 14.9 (q, C-18), 206.9 (d, C-19), 36.1 (d, C-20), 18.7 (q, C-21), 39.0 (t, C-22), 125.1 (d, C-23), 139.7 (d, C-24), 70.7 (s, C-25), 29.9 (q, C-26), 30.0 (q, C-27), 25.2 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.6 (s, 3-OAc), 21.9 (q, 3-OAc), 170.1 (s, 7-OAc), 21.3 (q, 7-OAc); EIMS m/z 478.3462 [M HOAc H2O].sup.+ (calcd for C.sub.32H.sub.48O.sub.4, 478.3447); FABMS m/z 579 [M + Na].sup.+, 595 [M + Kl].sup.+. Compound 5 [00009] Molecular formula C.sub.34H.sub.52O.sub.6; amorphous white powder; optical activity [].sup.26D 0.6 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,427, 2,926, 2,859, 2,353, 1,725, 1,544, 1,455, 1,373, 1,244, 1,016, 976, 673 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.66 (1H, m, H-1), 1.34 (1H, m, H-1), 1.24 (1H, m, H-2), 1.85 (1H, m, H-2), 4.82 (1H, br s, H-3), 5.86 (1H, d, J = 4.8 Hz, H-6), 5.21 (1H, d, J = 5.6 Hz, H-7), 1.89 (1H, s, H-8), 2.56 (1H, m, H-10), 1.46 (2H, m, H-11), 2.36 (2H, m, H-11), 1.60 (2H, m, H-12), 1.66 (2H, m, H-12), 1.45 (2H, m, H-15), 1.32 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.84 (3H, s, H-18), 9.78 (1H, s, H-19), 1.51 (1H, m, H-20), 0.94 (3H, d, J = 5.5 Hz, H-21), 1.80 (1H, m, H-22a), 1.10 (1H, m, H-22b), 4.46 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.08 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.71 (3H, d, J = 1.2 Hz, H-26), 1.68 (3H, d, J = 1.2 Hz, H-27), 1.24 (3H, s, H-28), 1.07 (3H, s, H-29), 0.80 (3H, s, H-30), 2.04 (s, 3-OAc), 2.03 (s, 7-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 21.5 (t, C-1), 26.1 (t, C-2), 77.9 (d, C-3), 40.1 (s, C-4), 148.1 (s, C-5), 119.5 (d, C-6), 68.7 (d, C-7), 46.4 (d, C-8), 49.7 (s, C-9), 35.9 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.5 (t, C-15), 27.5 (t, C-16), 50.3 (d, C-17), 14.7 (q, C-18), 206.4 (d, C-19), 32.7 (d, C-20), 18.9 (q, C-21), 41.9 (t, C-22), 69.4 (d, C-23), 124.6 (d, C-24), 135.7 (s, C-25), 18.3 (q, C-26), 25.6 (q, C-27), 25.0 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.6 (s, 3-OAc), 21.9 (q, 3-OAc), 170.2 (s, 7-OAc), 21.3 (q, 7-OAc); ESIMS m/z 579 [M + Na].sup.+; HRESIMS m/z 579.3654 [M + Na].sup.+. Compound 6 [00010] Molecular formula C.sub.34H.sub.52O.sub.6; amorphous white powder; optical activity [].sup.26.sub.D + 4.0 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,448 (br), 2,936, 2,348, 1,723, 1,455, 1,376, 1,249, 1,013, 986, 754 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.66 (1H, m, H-1), 1.34 (1H, m, H-1), 1.24 (1H, m, H-2), 1.85 (1H, m, H-2), 4.82 (1H, br s, H-3), 5.86 (1H, d, J = 4.8 Hz, H-6), 5.21 (1H, d, J = 5.6 Hz, H-7), 1.89 (1H, s, H-8), 2.56 (1H, m, H-10), 1.46 (2H, m, H-11), 2.36 (2H, m, H-11), 1.60 (2H, m, H-12), 1.66 (2H, m, H-12), 1.45 (2H, m, H-15), 1.32 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.84 (3H, s, H-18), 9.78 (1H, s, H-19), 1.51 (1H, m, H-20), 0.94 (3H, d, J = 5.5 Hz, H-21), 1.80 (1H, m, H-22), 1.10 (1H, m, H-22b), 5.58 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.08 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.71 (3H, d, J = 1.2 Hz, H-26), 1.68 (3H, d, J = 1.2 Hz, H-27), 1.24 (3H, s, H-28), 1.07 (3H, s, H-29), 0.80 (3H, s, H-30), 2.04 (s, 3-OAc), 2.02 (s, 23-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 21.5 (t, C-1), 26.1 (t, C-2), 77.9 (d, C-3), 40.1 (s, C-4), 148.1 (s, C-5), 119.5 (d, C-6), 68.7 (d, C-7), 46.4 (d, C-8), 49.7 (s, C-9), 35.9 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.5 (t, C-15), 27.5 (t, C-16), 50.3 (d, C-17), 14.7 (q, C-18), 206.4 (d, C-19), 32.7 (d, C-20), 18.9 (q, C-21), 41.9 (t, C-22), 69.4 (d, C-23), 124.6 (d, C-24), 135.7 (s, C-25), 18.3 (q, C-26), 25.6 (q, C-27), 25.0 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.6 (s, 3-OAc), 21.9 (q, 3-OAc), 170.6 (q, 23-OAc), 21.5 (s, 23-OAc); ESIMS m/z 579 [M + Na].sup.+; HRESIMS m/z 579.3654 [M + Na].sup.