Coix seed oil containing 8 triglycerides, and pharmaceutical preparation and use thereof

Abstract

The present invention relates to Coix seed oil extracted from Semen Coicis, pharmaceutical preparations thereof, and the use thereof in the treatment of tumors and inflammation. Specifically, the Coix seed oil contains 8 triglyceride ingredients in the following mass percentages: trilinolein 4.87-6.99%, 1-olein-2,3-dilinolein 13.00-18.69%, 1-palmitin-2,3-dilinolein 5.25-7.54%, 1,3-diolein-2-linolein 13.23-19.02%, 1-palmitin-2-linolein-3-olein 10.26-14.75%, 1,3-dipalmitin-2-linolein 2.28-3.28%, triolein 14.44-20.76%, and 1-palmitin-2,3-diolein 8.06-11.58%.

Claims

1. A Coix seed oil, comprising 8 triglyceride ingredients in the following mass percentages: trilinolein 4.87-6.99%, 1-olein-2,3-dilinolein 13.00-18.69%, 1-palmitin-2,3-dilinolein 5.25-7.54%, 1,3-diolein-2-linolein 13.23-19.02%, 1-palmitin-2-linolein-3-olein 10.26-14.75%, 1,3-dipalmitin-2-linolein 2.28-3.28%, triolein 14.44-20.76%, and 1-palmitin-2,3-diolein 8.06-11.58%; wherein, said 8 ingredients are obtained by alkali-refining from a crude coix seed oil which is extracted from coix seed powder by supercritical CO.sub.2 extraction.

2. The Coix seed oil of claim 1, wherein said triglyceride ingredients especially include 8 ingredients in the following mass percentages: trilinolein 5.47-6.69%, 1-olein-2,3-dilinolein 14.63-17.88%, 1-palmitin-2,3-dilinolein 5.90-7.21%, 1,3-diolein-2-linolein 14.88-18.19%, 1-palmitin-2-linolein-3-olein 11.55-14.11%, 1,3-dipalmitin-2-linolein 2.57-3.14%, triolein16.25-19.86% and 1-palmitin-2,3-diolein 9.07-11.08%.

3. The Coix seed oil of claim 1, wherein said triglyceride ingredients especially include 8 ingredients of the following mass percentages: trilinolein 5.96-6.20%, 1-olein-2,3-dilinolein 15.93-16.58%, 1-palmitin-2,3-dilinolein 6.43-6.69%, 1,3-diolein-2-linolein 16.20-16.87%, 1-palmitin-2-linolein-3-olein 12.57-13.09%, 1,3-dipalmitin-2-linolein 2.79-2.91%, triolein17.69-18.42% and 1-palmitin-2,3-diolein 9.87-10.27%.

4. The Coix seed oil of claim 1, having the following physicochemical constants based on the fatty oils: specific gravity at 20 C. 0.917-0.920, refractive index at 20 C. 1.471-1.474, acid value <0.2, iodine value 102-106, saponification value 188-195.

5. A pharmaceutical preparation, comprising a therapeutically effective amount of the Coix seed oil of claim 1 and one or more pharmaceutically acceptable carriers, wherein said pharmaceutically acceptable carriers are selected from pharmaceutical dilutions, excipients, fillers, emulsifiers, binders, absorption accelerators, surfactants, disintegrants, lubricants and antioxidants, flavoring agents, sweeteners, preservatives and coloring agents.

6. The pharmaceutical preparation of claim 5, wherein the pharmaceutically acceptable carriers are selected from one or more in the group consisting of: mannitol, sorbitol, sodium metabisulfite, sodium bisulfite, sodium thiosulfate, cysteine hydrochloride, thioglycolic acid, methionine, soybean lecithin, vitamin C, vitamin E, EDTA disodium, EDTA calcium sodium, a monovalent alkali metal carbonate, acetate, phosphate or its aqueous solution, hydrochloric acid, acetic acid, sulfuric acid, phosphoric acid, amino acids, sodium chloride, potassium chloride, sodium lactate, ethylparaben solution, benzoic acid, potassium sorbate, chlorhexidine acetate, xylitol, maltose, glucose, fructose, dextran, glycine, starch, sucrose, lactose, mannitol, and silicic derivatives, cellulose and its derivatives, alginates, gelatin, polyvinyl pyrrolidone, glycerin, Tween 80, agar-agar, calcium carbonate, calcium bicarbonate, surfactant, polyethylene glycol, cyclodextrin, -cyclodextrin, phospholipid material, kaolin, talc, and calcium stearate or magnesium stearate.

7. The pharmaceutical preparation of claim 5, wherein said pharmaceutical preparation is an oral solid preparation, an oral liquid preparation, or an injection.

8. The pharmaceutical preparation of claim 7, wherein: said oral solid preparation is selected from any one of capsules, tablets, dripping pills, granules, and concentrated pills; said oral liquid preparation is selected from any one of aqueous suspensions, oily suspensions, solutions, emulsions, syrups, elixirs; and said injection is selected from any one of nano suspensions, liposomes, emulsions, lyophilized powder for injection and aqueous injection.

9. The pharmaceutical preparation of claim 7, wherein said injection comprises the following components: TABLE-US-00049 Coix seed oil 50-350 g Soybean lecithin for Injection or 10-40 g soybean lecithin acceptable for injection Glycerin for Injection or 15-50 g glycerin acceptable for injection Water for injection adds to 1000 mL

10. The pharmaceutical preparation of claim 9, which is prepared by a method comprising steps of: adding appropriate amount of water for injection to soybean lecithin for injection or soybean lecithin acceptable for injection; dispersing the mixture with a high shear dispersing emulsifier to give a dispersion without bulks or granules; adding glycerin for injection or glycerin acceptable for injection; then adding water for injection to a specified amount, and stirring the mixture to give a water phase; weighing Coix seed oil; heating the weighed oil and the water phase separately to 60-70 C., then mixing them and emulsifying the mixture in a high pressure homogenizer, in which the low pressure is 5-12 MPa and the high pressure is 25-50 MPa; repeating the cycle of homogenization for 3-6 times until the amount of particles below 2 m is no less than 95% and particles above 5 m are undetectable; using NaOH or HCl to adjust the pH to 4.8 to 8.5; and filtering the resulting homogeneous emulsion by nitrogen pressure through a microporous filter of 3 m or less; filling the emulsion with nitrogen, sterilizing and cooling to afford the injection.

