Synthesis of the enantiomers of sclerosporin and sclerosporal to determine the absolute configuration of the natural products

Kitahara, Takeshi; Matsuoka, Tatsuji; Katayama, Masato; Marumo, Shingo; Mori, Kenji

doi:10.1016/s0040-4039(01)91234-1

Cited by 17 publications

(16 citation statements)

References 4 publications

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“…The referenced compounds were tested in antibacterial ( Escherichia coli , Bacillus megaterium ), antifungal ( Mycotypha microspora , Eurotium rubrum , and Microbotryum violaceum ), and antialgal ( Chlorella fusca ) assays,8,9 in protease elastase (HLE) inhibition assay,10 protein kinases (DYRK1A and CDK5) inhibition assay,11 3-T3-L1 murine adipocytes assay,12 cytotoxic activity assay against a panel of three cancer cell lines (NCI-H460, MCF7 and SF268),13 sporogenic activity assay,5,6 HIV-1 and HIV-2 virus assay,14 antiplasmodial activity assay against Plasmodium berghei on the liver stage,15 severe acute respiratory syndrome coronavirus (SARS) assay,16 Epstein-Barr virus (EBV) assay,17 and in two influenza viruses (Flu A and Flu B) assays 18…”

Section: Methodsmentioning

confidence: 99%

“…This substance, initially isolated from Sclerotinia fruticula showed an induction of asexual arthrospore formation in fungal mycelia 3,5. Interestingly, its (−)-form isolated from Diplocarpon mali did not showed sporogenic activity towards S. frutícula 5,6. During our search for new natural products produced from the marine-derived fungus Cadophora malorum , (+)-sclerosporin ( 1 ) and four new hydroxylated sclerosporin derivatives ( 2 – 5 ) were isolated from a spore culture on agar-BMS media supplemented with artificial sea salt.…”

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confidence: 99%

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Hydroxylated Sclerosporin Derivatives from the Marine-Derived Fungus Cadophora malorum

et al. 2010

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The marine-derived fungus Cadophora malorum was isolated from the green alga Enteromorpha sp. Growth on a biomalt medium supplemented with sea salt yielded an extract from which we have isolated sclerosporin and four new hydroxylated sclerosporin derivatives, namely 15-hydroxysclerosporin (2), 12-hydroxysclerosporin (3), 11-hydroxysclerosporin (4) and 8-hydroxysclerosporin (5). The compounds were evaluated in various biological activity assays. Compound 5 showed a weak fat-accumulation inhibitory activity against 3T3-L1 murine adipocytes.In recent years, research on the chemistry of marine organisms has experienced a tremendous increase, due to the need for compounds possessing bioactivity with possible pharmaceutical application or other economically useful properties. 1 From these organisms, marine fungi are recognized as a valuable source for new and bioactive secondary metabolites that have the potential to lead to innovations in drug therapy. 2 Sclerosporin is a rather rare antifungal and sporogenic cadinane-type sesquiterpene. 3,4 This substance, initially isolated from Sclerotinia fruticula showed an induction of asexual arthrospore formation in fungal mycelia.3 ,5 Interestingly, its (−)-form isolated from Diplocarpon mali did not showed sporogenic activity towards S. frutícula. 5,6 During our search for new natural products produced from the marinederived fungus Cadophora malorum, (+)-sclerosporin (1) and four new hydroxylated sclerosporin derivatives (2 -5) were isolated from a spore culture on agar-BMS media supplemented with artificial sea salt.The molecular formulae of compounds 2 -5 were deduced by HREIMS to be identical, i.e. C 15 H 22 O 3 , indicating five degrees of unsaturation. The 13 C NMR spectra for all four compounds showed 15 closely similar resonance signals, evidencing that each of the compound belonged to the same structural type. In each case a 13 C NMR downfield shifted resonance signal at δ 168 -170 was found, typical for a carboxylic acid functionality (C-14), whereas a further resonance signal at around δ 70 indicated a hydroxy substituted methylene for compounds 2 and 3, a hydroxy substituted methine for compound 5, and for compound 4 a hydroxylated quaternary carbon (see Table 1-Table 2, respectively). IR spectroscopic measurements showed a broad absorption band at 3300 cm −1 for 2 -5, also confirming the presence of a hydroxy substituent in each case. † Dedicated to the late Dr. John W. Daly of NIDDK, NIH, Bethesda, Maryland and to the late Dr. Richard E. Moore of the University of Hawaii at Manoa for their pioneering work on bioactive natural products. *To whom correspondence should be addressed. Tel.: +49228733747. Fax: +49228733250. g.koenig@uni-bonn.de. Supporting Information Available: 1 H and 13 C NMR, HREIMS, IR, CD spectra and other relevant information are included for compounds 1 -5. This material is available free of charge via the Internet at http://pubs.acs.org. NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2011 March 26....

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Hydroxylated Sclerosporin Derivatives from the Marine-Derived Fungus Cadophora malorum

et al. 2010

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“…19,20 Bioassay proved (+)-133 to be highly sporogenic, while (−)-133 was only marginally bioactive. 19,20 Bioassay proved (+)-133 to be highly sporogenic, while (−)-133 was only marginally bioactive.…”

Section: Sclerosporinmentioning

confidence: 99%

Synthesis of Biofunctional Molecules of Microbial Origin

Mori

2010

Chemical Synthesis of Hormones, Pheromones and Other Bioregulators

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“…The absolute configuration of (-)-sclerosporin was recently determined to be 1 by Kitahara et al 6 ) COOH Acknowledgments. The authors wish to express their sincere thanks to Dr. K. Sawamura and Dr. Y. Harada (Hirosaki University) for the kind gifts of D. mali.…”

Section: Micmentioning

confidence: 99%