+. Compound 7 [00011] Molecular formula C.sub.34H.sub.52O.sub.6; amorphous white powder; optical activity [].sup.26.sub.D + 83.1 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,461 (br), 2,948, 2,879, 2,357, 1,723, 1,451, 1,376, 1,244, 1,017, 934, 758 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.62 (1H, m, H-1), 1.54 (1H, m, H-1), 1.78 (1H, m, H-2), 1.94 (1H, m, H-2), 3.60 (1H, br s, H-3), 5.85 (1H, d, J = 5.2 Hz, H-6), 5.16 (1H, d, J = 5.2 Hz, H-7), 1.90 (1H, s, H-8), 2.53 (1H, m, H-10), 1.46 (2H, m, H-11), 2.36 (2H, m, H-11), 1.60 (2H, m, H-12), 1.66 (2H, m, H-12), 1.45 (2H, m, H-15), 1.32 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.84 (3H, s, H-18), 9.78 (1H, s, H-19), 1.51 (1H, m, H-20), 0.94 (3H, d, J = 5.5 Hz, H-21), 1.80 (1H, m, H-22a), 1.10 (1H, m, H-22b), 5.58 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.08 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.71 (3H, d, J = 1.2 Hz, H-26), 1.68 (3H, d, J = 1.2 Hz, H-27), 1.24 (3H, s, H-28), 1.07 (3H, s, H-29), 0.80 (3H, s, H-30), 2.00 (s, 7-OAc), 1.98 (s, 23-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 20.9 (t, C-1), 28.5 (t, C-2), 76.1 (d, C-3), 41.6 (s, C-4), 148.6 (s, C-5), 120.1 (d, C-6), 68.7 (d, C-7), 46.0 (d, C-8), 49.8 (s, C-9), 35.8 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.5 (t, C-15), 27.5 (t, C-16), 50.3 (d, C-17), 14.7 (q, C-18), 206.4 (d, C-19), 32.7 (d, C-20), 18.9 (q, C-21), 41.9 (t, C-22), 69.4 (d, C-23), 124.6 (d, C-24), 135.7 (s, C-25), 18.3 (q, C-26), 25.6 (q, C-27), 25.0 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.2 (s, 7-OAc), 21.3 (q, 7-OAc), 170.6 (q, 23-OAc), 21.5 (s, 23-OAc); ESIMS m/z 579 [M + Na].sup.+; HRESIMS m/z 579.3654 [M + Na].sup.+. Compound 8 [00012] Molecular formula C.sub.32H.sub.50O.sub.5; amorphous white powder; optical activity [].sup.26.sub.D + 115.8 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,448 (br), 2,947, 2,883, 2,356, 1,717, 1,460, 1,374, 1,235, 1,013, 939, 754 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.66 (1H, m, H-1), 1.57 (1H, m, H-1), 1.80 (1H, m, H-2), 1.96 (1H, m, H-2), 3.61 (1H, br s, H-3), 5.87 (1H, d, J = 5.6 Hz, H-6), 5.19 (1H, d, J = 5.6 Hz, H-7), 1.92 (1H, s, H-8), 2.55 (1H, m, H-10), 1.48 (2H, m, H-11), 2.36 (2H, m, H-11), 1.66 (2H, m, H-12), 1.72 (2H, m, H-12), 1.44 (2H, m, H-15), 1.40 (1H, m, H-16), 1.96 (1H, m, H-16), 1.50 (1H, m, H-17), 0.89 (3H, s, H-18), 9.79 (1H, s, H-19), 1.75 (1H, m, H-20), 0.99 (3H, d, J = 5.5 Hz, H-21), 1.65 (1H, m, H-22a), 1.04 (1H, m, H-22b), 4.46 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.19 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.70 (3H, d, J = 1.2 Hz, H-26), 1.69 (3H, d, J = 1.2 Hz, H-27), 1.26 (3H, s, H-28), 1.08 (3H, s, H-29), 0.81 (3H, s, H-30), 2.00 (s, 7-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 20.9 (t, C-1), 28.5 (t, C-2), 76.2 (d, C-3), 41.6 (s, C-4), 148.5 (s, C-5), 120.2 (d, C-6), 68.7 (d, C-7), 46.0 (d, C-8), 49.9 (s, C-9), 35.8 (d, C-10), 22.2 (t, C-11), 28.9 (t, C-12), 45.6 (s, C-13), 47.8 (s, C-14), 34.5 (t, C-15), 27.6 (t, C-16), 50.7 (d, C-17), 14.9 (q, C-18), 206.3 (d, C-19), 32.6 (d, C-20), 18.7 (q, C-21), 44.4 (t, C-22), 65.9 (d, C-23), 129.0 (d, C-24), 133.9 (s, C-25), 25.7 (q, C-26), 18.7 (q, C-27), 25.2 (q, C-28), 27.0 (q, C-29), 18.1 (q, C-30), 170.2 (s, 7-OAc), 21.3 (q, 7-OAc); ESIMS m/z 537 [M + Na].sup.+; HRESIMS m/z 537.3549 [M + Na].sup.+. Compound 9 [00013] Molecular formula C.sub.32H.sub.50O.sub.5; amorphous white powder; optical activity [].sup.26.sub.D 0.6 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,450 (br), 1,735, 1,720, 1,610, 1,470, 1,380, 1,260, 1,220, 1,190, 1,020, 990, 940, 920 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.62 (1H, m, H-1), 1.56 (1H, m, H-1), 1.93 (1H, m, H-2), 1.77 (1H, m, H-2), 3.62 (1H, br s, H-3), 5.88 (1H, d, J = 5.2 Hz, H-6), 5.19 (1H, d, J = 5.6 Hz, H-7), 1.91 (1H, s, H-8), 2.55 (1H, m, H-10), 1.42 (2H, m, H-11), 2.38 (2H, m, H-11), 1.56 (2H, m, H-12), 1.64 (2H, m, H-12), 1.43 (2H, m, H-15), 1.35 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.87 (3H, s, H-18), 9.80 (1H, s, H-19), 1.52 (1H, m, H-20), 0.91 (3H, d, J = 5.5 Hz, H-21), 1.72 (1H, m, H-22a), 2.15 (1H, m, H-22b), 5 (1H, ddd, J.sub.1 = 15.6 Hz, J.sub.2 = 8.4 Hz, J.sub.3 = 5.6 Hz, H-23), 5.59 (1H, d, J = 5.6 Hz, J, H-24), 1.31 (3H, d, J = 1.2 Hz, H-26), 1.31 (3H, d, J = 1.2 Hz, H-27), 1.26 (3H, s, H-28), 1.09 (3H, s, H-29), 0.81 (3H, s, H-30), 2.01 (s, 7-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 20.9 (t, C-1), 28.5 (t, C-2), 76.2 (d, C-3), 41.6 (s, C-4), 149.5 (s, C-5), 120.2 (d, C-6), 68.7 (d, C-7), 46.1 (d, C-8), 49.9 (s, C-9), 35.8 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.6 (t, C-15), 27.3 (t, C-16), 49.8 (d, C-17), 14.9 (q, C-18), 206.9 (d, C-19), 36.1 (d, C-20), 18.7 (q, C-21). 