11. The pharmaceutical preparation of claim 7, wherein said oral solid preparation comprises the following components: TABLE-US-00050 Coix seed oil 200-800 g Antioxidant(s) and/or emulsifier(s) 0.20-0.60 g to give 1000 capsules

12. The pharmaceutical preparation of claim 11, which is prepared by a method comprising steps of: preparing glue solution: weighing gelatin, purified water, glycerin and a preservative at a weight ratio of 1:0.6-1.2:0.3-0.8:0.0001-0.01; adding glycerin, purified water and preservative sequentially into a glue melting tank; heating to 70 C.-90 C.; then adding gelatin and constantly stirring the mixture under vacuum until the gelatin is completely dissolved; filtering the glue solution and storing the filtered glue solution at 56-62 C. for use; preparing drug liquid: adding Coix seed oil, antioxidant and/or emulsifier into an dosing tank, and stirring the mixture constantly until homogeneous mixing; and pressing capsules: choosing proper pellet dies according to the capsule size; pressing capsules in a temperature of 15-30 C. and a relative humidity of less than 35%; drying the pressed and shaped capsules; after removing capsules of abnormal size, washing the normal capsules with 95% medicinal ethanol, and drying them continuously to a moisture content of less than 12%; visually inspecting and removing unqualified capsules; finally printing and packaging to afford the pharmaceutical preparation.

13. The pharmaceutical preparation of claim 12, wherein: said preservative is selected from any one of 10% ethylparaben solution, benzoic acid, potassium sorbate and chlorhexidine acetate; said antioxidant is vitamin E; and said emulsifier is Tween 80.

Description

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Example 1 Preparation of Coix Seed Oil

(1) Supercritical carbon dioxide extraction: Coix seeds were crushed into 10 mesh powder and extracted using a supercritical CO.sub.2 extraction system. Coix seed powder was put in an extractor. The CO.sub.2 preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 40 and 45, respectively, and the outlet temperatures of separator I and separator II were kept 50 and 35, respectively. Flow rate of liquid CO.sub.2 was calculated based on the weight of Coix seed powder to be extracted. At a flow rate of 2.5 kg/h.Math.kg, carbon dioxide was pressed into the CO.sub.2 preheater via a high pressure pump, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO.sub.2 fluid at a pressure of 20 Mpa. Then the CO.sub.2 fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 7 Mpa to separate the oil. The CO.sub.2 gas out from the separation column entered sequentially into separator I and separator II, in which the pressure was sustained at 7 Mpa and 6 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO.sub.2 gas returned to liquid CO.sub.2 for reuse through a condenser. A continuous extraction for 2.5 h afforded a crude Coix seed oil.

(2) Refining: To the crude Coix seed oil obtained by supercritical CO.sub.2 extraction was added petroleum ether (60) of 51% of the oil weight. 2% NaOH aqueous solution of 45% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 20 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 22 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 46 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 80% of the oil weight. After standing for 3 h, the lower waste acetone was removed. The upper oil layer was added 5% of activated neutral alumina, stirred for 30 min, and filtered. The filtrate was heated, added with 4% of mixed adsorbent of activated kaolin:activated charcoal=1:1 by weight of crude oil, stirred for 30 min at 45, and then filtered. The filtrate was concentrated under a reduced pressure to remove the solvent, and washed again with purified water. After standing for 1 h, the lower waste water was removed. The upper oil was heated and vacuum dried under a nitrogen atmosphere. Then activated neutral alumina (10% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil underwent dry heat sterilization by vacuum at 165 for 2 h. After cooling, the oil was filtered through a 0.2 m microporous membrane and packed in 500 mL glass infusion bottles, and the bottles were sealed. The Coix seed oil was thus obtained in a yield of 4.5%. Physicochemical constants were detected as: specific gravity at 20, 0.917; refractive index at 20, 1.471; acid value 0.18; iodine value 102; and saponification value 190.

Example 2 Preparation of Coix Seed Oil

(3) Supercritical carbon dioxide extraction: Coix seeds were crushed into 20 mesh powder and extracted using a supercritical CO.sub.2 extraction system. Coix seed powder was put in an extractor. The CO.sub.2 preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 40 and 40, respectively, and the outlet temperatures of separator I and separator II were kept 20 and 15, respectively. Flow rate of liquid CO.sub.2 was calculated based on the weight of the Coix seed powder to be extracted. At a flow rate of 7.5 kg/h.Math.kg, carbon dioxide was pressed into the CO.sub.2 preheater via a high pressure pump, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO.sub.2 fluid at a pressure of 22 Mpa. Then the CO.sub.2 fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 8 Mpa to separate the oil. The CO.sub.2 gas out from the separation column was sequentially put into separator I and separator II, in which the pressure was sustained at 6 Mpa and 5 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO.sub.2 gas returned to liquid CO.sub.2 for reuse through a condenser. A continuous extraction for 2 h afforded a crude Coix seed oil.

