CN100516202C - Novel cell and its use for preparing gastrodin - Google Patents
Novel cell and its use for preparing gastrodin Download PDFInfo
- Publication number
- CN100516202C CN100516202C CNB2004100298286A CN200410029828A CN100516202C CN 100516202 C CN100516202 C CN 100516202C CN B2004100298286 A CNB2004100298286 A CN B2004100298286A CN 200410029828 A CN200410029828 A CN 200410029828A CN 100516202 C CN100516202 C CN 100516202C
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- CN
- China
- Prior art keywords
- cgmcc
- gastrodine
- datura
- cell
- strain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- PUQSUZTXKPLAPR-UJPOAAIJSA-N Gastrodin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(CO)C=C1 PUQSUZTXKPLAPR-UJPOAAIJSA-N 0.000 title claims description 38
- PUQSUZTXKPLAPR-KSSYENDESA-N 4-(beta-D-Glucopyranosyloxy) benzyl alcohol Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)c1ccc(CO)cc1 PUQSUZTXKPLAPR-KSSYENDESA-N 0.000 title 1
- 229930193974 gastrodin Natural products 0.000 title 1
- PUQSUZTXKPLAPR-NZEXEKPDSA-N helicidol Natural products O([C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O1)c1ccc(CO)cc1 PUQSUZTXKPLAPR-NZEXEKPDSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 241000208296 Datura Species 0.000 claims abstract description 12
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 24
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 19
- 235000015097 nutrients Nutrition 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- 240000007175 Datura inoxia Species 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 241000305492 Gastrodia Species 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 21
- 239000012141 concentrate Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000012258 culturing Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 235000006753 Platycodon grandiflorum Nutrition 0.000 description 1
- 240000003582 Platycodon grandiflorus Species 0.000 description 1
- 241000863480 Vinca Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
This invention relates to new cell from plants and its utilization in gastrodia tuber element and the preparation method. The plant cells of this invention are from Datura, especially the white and violet flower stramonium.
Description
Invention field
The present invention relates to new cell from plant, its preparation in the Gastrodine purposes and prepare the method for Gastrodine.Further, vegetable cell of the present invention is from the Solanaceae Datura, especially datura alba Nees and datura.
Background technology
Gastrodine (to hydroxymethyl benzene-β-O-pyranoglucose glucoside) is the main active ingredient of rhizoma Gastrodiae, has calmness, anti-inflammatory, anticonvulsion, analgesia and enhancing body immunity function.Gastrodine now has biology or the pharmacologically active identical with the Gastrodine of natural origin by the Gastrodine of chemosynthesis preparation and synthetic.But the synthetic Gastrodine technology of existing chemical combination exists the preparation cost height, and is raw materials used inflammable, environment vulnerable to pollution, defectives such as deficiency in economic performance.Therefore develop new economy, safe, pollution-free and efficiently the Gastrodine preparation method be very necessary.Dai Jungui etc. (2001,2002) studied the bio-transformation of balloonflower root and Vinca suspension culture to Gastrodine, it utilizes biological enzyme in the nutrient solution to remove glucosyl group in the Gastrodine molecular structure, and Gastrodine is converted into p-Hydroxybenzylalcohol, and then the chemosynthesis Gastrodine.
Summary of the invention
The objective of the invention is to develop new synthetic Gastrodine method.The present invention now unexpectedly finds to cultivate by the selectivity of the datura alba Nees in the Solanaceae Datura and datura being carried out on the cell levels after deliberation, obtained p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol directly effectively to be converted into the high reactivity cell (strain) of Gastrodine, this high reactivity cell (strain) is deposited in China Committee for Culture Collection of Microorganisms common micro-organisms center (CGMCC) on March 24th, 2003, preserving number is CGMCC No.1122 (from datura alba Nees (Dataurastramonium)), with be deposited in China Committee for Culture Collection of Microorganisms common micro-organisms center (CGMCC) on March 24th, 2004, preserving number is CGMCC No.1123 (from datura (Dataura tatula)).
Therefore, first aspect present invention relates to cell (strain), and its preserving number is: CGMCC No.1122 and/or CGMCC No.1123.
Further aspect of the present invention relates to cell (strain) CGMCC No.1122 and/or the purposes of CGMCC No.1123 in the preparation Gastrodine.
Further aspect of the present invention relates to the method for preparing Gastrodine, and it is included in the liquid nutrient medium existence down, and cell (strain) CGMCC No.1122 and/or CGMCC No.1123 are contacted with p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol.
According to the present invention, to cell of the present invention (strain) CGMCC No.1122 and/or the active any liquid nutrient medium that does not have influence of CGMCC No.1123, it includes but not limited to the LS liquid nutrient medium to the liquid nutrient medium described in the present invention, etc.
