Decalactone Derivatives from <i>Corynespora cassiicola</i>, an Endophytic Fungus of the Mangrove Plant <i>Laguncularia racemosa</i>

Ebrahim, Weaam; Aly, Amal H.; Mándi, Attila; Totzke, Frank; Kubbutat, Michael H.G.; Wray, Victor; Lin, Wen Han; Dai, Hao‐Fu; Proksch, Peter; Kurtán, Tibor; Debbab, Abdessamad

doi:10.1002/ejoc.201200245

Cited by 51 publications

(42 citation statements)

References 53 publications

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“…Many microorganisms isolated from marine sources are in fact already known from the terrestrial habitat and can be cultured without the presence of sea salt in the medium. This is especially common for marine-derived fungi and has been noted by many authors [39,40,41]. It is in fact often assumed that a large part of the microbes found in the sea are of terrestrial origin and may survive under marine conditions but are by no means obligatory marine [42,43,44].…”

Section: Introductionmentioning

confidence: 92%

Co-Cultivation—A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms

et al. 2014

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Marine-derived bacteria and fungi are promising sources of novel bioactive compounds that are important for drug discovery programs. However, as encountered in terrestrial microorganisms there is a high rate of redundancy that results in the frequent re-discovery of known compounds. Apparently only a part of the biosynthetic genes that are harbored by fungi and bacteria are transcribed under routine laboratory conditions which involve cultivation of axenic microbial strains. Many biosynthetic genes remain silent and are not expressed in vitro thereby seriously limiting the chemical diversity of microbial compounds that can be obtained through fermentation. In contrast to this, co-cultivation (also called mixed fermentation) of two or more different microorganisms tries to mimic the ecological situation where microorganisms always co-exist within complex microbial communities. The competition or antagonism experienced during co-cultivation is shown to lead to a significantly enhanced production of constitutively present compounds and/or to an accumulation of cryptic compounds that are not detected in axenic cultures of the producing strain. This review highlights the power of co-cultivation for increasing the chemical diversity of bacteria and fungi drawing on published studies from the marine and from the terrestrial habitat alike.

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Section: Introductionmentioning

confidence: 92%

Co-Cultivation—A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms

et al. 2014

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“…Very recently, the isolation of 1-3 belonging to the (14R) series has been reported from the heterologous production in Saccharomyces cerevisiae. [23][24][25] In order to test the applicability of the solution TDDFT-ECD calculation approach on exible RAL derivatives and explore the correlation between the stereochemistry and the characteristic ECD transitions, the solution conformers and ECD spectra of 1 and 3 were thus computed (SI-1, see ESI †). [23][24][25] In order to test the applicability of the solution TDDFT-ECD calculation approach on exible RAL derivatives and explore the correlation between the stereochemistry and the characteristic ECD transitions, the solution conformers and ECD spectra of 1 and 3 were thus computed (SI-1, see ESI †).…”

Section: Resultsmentioning

confidence: 99%

Structure, absolute configuration, and conformational study of resorcylic acid derivatives and related congeners from the fungus Penicillium brocae

et al. 2015

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In addition to three known resorcylic acid derivatives of the (14R) series (1-3), six new compounds including one new resorcylic acid derivative (13-hydroxydihydroresorcylide, 4) and five new loop-opened resorcylic acid-related congeners including brocapyrone A (5) and brocaketones A-D (6-9), were isolated and identified from the culture extract of a marine mangrove-derived endophytic fungus Penicillium brocae MA-192. Conformational analysis and TDDFT-ECD calculations of 1, 3, and 4 were carried out to confirm the (14R) absolute configuration and identify the solution conformers and factors that govern the correlation between stereochemistry and signs of the characteristic ECD bands. The single crystal X-ray of 3 and 5 allowed applying the solid-state TDDFT-ECD approach for 3 to compare the structures of solution and solid-state conformers and correlate the n-p* ECD transition of 5 with the helicity and absolute configuration of the dihydroisocoumarin moiety. All compounds were evaluated for antioxidant activity against DPPH and ABTS radicals. † Electronic supplementary information (ESI) available: The conformational analysis, solution ECD and computed ECD spectra of compounds 1, 3, and 4, selected 1D and 2D NMR spectra of compounds 4-9. CCDC 916585. For ESI and crystallographic data in CIF or other electronic format see

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“…Among these metabolites, xestodecalactone B (59) was found to have anti-fungal activity against Candida albicans [67] . Chemical investigation of the fungus Corynespora cassiicola resulted in the isolation of xestodecalactones D-F (61-63) [68] , whose absolute configurations were determined using the TDDFT ECD (time-dependent density functional theory electronic circular dichroism) method, proving that they belong to the (11S) series of xestodecalactones rather than possessing the (11R) configuration of the three former xestodecalactones 58-60.…”

Section: Structure and Bioactivitymentioning

confidence: 99%

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Jiang

Zhang

et al. 2014

Acta Pharmacol Sin

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Macrolides, which comprise a family of lactones with different ring sizes, belong to the polyketide class of natural products. Resorcinolic macrolides, an important subgroup, possess interesting structures and exhibit a wide variety of bioactivities, such as anti-tumor, anti-bacteria, and anti-malaria activities, etc. This review summarizes progress in isolation, bioactivity studies, biosynthesis, and representative chemical syntheses of this group of macrolides in recent decades, encompassing 63 naturally occurring macrolides published in 120 articles.

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Decalactone Derivatives from Corynespora cassiicola, an Endophytic Fungus of the Mangrove Plant Laguncularia racemosa

Cited by 51 publications

References 53 publications

Co-Cultivation—A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms

Co-Cultivation—A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms

Structure, absolute configuration, and conformational study of resorcylic acid derivatives and related congeners from the fungus Penicillium brocae

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

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