(4) Refining: To the crude Coix seed oil obtained by supercritical CO.sub.2 extraction was added petroleum ether (90) of 51% of the oil weight. 2% NaOH aqueous solution of 56% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 22 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 20 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 48 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 90% of the oil weight. After standing for 2 h, the lower waste acetone was removed. The upper layer of oil solution was added 8% of activated neutral alumina, stirred for 30 min, and filtered. The filtrate was heated, added 6% of mixed adsorbent of activated kaolin:activated charcoal=1:1, stirred for 30 min at 42, and then filtered. The filtrate was concentrated under a reduced pressure to remove the solvent, and washed again with purified water. After standing for 2 h, the lower waste water was removed. The upper oil was heated and vacuum dried under nitrogen atmosphere. Then activated neutral alumina (9% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil underwent dry heat sterilization by vacuum at 170 for 1.5 h. After cooling, the oil was filtered through a 0.2 m microporous membrane and packed in 500 mL glass infusion bottles, and the bottles were sealed. The product, the Coix seed oil, was thus obtained in a yield of 4.9%. Physicochemical constants were detected as: specific gravity at 20, 0.920; refractive index at 20, 1.473; acid value 0.19; iodine value 104; and saponification value 188.

Example 3 Preparation of Coix Seed Oil

(5) Supercritical carbon dioxide extraction: Coix seeds were crushed into 30 mesh powder and extracted using a supercritical CO.sub.2 extraction system. Coix seed powder was put in an extractor. The CO.sub.2 preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 33 and 39, respectively, and the outlet temperatures of separator I and separator II were kept 30 and 20, respectively. Flow rate of liquid CO.sub.2 was calculated based on the weight of the Coix seed powder to be extracted. At a flow rate of 5.5 kg/h.Math.kg, carbon dioxide was pressed into the CO.sub.2 preheater via a high pressure pump, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO.sub.2 fluid at a pressure of 19 Mpa. Then the CO.sub.2 fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 9 Mpa to separate the oil. The CO.sub.2 gas out from the separation column was sequentially put into separator I and separator II, in which the pressure was sustained at 5 Mpa and 4 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO.sub.2 gas returned to liquid CO.sub.2 for reuse through a condenser. A continuous extraction for 3 h afforded a crude Coix seed oil.

(6) Refining: To the crude Coix seed oil obtained by supercritical CO.sub.2 extraction was added petroleum ether (80) of 51% of the oil weight. 2% NaOH aqueous solution of 36% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 18 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 18 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 42 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 75% of the oil weight. After standing for 2 h, the lower waste acetone was removed. The upper layer of oil solution was added 3% of activated neutral alumina, stirred for 30 min, and filtered. The filtrate was heated, added 2% of mixed adsorbent of activated kaolin:activated charcoal=1:1, stirred for 30 min at 47, and then filtered. The filtrate was concentrated under a reduced pressure to remove the solvent, and washed again with purified water. After standing for 1 h, the lower waste water was removed. The upper oil was heated and vacuum dried under nitrogen atmosphere. Then activated neutral alumina (11% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil underwent dry heat sterilization by vacuum at 160 for 2 h. After cooling, the oil was filtered through a 0.2 m microporous membrane and packed in 500 mL glass infusion bottles, and the bottles were sealed. The product, the Coix seed oil, was thus obtained in a yield of 4.7%. Physicochemical constants were detected as: specific gravity at 20, 0.918; refractive index at 20, 1.474; acid value 0.15; iodine value 102; and saponification value 194.

Example 4 Preparation of Coix Seed Oil

(7) Supercritical carbon dioxide extraction: Coix seeds were crushed into 40 mesh powder and extracted using a supercritical CO.sub.2 extraction system. Coix seed powder was put in an extractor. The CO.sub.2 preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 35 and 42, respectively, and the outlet temperatures of separator I and separator II were kept 40 and 30, respectively. Flow rate of liquid CO.sub.2 was calculated based on the weight of the Coix seed powder to be extracted. At a flow rate of 4.5 kg/h.Math.kg, carbon dioxide was pressed into the CO.sub.2 preheater via a high pressure pump, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO.sub.2 fluid at a pressure of 21 Mpa. Then the CO.sub.2 fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 10 Mpa to separate the oil. The CO.sub.2 gas out from the separation column was sequentially put into separator I and separator II, in which the pressure was sustained at 7 Mpa and 5 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO.sub.2 gas returned to liquid CO.sub.2 for reuse through a condenser. A continuous extraction for 2 h afforded the crude Coix seed oil.

(8) Refining: To the crude Coix seed oil obtained by supercritical CO.sub.2 extraction was added petroleum ether (70) of 51% of the oil weight. 2% NaOH aqueous solution of 50% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 19 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 21 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 50 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 85% of the oil weight. After standing for 4 h, the lower waste acetone was removed. The upper layer of oil solution was added 6% of activated neutral alumina, stirred for 30 min, and filtered. The filtrate was heated, added 5% of mixed adsorbent of activated kaolin:activated charcoal=1:1, stirred for 30 min at 50, and then filtered. The filtrate was concentrated under a reduced pressure to remove the solvent, and washed again with purified water. After standing for 1.5 h, the lower waste water was removed. The upper oil was heated and vacuum dried under nitrogen atmosphere. Then activated neutral alumina (12% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil underwent dry heat sterilization by vacuum at 162 C. for 1 h. After cooling, the oil was filtered through a 0.2 m microporous membrane and packed in 500 mL glass infusion bottles, and the bottles were sealed. The product, the Coix seed oil, was thus obtained in a yield of 4.0%. Physicochemical constants were detected as: specific gravity at 20, 0.920; refractive index at 20, 1.471; acid value 0.16; iodine value 105; and saponification value 192.

