Virgatolides A<b>–</b>C, Benzannulated Spiroketals from the Plant Endophytic Fungus <i>Pestalotiopsis virgatula</i>

Li, Jian; Li, Li; Si, Youhui; Jiang, Xuejun; Guo, Liangdong; Che, Yongsheng

doi:10.1021/ol200770k

Cited by 82 publications

(46 citation statements)

References 30 publications

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“…A 6,6-spiro-ring system was constructed in consideration of the 13 C chemical shift value of C-15 at 101.9 p.p.m. [14][15][16][17][18][19] and the hydrogen deficiency index of 5, which was also confirmed by the correlations between H-12 and 14-Me, between H-17 and H-19 and between 14-Me and H-16eq in the ROESY spectrum (Supplementary Figure S7). These ROESY correlations suggested that the conformation around C-15 was restricted and they formed spiro-fused tetrahydropyrans.…”

Section: Resultssupporting

confidence: 54%

Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library

et al. 2011

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Two new 6,6-spiroacetal polyketides, spirotoamides A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces griseochromogenes JC82-1223 by screening of structurally unique compounds based on a search of spectral database. The fraction library was constructed using a systematic separation method to efficiently discover new metabolites from microbial sources such as actinomycetes and fungi. The structures of 1 and 2 were elucidated by 2D-NMR and mass spectrometric measurements. They belong to a class of polyketides, and contain a 6,6-spiroacetal core structure and a carboxamide group. The biosynthetic pathway of 1 and 2 is discussed in the text. Keywords: fraction library; microbial metabolite; spiroacetal polyketide; Streptomyces griseochromogenes; structure elucidation INTRODUCTION Microorganisms, such as actinomycetes and fungi, have a tremendous capacity to produce structurally diverse metabolites 1 with disparate activities, rendering them a significant source of pharmaceutical leads and therapeutic agents. 2,3 They are also used as potential bioprobes for chemical biology studies. 4,5 Many secondary metabolites have been reported, but not all have been isolated, nor have their wide-ranging physicochemical properties and low abundance been examined with regard to their potentially useful activities. Thus, we constructed a microbial metabolite fraction library by systematic separation with a spectral database, based on photodiode-array detector attached LC/MS analysis to discover structurally unique metabolites efficiently and rapidly. We discovered and isolated verticilactam 6 from S. spiroveticillatus JC-8444, a tautomycin producer, 7-9 and the new fraquinocins I and J 10 and 6-dimethylalylindole-3-carbaldehyde 11 from S. reveromyceticus SN-593, a reveromycin producer 12 by our methodology constructing the fraction library. Also, Bugni et al. 13 reported a marine natural products library by HPLC-MS fractionation for rapid drug discovery. These reports have demonstrated the advantage of fraction libraries in isolating and investigating the activities of natural products.Our microbial fraction library was developed on basic chromatographic techniques, comprizing two-step separation by middlepressure liquid chromatography (MPLC) and C 18 -HPLC, yielding 300-400 fractions from a single microbial strain with reproducibility. In addition to many known compounds, the fractions, which contain unidentified minor components, might contain valuable compounds

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Section: Resultssupporting

confidence: 54%

Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library

et al. 2011

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“…Compound 2 was obtained as a yellow oil, and its molecular formula was determined to be C 13 C NMR spectrum showed one methoxyl carbon at d C 60.9, three methyls at d C 18.0, 11.3, and 10.6, six carbon signals belonging to the arhamnose moiety at d C 106.4, 73.5, 72.4, 72.2, 72.0, and 18.0. The structure assembly of 2 was mainly achieved using the HMBC experiment.…”

Section: Resultsmentioning

confidence: 99%

Two new compounds from an endophytic fungusPestalotiopsis heterocornis

Xing

Deng

Luo

2011

Journal of Asian Natural Products Research

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Two new compounds, 7-hydroxy-5-methoxy-4,6-dimethyl-7-O-α-L-rhamnosyl-phthalide and 7-hydroxy-5-methoxy-4,6-dimethyl-7-O-β-D-glucopyranosyl-phthalide, along with one known and related metabolite 7-hydroxy-5-methoxy-4,6-dimethylphthalide were isolated from the EtOAc extract of fermentation broth of an endophytic fungus Pestalotiopsis heterocornis. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HR-ESI-MS, 1D NMR, and 2D NMR).

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“…32 exhibits moderate antifungal properties, with a minimum inhibitory concentration of approximately 10 g/mL to Pythium ultimum, and antioxidant activity 11 times greater than the vitamin E derivative trolox. Photinides A-F (33)(34)(35)(36)(37)(38), six new unique benzofuranone-derived -lactones, and a known compound 6-methoxy-9-methyl-4'-hydroxyaurone (39) have been isolated [19] …”

Section: Benzofuranonesmentioning

confidence: 99%

“…Virgatolides A-C (127-129), unique metabolites with a 3 , 4 , 5 , 6 -tetrahydrospiro [chroman-2, 2 -pyran]core, were isolated [39] from cultures of the plant endophytic fungus P. virgatula. 127-129 possess two previously undescribed skeletons originating from a benzannulated 6, 6-spiroketal and one (128 and 129) and two (127) -lactone units, respectively, and showed modest cytotoxicity against HeLa cells, with IC50 values of 19.0, 22.5, and 20.6 M, respectively.…”

Section: Spiroketal Compoundsmentioning

confidence: 99%

Bioactive Natural Compounds from the Plant Endophytic Fungi Pestalotiopsis spp.

Wang¹,

Lei²,

Ji³

et al. 2012

Mini Reviews in Medicinal Chemistry

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The plant-endophytic strains of the fungus Pestalotiopsis (Amphisphaeriaceae) are distributed throughout the world. Previous chemical investigation of members of the genus resulted in the discovery of various bioactive secondary metabolites including chromones, cytosporones, polyketides, terpenoids and coumarins with diverse structural features. The present report reviews the papers, which have appeared in the literature till now, concerning the isolation, structural elucidation, and biological activities of the secondary metabolites from Pestalotiopsis species.

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Virgatolides A–C, Benzannulated Spiroketals from the Plant Endophytic Fungus Pestalotiopsis virgatula

Cited by 82 publications

References 30 publications

Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library

Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library

Two new compounds from an endophytic fungusPestalotiopsis heterocornis

Bioactive Natural Compounds from the Plant Endophytic Fungi Pestalotiopsis spp.

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