39.0 (t, C-22), 125.1 (d, C-23), 139.7 (d, C-24), 70.7 (s, C-25), 29.9 (q, C-26), 30.0 (q, C-27), 25.2 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.1 (s, 7-OAc), 21.3 (q, 7-OAc); ESIMS m/z 537 [M + Na].sup.+; HRESIMS m/z 537.3549 [M + Na].sup.+. Compound 10 [00014] Molecular formula C.sub.32H.sub.50O.sub.5; amorphous white powder; optical activity [].sup.26.sub.D 110.2 (c = 0.1, MeOH); IR (KBr) v.sub.max 3,434 (br), 2,944, 2,353, 1,718, 1,647, 1,459, 1,376, 1,244, 1,113, 1,074, 973, 754 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 400 MHz) .sub.H 1.62 (1H, m, H-1), 1.54 (1H, m, H-1), 1.78 (1H, m, H-2), 1.94 (1H, m, H-2), 3.60 (1H, br s, H-3), 5.85 (1H, d, J = 5.2 Hz, H-6), 4.02 (1H, d, J = 5.2 Hz, H-7), 1.90 (1H, s, H-8), 2.53 (1H, m, H-10), 1.46 (2H, m, H-11), 2.36 (2H, m, H-11), 1.60 (2H, m, H-12), 1.66 (2H, m, H-12), 1.45 (2H, m, H-15), 1.32 (1H, m, H-16), 1.92 (1H, m, H-16), 1.48 (1H, m, H-17), 0.84 (3H, s, H-18), 9.78 (1H, s, H-19), 1.51 (1H, m, H-20), 0.94 (3H, d, J = 5.5 Hz, H-21), 1.80 (1H, m, H-22a), 1.10 (1H, m, H-22b), 5.58 (1H, ddd, J.sub.1 = 10 Hz, J.sub.2 = 8.8 Hz, J.sub.3 = 3.2 Hz, H-23), 5.08 (1H, dd, J.sub.1 = 8.8 Hz, J.sub.2 = 1.2 Hz, H-24), 1.71 (3H, d, J = 1.2 Hz, H-26), 1.68 (3H, d, J = 1.2 Hz, H-27), 1.24 (3H, s, H-28), 1.07 (3H, s, H-29), 0.80 (3H, s, H-30), 1.98 (s, 23-OAc); .sup.13C-NMR (CDCl.sub.3, 100 MHz) .sub.c 20.9 (t, C-1), 28.5 (t, C-2), 76.1 (d, C-3), 41.6 (s, C-4). 148.6 (s, C-5), 120.1 (d, C-6), 68.7 (d, C-7), 46.0 (d, C-8), 49.8 (s, C-9), 35.8 (d, C-10), 22.1 (t, C-11), 28.8 (t, C-12), 45.5 (s, C-13), 47.8 (s, C-14), 34.5 (t, C-15), 27.5 (t, C-16), 50.3 (d, C-17), 14.7 (q, C-18), 206.4 (d, C-19), 32.7 (d, C-20), 18.9 (q, C-21), 41.9 (t, C-22), 69.4 (d, C-23), 124.6 (d, C-24), 135.7 (s, C-25), 18.3 (q, C-26), 25.6 (q, C-27), 25.0 (q, C-28), 27.0 (q, C-29), 18.0 (q, C-30), 170.6 (q, 23-OAc), 21.5 (s, 23-OAc); ESIMS m/z 537 [M + Na].sup.+; HRESIMS m/z 537.3549 [M + Na].sup.+. Compound 11 [00015] Molecular formula C.sub.30H.sub.46O.sub.4; amorphous white powder; melt point 140-143 C.; optical activity [].sup.20.sub.D 5.9 (c = 0.13, MeOH); UV (MeOH) .sub.max (log ) 228 (3.6); IR (KBr) v.sub.max 3412, 2950, 2876, 1712, 1619, 1465, 1445, 1249, 1040, 944 cm.sup.1; .sup.1H-NMR (C.sub.5D.sub.5N, 500 MHz) .sub.H 2.09 (1H, m, H-1), 1.75 (1H, m, H-1), 2.09 (1H, m, H-2), 1.92 (1H, m, H-2), 3.82 (1H, br s, H-3), 6.28 (1H, br d, J = 4.7 Hz, H-6), 4.36 (1H, br d, J = 5.1 Hz, H-7), 2.37 (1H, s, H-8), 2.0 (1H, m, H-10), 2.66 (2H, m, H-11), 1.57 (2H, m, H-11), 1.60 (2H, m, H-12), 1.37 (2H, m, H-15), 1.94 (1H, m, H-16), 1.37 (1H, m, H-16), 1.57 (1H, m, H-17), 0.89 (3H, s, H-18), 10.65 (1H, s, H-19), 2.17 (1H, m, H-20), 1.03 (3H, d, J = 5.5 Hz, H-21), 2.54 (1H, d, J = 12.2 Hz, H-22), 2.17 (1H, m, H-22), 6.17 (1H, s, H-24), 1.75 (3H, s, H-26), 2.21 (3H, s, H-27), 1.19 (3H, s, H-28), 1.48 (3H, s, H-29), 0.86 (3H, s, H-30); .sup.13C-NMR (C.sub.5D.sub.5N, 125 MHz) .sub.C 21.8 (t, C-1), 29.9 (t, C-2), 75.7 (d, C-3), 41.8 (s, C-4), 145.8 (s, C-5), 124.3 (d, C-6), 65.7 (d, C-7), 50.7 (d, C-8), 50.6 (s, C-9), 36.9 (d, C-10), 22.7 (t, C-11), 29.5 (t, C-12), 45.9 (s, C-13), 48.4 (s, C-14), 34.9 (t, C-15), 28.0 (t, C-16), 50.7 (d, C-17), 14.7 (q, C-18), 207.8 (d, C-19), 33.5 (d, C-20), 20.0 (q, C-21), 51.9 (t, C-22), 200.7 (s, C-23), 124.9 (d, C-24), 154.1 (s, C-25), 27.3 (q, C-26), 20.6 (q, C-27), 27.4 (q, C-28), 26.2 (q, C-29), 18.3 (q, C-30); EIMS m/z 470 [M].sup.+; HRESIMS m/z 493.3297 [M + Na].sup.+ (calcd for C.sub.30H.sub.46O.sub.4Na, 493.3293). Compound 12 [00016] Molecular formula C.sub.36H.sub.58O.sub.9; amorphous white powder; optical activity [].sup.22.sub.D + 46.7 (c = 0.3, MeOH); .sup.1H-NMR (C.sub.5D.sub.5N, 500 MHz) .sub.H 0.86, 0.88, 1.16, 1.47 (each 3H, s), 1.18, 1.53, 1.57, 1.58, 1.93, 1.94, 1.96, 2.71 (each 1H), 1.35, 1.55, 1.93 (each 2H), 3.80 (1H, br s, H-3), 6.27 (1H, d, J = 4.4 Hz, H-6), 4.33 (1H, d, J = 4.6 Hz, H-7), 2.36 (1H, s, H-8), 2.71 (1H, m, H-10), 10.73, (1H, s, H-19), 2.06 (1H, m, H-20), 1.19 (3H, d, J = 6.6 Hz, H-21), 4.94 (1H, d, J = 7.8 Hz, H-23), 5.61 (1H, d, J = 7.8 Hz, H-24), 1.69, 1.75 (each 3H, s, H-26 and H-27), 4.94 (1H, d, J = 7.8 Hz, Glc-1), 4.01 (1H, br t, Glc-2), 4.21 (1H, d, Glc-3), 4.22 (1H, d, Glc-4), 3.88 (1H, br s, Glc-5), 4.34 (1H, dd, J.sub.1 = 9.1 Hz, J.sub.2 = 5.2 Hz, Glc-6a), 4.46 (1H, dd, J.sub.1 = 9.1 Hz, J.sub.2 = 1.9 Hz, Glc-6b); .sup.13C-NMR (C.sub.5D.sub.5N, 125 MHz) .sub.C 21.7 (t, C-1), 29.9 (t, C-2), 75.6 (d, C-3), 41.8 (s, C-4), 145.7 (s, C-5), 124.3 (d, C-6), 65.7 (d, C-7), 50.6 (d, C-8), 50.6 (s, C-9), 36.8 (d, C-10), 22.7 (t, C-11), 29.6 (t, C-12), 45.9 (s, C-13), 48.3 (s, C-14), 34.9 (t, C-15), 27.8 (t, C-16), 51.2 (d, C-17), 14.9 (q, C-18), 207.5 (d, C-19), 32.7 (d, C-20), 19.4 (q, C-21), 43.8 (t, C-22), 75.3 (d, C-23), 129.1 (d, C-24), 132.2 (s, C-25), 18.3 (q, C-26), 26.2 (q, C-27), 25.8 (q, C-28), 27.3 (q, C-29), 18.2 (q, C-30), 104.2 (d, Glc-1), 75.7 (d, Glc-2), 78.9 (d, Glc-3), 71.8 (d, Glc-4), 78.3 (d, Glc-5), 63.0 (d, Glc-6); ESIMS m/z 657 [M + Na].sup.+, 673 [M + K].sup.+; ESIMS m/z 633 [M H].sup.. Compound 13 [00017] Molecular formula C.sub.36H.sub.58O.sub.9; amorphous white powder; optical activity [].sup.22.sub.D + 90.0 (c = 0.1, MeOH); .sup.1H-NMR (C.sub.5D.sub.5N, 500 MHz) .sub.H 0.75, 0.89, 1.12, 1.43 (each 3H, s), 1.35, 1.55, 1.93 (each 2H), 1.16, 1.50, 1.53, 1.55, 1.90, 1.94, 1.96, 2.65 (each 1H), 3.81 (1H, br s, H-3), 6.16 (1H, d, J = 4.1 Hz, H-6), 4.62 (1H, d, J = 4.1 Hz, H-7), 2.53 (1H, s, H-8), 2.69 (1H, m, H-10), 10.56 (1H, s, H-19), 2.05 (1H, m, H-20), 1.10 (3H, d, J = 6.6 Hz, H-21), 4.78 (1H, dt, J.sub.1 = 8.1 Hz, J.sub.2 = 1.9 Hz, H-23), 5.60 (1H, d, J = 8.4 Hz, H-24), 1.68 (3H, s, H-26), 1.70 (3H, s, H-27), 4.95 (1H, d, J = 8.0 Hz, Glc-1), 4.02 (1H, br t, Glc-2), 4.27 (1H, d, Glc-3), 4.22 (1H, d, Glc-4), 3.88 (1H, br s, Glc-5), 4.41 (1H, dd, J.sub.1 = 12.4 Hz, J.sub.2 = 5.6 Hz, Glc-6a), 4.61 (1H, dd, J.sub.1 = 12.4 Hz, J.sub.2 = 1.2 Hz, Glc-6b); .sup.13C-NMR (C.sub.5D.sub.5N, 125 MHz) .sub.C 21.4 (t, C-1), 29.3 (t, C-2), 75.4 (d, C-3), 41.7 (s, C-4), 147.2 (s, C-5), 122.0 (d, C-6), 71.3 (d, C-7), 44.3 (d, C-8), 51.1 (s, C-9), 36.1 (d, C-10), 22.1 (t, C-11), 28.9 (t, C-12), 45.6 (s, C-13), 48.0 (s, C-14), 34.2 (t, C-15), 27.4 (t, C-16), 50.7 (d, C-17), 14.4 (q, C-18), 206.9 (d, C-19), 32.4 (d, C-20), 18.7 (q, C-21), 44.9 (t, C-22), 64.9 (d, C-23), 131.5 (d, C-24), 130.5 (s, C-25), 17.6 (q, C-26), 25.7 (q, C-27), 25.3 (q, C-28), 26.8 (q, C-29), 17.6 (q, C-30), 101.4 (d, Glc-1), 74.7 (d, Glc-2), 78.6 (d, Glc-3), 71.5 (d, Glc-4), 78.5 (d, Glc-5), 62.7 (d, Glc-6); ESIMS m/z 657 [M + Na].sup.+, 673 [M + K].sup.+; ESIMS m/z 633 [M H].sup.. Compound 14 [00018] Molecular formula C.sub.36H.sub.58O.sub.9; amorphous white powder; .sup.1H-NMR (C.sub.5D.sub.5N, 500 MHz) .sub.H 3.78 (1H, br s, H-3), 6.15 (1H, d, J = 4.7 Hz, H-6), 4.28 (1H, d, J = 5.3 Hz, H-7), 2.52 (1H, br s, H-8), 0.70 (3H, s, H-18), 10.49 (1H, s, H-19), 0.93 (3H, d, J = 5.8 Hz, H-21), 5.92 (2H, m, H-23), 5.92 (2H, m, H-24), 1.53 (3H, s, H-26), 1.53 (3H, s, H-27), 1.42 (3H, s, H-28), 1.11 (3H, s, H-29), 0.82 (3H, s, H-30), 4.95 (1H, d, J = 8.0 Hz, Glc-1), 4.02 (1H, br t, Glc-2), 4.27 (1H, d, Glc-3), 4.22 (1H, d, Glc-4), 3.88 (1H, br s, Glc-5), 4.41 (1H, dd, J.sub.1 = 12.4 Hz, J.sub.2 = 5.6 Hz, Glc-6a), 4.61 (1H, dd, J.sub.1 = 12.4 Hz, J.sub.2 = 1.2 Hz, Glc-6b); .sup.13C-NMR (C.sub.5D.sub.5N, 125 MHz) .sub.C 21.9 (t, C-1), 29.8 (t, C-2), 75.0 (d, C-3), 41.9 (s, C-4), 147.6 (s, C-5), 135.1 (d, C-6), 71.7 (d, C-7), 40.1 (d, C-8), 50.4 (s, C-9), 36.7 (d, C-10), 22.6 (t, C-11), 29.3 (t, C-12), 45.7 (s, C-13), 48.1 (s, C-14), 34.9 (t, C-15), 27.4 (t, C-16), 50.2 (d, C-17), 15.0 (q, C-18), 207.4 (d, C-19), 36.6 (d, C-20), 19.0 (q, C-21), 39.5 (t, C-22), 122.3 (d, C-23), 141.7 (d, C-24), 69.7 (s, C-25), 30.8 (q, C-26), 30.0 (q, C-27), 26.2 (q, C-28), 27.4 (q, C-29), 18.2 (q, C-30), 101.7 (d, Glc-1), 75.5 (d, Glc-2), 78.7 (d, Glc-3), 71.8 (d, Glc-4), 78.8 (d, Glc-5), 63.0 (d, Glc-6); ESITOFCMS m/z 657.2946 [M + Na].sup.+; 673.2549 [M + K].sup.+. Compound 15 [00019] Molecular formula C.sub.32H.sub.52O.sub.4; amorphous white powder; .