Example 5 Preparation of Coix Seed Oil

(9) Supercritical carbon dioxide extraction: Coix seeds were crushed into 50 mesh powder and extracted using a supercritical CO.sub.2 extraction system. Coix seed powder was put in an extractor. The CO.sub.2 preheater, extractor and separation column were heated by jacketed circulating hot water, so that the extraction temperature and separation temperature reached 42 and 45, respectively, and the outlet temperatures of separator I and separator II were kept 35 and 25, respectively. Flow rate of liquid CO.sub.2 was calculated based on the weight of the Coix seed powder to be extracted. At a flow rate of 6.5 kg/h.Math.kg, carbon dioxide was pressed into the CO.sub.2 preheater via a high pressure pump, turning into a fluid in supercritical state. In the extractor, an oil was extracted into the CO.sub.2 fluid at a pressure of 23 Mpa. Then the CO.sub.2 fluid with this oil entered a separation column, and the pressure of the separation column was controlled to 8 Mpa to separate the oil. The CO.sub.2 gas out from the separation column was sequentially put into separator I and separator II, in which the pressure was sustained at 6 Mpa and 4 Mpa, respectively. Impurities like water separated therefrom were discarded. The CO.sub.2 gas returned to liquid CO.sub.2 for reuse through a condenser. A continuous extraction for 2.5 h afforded the crude Coix seed oil.

(10) Refining: To the crude Coix seed oil obtained by supercritical CO.sub.2 extraction was added petroleum ether (80) of 51% of the oil weight. 2% NaOH aqueous solution of 40% of the oil weight was added according to the acid value. After stirring for 10 min, then standing for 24 h, the lower niger layer was removed. The upper layer was washed with purified water and let stand for 24 h. After the removal of the lower waste water, the upper layer went on a second washing. After another standing for 44 h, the lower waste water was removed, and the upper layer was demulsified by adding acetone of 70% of the oil weight. After standing for 3 h, the lower waste acetone was removed. The upper layer of oil solution was added 4% of activated neutral alumina, stirred for 30 min, and filtered. The filtrate was heated, added 3% of mixed adsorbent of activated kaolin:activated charcoal=1:1, stirred for 30 min at 40, and then filtered. The filtrate was concentrated under a reduced pressure to remove the solvent, and washed again with purified water. After standing for 2 h, the lower waste water was removed. The upper oil was heated and vacuum dried under nitrogen atmosphere. Then activated neutral alumina (8% of the oil weight) was added. The mixture was stirred, and allowed to stand at a cold place. After filtration, the filtrated oil underwent dry heat sterilization by vacuum at 165 for 2 h. After cooling, the oil was filtered through a 0.2 m microporous membrane and packed in 500 mL glass infusion bottles, and the bottles were sealed. The product, the Coix seed oil, was thus obtained in a yield of 4.3%. Physicochemical constants were detected as: specific gravity at 20, 0.917; refractive index at 20, 1.473; acid value 0.14; iodine value 103; and saponification value 192.

Example 6 Isolation and Identification of Trilinolein

(11) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C.sub.18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions were: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; and flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 12.6-14.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give the trilinolein.

(12) HR-EI-MS: m/z=878.7344 (Calcd.=878.7363, C.sub.57H.sub.98O.sub.6), Degree of unsaturation=9.

(13) IR (KBr film): 1746, 1170, 1098; 2928, 2856, 724; 3008, 1655 cm.sup.1 (weak).

(14) .sup.1H-NMR data are shown in Table 19.

(15) .sup.13C-NMR data are shown in Table 20.

(16) TABLE-US-00019 TABLE 19 .sup.1H-NMR spectral data of the compounds of Examples 6-13 No. G-H H 2-H 3-H 4-H 5-H 6-H 7-H 8-H 9-H 10-H 11-H 12-H 13-H 14-H 15-H 16-H 17-H 18-H A 4.30 LLL 5.27 2.32 3.61 1.32 2.05 5.36 2.77 5.36 2.05 3.32 0.89 4.15 B 4.29 2.77 5.37 2.04 OLL 5.27 2.32 1.61 1.33 2.04 5.37 1.33 0.88 4.14 2.04 1.33 C 4.30 2.05 5.36 2.77 5.36 2.05 1.31 0.88 PLL 5.27 2.31 3.61 1.31 4.15 1.31 1.31 0.88 D 4.30 2.87 1.52 OLO 5.27 2.32 3.61 1.32 2.05 5.36 3.32 0.89 4.15 2.77 5.36 2.05 E 4.15 2.04 5.35 2.94 1.28 3.28 0.88 PLO 5.27 2.31 1.63 1.28 2.77 5.35 2.04 3.08 4.30 1.28 0.88 F 4.15 1.28 0.88 PLP 5.27 2.31 1.61 1.28 2.05 5.36 2.77 5.36 2.05 1.28 0.88 4.30 1.18 0.88 G 4.15 OOO 5.27 2.31 3.61 1.28 2.00 2.00 1.28 0.88 4.30 5.34 H 4.15 2.04 5.34 2.04 1.27 0.88 POO 5.27 2.31 3.61 1.28 4.30 1.27 0.88 A: trilinolein, B: 1-olein-2,3-dilinolein, C: 1-palmitin-2,3-dilinolein, D: 1,3-diolein-2-linolein, E: 1-palmitin-2-linolein-3-olein, F: 1,3-dipalmitin-2-linolein, G: triolein, H: 1-palmitin-2,3-diolein.

