Chinese Journal of Organic Chemistry >
Fermentation Optimization of the Caerulomycin H and the Synthesis of Cyanogriside K
Received date: 2022-04-14
Revised date: 2022-06-06
Online published: 2022-06-17
Supported by
National Natural Science Foundation of China-Shandong Union Foundation(U1906213); Open Fund Projects from Key Laboratory of Synthetic Chemistry of Natural Substances(SIOC-2021-7)
Caerulomycin H (2) and its 4-yl α-L-rhamnopyranoside [cyanogriside K (1)] are two microbial natural products from marine-derived Actinoalloteichus cyanogriseus WH1-2216-6. Cyanogriside K (1) shows good antiproliferative activity against tumor cells, whereas the yield is very low and the synthesis has not been reported. Thus, enough caerulomycin H (2) was first obtained by optimazing the fermentation condition of the mutant strain CRM05 of A. cyanogriseus WH1-2216-6. The yield of caerulomycin H (2) reached 272 mg/L (increased by 5 times) in the optimal solid medium consisted of corn pellets (80 g) and liqiud medium 5# for actinomycetes (100 mL). Then cyanogriside K (1) was synthesized with 25.6% total yield from caerulomycin H (2) by six steps reactions including deoximation, rhamnosylation, oximation and deacetylation. The structure of cyanogriside K (1) was identified by NMR, HRESIMS and specific rotation data. It is the same compound as the reported natural product. Furthermore, cyanogriside K (1) showed good bioactivity against the proliferation of the tumor cell lines PATU8988T, 786-O, 5673, DU145, A-375, FaDu and SF126, with the half maximal inhibitory concentration (IC50) values ranging from 1.07 μmol/L to 1.78 μmol/L.
Yun Luo , Yukang Gao , Pengcheng Yan , Weiming Zhu . Fermentation Optimization of the Caerulomycin H and the Synthesis of Cyanogriside K[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2840 -2849 . DOI: 10.6023/cjoc202204035
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