Nodulisporisteroids C–L, new 4-methyl-progesteroid derivatives from Nodulisporium sp.

Zhao, Qing; Wang, Gao-Qian; Chen, Guodong; Hu, Dan; Li, Xiaoxia; Guo, Liangdong; Li, Yan; Yao, Xin‐Sheng; Gao, Hao

doi:10.1016/j.steroids.2015.08.004

Cited by 24 publications

(14 citation statements)

References 17 publications

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“…(no. 65-12-7-1) 41 , suggesting that the cleavage of the C20−C22 bond, to form the 20-keto, might be a key step in the divergence of furanosteroid biosynthesis from ergosterol biosynthesis. Based on these facts, we have proposed a reasonable early stage biosynthetic route for demethoxyviridin (Fig.…”

Section: Discussionmentioning

confidence: 99%

Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage

et al. 2018

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Furanosteroids, represented by wortmannin, viridin, and demethoxyviridin, are a special group of fungal-derived, highly oxygenated steroids featured by an extra furan ring. They are well-known nanomolar-potency inhibitors of phosphatidylinositol 3-kinase and widely used in biological studies. Despite their importance, the biosyntheses of these molecules are poorly understood. Here, we report the identification of the biosynthetic gene cluster for demethoxyviridin, consisting of 19 genes, and among them 15 biosynthetic genes, including six cytochrome P450 monooxygenase genes, are deleted. As a result, 14 biosynthetic intermediates are isolated, and the biosynthetic pathway for demethoxyviridin is elucidated. Notably, the pregnane side-chain cleavage requires three enzymes: flavin-dependent Baeyer-Villiger monooxygenase, esterase, and dehydrogenase, in sharp contrast to the single cytochrome P450-mediated process in mammalian cells. Structure–activity analyses of these obtained biosynthetic intermediates reveal that the 3-keto group, the C1β–OH, and the aromatic ring C are important for the inhibition of phosphatidylinositol 3-kinase.

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Section: Discussionmentioning

confidence: 99%

Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage

et al. 2018

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“…resulted in the isolation of two rarely 4-methyl-progesteroids ( 181 – 182 ) when grown in rice medium (Zheng et al, 2013). Whereas this strain could biosynthesize ten novel nodulisporisteroids ( 183 – 192 ) in shaking PDB medium (Zhao et al, 2015).…”

Section: Cultivation Conditionmentioning

confidence: 99%

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

et al. 2019

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Microbial secondary metabolites (MSMs) have played and continue to play a highly significant role in the drug discovery and development process. Genetically, MSM chemical structures are biologically synthesized by microbial gene clusters. Recently, however, the speed of new bioactive MSM discovery has been slowing down due to consistent employment of conventional cultivation and isolation procedure. In order to alleviate this challenge, a number of new approaches have been developed. The strategy of one strain many compounds (OSMAC) has been shown as a simple and powerful tool that can activate many silent biogenetic gene clusters in microorganisms to make more natural products. This review highlights important and successful examples using OSMAC approaches, which covers changing medium composition and cultivation status, co-cultivation with other strain(s), adding enzyme inhibitor(s) and MSM biosynthetic precursor(s). Available evidences had shown that variation of cultivation condition is the most effective way to produce more MSMs and facilitate the discovery of new therapeutic agents.

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“…4 Culture medium composition is one of the key factors that impact on metabolite production of a microorganism. 4,13 In this sense, the supplementation of different substances in the growth media was evaluated concerning metabolite production by the fungus P. brasilianum LaBioMMi 136, with the aim to induce new fungal metabolites coded on its genome but not expressed under standard Czapeck cultivation conditions.…”

Section: Resultsmentioning

confidence: 99%

“…fS36 isolated in Japan and was co-produced to other two cyclodepsipeptides JBIR 114 and JBIR 115 that differentiates in the composition and sequence of the amino-acid residues 13 ( Figure 5). This cyclodepsipeptides are structurally related to petrosifungins which are novel cyclodepsipeptides from Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis.…”

Section: Resultsmentioning

confidence: 99%

Copper and Manganese Cations Alter Secondary Metabolism in the FungusPenicillium brasilianum

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Pallini

Amaral

et al. 2016

Journal of the Brazilian Chemical Society

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The fungus Penicillium brasilianum LaBioMMi 136 was isolated as an endophyte from Melia azedarach and has shown to be a prominent producer of great diversity of secondary metabolites, although it does not express some biosynthetic routes to other natural compounds found in Penicillium genera. The present study aimed at the diversification of P. brasilianum secondary metabolism by varying the chemical composition used for its growth. Medium composition supplemented with CuSO 4 and MnSO 4 locked verruculogen biosynthesis and addressed proline to the production of a series of cyclodepsipeptides identified as JBIR 113, JBIR 114 and JBIR 115, never described for this species so far. The induced cyclodepsipeptide JBIR 113 was isolated by the use of combined chromatographic procedures and identified by spectroscopic methods. The unique structure with three neighboring cyclic amino acids proline and twice pipecolinic acid is rare as natural products and has been described for the first time in terrestrial organism. Verruculogen and JBIR 113 exhibited weak antiparasitary activity against Leishmania amazonensis.

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Nodulisporisteroids C–L, new 4-methyl-progesteroid derivatives from Nodulisporium sp.

Cited by 24 publications

References 17 publications

Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage

Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage

Exploring Structural Diversity of Microbe Secondary Metabolites Using OSMAC Strategy: A Literature Review

Copper and Manganese Cations Alter Secondary Metabolism in the FungusPenicillium brasilianum

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