(17) TABLE-US-00020 TABLE 20 .sup.13C-NMR spectral data of the compounds of Examples 6-13 No. Abb. G1-C C-1 C-2 C-3 C-4 C-5 C-6 C-7 C-8 C-9 C-10 C-11 A 62.12 173.28 34.05 24.86 29.05~29.62 27.21 130.01 128.08 25.64 LLL 68.91 172.87 34.21 24.90 129.98 128.09 B 62.12 173.28 34.04 24.86 29.07~29.79 27.22 130.03 128.08 25.65 OLL 68.89 172.87 34.21 24.90 27.19 130.00 128.10 173.29 129.73 130.03 27.22 C 62.12 173.30 34.04 24.89 29.06~29.72 27.21 130.02 128.08 25.64 PLL 68.90 172.88 34.20 24.85 129.99 128.09 173.34 34.07 24.88 29.06~29.72 D 62.12 173.29 34.05 24.86 29.07~29.79 27.20 129.73 130.03 27.24 OLO 68.89 172.87 34.21 24.90 27.22 130.00 128.10 25.65 E 62.11 173.28 34.04 24.85 29.06~29.78 27.18 129.71 130.01 27.21 PLO 68.91 172.86 34.20 24.87 27.21 129.98 128.09 25.64 173.32 34.06 24.88 29.06~29.78 F 62.09 173.32 34.05 24.86 29.05~29.70 29.05~29.70 PLP 68.89 172.86 34.19 24.88 27.20 129.97 128.08 25.63 G 62.12 173.29 34.04 24.86 29.07~9.78 27.19 129.72 130.02 27.24 OOO 68.90 172.87 34.21 24.90 129.69 130.03 H 62.12 173.31 34.04 24.88 29.06~29.78 129.72 130.02 POO 68.90 172.90 34.21 24.86 27.19 129.69 130.03 27.24 173.35 34.06 24.90 29.06~29.78 No. Abb. C-12 C-13 C-14 C-15 C-16 C-17 C-18 A 127.91 130.22 27.21 29.05~29.62 31.58 22.58 14.07 LLL 127.90 B 127.91 130.24 27.24 29.07~29.79 31.55 22.60 14.10 OLL 127.90 29.07~29.79 31.93 22.71 14.14 C 127.909 130.236 29.06~29.72 31.54 22.59 14.09 PLL 127.898 130.236 31.95 22.71 14.14 D 29.07~29.79 31.93 22.71 14.14 OLO 127.90 130.24 27.24 29.07~29.79 31.55 22.60 14.10 E 29.06~29.78 31.92 22.69 14.12 PLO 127.90 130.22 27.23 29.06~29.78 31.54 22.58 14.07 31.94 22.71 14.12 F 31.93 22.69 14.12 PLP 127.89 130.22 27.20 29.05~29.70 31.53 22.58 14.07 G 29.07~29.78 31.92 22.70 14.12 OOO H 29.06~29.78 31.92 POO 22.70 14.12 31.94 22.70 14.12 A: trilinolein, B: 1-olein-2,3-dilinolein, C: 1-palmitin-2,3-dilinolein, D: 1,3-diolein-2-linolein, E: 1-palmitin-2-linolein-3-olein, F: 1,3-dipalmitin-2-linolein, G: triolein, H: 1-palmitin-2,3-diolein.

Example 7 Isolation and Identification of 1-Olein-2,3-Dilinolein

(18) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 15.4-17.3 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-olein-2,3-dilinolein.

(19) HR-EI-MS: m/z=880.7518 (Calcd.=880.7520, C.sub.55H.sub.98O.sub.6), Degree of unsaturation=7.

(20) IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm.sup.1 (weak).

(21) .sup.1H-NMR data are shown in Table 19.

(22) .sup.13C-NMR data are shown in Table 20.

Example 8 Isolation and Identification of 1-Palmitin-2,3-Dilinolein

(23) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 17.4-18.1 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen to give a crude product.

(24) For the second purification, mobile phase A: acetonitrile, mobile phase B: acetonitrile-tetrahydrofuran (1:1). Solution of the above crude product was prepared with mobile phase B into 20 mg/mL. Injection volume of each separation was 1.5 mL. Column: Superstar Benetnach C.sub.18 (10 mm250 mm, 5 m); Gradient conditions: mobile phase B: 0-23 min: 50%-60%, 32-43 min: 60%-90%, 43-60 min: 100%; Flow rate: 3 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 31.2-34.7 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give the 1-palmitin-2,3-dilinolein.

(25) HR-EI-MS: m/z=854.7370 (Calcd.=854.7363, C.sub.55H.sub.98O.sub.6), Degree of unsaturation=7.

(26) IR (KBr Flim): 1746, 1165, 1095; 2926, 2854, 722; 3009, 1648 cm.sup.1 (weak).

(27) .sup.1H-NMR data are shown in Table 19.

(28) .sup.13C-NMR data are shown in Table 20.

Example 9 Isolation and Identification of 1,3-Diolein-2-Linolein

(29) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 18.4-20.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-olein-2,3-dilinolein.

(30) HR-EI-MS: m/z=882.7678 (Calcd.=882.7672, C.sub.57H.sub.102O.sub.6), Degree of unsaturation=7.

(31) IR (KBr film): 1747, 1163, 1097; 2925, 2855, 723; 3007, 1655 cm.sup.1 (weak).

(32) .sup.1H-NMR data are shown in Table 19.

(33) .sup.13C-NMR data are shown in Table 20.

Example 10 Isolation and Identification of 1-Palmitin-2-Linolein-3-Olein

(34) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL, Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 20.3-21.4 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-palmitin-2-linolein-3-olein.

(35) HR-EI-MS: m/z=856.7519 (Calcd.=856.7513, C.sub.55H.sub.100O.sub.6), Degree of unsaturation=6.

(36) IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm.sup.1 (weak).

(37) .sup.1H-NMR data are shown in Table 19.

(38) .sup.13C-NMR data are shown in Table 20.

Example 11 Isolation and Identification of 1,3-Dipalmitin-2-Linolein

(39) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 25.7-26.2 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1,3-dipalmitin-2-linolein.

(40) HR-EI-MS: m/z=830.7371 (Calcd.=830.7363, C.sub.53H.sub.98O.sub.6), Degree of unsaturation=5.

(41) IR (KBr film): 1747, 1164, 1098; 2925, 2854, 723; 3008, 1655 cm.sup.1 (weak).

