Curvulamine, a New Antibacterial Alkaloid Incorporating Two Undescribed Units from a <i>Curvularia</i> Species

Han, Wen Bo; Lu, Yan; Zhang, Ai Hua; Zhang, Gao Fei; Mei, Ya; Jiang, Nan; Lei, Xinxiang; Song, Yong; Ng, Seik Weng; Tan, Ren Xiang

doi:10.1021/ol502572g

Cited by 61 publications

(40 citation statements)

References 27 publications

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“…New metabolites 328-371 were also obtained from the genera Beauveria, Cladosporium, Cochliobolus, Curvularia, Dendrodochium, Diaporthaceae, Dichotomomyces, Emericella and Eurotium. [238][239][240][241][242][243][244][245][246][247][248][249][250] A pyrrolidinoindoline diketopiperazine dimer, cristatumin E, isolated from Eurotium herbariorum, 251 appears to be identical to the previously reported eurocristatine. 252 The genera Hansfordia, Humicola, Isaria, Neosartorya, Nigrospora, Paecilomyces and Paraconiothyrium also yielded the new metabolites 372-399.…”

Section: Marine-sourced Fungi (Excluding From Mangroves)supporting

confidence: 60%

Marine natural products

et al. 2016

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This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Marine-sourced Fungi (Excluding From Mangroves)supporting

confidence: 60%

Marine natural products

et al. 2016

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“…with an MIC value of 0.37 μM for all species. Curvulamine ( 23 ) has more selective antibacterial activity than tinidazole and is biosynthetically unique with a new extension formed through a decarboxylative condensation between an oligoketide motif and an alanine [ 27 ].…”

Section: New Antibacterial and Antifungal Compounds From Marine Fumentioning

confidence: 99%

Antibacterial and Antifungal Compounds from Marine Fungi

et al. 2015

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This paper reviews 116 new compounds with antifungal or antibacterial activities as well as 169 other known antimicrobial compounds, with a specific focus on January 2010 through March 2015. Furthermore, the phylogeny of the fungi producing these antibacterial or antifungal compounds was analyzed. The new methods used to isolate marine fungi that possess antibacterial or antifungal activities as well as the relationship between structure and activity are shown in this review.

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“…Inspired by the oxidation of I3C ( 1 ) into I3CA ( 2 ) 6 , the formation of 4 could be triggered by the decarboxylative Claisen condensation between 2 and 3 via a newly formed C 4 —C 3 , bond ( Scheme 1 ). Such a Claisen-condensing process was calculated to be energetically unfavorable 33. , 34.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by Daldinia eschscholzii

Lin

Jiang

Mei

et al. 2019

Acta Pharmaceutica Sinica B

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Two skeletally undescribed polyketide-indole hybrids (PIHs), named indolchromins A and B, were generated from indole-3-carbinol (I3C) in the fungal culture ( Daldinia eschscholzii ). The indolchromin structures were elucidated mainly by their 1D and 2D NMR spectra with the former confirmed by the single-crystal X-ray crystallographic analysis. Each indolchromin alkaloid was chirally separated into four isomers, whose absolute configurations were assigned by comparing the recorded circular dichroism (CD) spectra with the electronic CD (ECD) curves computed for all optional stereoisomers. Furthermore, the indolchromin construction pathways in fungal culture were clarified through enzyme inhibition, precursor feeding experiment, and energy calculation. The cascade reactions, including decarboxylative Claisen condensation catalyzed by 8-amino-7-oxononanoate synthase (AONS), C( sp 3 )-H activation, double bond migration, and Michael addition, all undergone compatibly during the fungal cultivation. In an MIC range of 1.3–8.6 μmol/L, (2 S ,4 R )- and (2 R ,4 S )-indolchromin A and (2 R ,4 S )-indolchromin B are inhibitory against Clostridium perfringens , Clostridium difficile , Veillonella sp., Bacteroides fragilis , and Streptococcus pyogenes . (2 R ,4 S )-Indolchromin A and (2 S ,4 S )-indolchromin B were cytotoxic against the human breast cancer cell line MDA-MB-231 with IC 50 values of 27.9 and 131.2 nmol/L, respectively, with the former additionally active against another human breast cancer cell line MCF-7 (IC 50 94.4 nmol/L).

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Curvulamine, a New Antibacterial Alkaloid Incorporating Two Undescribed Units from a Curvularia Species

Cited by 61 publications

References 27 publications

Marine natural products

Marine natural products

Antibacterial and Antifungal Compounds from Marine Fungi

Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by Daldinia eschscholzii

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