Bisvertinols: a new group of dimeric vertinoids from

Trifonov, Latchezar S.; Hilpert, Hans; Floersheim, Philipp; Dreiding, Aǹdré S.; Rast, Dora M.; Skřivanová, Romana; Hoesch, Lienhard

doi:10.1016/s0040-4020(01)87382-8

Cited by 66 publications

(80 citation statements)

References 9 publications

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“…The uv spectrum of 10 differs from the uv spectrum of octahydrotrichodimerol (6) and the other acetates (7,8,9), suggesting that one of the enolized P-diketone systems of 6 has been acetylated.…”

Section: Resultsmentioning

confidence: 91%

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The metabolites of Trichodermalongibrachiatum. Part 1. Isolation of the metabolites and the structure of trichodimerol

Andrade¹,

Ayer²,

Mebe³

1992

Can. J. Chem.

113

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. Can. J. Chem. 70, 2526Chem. 70, (1992. Tridzoderma longibrnchiaturn Rifai aggr. is a fungus reported to be antagonistic to the fungus Mycenn citricolor, the causative agent of the American leaf spot disease of coffee. We have investigated the metabolites produced when T. lorzgibrachiat~~rn is grown in liquid culture and have isolated the known compounds sorbicillin (Z), bisvertinol (3), and bisvertinolone (4) as well as several new compounds including trichodimerol (I), an interesting new natural product possessing a proper axis of symmetry. The structure of trichodimerol (1) was determined by a combination of spectroscopic techniques, including 'H and "C nuclear magnetic resonance, infrared, ultraviolet, circular dichroism, optical rotatory dispersion, and mass spectrometry, and by transformation to octahydrotrichodimerol (6) and symmetrical and unsymmetrical derivatives thereof. The relative stereochemistry of bisvertinol (3) and bisvertinolone (4) has been revised. The metabolites described are not biologically active against Mycena citricolor.ROMANO ANDRADE, WILLIAM A. AYER et PAUL P. MEBE. Can. J. Chem. 70, 2526 (1992) Le Trichodertna longibrachiatum Rifai aggr. est un champignon qui serait antagoniste du champignon Mycerla citricolor, l'agent causant des taches sur les feuilles de cafe amtricain. On a examint les mttabolites produits par culture liquide du T. longibrachiaturn et on a identifie la sorbicilline (Z), le bisvertinol (3) et la bisvertinolone (4), des composes connus, ainsi que plusieurs nouveaux compods, dont le trichodimCrol (I), un nouveau produit nature1 inttressant possCdant un axe de symttrie propre. On a determine la structure du trichodimCrol (1) par une combinaison de techniques spectroscopiques, dont la resonance magnttique nucltaire du 'H et du I3c, l'infrarouge, I'ultraviolet, le dichroi'sme circulaire, la dispersion rotatoire optique et la spectrometrie de masse ainsi que par la transformation de 1 en octahydrotrichodimCrol (6) et en des dtrivts symttriques et asymCtriques de ce dernier. On a revist la sttrtochimie relative du bisvertinol (3) et de la bisvertinolone (4). Les mttabolites dCcrits ne sont pas biologiquement actifs contre la Mycena citricolor.[Traduit par la redaction]

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Section: Resultsmentioning

confidence: 91%

“…It has also been isolated from Verticillium intertextum (8,9) and has been synthesized (10). Compound 2 was converted by catalytic hydrogenation to tetrahydrosorbicillin, similar in all respects to the product described by Dreiding and co-workers (9).…”

Section: Resultsmentioning

confidence: 99%

The metabolites of Trichodermalongibrachiatum. Part 1. Isolation of the metabolites and the structure of trichodimerol

Andrade¹,

Ayer²,

Mebe³

1992

Can. J. Chem.

113

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“…All of these compounds have been reported as inhibitors of lipid metabolism; [10][11][12][13][14][15] however, among inhibitors of lipid metabolism, lovastatin and triclosan had no effect on yellow pigment production.…”

Section: Screening Resultsmentioning

confidence: 99%

“…9) Based on this new concept, we established convenient assay systems to observe staphyloxanthin production by MRSA and started to search for inhibitors of staphyloxanthin production from natural sources. During this screening program, cerulenin (an inhibitor of fatty acid synthase), 10) dihydrobisvertinol, 11,12) xanthohumol (an inhibitor of diacylglycerol acyltransferase) 13,14) and zaragozic acid (an inhibitor of squalene synthase) 15) (Fig. 1), which are known as inhibitors of lipid metabolism, were selected from our natural product library.…”

mentioning

confidence: 99%

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Sakai

Koyama

Fukuda

et al. 2012

Biological & Pharmaceutical Bulletin

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Staphyloxanthin, a yellow pigment produced by methicillin-resistant Staphylococcus aureus (MRSA), is a virulent factor escaping from the host immune system. A new screening method for inhibitors of staphyloxanthin production by MRSA was established using paper disks. By this screening method, inhibitors of staphyloxanthin production were selected from the natural product library (ca. 300) and from actinomycete culture broths (ca. 1000). From the natural product library, four known inhibitors of lipid metabolism, cerulenin, dihydrobisvertinol, xanthohumol and zaragozic acid, were found to inhibit staphyloxanthin production; however, typical antibiotics used clinically, including vancomycin, had no effect on staphyloxanthin production. From actinomycete culture broths, two known anthraquinones, 6-deoxy-8-O-methylrabelomycin and tetrangomycin, were found to inhibit staphyloxanthin production by MRSA in the paper disk assay. These results suggested that this screening method is useful and effective to find compounds targeting staphyloxanthin production, leading to a new type of chemotherapeutics against MRSA infection.

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“…Compound 2 was obtained as an amorphous yellow powder and was shown to possess a molecular formula of C 28 H 34 O 8 by positive HRFABMS. The 1 H and 13 C NMR spectra of compound 2 displayed the characteristic paired signals including those of trichodimerol (1), suggesting that compound 2 is a modified trichodimerol (1) and is based on a bisorbicillinoid skeleton [16,21]. (1) is partially saturated.…”

Section: Structure Determinationmentioning

confidence: 99%

Fungal Metabolites, Sorbicillinoid Polyketides and Their Effects on the Activation of Peroxisome Proliferator-activated Receptor γ

Lee

Cai

et al. 2005

J Antibiot

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A new sorbicillinoid polyketide, dihydrotrichodimerol (2), along with known trichodimerol (1), and rezishanones C (3) and D (4) were isolated by bioassay-guided fractionation from an unidentified fungal strain. Dihydrotrichodimerol (2) specifically activated peroxisome proliferator-activated receptor g with an ED 50 value of 80 ng/ml as measured by a transactivation assay using a chimeric hPPAR/GAL4 system without affecting peroxisome proliferator-activated receptors a and d. On the other hand, compounds 1 and 2 suppressed the production of tumor necrosis factor-a and nitric oxide in LPSstimulated RAW264.7 cells to a similar extent.

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Bisvertinols: a new group of dimeric vertinoids from

Cited by 66 publications

References 9 publications

The metabolites of Trichodermalongibrachiatum. Part 1. Isolation of the metabolites and the structure of trichodimerol

The metabolites of Trichodermalongibrachiatum. Part 1. Isolation of the metabolites and the structure of trichodimerol

Search Method for Inhibitors of Staphyloxanthin Production by Methicillin-Resistant Staphylococcus aureus

Fungal Metabolites, Sorbicillinoid Polyketides and Their Effects on the Activation of Peroxisome Proliferator-activated Receptor γ

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