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Macrolactam compound FW05328-d and efficient fermentation method thereof

A technology of fw05328-d and macrocyclic lactam, which is applied in the field of structural analogues of macrocyclic lactam compound FW05328-1, can solve problems such as unstable properties, difficulty in large-scale preparation of FW05328-1, and achieve good medical value Effect

Pending Publication Date: 2021-06-11
FUJIAN INST OF MICROBIOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its polyene structure, FW05328-1 is unstable and prone to structural transformation and degradation. The reported macrolactam compounds Micromonolactam and Salinilactam A also exhibit the same properties, which gives the preparation of compound FW05328-1 Especially large-scale preparation brings great difficulties

Method used

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  • Macrolactam compound FW05328-d and efficient fermentation method thereof
  • Macrolactam compound FW05328-d and efficient fermentation method thereof
  • Macrolactam compound FW05328-d and efficient fermentation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Shake flask fermentation of embodiment 1 compound FW05328-d

[0043] The preserved Micromonospora marine strain Micromonospora sp.FIM-MA181224 was cultured on a high asparagine solid medium at 35°C for 15 days to obtain a fresh slant of Micromonospora marine micromonospora sp.FIM-MA181224.

[0044] Inoculate the fresh slant excavated pieces (0.5cm×0.5cm) of Micromonospora marine Micromonospora sp.FIM-MA181224 in the shake flask seed medium, and cultivate them at 30°C and 240r / min for 72h to obtain the shake flask seed culture solution. The shake flask seeds were inoculated into the shake flask fermentation medium according to the inoculum amount of 4%, cultured at 32°C and 260r / min for 5 days, and then placed in the bottle, and the content of FW05328-d in the fermentation broth was determined by HPLC.

[0045] Seed medium preparation method: soluble starch 15g, glucose 5g, peptone 5g, yeast powder 5g, (NH 4 ) 2 SO 4 0.5g, K 2 HPO 4 ·3H 2 O 0.5g, CaCO 3 2g, sea s...

Embodiment 2

[0048] Purification and preparation of embodiment 2 compound FW05328-d

[0049] Take 10L of the fermentation product of Micromonospora sp. FIM-MA181224 in the above-mentioned Example 1 and centrifuge at 4500rpm to obtain mycelium, which is extracted with 1.5 times the volume of acetone (1:1, V:V) , the extract was concentrated under reduced pressure at less than 40°C to remove acetone to obtain an extract (5g). After dissolving the extract with appropriate distilled water, it was adsorbed with HP20 macroporous resin, eluted with 3 times the column volume of deionized water, and then used Gradient elution of 30%-75% alcohol concentration, HPLC detection and tracking, respectively pooled fractions containing component FW05328-d.

[0050] Then choose reverse C18 packing, prepacked column with diameter-to-height ratio of 1:3, absorb the above-mentioned substances on medium-pressure reverse C18 column, use methanol water 40%-80% gradient elution, HPLC detection and tracking, respec...

Embodiment 3

[0052] The structure identification of embodiment 3 compound FW05328-d

[0053] The compound FW05328-d obtained above is a light yellow amorphous powder. The structure of the target compound FW05328-d was identified by combining the data of mass spectrum, ultraviolet spectrum and nuclear magnetic resonance.

[0054] Such as figure 1 The ultraviolet absorption spectrum shown, UV(MeOH), λmax: 294 nm.

[0055] Such as figure 2 The shown HR-TOF-MS spectrum, HR-ESI-MS (m / z 490.2946[M+Na]+; molecular formula is C29H41NO4; calculated unsaturation is 10.

[0056] Such as image 3 shown 1 H-NMR (600MHz, in DMSO-d6) spectrum, it can be seen that the high field area shows two sets of double peak methyl hydrogen signals [δ1.03(3H,d,J=6.6Hz) and δ1.11(3H,d,J =7.0Hz)] and 2 sets of unimodal methyl hydrogen signals [δ1.56(3H,s) and δ1.72(3H,s)], there are multiple sets of ene hydrogen proton signals and 1 set of active hydrogen protons in the low field area Signal δ 7.55 (IH, d, J = ...

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Abstract

The invention belongs to the technical field of microbial fermentation, particularly relates to a structural analogue FW05328-d of a macrolactam compound FW05328-1, and further discloses an efficient fermentation method of the structural analogue by utilizing amino acid induction. The macrolactam compound FW05328-d is the structural analogue of the developed macrocyclic lactam compound FW05328-1, the structure of the compound FW05328-d is one -OH less than that of the compound FW05328-1 on the tenth site, the substance structure and chemical performance of the compound FW05328-d are more stable, and the macrolactam compound FW05328-d is more suitable for large-scale production. The antitumor activity test of the macrolactam compound FW05328-d proves that the compound has the activity of resisting mouse melanoma cell strains, human esophageal cancer cell strains and human colon cancer cell strains, and has better medical value.

Description

technical field [0001] The invention belongs to the technical field of microbial fermentation, specifically relates to a structural analog FW05328-d of a macrocyclic lactam compound FW05328-1, and further discloses a method for inducing efficient fermentation of the structural analog by using amino acids. Background technique [0002] With the continuous advancement of medical technology, more and more medical problems have been overcome, and human life expectancy has been greatly extended. However, cancer is still one of the major medical problems that humans need to overcome. Whether in developed or developing countries, cancer is the disease with the highest mortality rate, and its incidence and mortality are still increasing. At present, the main treatments for cancer include surgery, radiotherapy and antineoplastic drug therapy, especially antineoplastic drug therapy. The continuous growth of the global cancer incidence will promote the rapid development of the antineop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D225/02A61P35/00C12P17/10C12R1/29
CPCC07D225/02A61P35/00C12P17/10
Inventor 孙菲陈丽赵薇周剑方志楷江红
Owner FUJIAN INST OF MICROBIOLOGY
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