CN101274883B - Process for preparing kamebakaurin from isodon excisa(maxin.)hara - Google Patents
Process for preparing kamebakaurin from isodon excisa(maxin.)hara Download PDFInfo
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- CN101274883B CN101274883B CN2008101002511A CN200810100251A CN101274883B CN 101274883 B CN101274883 B CN 101274883B CN 2008101002511 A CN2008101002511 A CN 2008101002511A CN 200810100251 A CN200810100251 A CN 200810100251A CN 101274883 B CN101274883 B CN 101274883B
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- amethystoidin
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Abstract
The invention pertains to the filed of natural medicine. The invention relates to a new technology for preparing Kamebakaurin by taking the cauline leaf of Isodon excise (Maxin.) Hara as raw material.The extraction method is an ultrasonic extraction method, with the extraction frequency of 100Hz, the temperature of 50 DEG C, the extraction time of 30min, the extraction of three times and the extraction solution being ethanol of 70 percent; a separation method adopts D101 macropore to adsorb resin and JTY-1 reversed-phase resin column and then carries out silica gel column chromatography and is combined with recrystallization to obtain a compound with the purity being more than 98 percent. The compound belongs to diterpenoid, the type of structure belongs to kaurane, the structure of exomethylene cyclopentanone exists in the molecular structure of the compound and the compound can be used as a lead compound of antitumor drugs. The technology of the invention aims at meeting the quantity demanded of production and scientific research, increasing yield and reducing cost.
Description
Technical field
The invention belongs to natural medicine field.The present invention relates to a kind of is the technology of feedstock production calyx west Amethystoidin A (Kamebakaurin) with rabdosiaexcisa Isodon excise (Maxim.) Hara cauline leaf, and its purity reaches more than 98%.This kind compound is the diterpenes material, and structure type belongs to kaurane type, has the structure of methylene radical cyclopentanone outside the ring in its molecular structure, and this compounds can be used as the lead compound of antitumor drug.
Background technology
Rabdosiaexcisa Isodon excisa (Maxim.) Hara, have another name called tortoise leaf grass, dog day grass, wild perillaseed, flavor cool in nature is sweet, be per nnial herb, be distributed in the provinces such as Jilin, Shanxi, Shaanxi, Gansu of China, also there are certain distribution in Korea, the Soviet Union and Japan in the Asia, growth height above sea level is 550-1100m, major part grows in thick grass, roadside, the woods and cloudy dried rhizome of rehmannia band such as border, have distribute wide, the characteristics that output is big.A kind of as in the numerous plants of Rabdosia, rabdosiaexcisa has good physiologically active equally, China among the people be used to very early treat rheumatism flu, swelling and pain in the throat, gastritis, bladder distending pain, arthralgia, through close, mazoitis, wound, snake bite and insect sting etc., this plant also has tangible anticancer physiological action, depends primarily on its main component---diterpene-kind compound.A constructional feature of this type of diterpene-kind compound maximum is exactly the ring texture with the outer methylene radical cyclopentanone of a ring.Existing a large amount of molecular structure and medicine efficacy relation research experiments proves, the good antitumour activity that most Rabdosia plant is had, and its active centre is exactly the ring texture of the outer methylene radical cyclopentanone of this ring.
To the chemical constitution study of Rabdosia plant with drug effect, start from Japanese scholar's Yagi spark gap and equal from prolong the life grass, to separate in 1910 and obtain crystallization amaroid plectranthin.Takahashi in 1958 etc. from prolong the life grass, separate in (Isodon.japonica) first obtain having antivirus action kaurene type diterpene (ent-kaurene diterpene) compounds enmein (enmein); because these bitter taste diterpene compounds present anti-microbial activity and the anti-tumor activity of highly selecting to gram-positive microorganism; therefore, from the 1980s Labiatae Herba Rabdosiae glaucocalycis plant chemical ingredient research very active.Up to the present, people are divided into from rabdosiaexcisa from having identified 23 diterpenes compositions.
The means that obtain above composition at present all are to use classical extraction and separation method, and the organic solvent of promptly selecting opposed polarity obtains the component of opposed polarity as extraction solvent, and different components carries out the separation of monomeric compound again by silicagel column.
1, the extraction of diterpene-kind compound
Methyl alcohol or extraction using alcohol, alcohol extract is concentrated into certain volume, and adjusts suitable determining alcohol, and the lipotropy organic solvent with opposed polarity extracts successively by the ascending incremental order of polarity again, obtains different fat-soluble terpene extracts.