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 1.50 (2H, m, H-1), 1.80 (2H, m, H-2), 3.43 (1H, br s, H-3), 5.63 (1H, dd, J.sub.1 = 3.0 Hz, J.sub.2 = 9.3 Hz, H-6), 5.96 (1H, dd, J.sub.1 = 3.3 Hz, J.sub.2 = 9.3 Hz, H-7), 2.89 (1H, br s, H-8), 2.40 (1H, m, H-10), 1.74 (1H, m H-11), 1.61 (1H, m H-11), 1.61 (2H, m, H-12), 1.31 (2H, m, H-15), 1.92 (2H, m, H-16), 1.40 (1H, m, H-17), 0.88 (3H, s, H-18), 4.65 (1H, s, H-19), 5.45 (1H, m, H-23), 5.40 (1H, d, H-24), 1.23 (3H, s, H-26), 1.23 (3H, s, H-27), 3.37 (3H, s, 19-OMe), 3.13 (3H, s, 25-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 17.4 (t, C-1), 27.2 (t, C-2), 76.5 (d, C-3), 37.3 (s, C-4), 86.8 (s, C-5), 132.8 (d, C-6), 130.9 (d, C-7), 41.6 (d, C-8), 48.3 (s, C-9), 40.5 (d, C-10), 23.2 (t, C-11), 30.7 (t, C-12), 45.1 (s, C-13), 48.0 (s, C-14), 33.4 (t, C-15), 28.0 (t, C-16), 51.0 (d, C-17), 14.7 (q, C-18), 112.1 (d, C-19), 37.9 (d, C-20), 18.7 (q, C-21), 27.1 (t, C-22), 128.4 (d, C-23), 136.8 (d, C-24), 74.9 (s, C-25), 26.1 (q, C-26), 25.8 (q, C-27), 20.6 (3q, C-28), 24.4 (q, C-29), 19.9 (q, C-30), 57.3 (q, 19-OMe), 50.3 (q, 25-OMe); HRMS m/z 500.3874 [M].sup.+ (calcd for C.sub.32H.sub.52O.sub.4, 500.3865). Compound 16 [00020] Molecular formula C.sub.32H.sub.52O.sub.4; amorphous white powder; optical activity [].sup.20.sub.D 74 (c = 0.2, cyclohexane); UV (cyclohexane) .sub.max (log ) 210.4 (3.20) nm; IR (KBr) v.sub.max 3471, 2926, 2882, 1732, 1647, 1469, 1383, 1115, 1084 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 1.50 (2H, m, H-1), 1.80 (2H, m, H-2), 3.43 (1H, br s, H-3), 5.63 (1H, dd, J.sub.1 = 3.0 Hz, J.sub.2 = 9.3 Hz, H-6), 5.96 (1H, dd, J.sub.1 = 3.3 Hz, J.sub.2 = 9.3 Hz, H-7), 2.89 (1H, br s, H-8), 2.40 (1H, m, H-10), 1.74 (1H, m H-11), 1.61 (1H, m H-11), 1.61 (2H, m, H-12), 1.31 (2H, m, H-15), 1.92 (2H, m, H-16), 1.40 (1H, m, H-17), 0.88 (3H, s, H-18), 4.65 (1H, s, H-19), 1.73 (1H, m, H-20), 0.96 (3H, d, J = 6.6 Hz, H-21), 1.69 (1H, m, H-22), 1.00 (1H, m, H-22), 3.95 (1H, dt, J.sub.1 = 3.0 Hz, J.sub.2 = 9.3 Hz, H-23), 5.02 (1H, br d, J = 8.4 Hz, H-24), 1.74 (3H, s, H-26), 1.68 (3H, s, H-27), 0.85 (3H, s, H-28), 1.22 (3H, s, H-29), 0.85 (3H, s, H-30), 3.43 (3H, s, 19-OMe), 3.21 (3H, s, 23-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 17.4 (t, C-1), 27.2 (t, C-2), 76.5 (d, C-3), 37.3 (s, C-4), 86.8 (s, C-5), 132.8 (d, C-6), 130.9 (d, C-7), 41.6 (d, C-8), 48.3 (s, C-9), 40.5 (d, C-10), 23.2 (t, C-11), 30.7 (t, C-12), 45.1 (s, C-13), 48.0 (s, C-14), 33.4 (t, C-15), 28.0 (t, C-16), 51.0 (d, C-17), 14.7 (q, C-18), 112.1 (d, C-19), 32.5 (d, C-20), 18.7 (q, C-21), 42.8 (t, C-22), 74.7 (d, C-23), 128.0 (d, C-24), 134.5 (s, C-25), 25.8 (q, C-26), 18.1 (q, C-27), 24.1 (3q, C-28), 20.5 (q, C-29), 19.8 (q, C-30), 58.2 (q, 19-OMe), 55.6 (q, 23-OMe); HRESIMS m/z 523.3752 [M + Na].sup.+ (calcd for C.sub.32H.sub.52O.sub.4Na, 523.3758). Compound 17 [00021] Molecular formula C.sub.32H.sub.52O.sub.4; amorphous white powder; optical activity [].sub.D 37.1 (c = 0.054, CHCl.sub.3); IR (KBr) v.sub.max 3516, 2926, 1377, 1109, 1070 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 0.90, 0.88, 0.87, 0.86, 0.83 (each 3H), 3.48 (1H, m, H-3), 6.07 (1H, dd, J.sub.1 = 9.8 Hz, J.sub.2 = 2.3 Hz, H-6), 5.50 (1H, m, H-7), 2.24 (1H, m, H-8), 2.15 (1H, m, H-10), 4.40 (1H, s, H-19), 5.45 (1H, m, H-23), 5.40 (1H, d, H-24), 1.23 (3H, s, H-26), 1.23 (3H, s, H-27), 3.37 (3H, s, 19-OMe), 3.13 (3H, s, 25-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 16.5 (t, C-1), 21.4 (t, C-2), 76.2 (d, C-3), 45.1 (s, C-4), 85.1 (s, C-5), 133.5 (d, C-6), 130.5 (d, C-7), 49.8 (d, C-8), 48.9 (s, C-9), 36.1 (d, C-10), 30.4 (t, C-11), 39.4 (t, C-12), 37.1 (s, C-13), 48.0 (s, C-14), 33.5 (t, C-15), 27.8 (t, C-16), 50.0 (d, C-17), 15.0 (q, C-18), 114.7 (d, C-19), 37.9 (d, C-20), 18.7 (q, C-21), 27.1 (t, C-22), 128.4 (d, C-23), 136.8 (d, C-24), 74.9 (s, C-25), 26.1 (q, C-26), 25.8 (q, C-27), 20.6 (3q, C-28), 24.4 (q, C-29), 19.9 (q, C-30), 57.3 (q, 19-OMe), 50.3 (q, 25-OMe); HRMS m/z 500.3874 [M].sup.+ (calcd for C.sub.32H.sub.52O.sub.4, 500.3865). Compound 18 [00022] Molecular formula C.sub.32H.sub.52O.sub.4; amorphous white powder; optical activity [].sup.20.sub.D 26.5 (c = 0.2, cyclohexane); UV (cyclohexane) .sub.max (log ) 210.8 (3.20) nm; IR (KBr) v.sub.max 3525, 2939, 2875, 1732, 1647, 1466, 1382, 1113, 1083 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 1.35 (1H, m, H-1), 2.03 (1H, m, H-1), 1.74 (2H, m, H-2), 3.44 (1H, br s, H-3), 6.08 (1H, dd, J.sub.1 = 1.5 Hz, J.sub.2 = 9.6 Hz, H-6), 5.51 (1H, dd, J.sub.1 = 3.6 Hz, J.sub.2 = 9.9 Hz, H-7), 2.26 (1H, br s, H-8), 2.31 (1H, dd, J.sub.1 = 6 Hz, J.sub.2 = 12 Hz, H-10), 1.74 (1H, m, H-11), 1.65 (1H, m, H-11), 