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Polyketone indole alkaloid as well as preparation method and application thereof

An alkaloid and indole technology, applied in the field of microbial engineering technology and pharmacology, can solve the problems of drug resistance, low treatment efficiency, restricting the treatment effect and quality of life of tumor patients, and achieve guaranteed source, low cost, short cycle effect

Active Publication Date: 2018-12-28
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current chemotherapy drugs still have problems such as low treatment efficiency and drug resistance, which seriously restrict the treatment effect and quality of life of cancer patients.

Method used

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  • Polyketone indole alkaloid as well as preparation method and application thereof
  • Polyketone indole alkaloid as well as preparation method and application thereof
  • Polyketone indole alkaloid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Liquid fermentation and feeding of mantis intestinal bacteria IFB-T01 (Daldinia eschscholzii)

[0032] The bacterial block of Daldinia eschscholzii IFB-TL01 derived from the intestinal bacteria of the activated mantis mantis was inoculated in 1L Erlenmeyer flasks, each containing 400mL of malt culture medium, inoculated 10 flasks on a shaker, and cultured at 200rpm, 28‐30℃ for 2 ~3 days, as the seed solution, and then inoculate the seed solution in a new malt culture medium (400mL / bottle×200 bottles) with an inoculation amount of 20mL, and continue to cultivate for 2 days at 200rpm and 28 to 30°C. Feed indole-3-carbinol at 24, 48, and 72 hours respectively until the final concentration of indole-3-carbinol in the solution is 1.0 mM, 200 rpm, and then continue fermentation at 28-30°C for 10 days.

Embodiment 2

[0033] Embodiment 2: Extraction and separation of indole polyketide alkaloids

[0034] Get the fermented liquid in Example 1 and filter it through gauze, extract the filtrate with ethyl acetate, and centrifuge and concentrate to obtain black extract A (83g); extract A is subjected to silica gel column chromatography segmentation, and petroleum ether: acetone (volume ratio: 100:2, 100:5, 10:1, 5:1, 3:1, 2:1, 1:1) for gradient elution to obtain 7 eluted fractions A1-A7;

[0035] Section A4 (petroleum ether: acetone = 5:1 part) continued to be eluted with petroleum ether: acetone (100:2→1:1) gradient to obtain a total of 7 fractions F1-F7.

[0036] Among them, F3 (20:1) and F4 (10:1) fractions were subjected to Sephadex LH-20 column chromatography (methanol elution), and high-pressure preparative liquid phase [chromatographic column: ODS-2Hy0persil columns (5 μm, 250 × 10mm) ], MeOH / H 2 O (70:30 and 65:35) elution purification, respectively to obtain the racemate (8mg, yield ...

Embodiment 3

[0038] Embodiment 3: Structural identification of indole polyketide alkaloids

[0039] The structures of indolepolyketone alkaloids were determined based on their mass spectrum, nuclear magnetic resonance spectrum, and X-ray single crystal diffraction analysis.

[0040] The spectroscopic data are as follows:

[0041] Dalesindole B, from CH 2 Cl 2 / MeOH (1:1) yellow single crystal, high resolution electrospray mass spectrometry HR / ESIMS: m / z 302.1156; infrared (KBr)ν max (cm -1 ):3409,2971,2913,1616,1587,1464,744. 1 H and 13 C NMR is shown in Table 1.

[0042] Chiral resolution of racemate A obtained two enantiomers {(+)-(2S,4R), light gray powder, high resolution electrospray mass spectrometry HR / ESIMS: m / z 302.1159; optical rotation [α] 25D +25.3°(c=0.15, MeOH), circular dichroism CD(MeOH)λ max (Δε)=204(5.5), 228(-6.1), 270(1.38)nm; (–)-(2R,4S), light gray powder, high resolution electrospray mass spectrometry HR / ESIMS: m / z 302.1154; optical rotation [α]25D–20.0°(c=0...

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Abstract

The invention discloses a class of indole polyketone alkaloids. The class of indole polyketone alkaloids is extracted from fermentation broth of daldinia eschscholzii IFB-TL01 coming from intestinal fungi of tenodera aridifolia sinensis fed with indole-3-methanol. The indole polyketone alkaloids provided by the invention are compounds with a new skeleton; results of pharmacological experiments show that the indole polyketone alkaloids have inhibition activity on the proliferation of various tumor cells, in particular, can selectively inhibit tumor cells of MCF-7 and MDA-MB-231, therefore, theindole polyketone alkaloids can be used as antitumor drugs, especially as a lead compound for the production of anti-breast cancer drugs, and are used in the antitumor drugs.

Description

technical field [0001] The invention belongs to the field of microbial engineering technology and pharmacology, and in particular relates to the fermentation liquid obtained from the intestinal fungus Daldinia genus Daldinia (Daldinia) light wheel charcoal shell IFB-TL01 (Daldinia eschscholzii) fed with indole-3-carbinol A class of extracted indole polyketide alkaloids and its preparation method and application. Background technique [0002] The discovery and application of new skeleton compounds play a vital role in the development of drugs. Polyketides are a large class of secondary metabolites synthesized by bacteria, fungi, and plants. They have unique structures and biological activities and have attracted extensive attention. The polyketide synthase biosynthesis production line is used for the construction and assembly of a series of new backbone compounds, which is a huge treasure trove to be excavated. By adding active exogenous substances and cleverly utilizing t...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D405/14A61K31/404A61P35/00
CPCA61P35/00C07D405/04C07D405/14C07B2200/07
Inventor 谭仁祥林丽萍
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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