(42) .sup.1H-NMR data are shown in Table 19.

(43) .sup.13C-NMR data are shown in Table 20.

Example 12 Isolation and Identification of Triolein

(44) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 26.6-27.7 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give triolein.

(45) HR-EI-MS: m/z=884.7851 (Calcd.=884.7833, C.sub.57H.sub.104O.sub.6), Degree of unsaturation=6.

(46) IR (KBr film):1749, 1165, 1095; 2925, 2854, 723; 3004, 1654 cm.sup.1 (weak).

(47) .sup.1H-NMR data are shown in Table 19.

(48) .sup.13C-NMR data are shown in Table 20.

Example 13 Isolation and Identification of 1-Palmitin-2,3-Diolein

(49) Isolation was carried out on P3000A preparative high performance liquid chromatography (Column: Superstar Benetnach C18, 20 mm150 mm, 5 m; Mobile phase A: acetonitrile, Mobile phase B: acetonitrile/tetrahydrofuran (1:1)). Coix seed oil solution was prepared with mobile phase B into 50 mg/mL. Injection volume of each separation was 1.5 mL. Gradient conditions: mobile phase B: 0-27 min: 50%-60%, 27-35 min: 90%, 35-45 min: 100%; Flow rate: 18 mL/min. UV detection wavelength: 208 nm. Peak fractions at retention time of 28.2-29.3 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen to give crude product.

(50) For the second purification, mobile phase A: acetonitrile, mobile phase B: acetonitrile/tetrahydrofuran (1:1). Solution of the above crude product was prepared with mobile phase B into 20 mg/mL. Injection volume of each separation was 1.5 mL. Column: Superstar Benetnach C.sub.18 (10 mm250 mm, 5 m); Gradient conditions: mobile phase B: 0-23 min: 50%-60%, 32-43 min: 60%-90%, 43-60 min: 100%; Flow rate: 3 mL/min; UV detection wavelength: 208 nm. Peak fractions at retention time of 32.9-35.1 min were collected, and concentrated using a rotary evaporator in vacuum under nitrogen. Residues were transferred with chloroform to a 10 mL vial, and dried in a vacuum oven at 35 C. for 6 h. After filling with nitrogen, the dried samples were frozen in a refrigerator to give 1-palmitin-2,3-diolein.

(51) HR-EI-MS: m/z=858.7672 (Calcd.=858.7676, C.sub.55H.sub.102O.sub.6), Degree of unsaturation=5.

(52) IR (KBr film): 1747, 1166, 1095; 2926, 2854, 722; 3003, 1654 cm.sup.1 (weak).

(53) .sup.1H-NMR data are shown in Table 19.

(54) .sup.13C-NMR data are shown in Table 20.

Example 14 Preparation of Coix Seed Oil Injection of the Invention

(55) Formulation:

(56) TABLE-US-00021 Coix seed oil 100 g Soybean lecithin for injection 10 g Glycerin for injection 15 g Water for injection adds to 1000 mL

(57) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(58) TABLE-US-00022 Trilinolein 6.10% 1-Olein-2,3-dilinolein 16.18% 1-Palmitin-2,3-dilinolein 6.56% 1,3-Diolein-2-linolein 16.69% 1-Palmitin-2-linolein-3-olein 12.96% 1,3-Dipalmitin-2-linolein 2.88% Triolein 18.30% 1-Palmitin-2,3-diolein 10.18%

(59) Process:

(60) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection was added to a specified amount, and the mixture was stirred to give a water phase.

(61) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 60, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 6 MPa and the high pressure was 30 MPa. The homogenization was repeated for 4 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 8.5.

(62) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 15 Preparation of Coix Seed Oil Injection of the Invention

(63) Formulation:

(64) TABLE-US-00023 Coix seed oil 300 g Soybean lecithin acceptable for injection 40 g Glycerin acceptable for injection 50 g Water for injection adds to 1000 mL

(65) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(66) TABLE-US-00024 Trilinolein 4.87% 1-Olein-2,3-dilinolein 13.00% 1-Palmitin-2,3-dilinolein 5.25% 1,3-Diolein-2-linolein 15.13% 1-Palmitin-2-linolein-3-olein 10.26% 1,3-Dipalmitin-2-linolein 3.05% Triolein 20.46% 1-Palmitin-2,3-diolein 11.50%

(67) Process:

(68) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase.

(69) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 70, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 12 MPa and the high pressure was 45 MPa. The homogenization was repeated for 3 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 7.1.

(70) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 16 Preparation of Coix Seed Oil Injection of the Invention

(71) Formulation:

(72) TABLE-US-00025 Coix seed oil 200 g Soybean lecithin for injection 25 g Glycerin acceptable for injection 30 g Water for injection adds to 1000 mL

(73) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(74) TABLE-US-00026 Trilinolein 5.47% 1-Olein-2,3-dilinolein 14.75% 1-Palmitin-2,3-dilinolein 6.01% 1,3-Diolein-2-linolein 18.19% 1-Palmitin-2-linolein-3-olein 14.11% 1,3-Dipalmitin-2-linolein 2.60% Triolein 16.25% 1-Palmitin-2,3-diolein 9.11%

(75) Process:

(76) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase.

(77) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 65, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 10 MPa and the high pressure was 30 MPa. The homogenization was repeated for 5 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 4.8.

(78) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 17 Preparation of Coix Seed Oil Injection of the Invention

(79) Formulation:

(80) TABLE-US-00027 Coix seed oil 150 g Soybean lecithin acceptable for injection 35 g Glycerin for injection 30 g Water for injection adds to 1000 mL

(81) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(82) TABLE-US-00028 Trilinolein 5.96% 1-Olein-2,3-dilinolein 15.93% 1-Palmitin-2,3-dilinolein 6.43% 1,3-Diolein-2-linolein 16.20% 1-Palmitin-2-linolein-3-olein 12.57% 1,3-Dipalmitin-2-linolein 2.79% Triolein 17.69% 1-Palmitin-2,3-diolein 9.87%

(83) Process:

(84) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase.

