Structural elucidation and NMR assignments of four aromatic lactones from a mangrove endophytic fungus (No. GX4‐1B)

Huang, Hongbo; Li, Qing; Feng, Xiaohai; Chen, Bin; Wang, Jun; Liu, Lan; She, Zhigang; Lin, Yongcheng

doi:10.1002/mrc.2605

Cited by 15 publications

(16 citation statements)

References 13 publications

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“…An HMBC correlation from H-7 (δ 7.56) to C-6 (δ 156.1) and from H-8 to C-6 ( 4 J ), and the 13 C chemical shift of C-4a (δ 155.8), an oxygenated sp 2 carbon, revealed that C-4a and C-6a were connected via C-6 by an ester bond. Therefore, one remaining carbonyl group (δ 181.0, C-11) was inevitably attached between C-10a and C-11a [6,7,8,9]. This assignment was supported by an HMBC correlation from H-7 to C-11 ( 4 J ).…”

Section: Resultsmentioning

confidence: 85%

“…Dibenz[ b , e ]oxepines are rare metabolites, and, thus far, only six natural products ( 4 – 9 , Figure 3) have been reported [6,7,8,9]. Compound 1 is, therefore, the seventh example of this class of natural products.…”

Section: Resultsmentioning

confidence: 99%

“…The structure of compound 1 was elucidated as 1-hydroxy-10-methoxy-dibenz[ b , e ]oxepin-6,11-dione (Figure 1) by the analysis of its spectroscopic data. Natural products possessing a dibenz[ b , e ]oxepine structure are quite rare, and only six compounds have been reported as natural products in scientific journals [6,7,8,9]. Antifungal and cytotoxic activities were exhibited by two known compounds ( 2 and 3 ).…”

Section: Introductionmentioning

confidence: 99%

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A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942

et al. 2012

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1-Hydroxy-10-methoxy-dibenz[b, e]oxepin-6,11-dione (1) was obtained from the culture broth of a marine-derived fungus, Beauveria bassiana TPU942, isolated from a marine sponge collected at Iriomote Island in Okinawa, together with two known compounds, chrysazin (2) and globosuxanthone A (3). The structure of 1 was elucidated on the basis of its spectroscopic data (HREIMS, 1D and 2D NMR experiments including 1H–1H COSY, HMQC and HMBC spectra). Dibenz[b, e]oxepines are rare in nature, and only six natural products have been reported. Therefore, compound 1 is the seventh natural product in this class. Compounds 2 and 3 showed an antifungal activity against Candida albicans, and 3 inhibited the cell growth against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma). Compound 1 did not show an apparent activity in the same bioassays.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942

et al. 2012

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“…Two new aromatic lactones, 1,10-dihydroxy-8-methyl-dibenz[ b , e ]oxepin-6,11-dione ( 54 ) and 6-hydroxy-4-hydroxymethyl-8-methoxy-3-methylisocoumarin ( 55 ), along with two known compounds, 3-hydroxymethyl-6,8-dimethoxycoumarin ( 56 ) and 1,10-dihydroxy-dibenz[ b , e ]oxepin-6,11-dione ( 57 ), were collected from an unidentified endophytic fungus No. GX4-1B, which was obtained from Bruguiera gymnoihiza (L.), but their bioactivities have not been examined in this research [ 40 ].…”

Section: Metabolites Derived From the Mangrove Fungi In The South mentioning

confidence: 99%

Advances in the Study of the Structures and Bioactivities of Metabolites Isolated from Mangrove-Derived Fungi in the South China Sea

et al. 2013

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Many metabolites with novel structures and biological activities have been isolated from the mangrove fungi in the South China Sea, such as anthracenediones, xyloketals, sesquiterpenoids, chromones, lactones, coumarins and isocoumarin derivatives, xanthones, and peroxides. Some compounds have anticancer, antibacterial, antifungal and antiviral properties, but the biosynthesis of these compounds is still limited. This review summarizes the advances in the study of secondary metabolites from the mangrove-derived fungi in the South China Sea, and their biological activities reported between 2008 and mid-2013.

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“…Alcohols containing four, five and six carbon atoms are the most abundant odour and flavour components of fermentation beverages . In addition to such volatile compounds, some phenolic derivatives can also be found as products of fermentation processes …”

Section: Introductionmentioning

confidence: 99%

Matrix‐assisted diffusion‐ordered spectroscopy: application of surfactant solutions to the resolution of isomer spectra

Tormena

Evans

Haiber

et al. 2012

Magnetic Reson in Chemistry

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The component spectra of a mixture of isomers with nearly identical diffusion coefficients cannot normally be distinguished in a standard diffusion-ordered spectroscopy (DOSY) experiment but can often be easily resolved using matrix-assisted DOSY, in which diffusion behaviour is manipulated by the addition of a co-solute such as a surfactant. Relatively little is currently known about the conditions required for such a separation, for example, how the choice between normal and reverse micelles affects separation or how the isomer structures themselves affect the resolution. The aim of this study was to explore the application of sodium dodecyl sulfate (SDS) normal micelles in aqueous solution and sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) aggregates in chloroform, at a range of concentrations, to the diffusion resolution of some simple model sets of isomers such as monomethoxyphenols and short chain alcohols. It is shown that SDS micelles offer better resolution where these isomers differ in the position of a hydroxyl group, whereas AOT aggregates are more effective for isomers differing in the position of a methyl group. For both the normal SDS micelles and the less well-defined AOT aggregates, differences in the resolution of the isomers can in part be rationalised in terms of differing degrees of hydrophobicity, amphiphilicity and steric effects.

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Structural elucidation and NMR assignments of four aromatic lactones from a mangrove endophytic fungus (No. GX4‐1B)

Cited by 15 publications

References 13 publications

A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942

A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942

Advances in the Study of the Structures and Bioactivities of Metabolites Isolated from Mangrove-Derived Fungi in the South China Sea

Matrix‐assisted diffusion‐ordered spectroscopy: application of surfactant solutions to the resolution of isomer spectra

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