Ten-Membered Lactones from the Marine-Derived Fungus <i>Curvularia</i> sp.

Greve, Hendrik; Schupp, Peter J.; Eguereva, Ekaterina; Kehraus, Stefan; König, Gabriele M.

doi:10.1021/np8003326

Cited by 50 publications

(53 citation statements)

References 20 publications

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“…Their structures were characterized using 2D NMR spectroscopic analyses. The relative configuration of the stereogenic carbons was determined by comparison of the 3 J H,H spin systems with those of herbarumin (40), putaminoxin (35), and/or modiolide A (8), and further confirmed by a NOE experiment [33,34]. Investigation of the secondary metabolites of the marinederived fungus Curvularia sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 97%

“…NMR spectroscopy in combination with X-ray crystal structure analyses, Mosher's method, [ ] D values, CD, or quantum chemical CD calculations were extensively used in the elucidation of the relative and absolute configurations of nonanolides. In some cases, the absolute stereochemistry of nonanolides, for example putaminoxin (35) [44], mueggelone (39) [45], sporostatin (53) [46], multiplolide A (4) [47], xestodecalactones A, B and C (54)(55)(56) [48][49][50], and achaetolide (49) [41,51] were established by stereoselective total synthesis. The nonanolide class of metabolites is classified according to the previously established criteria: (i) simple nonanolides with methyl and oxygen substituents (Fig.…”

Section: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

“…Putaminoxin (35), putaminoxins B, D, E (36)(37)(38) Phoma putaminum Fungal pathogen [15][16][17] Colletofragarones A1, A2 (50,51) Colletotrichum fragariae Fungus [18] Mueggelone (gloeolactone) (39) Aphanizomenon flos-aquae (Gloeotrichia sp.) Cyanobacterium [8,9] Aspinolides A-C (1-3) Aspergillus chraceus (DSM-7428) Fungus [19] Sporostatin (M5032) (53) Sporormiella sp.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…Investigation of the secondary metabolites of the marinederived fungus Curvularia sp. isolated from the red alga Acanthophora spicifera, yielded curvulides A, B 1 , and B 2 (24)(25)(26), and an unnamed 10-membered lactone (27), along with modiolide A (8) [35]. The structures of 24-27 were characterized based on NMR spectroscopic and MS data.…”

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

“…Phoma putaminum, a causal agent of leaf necrosis of Erigeron annuus, produced several phytotoxic macrolides named putaminoxin, and putaminoxins B, D, and E (35)(36)(37)(38). Their structures were characterized, using spectroscopic and chemical methods, as new nonanolides with a propyl or pentyl group at the C-9 position [15][16][17].…”

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

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Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 97%

Section: Structures and Classification Of Nonano-lidesmentioning

confidence: 99%

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

Section: Simple Nonanolides With Methyl and Oxygen Substituentsmentioning

confidence: 99%

Section: Nonanolides With Extended Alkyl Chainsmentioning

confidence: 99%

See 3 more Smart Citations

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Merosesquiterpenoids and Ten‐Membered Macrolides from a Soft Coral‐Derived Lophiostoma sp. Fungus

Zheng

Shao

Chen

et al. 2015

Chemistry & Biodiversity

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One new merosesquiterpenoid, craterellin D (1), along with one known analog, craterellin A (2), and five known ten-membered macrolides, 3-7, were isolated from a soft coral-derived Lophiostoma sp. fungus. The absolute configuration of 1 was established based on biogenetic consideration with the co-isolated analog 2, whose configuration was determined by modified Mosher's method and single-crystal X-ray diffraction analysis using CuKα radiation. The absolute configuration of 3 was determined by X-ray diffraction analysis using CuKα radiation. Compounds 2 and 3 showed antibacterial activities against Bacillus cereus with a MIC value of 3.12 μM.

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Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

Kurtán

Yang

et al. 2011

Eur J Org Chem

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Cytospolides A-E (1-5), five new nonanolides with an unprecedented 15-carbon skeleton with the unique chemical feature of a C-2 methyl group, were isolated from the endophytic fungus Cytospora sp. The structures were elucidated by spectroscopic analysis, chemical interconversion, and single-crystal XRD. The solution and solid state conformers were compared by experimental methods (X-ray, NMR) and solvent and gas phase DFT calculations. The absolute configurations were assigned by time dependent (TD)-DFT calculations of CD spectra, including solution and solid state CD/

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Ten-Membered Lactones from the Marine-Derived Fungus Curvularia sp.

Cited by 50 publications

References 20 publications

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Merosesquiterpenoids and Ten‐Membered Macrolides from a Soft Coral‐Derived Lophiostoma sp. Fungus

Cytospolides A–E, New Nonanolides from an Endophytic Fungus, Cytospora sp.

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