2, the separation of diterpene-kind compound
(1) column chromatography separation sorbent material commonly used is silica gel, neutral alumina, and wherein silica gel is most widely used.Eluent commonly used is many with sherwood oil, normal hexane, hexanaphthene equal solvent or with chloroform-ethanol elution.
(2) the crystallization process separation concentrates its extracting solution, again with appropriate solvent or method recrystallization.
It is less to adopt the said extracted method to obtain the pure product amount of calyx west Amethystoidin A (Kamebakaurin) monomer, can not satisfy and produce and the scientific research needs.
Summary of the invention
The present invention relates to a kind of is the technology of feedstock production calyx west Amethystoidin A (Kamebakaurin) with rabdosiaexcisa Isodon excise (Maxim.) Hara cauline leaf, and its purity reaches more than 98%.This kind compound is the diterpenes material, and structure type belongs to kaurane type, has the structure of methylene radical cyclopentanone outside the ring in its molecular structure, and this compounds can be used as the lead compound of antitumor drug.The objective of the invention is to improve yield, reduce cost for satisfying the demand in production and the scientific research.
(1) the present invention removes the foreign material in the rabdosiaexcisa cauline leaf, dries then or dries, and is ground into 40 order powder, take ultrasonic extraction, the extraction frequency is 100Hz, and temperature is 50 ℃, extraction time is 30min, extracts 3 times, and the extraction solvent is 70% ethanol.
(2) ethanol extract of 70% in (1) is merged, is evaporated to small volume, behind petroleum ether degreasing, add the water of 2 times of volumes, put into refrigerator 12h after, centrifugal, must supernatant liquor.
(3) supernatant liquor in (2) is passed through D
101Macroporous adsorptive resins absorption washes with water earlier, removes partial pigment and impurity, and then is respectively 10%, 40%, 60% ethanolic soln wash-out with concentration, the fraction collection ethanol eluate.
(4) 60% ethanol eluate in (3) is reclaimed alcohol solvent, obtain the khaki color powder.
(5) the khaki color powder in (4) is admixed the reversed-phase resin of equivalent, last JTY-1 reversed-phase resin post.With 20%-30% ethanolic soln wash-out, merge ethanolic soln, behind the recovery alcohol solvent, get white powder.
(6) white powder in (5) is carried out silica gel column chromatography again, use the solvent systems chloroform: acetone: ethyl acetate=3: 1: 1 eluant solutions, elute soln is placed, and has the crystalloid material to separate out.
(7) the crystalloid material in (6) is carried out recrystallization with 95% ethanol, obtain compound calyx west Amethystoidin A (Kamebakaurin), its purity reaches more than 98%.
According to the present invention, " % " among the present invention is weight percent.
Embodiment
The following examples can further specify the present invention, but do not limit the present invention in any way.
Embodiment 1:
(1) get rabdosiaexcisa cauline leaf 2000g, remove foreign material wherein, dry then, be ground into 40 order powder, take ultrasonic extraction, the extraction frequency is 100Hz, and temperature is 50 ℃, and extraction time is 30min, extracts 3 times, and the extraction solvent is 70% ethanol.
(2) ethanol extract of 70% in (1) is merged, is evaporated to small volume, behind petroleum ether degreasing, add the water of 2 times of volumes, put into refrigerator 12h after, centrifugal, must supernatant liquor.
(3) supernatant liquor in (2) is passed through D
101Macroporous adsorptive resins absorption washes with water earlier, removes partial pigment and impurity, and then is respectively 10%, 40%, 60% ethanolic soln wash-out with concentration, the fraction collection ethanol eluate.
(4) 60% ethanol eluate in (3) is reclaimed alcohol solvent, obtain the khaki color powder.
(5) the khaki color powder in (4) is admixed the reversed-phase resin of equivalent, last JTY-1 reversed-phase resin post.With 20%-30% ethanolic soln wash-out, merge ethanolic soln, behind the recovery alcohol solvent, get white powder.
(6) white powder in (5) is carried out silica gel column chromatography again, use the solvent systems chloroform: acetone: ethyl acetate=3: 1: 1 eluant solutions, elute soln is placed, and has the crystalloid material to separate out.
(7) the crystalloid material in (6) is carried out recrystallization with 95% ethanol, obtain compound calyx west Amethystoidin A (Kamebakaurin) (61mg), its purity reaches more than 98%.
Embodiment 2:
(1) get rabdosiaexcisa cauline leaf 2000g, remove foreign material wherein, oven dry is ground into 40 order powder then, takes ultrasonic extraction, and the extraction frequency is 100Hz, and temperature is 50 ℃, and extraction time is 30min, extracts 3 times, and the extraction solvent is 70% ethanol.