1.63 (2H, m, H-12), 1.29 (2H, m, H-15), 1.93 (2H, m, H-16), 1.40 (1H, m, H-17), 0.88 (3H, s, H-18), 4.42 (1H, s, H-19), 1.74 (1H, m, H-20), 0.94 (3H, d, J = 6.3 Hz, H-21), 1.70 (1H, m, H-22), 1.00 (1H, m, H-22), 3.94 (1H, dt, J.sub.1 = 3.0 Hz, J.sub.2 = 9.3 Hz, H-23), 5.02 (1H, br d, J = 8.7 Hz, H-24), 1.74 (3H, s, H-26), 1.68 (3H, s, H-27), 0.88 (3H, s, H-28), 1.25 (3H, s, H-29), 0.85 (3H, s, H-30), 3.40 (3H, s, 19-OMe), 3.21 (3H, s, 23-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 16.5 (t, C-1), 27.4 (t, C-2), 76.2 (d, C-3), 37.1 (s, C-4), 85.0 (s, C-5), 133.0 (d, C-6), 130.5 (d, C-7), 49.8 (d, C-8), 49.0 (s, C-9), 37.9 (d, C-10), 21.4 (t, C-11), 30.6 (t, C-12), 45.2 (s, C-13), 48.1 (s, C-14), 33.4 (t, C-15), 27.9 (t, C-16), 51.0 (d, C-17), 15.0 (q, C-18), 114.7 (d, C-19), 32.5 (d, C-20), 18.7 (q, C-21), 42.8 (t, C-22), 74.6 (d, C-23), 127.0 (d, C-24), 134.0 (s, C-25), 25.8 (q, C-26), 18.1 (q, C-27), 24.4 (3q, C-28), 20.6 (q, C-29), 19.9 (q, C-30), 57.2 (q, 19-OMe), 55.7 (q, 25-OMe); HRESIMS m/z 523.3750 [M + Na].sup.+ (calcd for C.sub.32H.sub.52O.sub.4Na, 523.3758). Compound 19 [00023] Molecular formula C.sub.31H.sub.50O.sub.4; amorphous white powder; .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 1.50 (2H, m, H-1), 1.80 (2H, m, H-2), 3.43 (1H, br s, H-3), 5.63 (1H, dd, J.sub.1 = 3.0 Hz, J.sub.2 = 9.3 Hz, H-6), 5.96 (1H, dd, J.sub.1 = 3.3 Hz, J.sub.2 = 9.3 Hz, H-7), 2.89 (1H, br s, H-8), 2.40 (1H, m, H-10), 1.74 (1H, m, H-11), 1.61 (1H, m, H-11), 1.61 (2H, m, H-12), 1.31 (2H, m, H-15), 1.92 (2H, m, H-16), 1.40 (1H, m, H-17), 0.88 (3H, s, H-18), 4.65 (1H, s, H-19), 1.23 (3H, d, H-21), 5.57 (2H, m, H-24), 5.57 (2H, m, H-24), 1.29 (3H, s, H-26), 1.29 (3H, s, H-27), 3.37 (3H, s, 19-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 17.4 (t, C-1), 27.2 (t, C-2), 76.5 (d, C-3), 37.3 (s, C-4), 86.8 (s, C-5), 132.8 (d, C-6), 130.9 (d, C-7), 41.6 (d, C-8), 48.3 (s, C-9), 40.5 (d, C-10), 23.2 (t, C-11), 30.7 (t, C-12), 45.1 (s, C-13), 48.0 (s, C-14), 33.4 (t, C-15), 28.0 (t, C-16), 51.0 (d, C-17), 14.7 (q, C-18), 112.1 (d, C-19), 36.2 (d, C-20), 18.6 (q, C-21), 27.1 (t, C-22), 125.3 (d, C-23), 139.5 (d, C-24), 70.7 (s, C-25), 29.9 (2q, C-26, 27), 30.0, 20.6 (q, C-28), 24.4 (q, C-29), 20.5 (q, C-30), 57.3 (q, 19-OMe) Compound 20 [00024] Molecular formula C.sub.31H.sub.50O.sub.4; amorphous white powder; melt point 102-104 C.; optical activity [].sub.D 52.8 (c = 0.036, CHCl.sub.3); .sup.1H-NMR (CDCl.sub.3, 300 MHz) .sub.H 0.88, 0.86, 0.83, 0.84 (each 3H, s, 4 CH.sub.3), 3.41 (1H, br s, J = 6.7 Hz, H-3), 6.10 (1H, dd, J.sub.1 = 9.71 Hz, J.sub.2 = 2.30 Hz, H-6), 5.50 (1H, dd, J.sub.1 = 9.71 Hz, J.sub.2 = 3.72 Hz, H-7), 2.13 (1H, br s, H-8), 2.29 (1H, m, H-10), 4.40 (1H, s, H-19), 1.23 (3H, d, H-21), 5.57 (1H, m, H-23), 5.57 (1H, m, H-24), 1.29 (3H, s, H-26), 1.29 (3H, s, H-27), 3.37 (3H, s, 19-OMe); .sup.13C-NMR (CDCl.sub.3, 75 MHz) .sub.C 16.5 (t, C-1), 21.4 (t, C-2), 76.2 (d, C-3), 45.1 (s, C-4), 85.1 (s, C-5), 133.0 (d, C-6), 130.5 (d, C-7), 49.8 (d, C-8), 48.9 (s, C-9), 37.9 (d, C-10), 30.4 (t, C-11), 39.1 (t, C-12), 37.1 (s, C-13), 47.9 (s, C-14), 33.5 (t, C-15), 27.8 (t, C-16), 50.1 (d, C-17), 15.0 (q, C-18), 114.7 (d, C-19), 36.2 (d, C-20), 18.6 (q, C-21), 27.1 (t, C-22), 125.3 (d, C-23), 139.5 (d, C-24), 70.7 (s, C-25), 29.9 (q, C-26), 30.0 (q, C-27), 20.6 (q, C-28), 24.4 (q, C-29), 20.5 (q, C-30), 57.3 (q, 19-OMe); HRMS m/z 486.3725 [M].sup.+ (calcd for C.sub.31H.sub.50O.sub.4, 486.3709). Compound 21 [00025] Molecular formula C.sub.31H.sub.50O.sub.4; amorphous white powder; optical activity [].sup.19.8.sub.D 62 (c = 0.19, MeOH); UV (MeOH) .sub.max (log ) 229 (4.03), 202 (4.36) nm; IR (KBr) v.sub.max 3444, 2950, 1639, 1383, 1081 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 600 MHz) .sub.H 1.36 (1H, m, H-1), 1.95 (1H, m, H-1), 1.71 (1H, m, H-2), 1.75 (1H, m, H-2), 3.41 (1H, d, 7 = 9.2 Hz, H-3), 6.09 (1H, dd, J.sub.1 = 1.6 Hz, J.sub.2 = 9.7 Hz, H-6), 5.51 (1H, dd, J.sub.1 = 3.5 Hz, J.sub.2 = 9.7 Hz, H-7), 2.26 (1H, m, H-8), 2.28 (1H, m, H-10), 1.61 (1H, m, H-11), 1.72 (1H, m, H-11), 1.63 (1H, m, H-12), 2.17 (1H, s, H-12), 1.31 (2H, m, H-15), 1.39 (1H, m, H-16), 1.95 (1H, m, H-16), 1.44 (1H, m, H-17), 0.90 (3H, s, H-18), 4.41 (1H, s, H-19), 1.70 (1H, s, H-20), 0.98 (3H, d, J = 6.4 Hz, H-21), 