ArticleScientific reports2017
Structural diversity of anti-pancreatic cancer capsimycins identified in mangrove-derived Streptomyces xiamenensis 318 and post-modification via a novel cytochrome P450 monooxygenase.
Article in Scientific reports, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Actinomycetota-Derived Metabolites in Pancreatic Cancer: Chemical Diversity, Metabolic Vulnerability, and Translational Barriers.Current oncology reports · 2026Review
- Chlokamycins B-D: Chlorohydrin-Containing Polycyclic Tetramate Macrolactams with Cytotoxic Activity from the Marine Sponge-DerivedMarine drugs · 2026Article
- A plug-and-play system for polycyclic tetramate macrolactam production and functionalization.Microbial cell factories · 2025Article
- Critical analysis of polycyclic tetramate macrolactam biosynthetic gene cluster phylogeny and functional diversity.Applied and environmental microbiology · 2024Article
- Biotechnological potential of actinomycetes in the 21st century: a brief review.Antonie van Leeuwenhoek · 2024Review
- New polycyclic tetramate macrolactams with antimycobacterial activity produced by marine-derived Streptomyces sp. KKMA-0239.The Journal of antibiotics · 2024Article
- Taxonomy and anticancer potential of Streptomyces niphimycinicus sp. nov. against nasopharyngeal carcinoma cells.Applied microbiology and biotechnology · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- An Antifungal Polycyclic Tetramate Macrolactam, Heat-Stable Antifungal Factor (HSAF), Is a Novel Oxidative Stress Modulator in Lysobacter enzymogenes.Applied and environmental microbiology · 2021Article
- Anticancer Drug Discovery from Microbial Sources: The Unique Mangrove Streptomycetes.Molecules (Basel, Switzerland) · 2020Review
- The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms.Marine drugs · 2020Review
- Dynamical modelling of secondary metabolism and metabolic switches inRoyal Society open science · 2019Article
- A Novel AdpA Homologue Negatively Regulates Morphological Differentiation in Streptomyces xiamenensis 318.Applied and environmental microbiology · 2019Article
- Biosynthesis of the Polycyclic System in the Antifungal HSAF and Analogues from Lysobacter enzymogenes.Angewandte Chemie (International ed. in English) · 2018Article
- Diverse Cone-Snail Species Harbor Closely RelatedFrontiers in microbiology · 2017Article
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Authors and funding
11 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Polycyclic tetramate macrolactams (PTMs) were identified as distinct secondary metabolites of the mangrove-derived Streptomyces xiamenensis 318. Together with three known compounds-ikarugamycin (1), capsimycin (2) and capsimycin B (3)-two new compounds, capsimycin C (4) with trans-diols and capsimycin D (5) with trans-configurations at C-13/C-14, have been identified. The absolute configurations of the tert/tert-diols moiety was determined in 4 by NMR spectroscopic analysis, CD spectral comparisons and semi-synthetic method. The post-modification mechanism of the carbocyclic ring at C-14/C-13 of compound 1 in the biosynthesis of an important intermediate 3 was investigated. A putative cytochrome P450 superfamily gene, SXIM_40690 (ikaD), which was proximally localized to the ikarugamycin biosynthetic pathway, was characterized. In vivo gene inactivation and complementation experiment confirmed that IkaD catalysed the epoxide-ring formation reaction and further hydroxylation of ethyl side chain to form capsimycin G (3'). Binding affinities and kinetic parameters for the interactions between ikarugamycin (1) and capsimycin B (3) with IkaD were measured with Surface Plasmon Resonance. The intermediate compound 3' was isolated and identified as 30-hydroxyl-capsimycin B. The caspimycins 2 and 3, were transferred to methoxyl derivatives, 6 and 7, under acidic and heating conditions. Compounds 1-3 exhibited anti-proliferative activities against pancreatic carcinoma with IC
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