Novel Polyketide Metabolites from a Species of Marine Fungi

Smith, Cameron J.; Abbanat, Darren; Bernan, Valerie S.; Maiese, William M.; Greenstein, Michael; Jompa, Jamaluddìn; Tahir, Akbar; Ireland, Chris M.

doi:10.1021/np990361w

Cited by 119 publications

(83 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some of them also occur in nature [2]. It is interesting to note that butenolides are often encountered among fungi [3], bacteria [4] and gorgonians [5], etc. The saturated analogues of these compounds are reported to act as signaling substances in bacteria [6] and enhance spore formation in streptomycetes or induce metabolite production [7].…”

Section: Introductionmentioning

confidence: 99%

<b>Synthesis of new α, β -unsaturated butenolides</b>

Joshi

Chamoli

2010

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

<b>Synthesis of new α, β -unsaturated butenolides</b>

Joshi

Chamoli

2010

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

show abstract

“…More recently, these studies have expanded to include marine-derived species (e.g. Shin and Fenical, 1987;Adam et al, 1996;Smith et al, 2000;Cueto et al, 2001 andWu et al, 2005). As part of our ongoing studies to develop the biomedical potential of marine microorganisms (e.g.…”

Section: Introductionmentioning

confidence: 99%

Secondary metabolite chemistry of the marine-derived fungus Massarina sp., strain CNT-016

et al. 2007

View full text Add to dashboard Cite

Chemical investigation of the culture broth extracts of the marine-derived fungus Massarina sp.(strain CNT-019) has yielded two new secondary metabolites, spiromassaritone (1) and massariphenone (2), as well as the previously reported fungal metabolites 6-epi-5′-hydroxymycosporulone (3) and enalin A (4). The structures of these compounds were established by a variety of one-and two-dimensional NMR experiments, while the relative configuration of spiromassaritone (1) was determined by X-ray crystallographic methods. The fungal strain was isolated as a sterile mycelium from an ocean mud sample and identified using ITS sequence analysis.

show abstract

“…2 Corresponding epoxides have not yet been reported; however, the epoxyrollins 11 A and B with epoxides in C-2 side chains are related structures.…”

mentioning

confidence: 99%

New Butenolides from Two Marine Streptomycetes

et al. 2000

View full text Add to dashboard Cite

Chemical examination of two marine Streptomycetes has resulted in the isolation of four new butenolides, namely 4,10-dihydroxy-10-methyl-dodec-2-en-1,4-olide (1), two diastereomeric 4,11-dihydroxy-10-methyldodec-2-en-1,4-olides (2/3), and 4-hydroxy-10-methyl-11-oxo-dodec-2-en-1,4-olide (4). The structures were identified by interpretation of the 2D NMR and mass spectral data.Butenolides, a family of R, -unsaturated lactones, are often encountered among fungi, 2 bacteria, 3 and gorgonians, 4 to name a few. Their saturated analogues act as signaling substances in bacteria 5 and enhance spore formation of Streptomycetes or induce metabolite production. 6 In a continuing search for bioactive constituents from marine microorganisms, we found that extracts from the Streptomycete strains B 5632 and B 3497 from marine sediments formed several new butenolides.The isolate B 5632 was fermented in a 20-L scale on YMG medium with artificial seawater for 3 days. The fermentation broth was filtered over Celite and exhaustively extracted with ethyl acetate. This extract was partitioned between methanol and cyclohexane for defatting, and the methanol layer, after concentration, was chromatographed on a flash column. Bioassay-guided fractionation led to the localization of the activity from which four known antimycins and three new butenolides (1-3) were obtained. In a similar way, strain B 3497 delivered a new keto butenolide (4) in addition to antimycin A. The antimycins were responsible for the strong antifungal activity of the extracts against Mucor miehei (Tü 284).Analytical HPLC indicated that the butenolide fraction (localized by a strong blue-violet color on spraying with anisaldehyde) contained two related compounds. Compound 1 was obtained as an oil by preparative HPLC. Under EIMS conditions, no molecular ion was visible; however, its molecular mass was fixed as 226 Da by pseudomolecular ions at m/z 244 [M + + NH 4 ] and 226 [M + + NH 4 -H 2 O] on CIMS. An APT spectrum showed that the compound contained two methyl, six methylene, three methine, and two quaternary carbons, according to a formula C 13 H 22 O 3 , in agreement with chemical shifts. The proton signals at δ 7.44 and 6.11 and a carbon signal at δ 173.2 indicated that the compound had an R, -unsaturated lactone, ester, or acid moiety. The molecular formula demands three double-bond equivalents. As two are accounted for by an ester or lactone carbonyl and a double bond, the molecule must be monocyclic. The H-H COSY spectrum showed couplings between the two olefinic protons and a multiplet at δ 5.01, indicating an oxygenated carbon next to the double bond. This methine showed further coupling to two methylene protons, which, in turn, were coupled to another methylene group. An HMQC spectrum correlated the proton signal at δ 5.01 to a methine signal at δ 83.4. This sequence resulted in fragment a.Additionally, the 1 H NMR spectrum showed a clear quartet and a triplet, indicating the presence of an isolated ethyl group in the molecule. A signal for an isolated me...

show abstract

Novel Polyketide Metabolites from a Species of Marine Fungi

Cited by 119 publications

References 8 publications

<b>Synthesis of new α, β -unsaturated butenolides</b>

<b>Synthesis of new α, β -unsaturated butenolides</b>

Secondary metabolite chemistry of the marine-derived fungus Massarina sp., strain CNT-016

New Butenolides from Two Marine Streptomycetes

Contact Info

Product

Resources

About

Novel Polyketide Metabolites from a Species of Marine Fungi

Cited by 119 publications

References 8 publications

<b>Synthesis of new &alpha;, &beta; -unsaturated butenolides</b>

<b>Synthesis of new &alpha;, &beta; -unsaturated butenolides</b>

Secondary metabolite chemistry of the marine-derived fungus Massarina sp., strain CNT-016

New Butenolides from Two Marine Streptomycetes

Contact Info

Product

Resources

About

<b>Synthesis of new α, β -unsaturated butenolides</b>

<b>Synthesis of new α, β -unsaturated butenolides</b>