(85) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 68, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 7 MPa and the high pressure was 35 MPa. The homogenization was repeated for 3 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.8.

(86) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 18 Preparation of Coix Seed Oil Capsule of the Invention

(87) Formulation:

(88) TABLE-US-00029 Coix seed oil 200 g Vitamine E 0.20 g to give 1000 capsules

(89) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(90) TABLE-US-00030 Trilinolein 6.20% 1-Olein-2,3-dilinolein 16.58% 1-Palmitin-2,3-dilinolein 6.69% 1,3-Diolein-2-linolein 16.87% 1-Palmitin-2-linolein-3-olein 13.09% 1,3-Dipalmitin-2-linolein 2.91% Triolein 18.42% 1-Palmitin-2,3-diolein 10.27%

(91) Process:

(92) Glue formulation: Gelatin, purified water, glycerin and 10% ethylparaben solution were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and 10% ethylparaben solution were sequentially added into a glue melting tank and heated to 70. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 60 for use.

(93) Drug formulation: Formulated amount of Coix seed oil and vitamin E were added into an ingredient tank and stirred constantly until thoroughly mixed.

(94) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 18 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 19 Preparation of Coix Seed Oil Capsule of the Invention

(95) Formulation:

(96) TABLE-US-00031 Coix seed oil 800 g Tween 80 0.60 g to give 1000 capsules

(97) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(98) TABLE-US-00032 Trilinolein 6.69% 1-Olein-2,3-dilinolein 17.88% 1-Palmitin-2,3-dilinolein 7.21% 1,3-Diolein-2-linolein 14.92% 1-Palmitin-2-linolein-3-olein 11.55% 1,3-Dipalmitin-2-linolein 3.14% Triolein 19.86% 1-Palmitin-2,3-diolein 11.08%

(99) Process:

(100) Glue formulation: Gelatin, purified water, glycerin and benzoic acid were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and benzoic acid were sequentially added into a glue melting tank and heated to 90. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 56 for use.

(101) Drug formulation: Formulated amount of Coix seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed.

(102) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 26 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 20 Preparation of Coix Seed Oil Capsule of the Invention

(103) Formulation:

(104) TABLE-US-00033 Coix seed oil 500 g Vitamine E 0.40 g to give 1000 capsules

(105) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(106) TABLE-US-00034 Trilinolein 6.99% 1-Olein-2,3-dilinolein 18.69% 1-Palmitin-2,3-dilinolein 7.54% 1,3-Diolein-2-linolein 19.02% 1-Palmitin-2-linolein-3-olein 14.75% 1,3-Dipalmitin-2-linolein 3.28% Triolein 15.96% 1-Palmitin-2,3-diolein 9.70%

(107) Process:

(108) Glue formulation: Gelatin, purified water, glycerin and potassium sorbate were weighed at a weight ratio of 1:0.9:0.6:0.005. Glycerin, purified water and potassium sorbate were sequentially added into a glue melting tank and heated to 80. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 62 for use.

(109) Drug formulation: Formulated amount of Coix seed oil and Vitamin E were added into an ingredient tank and stirred constantly until thoroughly mixed.

(110) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 28 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 21 Preparation of Coix Seed Oil Capsule of the Invention

(111) Formulation:

(112) TABLE-US-00035 Coix seed oil 600 g Tween 80 0.3 g to give 1000 capsules

(113) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(114) TABLE-US-00036 Trilinolein 6.15% 1-Olein-2,3-dilinolein 16.31% 1-Palmitin-2,3-dilinolein 6.66% 1,3-Diolein-2-linolein 16.77% 1-Palmitin-2-linolein-3-olein 12.89% 1,3-Dipalmitin-2-linolein 2.88% Triolein 18.30% 1-Palmitin-2,3-diolein 10.18%

(115) Process:

(116) Glue formulation: Gelatin, purified water, glycerin and chlorhexidine acetate were weighed at a weight ratio of 1:1.0:0.5:0.008. Glycerin, purified water and chlorhexidine acetate were sequentially added into a glue melting tank and heated to 85. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 56 for use.

(117) Drug formulation: Formulated amount of Coix seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed.

(118) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 30 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 22 Preparation of Coix Seed Oil Injection of the Invention

(119) Formulation:

(120) TABLE-US-00037 Coix seed oil 100 g Soybean lecithin for injection 10 g Glycerin for injection 15 g Water for injection adds to 1000 mL

(121) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(122) TABLE-US-00038 Trilinolein 5.13% 1-Olein-2,3-dilinolein 14.09% 1-Palmitin-2,3-dilinolein 5.74% 1,3-Diolein-2-linolein 15.01% 1-Palmitin-2-linolein-3-olein 10.95% 1,3-Dipalmitin-2-linolein 2.88% Triolein 20.75% 1-Palmitin-2,3-diolein 8.69%

(123) Process:

(124) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin for injection was added. Then water for injection was added to a specified amount, and the mixture was stirred to give a water phase.

(125) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 60, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 7 MPa and the high pressure was 26 MPa. The homogenization was repeated for 5 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.8.

(126) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 23 Preparation of Coix Seed Oil Injection of the Invention

(127) Formulation:

(128) TABLE-US-00039 Coix seed oil 300 g Soybean lecithin acceptable for injection 40 g Glycerin acceptable for injection 50 g Water for injection adds to 1000 mL

(129) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(130) TABLE-US-00040 Trilinolein 5.71% 1-Olein-2,3-dilinolein 15.11% 1-Palmitin-2,3-dilinolein 6.02% 1,3-Diolein-2-linolein 15.45% 1-Palmitin-2-linolein-3-olein 14.20% 1,3-Dipalmitin-2-linolein 3.20% Triolein 17.14% 1-Palmitin-2,3-diolein 9.22%

(131) Process:

(132) To a formulated amount of soybean lecithin acceptable for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin acceptable for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase.

