Cytotoxic sesterterpenes, 6-epi-ophiobolin G and 6-epi-ophiobolin N, from marine derived fungus Emericella variecolor GF10

Wang, Hong; Ito, Takuya; Kinoshita, Masahiro; Nakai, Y.; Kurotaki, Mineko; Kobayashi, Mariko

doi:10.1016/j.tet.2004.05.021

Cited by 94 publications

(117 citation statements)

References 12 publications

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“…The NOE correlations between H-1a/H-10, H-1a/H-6, H-10/H-14 suggested a syn orientation of them, and H-1b, H-2, and C-22 were oriented on the opposite face relative to the above protons based on NOE correlations between H-2/H-1b, H-2/H-22. The relative configurations at C-10, C-14, and C-15 were supported by the identical NMR data with those reported for 6-epiophiobolin G. 8 Additionally, the double bond at C-16 was correlations (Fig. 2), the double bond at C-3 in 8 was found to be no longer present and instead a new double bond appeared between C-2/C-6 in 5.…”

supporting

confidence: 77%

“…The total EtOAc-soluble fraction (35.5 g) was subjected to stepgradient silica gel column chromatography (CC) with a solvent system consisting of 0-100% petroleum ether (PE)-EtOAc to afford 14 fractions (Frs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] on the basis of TLC analysis. Fr.…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…2) further confirmed the structures of 13 and 14 to be (6-Strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids. The remaining known compounds, including (6a)-21,21-O-dihydroophiobolin G (8), 3 (5a,6a)-ophiobolin H (9), 3 ophiobolin H (10), 8 ophiobolin F (11), 9 3b,9a,11-trihydroxy-6-oxodrim-7-ene (12), 4 (6-strobilactone-B) esters of (E,E)-6,7-dihydroxy-2,4-octadienoic acids (15 and 16), 4 (6-strobilactone-B) ester of (E,E)-6-oxo-2,4-hexadienoic acid (17, Ustusolate 10 and (29E,49E,69E)-6-(19-carboxyocta-29,49,69-triene)-11,12-epoxy-9,11-dihydroxydrim-7-ene (20), 10 were identified by detailed NMR data comparison with literature values.…”

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confidence: 99%

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Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

et al. 2013

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One new meroterpene, 1,2-dihydroterretonin F (2), five new sesterterpenes, (6a)-21-deoxyophiobolin G(3), (6a)-16,17-dihydro-21-deoxyophiobolin G (4), ophiobolin U (5), ophiobolin V (6), and ophiobolin W (7), two new sesquiterpenes, (6-strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids (13 and 14), and twelve known terpenes (1, 8-12, and 15-20) were isolated from Aspergillus ustus, a fungus from the fresh tissue of marine green alga Codium fragile. Their structures and absolute configurations were identified by NMR and mass spectroscopic methods as well as quantum chemical calculations. Some of the isolates exhibited antibacterial activity and brine shrimp toxicity.

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confidence: 77%

Section: Extraction and Isolationmentioning

confidence: 99%

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confidence: 99%

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Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

et al. 2013

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“…Marine microorganism is a rich source of secondary metabolites with diverse structures and various biological activities, such as cytotoxic [1], antitumor [2], antimicrobial [3], and antimycobacterial [4] activities. In our continuing research on antitumor secondary metabolites from marine-derived microorganisms, a culture extract of an Aspergillus carbonarius strain isolated from the marine sediment collected at Weizhou Island, China, showed significant cytotoxic activity against K562 cell line at 10.0 m g/ml.…”

Section: Introductionmentioning

confidence: 99%

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

et al. 2007

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Two new secondary metabolites, carbonarones A (1) and B (2), were obtained from the culture of the marine-derived fungus Aspergillus carbonarius isolated from the marine sediment collected at Weizhou island of China. Based on ESIMS, 1D and 2D NMR data, and the X-ray crystallographic analysis, their structures were elucidated as 6-benzyl-4-oxo-4H-pyran-3-carboxamide and 6-benzyl-4-hydroxy-2-oxo-1, 2-dihydropyridine-3-carbaldehyde, respectively. 1 and 2 showed moderate cytotoxicity against K562 cells with IC 50 values of 56.0 and 27.8 mg/ml, respectively. [7]. The latter were effectively used to control Coleopteran and Lepidopteran insects. Further chemical investigation on metabolites of this fungal species was carried out, which led to the isolation and structural elucidation of two new compounds, carbonarones A (1) and B (2), (Fig. 1) via bioassay-guided isolation procedure. KeywordsThe bioactive secondary metabolites of the A. carbonarius were obtained from the EtOAc extract of the fermentation broth and mycelia. Isolation of the compounds was achieved by repeated chromatographic steps, including column chromatography on silica gel, Sephadex LH-20 and reversed-phase semipreparative HPLC. Materials and Methods StrainThe fungus strain Aspergillus carbonarius WZ-4-11 was isolated from the marine sediments collected in Nov.

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“…The gross structure of 1 was very similar to that of the known compound ophiobolin H (¼ (1R,2aS,6aS,7R,9aR,10aS,10bS)-7-[(1S,2Z)-1,5-dimethylhexa-2,4-dien-1-yl]-1,2,4,6,6a,7,8,9,9a,10,10a,10b-dodecahydro-1,9a-dimethyl-2aH-3-oxacyclopenta [5,6]cycloocta [1,2,3-cd]pentalene-1,2a-diol), previously isolated from the same fungus, based on 2D-NMR data analysis (Fig. 2) and by comparison with literature data [14] [15]. However, the ROESY interactions HÀC(6)/HÀC(10), HÀC(10)/H a ÀC(9), HÀC(2)/Me(22), and Me(22)/H b ÀC (9), and the absence of a ROESY correlation HÀC(6)/HÀC(2) (Fig.…”

mentioning

confidence: 99%

Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge‐Derived Fungus Aspergillus ustus

Liu

Edrada-Ebel

Ebel

et al. 2011

Helvetica Chimica Acta

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Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin-type sesterterpenoids 1 -5 and the two new pyrrolidine alkaloids 6 and 7, together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopicdata analysis (1D-and 2D-NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y.

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Cytotoxic sesterterpenes, 6-epi-ophiobolin G and 6-epi-ophiobolin N, from marine derived fungus Emericella variecolor GF10

Cited by 94 publications

References 12 publications

Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

Carbonarones A and B, New Bioactive γ-Pyrone and α-Pyridone Derivatives from the Marine-derived Fungus Aspergillus carbonarius

Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge‐Derived Fungus Aspergillus ustus

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