1.03 (1H, m, H-22), 1.64 (1H, m, H-22), 4.46 (1H, m, H-23), 5.19 (1H, d, J = 8.4 Hz, H-24), 1.68 (3H, s, H-26), 1.70 (3H, s, H-27), 0.88 (3H, s, H-28), 1.24 (3H, s, H-29), 0.8 (3H, s, H-30), 3.39 (3H, s, 19-OMe); .sup.13C-NMR (CDCl.sub.3, 150 MHz) .sub.C 16.5 (t, C-1), 27.1 (t, C-2), 76.2 (d, C-3), 37.1 (s, C-4), 85.1 (s, C-5), 133.0 (d, C-6), 130.5 (d, C-7), 49.8 (d, C-8), 49.0 (s, C-9), 37.9 (d, C-10), 21.4 (t, C-11), 30.5 (t, C-12), 45.2 (s, C-13), 48.1 (s, C-14), 33.4 (t, C-15), 28.1 (t, C-16), 50.9 (d, C-17), 15.0 (q, C-18), 114.7 (d, C-19), 32.6 (d, C-20), 18.6 (q, C-21), 44.4 (t, C-22), 65.9 (d, C-23), 128.9 (d, C-24), 133.9 (s, C-25), 18.1 (q, C-26), 25.7 (q, C-27), 24.4 (3q, C-28), 20.6 (q, C-29), 19.9 (q, C-30), 57.3 (q, 19-OMe); ESIMS m/z 509 [M + Na].sup.+; HRESIMS m/z 509.3611 [M + Na].sup.+ (calcd for C.sub.31H.sub.50O.sub.4Na 509.3601). Compound 22 [00026] Molecular formula C.sub.31H.sub.50O.sub.4; amorphous white powder; optical activity [].sup.19.9.sub.D 102 (c = 0.08, MeOH); UV (MeOH); UV (MeOH) .sub.max (log ) 228 (4.69), 202 (4.54) nm; IR (KBr) v.sub.max 3441, 2946, 1635, 1449, 1184, 1115, 1083 cm.sup.1; .sup.1H-NMR (CDCl.sub.3, 600 MHz) .sub.H 1.49 (1H, m, H-1), 1.77 (1H, m, H-1), 1.75 (1H, m, H-2), 1.78 (1H, m, H-2), 3.41 (1H, d, J = 9.2 Hz, H-3), 5.99 (1H, d, J = 9.8 Hz, H-6), 5.62 (1H, dd, J.sub.1 = 3.5 Hz, J.sub.2 = 9.7 Hz, H-7), 2.89 (1H, br s, H-8), 2.40 (1H, m, H-10), 1.62 (1H, m, H-11), 1.75 (1H, m, H-11), 1.62 (1H, m, H-12), 2.17 (1H, s, H-12), 1.31 (1H, m, H-15), 1.36 (1H, m, H-15), 1.38 (1H, m, H-16), 1.95 (1H, m, H-16), 1.42 (1H, m, H-17), 0.89 (3H, s, H-18), 4.65 (1H, s, H-19), 1.70 (1H, s, H-20), 0.99 (3H, d, J = 6.4 Hz H-21), 1.03 (1H, m, H-22), 1.64 (1H, m, H-22), 4.47 (1H, m, H-23), 5.20 (1H, d, J = 8.4 Hz, H-24), 1.69 (3H, s, H-26), 1.70 (3H, s, H-27), 0.84 (3H, s, H-28), 1.21 (3H, s, H-29), 0.84 (3H, s, H-30), 3.43 (3H, s, 19-OMe); .sup.13C-NMR (CDCl.sub.3, 150 MHz) .sub.C 17.4 (t, C-1), 27.2 (t, C-2), 76.2 (d, C-3), 37.3 (s, C-4), 86.7 (s, C-5), 130.9 (d, C-6), 132.7 (d, C-7), 41.6 (d, C-8), 48.3 (s, C-9), 40.5 (d, C-10), 23.2 (t, C-11), 30.7 (t, C-12), 45.1 (s, C-13), 48.0 (s, C-14), 33.4 (t, C-15), 28.2 (t, C-16), 50.9 (d, C-17), 14.7 (q, C-18), 112.1 (d, C-19), 32.6 (d, C-20), 18.6 (q, C-21), 44.4 (t, C-22), 65.9 (d, C-23), 129.0 (d, C-24), 133.8 (s, C-25), 18.1 (q, C-26), 25.7 (q, C-27), 24.1 (q, C-28), 20.5 (q, C-29), 19.7 (q, C-30), 58.2 (q, 19-OMe); ESIMS m/z 509 [M + Na].sup.+; HRESIMS m/z 509.3609 [M + Na].sup.+ (calcd for C.sub.31H.sub.50O.sub.4Na, 509.3601). Compound 23 [00027] Molecular formula C.sub.32H.sub.52O.sub.4; amorphous white powder; melt point 104-107 C.; optical activity [].sup.25.sub.D + 25.9 (c = 0.26, CHCl.sub.3); IR (KBr) v.sub.max 3444, 2929, 1712, 845, 820 cm.sup.1; .sup.1H-NMR (C.sub.5D.sub.5N, 600 MHz) .sub.H 1.69 (1H, m, H-1), 2.01 (1H, m, H-1), 1.90 (1H, m, H-2), 2.05 (1H, m, H-2), 3.81 (1H, br s, H-3), 6.15 (1H, d, J = 5.4 Hz, H-6), 3.55 (1H, br d, J = 5.4 Hz, H-7), 2.23 (1H, s, H-8), 2.65 (1H, m, H-10), 1.54 (1H, m, H-11), 1.95 (1H, m, H-11), 1.60 (2H, s, H-12), 1.35 (2H, m, H-15), 1.36 (1H, m, H-16), 1.95 (1H, m, H-16), 1.56 (1H, m, H-17), 0.95 (3H, s, H-18), 10.31 (1H, s, H-19), 1.55 (1H, s, H-20), 1.00 (3H, d, J = 5.9 Hz, H-21), 1.85 (1H, m, H-22), 2.24 (1H, m, H-22), 5.66 (1H, ddd, J.sub.1 = 5.4 Hz, J.sub.2 = 8.3 Hz, J.sub.3 = 15.8 Hz, H-23), 5.57 (1H, d, J = 15.8 Hz, H-24), 1.34 (3H, s, H-26), 1.34 (3H, s, H-27), 1.1 (3H, s, H-28), 1.50 (3H, s, H-29), 0.81 (3H, s, H-30), 3.29 (3H, s, 19-OMe), 3.23 (3H, s, 25-OMe); .sup.13C-NMR (C.sub.5D.sub.5N, 150 MHz) .sub.C 21.6 (t, C-1), 29.8 (t, C-2), 75.6 (d, C-3), 42.0 (s, C-4), 147.7 (s, C-5), 121.1 (d, C-6), 75.7 (d, C-7), 45.8 (d, C-8), 50.3 (s, C-9), 36.8 (d, C-10), 22.6 (t, C-11), 29.4 (t, C-12), 45.9 (s, C-13), 47.9 (s, C-14), 35.1 (t, C-15), 27.7 (t, C-16), 50.3 (d, C-17), 15.0 (q, C-18), 207.2 (d, C-19), 36.4 (d, C-20), 19.0 (q, C-21), 39.7 (t, C-22), 128.4 (d, C-23), 137.8 (d, C-24), 74.9 (s, C-25), 26.1 (q, C-26), 26.5 (q, C-27), 27.3 (q, C-28), 26.2 (q, C-29), 18.2 (q, C-30), 55.9 (q, 19-OMe), 50.2 (q, 25-OMe); EIMS m/z 482 [M H.sub.2O].sup.+; 440 [M H.sub.2O MeOH].sup.+; HREIMS m/z 482.3759 [M H.sub.2O].sup.+ (calcd for C.sub.32H.sub.50O.sub.3, 482.3760); FABMS m/z 539 [M + K].sup.+.