(2) ethanol extract of 70% in (1) is merged, is evaporated to small volume, behind petroleum ether degreasing, add the water of 2 times of volumes, put into refrigerator 12h after, centrifugal, must supernatant liquor.
(3) supernatant liquor in (2) is passed through D
101Macroporous adsorptive resins absorption washes with water earlier, removes partial pigment and impurity, and then is respectively 10%, 40%, 60% ethanolic soln wash-out with concentration, the fraction collection ethanol eluate.
(4) 60% ethanol eluate in (3) is reclaimed alcohol solvent, obtain the khaki color powder.
(5) the khaki color powder in (4) is admixed the reversed-phase resin of equivalent, last JTY-1 reversed-phase resin post.With 20%-30% ethanolic soln wash-out, merge ethanolic soln, behind the recovery alcohol solvent, get white powder.
(6) white powder in (5) is carried out silica gel column chromatography again, use the solvent systems chloroform: acetone: ethyl acetate=3: 1: 1 eluant solutions, elute soln is placed, and has the crystalloid material to separate out.
(7) the crystalloid material in (6) is carried out recrystallization with 95% ethanol, obtain compound calyx west Amethystoidin A (Kamebakaurin) (59mg), its purity reaches more than 98%.
Claims (2)
1. one kind is the technology of feedstock production calyx west Amethystoidin A with the rabdosiaexcisa cauline leaf, it is characterized in that may further comprise the steps:
Step (one): remove the foreign material in the rabdosiaexcisa cauline leaf, dry then or dry, be ground into 40 order powder, take ultrasonic extraction to extract, the extraction frequency is 100Hz, and temperature is 50 ℃, extraction time is 30min, extracts 3 times, and the extraction solvent is 70% ethanol;
Step (two): the ethanol extract of 70% in the step () is merged, is evaporated to small volume, behind petroleum ether degreasing, add the water of 2 times of volumes, put into refrigerator 12h after, centrifugal, must supernatant liquor;
Step (three): the supernatant liquor in the step (two) is passed through D
101Macroporous adsorptive resins absorption washes with water earlier, removes partial pigment and impurity, and then is respectively 10%, 40%, 60% ethanolic soln wash-out with concentration, the fraction collection ethanol eluate;
Step (four): 60% ethanol eluate in the step (three) is reclaimed alcohol solvent, obtain the khaki color powder;
Step (five): the khaki color powder in the step (four) is admixed the reversed-phase resin of equivalent, and last JTY-1 reversed-phase resin post with 20%-30% ethanolic soln wash-out, merges ethanolic soln, reclaim alcohol solvent after, white powder;
Step (six): the white powder in the step (five) is carried out silica gel column chromatography again, use the solvent systems chloroform: acetone: ethyl acetate=3: 1: 1 eluant solutions, elute soln is placed, and has the crystalloid material to separate out;
Step (seven): the crystalloid material in the step (six) is carried out recrystallization, obtain compound calyx west Amethystoidin A, its purity all reaches more than 98%.
2. preparation technology according to claim 1, the raw material of preparation calyx west Amethystoidin A is the cauline leaf of rabdosiaexcisa Isodon excisa (Maxin.) Hara.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2008101002511A CN101274883B (en) | 2008-05-15 | 2008-05-15 | Process for preparing kamebakaurin from isodon excisa(maxin.)hara |
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| CN2008101002511A CN101274883B (en) | 2008-05-15 | 2008-05-15 | Process for preparing kamebakaurin from isodon excisa(maxin.)hara |
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| CN101274883A CN101274883A (en) | 2008-10-01 |
| CN101274883B true CN101274883B (en) | 2010-06-09 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1566061A (en) * | 2003-06-30 | 2005-01-19 | 桂明玉 | Novel natural drug effective region of rabdosiaexcisa total diterpene |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1566061A (en) * | 2003-06-30 | 2005-01-19 | 桂明玉 | Novel natural drug effective region of rabdosiaexcisa total diterpene |
Non-Patent Citations (4)
| Title |
|---|
| JEONG-HYUNG LEE, et al..THE JOURNAL OF BIOLOGICAL CHEMISTRY27 21.2002,27(21),18411-18420. |
| JEONG-HYUNG LEE, et al..THE JOURNAL OF BIOLOGICAL CHEMISTRY27 21.2002,27(21),18411-18420. * |
| 张崇禧等.长白山地区尾叶香茶菜化学成分的研究.中成药30 1.2008,30(1),102-105. |
| 张崇禧等.长白山地区尾叶香茶菜化学成分的研究.中成药30 1.2008,30(1),102-105. * |
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