Isolation, structure elucidation and biosynthesis of benzo[b]fluorene nenestatin A from deep-sea derived Micromonospora echinospora SCSIO 04089

Jiang, Xiaoling; Zhang, Qingbo; Zhu, Yiguang; Nie, Fangling; Wu, Zhiwei; Yang, Chunfang; Zhang, Liping; Tian, Xinpeng

doi:10.1016/j.tet.2017.03.054

Cited by 41 publications

(43 citation statements)

References 45 publications

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“…Compound 35 displayed moderate cytotoxic activity against the human tumor cell lines BGC 823, HepG2, and A375 (IC 50 values: 11.03, 17.36 and 17.5 mM, respectively). 17 The same rare actinobacterium also yielded two new angucyclines, named (2R,3R)-2hydroxy-8-O-methyl-tetrangomycin (36) and (2R,3R)-2-hydroxy-5-O-methyltetrango-mycin (37), together with eight known compounds (38)(39)(40)(41)(42)(43)(44)(45). Compounds 38, 39, 43 and 44 displayed signicant cytotoxic activities against HeLa cells and the IC 50 values were 0.27, 0.11, 0.56, and 0.39 mM, respectively.…”

Section: Introductionmentioning

confidence: 99%

The secondary metabolites of rare actinomycetes: chemistry and bioactivity

et al. 2019

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Section: Introductionmentioning

confidence: 99%

The secondary metabolites of rare actinomycetes: chemistry and bioactivity

et al. 2019

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“…Benzofluorene-containing atypical angucyclines are widely distributed in nature 1 with lomaiviticin A ( 1 ) 2 , kinamycin A ( 2 ) 3 , nenestatin A ( 3 ) 4 , and fluostatins (FSTs, such as 4 – 6 ) as representative examples (Fig. 1 ) 5 – 11 .…”

Section: Introductionmentioning

confidence: 99%

“…There has thus been significant interest in the biosynthesis of these compounds given their structural complexity and pharmaceutical potency. Recent progress in this regard includes identification of the biosynthetic gene clusters for the kinamycins ( alp ) 15 , 16 , the lomaiviticins ( lom ) 17 , 18 , nenestatin A ( nes ) 4 , and the fluostatins ( fls ) 8 , 11 . More recent biochemical experiments have also demonstrated that the oxidative ring contraction during kinamycin biosynthesis is catalyzed by the flavin-dependent monooxygenase AlpJ 19 – 21 and that hydrolysis of the epoxide moiety is catalyzed by the α/β hydrolase Alp1U 3 .…”

Section: Introductionmentioning

confidence: 99%

Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines

et al. 2018

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Lomaiviticin A and difluostatin A are benzofluorene-containing aromatic polyketides in the atypical angucycline family. Although these dimeric compounds are potent antitumor agents, how nature constructs their complex structures remains poorly understood. Herein, we report the discovery of a number of fluostatin type dimeric aromatic polyketides with varied C−C and C−N coupling patterns. We also demonstrate that these dimers are not true secondary metabolites, but are instead derived from non-enzymatic deacylation of biosynthetic acyl fluostatins. The non-enzymatic deacylation proceeds via a transient quinone methide like intermediate which facilitates the subsequent C–C/C−N coupled dimerization. Characterization of this unusual property of acyl fluostatins explains how dimerization takes place, and suggests a strategy for the assembly of C–C and C–N coupled aromatic polyketide dimers. Additionally, a deacylase FlsH was identified which may help to prevent accumulation of toxic quinone methides by catalyzing hydrolysis of the acyl group.

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“…A biosynthetic intermediate homo‐dehydrorabelomycin E ( 79 ) was obtained from the Δnes 27 mutant. Compound 79 exhibited antibacterial activities against S. aureus (MIC=1 mg/mL) and Micrococcus luteus (MIC=8 mg/mL), while nenestatin A ( 78 ) had no activity against these indicator strains (MIC>64 mg/mL) …”

Section: Polyketidesmentioning

confidence: 99%

Secondary Metabolites from Marine Micromonospora: Chemistry and Bioactivities

Gui

et al. 2020

Chemistry & Biodiversity

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Marine Micromonospora was revealed to be a rather untapped and a rich source of chemically diverse and unique bioactive natural products. This review is aimed to make a comprehensive survey of secondary metabolites that were derived from marine Micromonospora including chemical diversity and biological activities. A total of 116 compounds from 41 marine Micromonospora species have been reported, covering the literatures from 1997 to 2019. These compounds contain several structural classes such as polyketides (PKS), nonribosomal peptides (NRPS), PKS-NRPS hybrids, terpenes and others, and they present cytotoxic, antibacterial, antiparasitic, chemopreventive or antioxidant activities.

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Isolation, structure elucidation and biosynthesis of benzo[b]fluorene nenestatin A from deep-sea derived Micromonospora echinospora SCSIO 04089

Cited by 41 publications

References 45 publications

The secondary metabolites of rare actinomycetes: chemistry and bioactivity

The secondary metabolites of rare actinomycetes: chemistry and bioactivity

Molecular basis of dimer formation during the biosynthesis of benzofluorene-containing atypical angucyclines

Secondary Metabolites from Marine Micromonospora: Chemistry and Bioactivities

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