Example 1-23

[0106] For the obtained compounds 1 to 23, cancer cell viability tests were performed by the above-described <Cancer cell viability tests>. The results are shown in FIG. 4 to 26.

[0107] In addition, inhibitory concentrations of cell growth activity IC50 (M) (i.e., minimum concentration of the compound required for 50% inhibition of cell growth activity) for the compounds 1 to 23 were calculated according to the cancer cell viability tests shown in FIG. 4 to 26. By conversion of the results, inhibitory concentrations of cell growth activity (IC50) of compounds 1 to 23 are shown in Table 2 below, respectively.

TABLE-US-00002 TABLE 2 Example Example Example Example Example Example Example Example 1 2 3 4 5 6 7 8 Compound Compound Compound Compound Compound Compound Compound Compound Cell line 1 2 3 4 5 6 7 8 Vero ** 12.8 ** 35.3 25.26 23.08 23.19 24.15 MDA-MB-231 ** 4.44 5.2 12.08 8.07 23.51 6.0 5.19 U87-MG 150.5 7.52 6.82 14.37 8.8 23.42 8.51 7.54 MDA-MB-468 ** 7.25 10.41 18.6 16.76 13.95 13.94 9.81 Mahlavu ** 11.27 23 29.42 18.52 16.23 11.94 11.5 A549 ** 4.16 12.18 12.9 11.99 5.43 6.26 4.86 SW480 ** 13.06 18.22 12.95 16.37 14.91 13.49 13.8 U937 36.63 0.05 3.45 8.08 3.67 1.57 5.52 5.39 Example Example Example Example Example Example Example Example 9 10 11 12 13 14 15 16 Compound Compound Compound Compound Compound Compound Compound Compound Cell line 9 10 11 12 13 14 15 16 Vero 25.88 19.19 ** 124.42 ** ** ** ** MDA-MB-231 18.33 10.66 ** 41.71 59.42 32.81 ** ** U87-MG 15.55 10.68 ** 49.03 102.96 58.47 ** ** MDA-MB-468 26.77 20.33 ** 56.52 58.34 39.26 ** ** Mahlavu 5.07 19.37 ** 70.31 ** ** ** ** A549 24.41 9.81 ** 100.38 198.3 171.06 ** ** SW480 31.82 17.87 ** 98.6 67.15 64.24 ** ** U937 11.15 5.92 84.21 58.6 32.52 19.8 4.28 97.9 Example Example Example Example Example Example Example 17 18 19 20 21 22 23 Compound Compound Compound Compound Compound Compound Compound Cell line 17 18 19 20 21 22 23 Vero ** ** 36.14 12.5 ** ** 15.88 MDA-MB-231 ** ** 22.6 10.44 130 ** 7.91 U87-MG ** ** 25 12.16 83.46 ** 7.65 MDA-MB-468 9.4 ** 24.35 6.9 35.4 ** 7.55 Mahlavu ** ** 20.73 19.65 ** ** 15.44 A549 ** ** 45.64 20.06 ** ** 15.34 SW480 ** ** 16.61 12.6 117.8 ** 7.56 U937 12.20 ** 11.88 4.33 6.19 6.17 5.75 ** indicates that the inhibitory concentration of cell growth activity (IC50) of the compound is much greater than 256 M, and has no inhibition effect.

[0108] Then, for the obtained compounds 1 to 23, the compounds were evaluated for their ability to inhibit cell growth activity according to the following evaluation criteria with reference to the data in Table 2 above.

[0109] That is, when the inhibitory concentration of cell growth activity (IC50) of the compound listed in Table 2 above is greater than 256 M, the ability of the compound to inhibit cell growth activity is evaluated to be very poor (X X); when the inhibitory concentration of cell growth activity (IC50) is between 64 and 256 M, the ability of the compound to inhibit cell growth activity is evaluated to be poor (X); when the inhibitory concentration of cell growth activity (IC50) is between 16 and 64 M, the ability of the compound to inhibit cell growth activity is evaluated to be acceptable (); when the inhibitory concentration of cell growth activity (IC50) is between 8 and 16 M, the ability of the compound to inhibit cell growth activity is evaluated to be good (); and when the inhibitory concentration of cell growth activity (IC50) is less than 8 M, the ability of the compound to inhibit cell growth activity is evaluated to be excellent (). The individual evaluation results of these compounds are shown in Table 3 respectively.

TABLE-US-00003 TABLE 3 Example Example Example Example Example Example Example Example 1 2 3 4 5 6 7 8 Compound Compound Compound Compound Compound Compound Compound Compound Cell line 1 2 3 4 5 6 7 8 Vero X X X X MDA-MB-231 X X U87-MG X MDA-MB-468 X X Mahlavu X X A549 X X SW480 X X U937 Example Example Example Example Example Example Example Example 9 10 11 12 13 14 15 16 Compound Compound Compound Compound Compound Compound Compound Compound Cell line 9 10 11 12 13 14 15 16 Vero X X X X X X X X X X X MDA-MB-231 X X X X X X U87-MG X X X X X X X MDA-MB-468 X X X X X X Mahlavu X X X X X X X X X X X A549 X X X X X X X X X SW480 X X X X X X X X X U937 X X Example Example Example Example Example Example Example 17 18 19 20 21 22 23 Compound Compound Compound Compound Compound Compound Compound Cell line 17 18 19 20 21 22 23 Vero X X X X X X X X MDA-MB-231 X X X X X X X U87-MG X X X X X X X MDA-MB-468 X X X X Mahlavu X X X X X X X X A549 X X X X X X X X SW480 X X X X X X X U937 X X

[0110] From the evaluation results of inhibitory ability of cell growth activity (IC50) listed in Table 3 above, it is clearly known that for inhibition of human Glioblastoma cells U87-MG, compounds 4, 5, 7, 9, 10, and 20 have good () inhibitory ability of cell growth of human Glioblastoma cells, while compounds 2, 3, 8, and 23 have excellent () inhibitory ability of cell growth of human Glioblastoma cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting Glioblastoma or treating Glioblastoma.

[0111] For inhibition of human liver cancer cells Mahlavu, compounds 2, 7, 8, and 23 have good () inhibitory ability of cell growth of human liver cancer cells, while compound 9 have excellent () inhibitory ability of cell growth of human liver cancer cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting liver cancer or treating liver cancer.

[0112] For inhibition of human colorectal cancer cells SW-480, compounds 2, 4, 6, 7, 8, and 20 have good () inhibitory ability of cell growth of human colorectal cancer cells, while compound 23 have excellent () inhibitory ability of cell growth of human colorectal cancer cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting colorectal cancer or treating colorectal cancer.

[0113] For inhibition of human lung cancer cells A549, compounds 3, 4, 5, 10, and 223 have good () inhibitory ability of cell growth of human lung cancer cells, while compounds 2, 6, 7, and 8 have excellent () inhibitory ability of cell growth of human lung cancer cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting lung cancer or treating lung cancer.

[0114] For inhibition of human lung cancer cells A549, compounds 3, 4, 5, 10, and 23 have good () inhibitory ability of cell growth of human lung cancer cells, while compounds 2, 6, 7, and 8 have excellent () inhibitory ability of cell growth of human lung cancer cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting lung cancer or treating lung cancer.

[0115] For inhibition of human leukemia cells U937, compounds 4, 9, 17, and 19 have good () inhibitory ability of cell growth of human leukemia cells, while compounds 2, 3, 5, 6, 7, 8, 10, 15, and 20 to 23 have excellent () inhibitory ability of cell growth of human leukemia cells. In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting leukemia or treating leukemia.

[0116] For inhibition of human breast cancer cells MDA-MB-231, compounds 4, 5, 10, and 20 have good () inhibitory ability of cell growth of human breast cancer cells, while compounds 2, 3, 7, 8, and 23 have excellent () inhibitory ability of cell growth of human breast cancer cells; in addition, for inhibition of human breast cancer cells MDA-MB-468, compounds 3, 6, 7, 8, and 17 have good () inhibitory ability of cell growth of human breast cancer cells, while compounds 2, 20, and 23 have excellent () inhibitory ability of cell growth of human breast cancer cells In other words, momordicin and derivatives thereof obtained by the present invention are effective components for pharmaceutically resisting breast cancer or treating breast cancer. From exemplification of examples 1 to 23 above, it can be clearly confirmed that for the pharmaceutical compounds for treating cancer of this invention, due to having chemical structures represented by formula (I) or (II) and having excellent inhibitory ability of cell growth activity for various human cancer cells, the compound of this invention is an active ingredient effective to treat cancer, and may be prepared into a pharmaceutical compound or pharmaceutical compound composition for treating cancer.

[0117] While specific examples of the invention have been disclosed in the forgoing detailed description of the invention, it is understood that these examples are not intended to limit the invention, and various variations and modifications can be made thereto by one of ordinary skill in the art to which this invention belongs, without departing the principle and spirit of this invention. Thus, the scope of this invention is defined by the appended claims.