ArticleNature communications2018
Biosynthetic pathway for furanosteroid demethoxyviridin and identification of an unusual pregnane side-chain cleavage.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed, 63 citations in OpenAlex.
- Biomimetic Synthesis of Seven Halenaquinone Meroterpenoids.Journal of the American Chemical Society · 2026Article
- Nucleophilic addition promoted ring rearrangement-aromatization in aza-/thio-sesquiterpenoid biosynthesis.Nature communications · 2025Article
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens.Scientific reports · 2025Article
- A new tetracyclic triterpenoid from endophytic fungusChinese herbal medicines · 2024Article
- The expanded CRISPR toolbox for constructing microbial cell factories.Trends in biotechnology · 2024Review
- New Report: Genome Mining Untaps the Antibiotics Biosynthetic Gene Cluster of Pseudoalteromonas xiamenensis STKMTI.2 from a Mangrove Soil Sediment.Marine biotechnology (New York, N.Y.) · 2022Article
- Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme.Beilstein journal of organic chemistry · 2022Article
- Genome mining methods to discover bioactive natural products.Natural product reports · 2021Review
- Article
- Secondary metabolite biosynthetic diversity in the fungal familyStudies in mycology · 2021Article
- Wortmannin and Wortmannine Analogues from an Undescribed Niesslia sp.Journal of natural products · 2019Article
- Biosynthesis of clinically used antibiotic fusidic acid and identification of two short-chain dehydrogenase/reductases with converse stereoselectivity.Acta pharmaceutica Sinica. B · 2019Article
- Study of the Binding Interaction between Wortmannin and Calf Thymus DNA: Multispectroscopic and Molecular Docking Studies.Evidence-based complementary and alternative medicine : eCAM · 2019Article
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Authors and funding
11 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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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