According to the present invention, preparing in the Gastrodine process with cell of the present invention (strain) CGMCC No.1122 and/or CGMCCNo.1123, temperature is generally envrionment temperature, as 20-25 ℃.After Gastrodine is with generation, the mixture of available energy dissolving Gastrodine organic solvent or organic solvent and water extracts the Gastrodine in the conversion fluid, uses chromatography then, as silica gel column chromatography, high pressure liquid chromatography, macroporous resin etc. further separate Gastrodine in the extracting solution.Wherein act on organic solvent and include but not limited to straight or branched C
1-6Alkyl alcohol, acetone, methylene dichloride, chloroform, acetonitrile etc.; C
1-6Alkyl alcohol has been said methyl alcohol, ethanol, propyl alcohol, propyl carbinol etc. for example.Gastrodine after the separation can carry out recrystallization.
According to the present invention, in with cell (strain) (CGMCC No.1122 and/or CGMCC No.1123) preparation Gastrodine process, can be earlier liquid nutrient medium such as LS and cell (strain) (CGMCCNo.1122 and/or CGMCC No.1123) be mixed and be incorporated in the shaking table rotation 4-5 days, shaking speed is 100-120 rev/min, and then adds p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol; Perhaps liquid nutrient medium and cell (strain) (CGMCC No.1122 and/or CGMCC No.1123) and p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol are mixed in shaking table simultaneously and rotate, rotating speed can be 100-120 rev/min.But the order by merging of above these factors such as raw material, the rotating speed of shaking table, temperature, can extracting mode etc. can be selected or be changed p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol being converted into Gastrodine with cell (strain) CGMCC No.1122 and/or CGMCC No.1123.
According to the present invention, raw materials used among the present invention all is known as p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol or liquid nutrient medium LS, and can or can buy from the market by the means known in the art preparation.
The preservation of biomaterial
CGMCC No.1122 is deposited in China Committee for Culture Collection of Microorganisms common micro-organisms center (CGMCC) on March 24th, 2004.
CGMCC No.1123 is deposited in China Committee for Culture Collection of Microorganisms common micro-organisms center (CGMCC) on March 24th, 2004.
The following examples are used for describing in further detail the present invention, but it does not mean that the present invention only limits to this.
The preparation of embodiment 1. Gastrodines
In the 250ml triangular flask, add 100ml LS liquid nutrient medium and 15g cell (strain) (CGMCC No.1122), add again the 70.00mg p-Hydroxybenzaldehyde in room temperature shaking table rotating and culturing 12 days, rotating speed 100-120 rev/min.Use the n-butanol extraction conversion fluid, concentrate n-butanol extracting liquid then, concentrate back resistates chromatography on silica gel column chromatography, use trichloromethane: methyl alcohol (9: 1, v/v) wash-out, concentrate eluant gets the Gastrodine crude product, uses trichloromethane: methyl alcohol (9: 1, v/v) recrystallization, get Gastrodine 56.66mg, productive rate 80.95%, fusing point 154-156 ℃.
The preparation of embodiment 2. Gastrodines
In the 250ml triangular flask, add 100ml LS liquid nutrient medium and 15g cell (strain) (CGMCC No.1122), in shaking table, rotated 4-5 days in room temperature, rotating speed 100-120 rev/min, and then add the 30.00mg p-Hydroxybenzaldehyde in room temperature shaking table rotating and culturing 10 days, rotating speed 100-120 rev/min.Use the n-butanol extraction conversion fluid, concentrate n-butanol extracting liquid then, concentrate back resistates chromatography on silica gel column chromatography, use trichloromethane: methyl alcohol (9: 1, v/v) wash-out, concentrate eluant gets the Gastrodine crude product, uses trichloromethane: methyl alcohol (9: 1, v/v) recrystallization, get Gastrodine 24.89mg, productive rate 82.96%, fusing point 154-156 ℃.
The preparation of embodiment 3. Gastrodines
In the 250ml triangular flask, add 100ml LS liquid nutrient medium and 10g cell (strain) (CGMCC No.1123), in shaking table, rotated 4-5 days in room temperature, rotating speed 100-120 rev/min, and then add the 30.00mg p-Hydroxybenzaldehyde in room temperature shaking table rotating and culturing 10 days, rotating speed 100-120 rev/min.Use the n-butanol extraction conversion fluid, concentrate n-butanol extracting liquid then, concentrate back resistates chromatography on silica gel column chromatography, use trichloromethane: methyl alcohol (9: 1, v/v) wash-out, concentrate eluant gets the Gastrodine crude product, uses trichloromethane: methyl alcohol (9: 1, v/v) recrystallization, get Gastrodine 25.80mg, productive rate 86.00%, fusing point 154-156 ℃.
The preparation of embodiment 4. Gastrodines
With p-Hydroxybenzylalcohol is raw material.
In the 500ml triangular flask, add 300ml LS liquid nutrient medium and 100g cell (strain) (CGMCC No.1123), in shaking table, rotated 4-5 days in room temperature, rotating speed 100-120 rev/min, and then add the 40.00mg p-Hydroxybenzaldehyde in room temperature shaking table rotating and culturing 10 days, rotating speed 100-120 rev/min.Use the n-butanol extraction conversion fluid, concentrate n-butanol extracting liquid then, concentrate back resistates chromatography on silica gel column chromatography, use trichloromethane: methyl alcohol (9: 1, v/v) wash-out, concentrate eluant gets the Gastrodine crude product, uses trichloromethane: methyl alcohol (9: 1, v/v) recrystallization, get Gastrodine 30.00mg, productive rate 75.00%, fusing point 154-156 ℃.
