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Conversion preparation method of euphorbia lathyris diterpene compound

A technology of capers and compounds, applied in the field of biopharmaceuticals, can solve the problems that have not yet been reported on the microbial transformation of capers diterpenoids

Active Publication Date: 2017-05-24
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Therefore, the use of microorganisms to carry out transformation research on the diterpene-type compounds of caperia, in order to obtain some transformation products at specific sites (especially C-8 and C-18 low-activity carbon sites) that are difficult to prepare by traditional chemical synthesis, Combined with the chemical synthesis method, the microbial transformation product is further chemically modified. So far, there has been no report on the microbial transformation of caperia diterpenoids.

Method used

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  • Conversion preparation method of euphorbia lathyris diterpene compound
  • Conversion preparation method of euphorbia lathyris diterpene compound
  • Conversion preparation method of euphorbia lathyris diterpene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Examination of the transformation results of Mucor circinelloides CICC 40242 on Lathyrol and Euphorbia Factor L3

[0038] The present invention transforms and screens 20 bacterial strains, and the result shows that the Mucor circinatus has strong transformation ability to the capricorn diterpene alcohol and euphorbia factor L3.

[0039] 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;

[0040] 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 fo...

Embodiment 2

[0042] Example 2 Preparation of 8α-hydroxyeuphorbia factor L3(1) and 18-hydroxyeuphorbia factor L3(2)

[0043] 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 Euphorbia factor L3 ethanol solution to the bacterial solution, and the final concentration is 0.1 mg / mL. After culturing under the same conditions for 72 hours, the fermentation broth was suction-filtered, the filtrate was extracted with ethyl acetate for 3 times, and the ethyl acetate was recovered after merging to obtain the total extract of the fermentation broth;

[0044] The total extract of the fermentation broth was dissolved with a small amount of ethyl acetate, mixed with 1g of silica gel (100-200 mesh), and loaded with dichloromethane wet method on a silica gel column equipped...

Embodiment 3

[0045] Example 3 Preparation of 8α-Hydroxy Capper Diterpene Alcohol (3)

[0046] 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 Caperia spp. diterpene alcohol to the bacterial liquid, the final concentration is 0.1 mg / mL, after 72 hours of cultivation under the same conditions, the fermentation liquid is suction-filtered, and the filtrate is extracted with ethyl acetate for 3 times, and the ethyl acetate is recovered after merging ester, to obtain the total extract of the fermentation broth;

[0047] The total extract of the fermentation broth is dissolved with a small amount of ethyl acetate, mixed with 1g of silica gel (100-200 mesh), the sample is loaded in dichloromethane wet method, and in a silica gel column equipped...

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Abstract

The invention relates to the field of biological medicines, and relates to a conversion method of a euphorbia lathyris diterpene compound. The method comprises the following steps of utilizing a known microorganism to perform microorganism conversion on the euphorbia lathyris phorbol and a derivative thereof, and combining with chemical acylation, so as to prepare a euphorbia lathyris diterpene derivative compound; especially, utilizing a mucor circinelloides (CICC40242) microorganism to perform hydroxylation biological conversion on the euphorbia lathyris phorbol and euphorbia factor L3, and performing chemical acylation on hydroxyls introduced by C8 and C18, so as to obtain three hydroxylated products and six C8 alcohol esterified products. The method has the advantages that the water solubility of the euphorbia factor L3 is improved by the hydroxylation at site, and the druggability is improved; furthermore, the prepared euphorbia lathyris diterpene compound can be used for preparing anti-tumor activity and anti-tumor multidrug resistance type pharmaceutical compositions. The chemical formula is shown in the specification.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, and relates to a conversion method of caperia diterpene compounds, in particular to the preparation of caperia caperis diterpene alcohols and their derivatives by utilizing known microorganisms, combined with chemical acylation A method for diterpenoid-type derivatives. 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 anti-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] The study disclosed that the diterpenoid compound of caperia was isolated for the first time from Euphorbia lathyris L. (Tetrahedron Letters, 1971, 18:1325-1328). Subsequently, a variety of c...

Claims

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Application Information

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IPC IPC(8): C12P7/62C12P7/26C12P17/12C12P17/04A61K31/235A61K31/122A61K31/4406A61K31/341A61P35/00C12R1/785
Inventor 程志红吴亦晴
Owner FUDAN UNIV
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