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Transformation method and application of structurally rearranged derivatives of diterpene-type compounds of caperia

A technology for compounds and diterpenes, applied in the field of structural rearrangement derivatives, can solve the problems that have not yet been seen, and achieve the effects of improving druggability and enhancing water solubility

Active Publication Date: 2020-07-14
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report about capricorn diterpenoids with three-membered ring opening of the diterpene skeleton

Method used

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  • Transformation method and application of structurally rearranged derivatives of diterpene-type compounds of caperia
  • Transformation method and application of structurally rearranged derivatives of diterpene-type compounds of caperia
  • Transformation method and application of structurally rearranged derivatives of diterpene-type compounds of caperia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 High Performance Liquid Chromatography (HPLC) Examination of Mortierella ramanniana Transforming Lathyrol and 7β-Hydroxystephanol into Rearranged Products

[0028] The strain screening medium is a potato medium: cut 200g of peeled potatoes into small cubes of 1 cubic centimeter, boil them with 1L of water for 20 minutes, add 20g of glucose after filtering the potato liquid, and distribute them in 250mL Erlenmeyer flasks, 50mL per bottle , sterilized at 121°C, 0.15Mpa for 20 minutes;

[0029] The strains were inoculated on the slant solid medium, cultured at 28°C for 7 days, and stored in a refrigerator at 4°C. The strains were activated by a two-step activation method. First, the strains were inoculated on the potato medium, and the flask was shaken at 28°C and 180rpm. After culturing for 48 hours, obtain the seed solution; inoculate the seed solution in another potato medium at a volume ratio of 1%-3%, and cultivate under the same conditions for 48 hours, and...

Embodiment 2

[0035] Embodiment 2 prepares the structural rearrangement product (1) of diterpene alcohol

[0036]The two-step activation method was used to activate the strains, and the obtained seed solution was inoculated into 250mL potato medium with a volume ratio of 1L in a 1L Erlenmeyer flask at a volume ratio of 1%, and was shaken at 28°C for 48h under the condition of 180rpm. Add 5mg / mL ethanol solution of stephenae diterpene alcohol to the bacterial solution, the final concentration is 0.1mg / mL, after 108 hours of cultivation under the same conditions, the fermentation broth is suction-filtered, the filtrate is extracted with ethyl acetate for 3 times, and ethyl acetate is recovered after combination , to obtain the total extract of the fermentation broth;

[0037] The total extract of the fermentation broth was dissolved with a small amount of ethyl acetate, mixed with 1g of silica gel, and wet-loaded with dichloromethane on a silica gel column equipped with 40g of column chromato...

Embodiment 3

[0038] Example 3 Preparation of Structural Rearrangement Product (2) of 7β-Hydroxystephania Diterpene Alcohol

[0039] The two-step activation method was used to activate the strains, and the obtained seed solution was inoculated into 250mL potato medium with a volume ratio of 1L in a 1L Erlenmeyer flask at a volume ratio of 1%, and was shaken at 28°C for 48h under the condition of 180rpm. Add 5 mg / mL ethanol solution of 7β-hydroxystephinol diterpene alcohol to the bacterial liquid, the final concentration is 0.1 mg / mL, after 108 hours of culture under the same conditions, the fermentation liquid is suction filtered, and the filtrate is extracted with ethyl acetate for 3 times, combined and recovered Ethyl acetate to obtain the total extract of the fermentation broth;

[0040] The total extract of the fermentation broth was dissolved in a small amount of ethyl acetate, mixed with 1g of silica gel, wet loaded with dichloromethane into a silica gel column equipped with 40g of co...

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Abstract

The invention belongs to the field of biological drugs, and relates to preparation of a novel euphorbia lathyris diterpane type compound and application in antitumor drugs. The compound is structurally characterized in that parallel three-membered rings in euphorbia lathyris diterpane are subjected to ring opening and rearrangement, and a hydroxyl and allyl substituted ring opening compound is obtained. The compound is obtained by Mortierella rammanniana biological conversion of the euphorbia lathyris diterpane type compound of a 5 / 11 / 3 ring system; after the euphorbia lathyris diterpane type compound is rearranged and hydroxylated, the water solubility is enhanced, and the druggability is improved. Furthermore, the compound can be used for preparing drugs or drug compositions capable of resisting tumor activities. The chemical formula of the compound is shown in the specification.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, and relates to a method for transforming caperia diterpenes, in particular to using known microorganisms to transform caperia diterpenes to prepare structurally rearranged derivatives with anticancer activity. Background technique [0002] It is disclosed in the prior art that the diterpene-type compound of Caperia spp. belongs to the natural product of the diterpene skeleton, and has obvious anti-tumor activity and the activity of reversing tumor multidrug resistance (MDR). The study of structure-activity relationship shows that the difference of substituents on the core can obviously change the antitumor activity and MDR activity of this kind of compound. [0003] Some studies have disclosed that the diterpene-type compound of caperia was first isolated from Euphorbia lahyris L. (Tetrahedron Letters, 1971, 18:1325-1328); A kind of capricorn diterpene derivatives, such as five capricorn diterp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/743C12P7/26A61K31/122A61P35/00C12R1/645
CPCC07C49/743C12P7/26
Inventor 程志红吴亦晴
Owner FUDAN UNIV
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