(133) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 70, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 11 MPa and the high pressure was 48 MPa. The homogenization was repeated for 6 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 7.5.

(134) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 24 Preparation of Coix Seed Oil Injection of the Invention

(135) Formulation:

(136) TABLE-US-00041 Coix seed oil 200 g Soybean lecithin for injection 25 g Glycerin acceptable for injection 30 g Water for injection adds to 1000 mL

(137) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(138) TABLE-US-00042 Trilinolein 6.18% 1-Olein-2,3-dilinolein 16.03% 1-Palmitin-2,3-dilinolein 6.51% 1,3-Diolein-2-linolein 16.30% 1-Palmitin-2-linolein-3-olein 12.83% 1,3-Dipalmitin-2-linolein 2.81% Triolein 18.10% 1-Palmitin-2,3-diolein 9.95%

(139) Process:

(140) To a formulated amount of soybean lecithin for injection was added an appropriate amount of water for injection. The mixture was dispersed with a high shear dispersing emulsifier into a dispersion without bulks or granules. Formulated amount of glycerin acceptable for injection was added. Then water for injection is added to a specified amount, and the mixture was stirred to give a water phase.

(141) A formulated amount of Coix seed oil was weighed. The weighed oil and the water phase prepared above were heated separately to 65, then mixed and emulsified in a high pressure homogenizer, in which the low pressure was 8 MPa and the high pressure was 40 MPa. The homogenization was repeated for 4 times until the amount of particles below 2 m was no less than 95% and particles above 5 m were undetectable. If necessary, NaOH or HCl was used to adjust the pH to 6.5.

(142) The resulting homogeneous emulsion was filtered by nitrogen pressure through a microporous filter of 3 m or less, then filled under nitrogen, and finally sterilized and cooled to afford the injection.

Example 25 Preparation of Coix Seed Oil Capsule of the Invention

(143) Formulation:

(144) TABLE-US-00043 Coix seed oil 200 g Vitamine E 0.20 g to give 1000 capsules

(145) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(146) TABLE-US-00044 Trilinolein 6.51% 1-Olein-2,3-dilinolein 17.26% 1-Palmitin-2,3-dilinolein 6.84% 1,3-Diolein-2-linolein 17.65% 1-Palmitin-2-linolein-3-olein 13.56% 1,3-Dipalmitin-2-linolein 3.07% Triolein 19.33% 1-Palmitin-2,3-diolein 10.80%

(147) Process:

(148) Glue formulation: Gelatin, purified water, glycerin and 10% ethylparaben solution were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and 10% ethylparaben solution were sequentially added into a glue melting tank and heated to 70. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 59 for use.

(149) Drug formulation: Formulated amount of Coix seed oil and Vitamin E were added into an ingredient tank and stirred constantly until thoroughly mixed.

(150) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 16 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 26 Preparation of Coix Seed Oil Capsule of the Invention

(151) Formulation:

(152) TABLE-US-00045 Coix seed oil 800 g Tween 80 0.60 g to give 1000 capsules

(153) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(154) TABLE-US-00046 Trilinolein 6.71% 1-Olein-2,3-dilinolein 18.01% 1-Palmitin-2,3-dilinolein 7.25% 1,3-Diolein-2-linolein 18.50% 1-Palmitin-2-linolein-3-olein 11.90% 1,3-Dipalmitin-2-linolein 2.63% Triolein 19.91% 1-Palmitin-2,3-diolein 11.21%

(155) Process:

(156) Glue formulation: Gelatin, purified water, glycerin and benzoic acid were weighed at a weight ratio of 1:1.2:0.8:0.01. Glycerin, purified water and benzoic acid were sequentially added into a glue melting tank and heated to 90. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 60 for use.

(157) Drug formulation: Formulated amount of Coix seed oil and Tween 80 were added into an ingredient tank and stirred constantly until thoroughly mixed.

(158) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 26 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.

Example 27 Preparation of Coix Seed Oil Capsule of the Invention

(159) Formulation:

(160) TABLE-US-00047 Coix seed oil 500 g Vitamine E 0.40 g to give 1000 capsules

(161) wherein, the Coix seed oil contains triglyceride ingredients as follows:

(162) TABLE-US-00048 Trilinolein 6.85% 1-Olein-2,3-dilinolein 18.24% 1-Palmitin-2,3-dilinolein 7.25% 1,3-Diolein-2-linolein 18.61% 1-Palmitin-2-linolein-3-olein 12.03% 1,3-Dipalmitin-2-linolein 3.01% Triolein 18.60% 1-Palmitin-2,3-diolein 11.21%

(163) Process:

(164) Glue formulation: Gelatin, purified water, glycerin and potassium sorbate were weighed at a weight ratio of 1:0.9:0.6:0.005. Glycerin, purified water and potassium sorbate were sequentially added into a glue melting tank and heated to 80. Then gelatin was added and constantly stirred under vacuum until the gelatin was completely dissolved. The glue was filtered and stored at 62 for use.

(165) Drug formulation: Formulated amount of Coix seed oil and Vitamin E were added into an ingredient tank and stirred constantly until thoroughly mixed.

(166) Capsule pressing: Proper pellet dies were chosen according to the capsule size. Capsules were pressed under a temperature of 20 and a relative humidity of less than 35%, then shaped and dried. After excluding capsules of abnormal size, normal capsules were washed with 95% medicinal ethanol and dried continuously till the moisture content was less than 12%. Unqualified capsules were removed by visual inspection, and the final products were printed and packaged.