Sesquiterpenoids and Benzofuranoids from the Marine-Derived Fungus <i>Aspergillus ustus</i> 094102

Lu, Zhenyu; Wang, Yi; Miao, Chengdu; Li, Peipei; Hong, Kui; Zhu, Weiming

doi:10.1021/np900268z

Cited by 86 publications

(90 citation statements)

References 20 publications

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“…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%

“…1,2 Aspergillus ustus (A. insuetus) has been proven to be a prolific producer of terpenes, containing sesquiterpenes, sesterterpenes, and meroterpenes. [3][4][5][6][7] However, most of them have been assigned only relative configurations, and their absolute configurations remain unresolved. In our ongoing program to discover new bioactive compounds from marine algae and their associated fungi, a fungus A. ustus isolated from the marine green alga Codium fragile was investigated.…”

Section: Introductionmentioning

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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Section: Extraction and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2013

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“…13) The structure of 1 was further confirmed by 1 H-1 H correlation spectroscopy (COSY) and heteronuclear multiple bond connectivity (HMBC) correlations (Fig. 2).…”

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confidence: 83%

“…The remaining known metabolites were identified by comparing their spectroscopic data with that reported in the literature. 1,[7][8][9][10][11][12] All compounds were evaluated for their cytotoxicities against P388, HL-60, K562 and BEL-7402 cell lines using the sulforhodamine B (SRB) 14) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) 14) methods. Only compound 4 exhibited moderate cytotoxicity against the P388 cell line with IC 50 value of 8.7 mM.…”

Section: )mentioning

confidence: 99%

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Drimane Sesquiterpenoids from the Mangrove-Derived Fungus Aspergillus ustus

Zhou

Zhu

Cai

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Fungi from mangrove have attracted much attention for their unique living conditions of wave-energy tidal mudflats, high moisture level, high salt concentration and lack of oxygen.1) This fungal group has been widely recognized as rich source of active secondary metabolites.2,3) As part of our ongoing search for novel bioactive compounds from microorganisms isolated from unusual or specialized ecological niches, 4-6) the culture extract of a fungus strain (Aspergillus ustus), isolated from the rhizosphere soil of the mangrove Acrostichum aureurm grown in Guangxi Province of China, showed cytotoxic activity against P388 (mice lymphocytic leukemia) cell line. The chemical composition research on the EtOAc extract of the A. ustus fermentation led us to identify five new drimane sesquiterpenes (1-5) together with 14 known analogues (Fig. 1).1,7-12) Herein, we report the structural elucidations and cytotoxic activities of these metabolites against P388, HL-60 (human promyelocytic leukemia cells), K562 (human erythromyeloblastoid leukemia cells) and BEL-7402 (human hepatoma cells).Compound 1 was obtained as a white powder. The molecular formula was determined as C 16 H 28 O 3 on the basis of its high resolution-electrospray ionization-mass spectra (HR-ESI-MS) peak at m/z 291.1930 [MϩNa] ϩ (Calcd for C 16 C-NMR (distortionless enhancement by polarization transfer (DEPT)) spectrum (Table 2) displayed 16 carbon resonances, assignable to five methyls, four methylenes, three methines and four quaternary carbons. Apart from one degree of unsaturation occupied by a double bond, the remaining two degrees of unsaturation required 1 to contain a bicyclic core ring system. The aforementioned data implied that 1 was a drimane sesquiterpense.13) The NMR resonances were similar to those reported for albrassitriol (20), but replacing one of the OHs by a methoxyl group.13) The structure of 1 was further confirmed by 1 H-1 H correlation spectroscopy (COSY) and heteronuclear multiple bond connectivity (HMBC) correlations (Fig. 2). The connection of C-11 and C-9 was determined by the HMBC correlations from H-11 to C-8 and C-10, and the location of -OCH 3 at C-6 was deduced via a correlation between the methoxy protons and C-6.The relative configuration of 1 was determined by the nuclear Overhauser effect spectroscopy (NOESY) spectrum. Correlations between H-13 and H-1b (eq) and between H-5 and H-1a (ax) suggested a trans-fused decalin nucleus.1) The correlation between H-5 and 6-OCH 3 indicated the configu- Five new drimane sesquiterpenes (1-5) together with 14 known analogues (6-19) were isolated from laboratory cultures of a mangrove-derived fungus Aspergillus ustus. Their structures were established by spectroscopic methods and antitumor activities were evaluated by sulforhodamine B (SRB) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) methods.

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Fungi

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: The Fungal Kingdom: The Concept of Marine Fungi Mastigomycetes and Eumycetes (True Fungi) Elements of Classification of Eumycetes Background Information on the Structure of Chitin Fatty Acids Sterols Membrane Peptides of Fungi: Peptaibols General Comments on Secondary Metabolites of Marine Fungi Substances Isolated from Fungi Collected from the Surface of the Sea Substances Isolated from Fungi from Sediments and other Inert Substrates Substances Isolated from Fungi Associated with Cyanobacteria Algicolous Fungi: General Remarks Substances Isolated from Fungi Associated with Green Algae and Marine Spermatophyta Substances Isolated from Fungi Associated with Red Algae Substances Isolated from Fungi Associated with Brown Algae Substances Isolated from Lignicolous Fungi Substances Isolated from Fungi Associated with Sponges Substances Isolated from Fungi Associated with Cnidarians Substances Isolated from Fungi Associated with Mollusks Substances Isolated from Fungi Associated with Bryozoans Substances Isolated from Fungi Associated with Echinoderms Substances Isolated from Fungi Associated with Crustaceans Substances Isolated from Fungi Associated with Tunicates (Ascidians) Substances Isolated from Fungi Associated with Fish Summary of Marine‐Derived Fungi

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Sesquiterpenoids and Benzofuranoids from the Marine-Derived Fungus Aspergillus ustus 094102

Cited by 86 publications

References 20 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

Drimane Sesquiterpenoids from the Mangrove-Derived Fungus Aspergillus ustus

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