The preparation of embodiment 5. Gastrodines
With p-Hydroxybenzylalcohol is raw material.
In the 2000ml triangular flask, add 1700ml LS liquid nutrient medium and 350g cell (strain) (CGMCC No.1123), in shaking table, rotated 4-5 days in room temperature, rotating speed 100-120 rev/min, and then add the 900.00mg p-Hydroxybenzaldehyde in room temperature shaking table rotating and culturing 10 days, rotating speed 100-120 rev/min.Use the n-butanol extraction conversion fluid, concentrate n-butanol extracting liquid then, concentrate back resistates chromatography on silica gel column chromatography, use trichloromethane: methyl alcohol (9: 1, v/v) wash-out, concentrate eluant gets the Gastrodine crude product, uses trichloromethane: methyl alcohol (9: 1, v/v) recrystallization, get Gastrodine 240.00mg, productive rate 27.00%, fusing point 154-156 ℃.
Claims (10)
1. cell strain CGMCC No.1122 or CGMCC No.1123.
2. cell strain CGMCC No.1122 and/or CGMCC No.1123 are in the purposes of preparation in the Gastrodine.
3. the preparation method of Gastrodine, it is included in liquid nutrient medium and exists down, and cell strain CGMCC No.1122 and/or CGMCC No.1123 are contacted with p-Hydroxybenzaldehyde or p-Hydroxybenzylalcohol.
4. the cell strain of claim 1, wherein said cell strain is from Datura.
5. the cell strain of claim 1, wherein CGMCC No.1122 is from datura alba Nees, and CGMCC No.1123 is from datura.
6. the purposes of claim 2, wherein said cell strain is from Datura.
7. the purposes of claim 2, wherein CGMCC No.1122 is from datura alba Nees, and CGMCC No.1123 is from datura.
8. the method for claim 3, wherein liquid nutrient medium is LS.
9. the method for claim 3, wherein said cell strain is from Datura.
10. the method for claim 3, wherein CGMCC No.1122 is from datura alba Nees, and CGMCC No.1123 is from datura.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100298286A CN100516202C (en) | 2004-03-29 | 2004-03-29 | Novel cell and its use for preparing gastrodin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100298286A CN100516202C (en) | 2004-03-29 | 2004-03-29 | Novel cell and its use for preparing gastrodin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1676601A CN1676601A (en) | 2005-10-05 |
| CN100516202C true CN100516202C (en) | 2009-07-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100298286A Expired - Lifetime CN100516202C (en) | 2004-03-29 | 2004-03-29 | Novel cell and its use for preparing gastrodin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100516202C (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999750B (en) * | 2007-01-10 | 2010-07-14 | 浙江大学 | Process of synthesizing gastrodiacin by microorganism cell biological transferring parhydroxy benzyl methylol |
| CN103224539B (en) * | 2013-05-23 | 2015-09-09 | 湖北济生医药有限公司 | A kind of Gastrodine compound and pharmaceutical composition thereof |
| CN103788148B (en) * | 2014-02-13 | 2015-11-04 | 悦康药业集团有限公司 | Gastrodin compound and preparation thereof |
| CN109609434B (en) * | 2018-11-23 | 2022-08-30 | 湖南中医药大学 | Method for synthesizing gastrodin through biotransformation and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1256925A (en) * | 1998-12-11 | 2000-06-21 | 涂远生 | Medicine for stopping drug-taking |
| JP2003048848A (en) * | 2001-08-01 | 2003-02-21 | Taisho Pharmaceut Co Ltd | Medical composition |
-
2004
- 2004-03-29 CN CNB2004100298286A patent/CN100516202C/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1256925A (en) * | 1998-12-11 | 2000-06-21 | 涂远生 | Medicine for stopping drug-taking |
| JP2003048848A (en) * | 2001-08-01 | 2003-02-21 | Taisho Pharmaceut Co Ltd | Medical composition |
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| Publication number | Publication date |
|---|---|
| CN1676601A (en) | 2005-10-05 |
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| C14 | Grant of patent or utility model | ||
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| C56 | Change in the name or address of the patentee |
Owner name: KPC CO., LTD. Free format text: FORMER NAME: KUNMING PHARMACEUTICAL INDUSTRY GROUP CORP., LTD. |
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| CP03 | Change of name, title or address |
Address after: 650106 Kunming science and Technology Industrial Development Zone, Yunnan Province Road No. 166 Patentee after: KPC PHARMACEUTICALS, Inc. Address before: 650106 No. 166, medical Road, Kunming hi tech Industrial Development Zone, Yunnan, China Patentee before: KUNMING PHARMACEUTICAL Corp. |
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Granted publication date: 20090722 |