The biosynthesis of phenols—XVII

Ballantine, James A.; Hassall, C. H.; Jones, Ben

doi:10.1016/s0031-9422(00)88601-x

Cited by 19 publications

(21 citation statements)

References 9 publications

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“…The 1 H-, 13 C-and 2D-NMR data (including COSY, NOESY, HMQC, and HMBC) indicated that this compound possessed 4-O-methyl-b-glucopyranose unit attached to a 3,3Ј-dihydroxy-5,5Ј-dimethyl diphenyl ether (diorcinol). 11,12) The aglycone composed of six aromatic methine carbons, six aromatic quaternary carbons and two methyl carbons as observed from 13 C-NMR/DEPT spectra. The 1 H-1 H COSY cross signals were detected between H-2/H-4, H-2/H-6, H-4/H-7, H-6/H-7, H-2Ј/H-4Ј, H-2Ј/H-6Ј, H-4Ј/H-7Ј, and H-6Ј/H-7Ј.…”

Section: Resultsmentioning

confidence: 93%

“…The vicinal coupling constants (J 1Љ,2Љ ϭ7.9 Hz, J 2Љ,3Љ ϭ9.2 Hz, J 3Љ,4Љ ϭ9.1 Hz, J 4Љ,5Љ ϭ9.6 Hz) revealed that H-1Љ to H-5Љ were all oriented in the axial positions of a pyranose ring. The attach-ment of a methoxyl at C-4Љ was assigned from HMBC spectrum in which correlations were observed from methoxyl protons 15) The aglycone, obtained by acid hydrolysis of 1, was spectroscopically identical to diorcinol (4), 11,12) which was also isolated as a co-metabolite from the fungus BCC 1861.…”

Section: Resultsmentioning

confidence: 99%

“…Cordyol B (2) Three known compounds, diorcinol (4), 11,12) violaceol-I (5) and violaceol-II (6), 13,14) were also isolated from Cordyceps sp. BCC 1861.…”

Section: Resultsmentioning

confidence: 99%

“…The organic layer was evaporated to dryness to obtain aglycone (37.5 mg) whose 1 H-NMR data was identical to the isolate 4 as well as literature data of diorcinol. 11,12) Biological Assays Antimalarial activity against Plasmodium falciparum K1 was conducted by using microculture radioisotope technique.…”

Section: )mentioning

confidence: 99%

“…As part of our ongoing research program on bioactive constituents of insect pathogenic fungi, 1) we describe herein the isolation of two novel diphenyl ether glycosides, cordyols A (1) and B (2), a new diphenyl ether, cordyol C (3), together with three known diphenyl ethers, diorcinol (4), 11,12) violaceol-I (5) and violaceol-II (6), 13,14) from Cordyceps sp. BCC 1861.…”

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confidence: 99%

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New Diphenyl Ethers from the Insect Pathogenic Fungus Cordyceps sp. BCC 1861

et al. 2007

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Two novel diphenyl ether glycosides and a new diphenyl ether, cordyol A-C (1-3), were isolated from the insect pathogenic fungus Cordyceps sp. BCC 1861. Structures of these compounds were elucidated by NMR and MS spectral analyses. Cordyol C (3) exhibited significant anti-HSV-1 activity with an IC 50 value of 1.3 m mg/ml, and cytotoxic activity against BC and NCI-H187 cancer cell lines with IC 50 values of 8.65 and 3.72 m mg/ml, respectively. Cordyol A (1) displayed weak antimycobacterial activity with a MIC value of 100 m mg/ml.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

“…Cordyol B (2) Three known compounds, diorcinol (4), 11,12) violaceol-I (5) and violaceol-II (6), 13,14) were also isolated from Cordyceps sp. BCC 1861.…”

Section: Resultsmentioning

confidence: 99%

Section: )mentioning

confidence: 99%

mentioning

confidence: 99%

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New Diphenyl Ethers from the Insect Pathogenic Fungus Cordyceps sp. BCC 1861

et al. 2007

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Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

Zhou

Zhu

et al. 2015

Chemistry & Biodiversity

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A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.

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Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii

Gao

Tian

Liao

et al. 2020

Chemistry & Biodiversity

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The chemical investigation on endophytic fungus Annulohypoxylon cf. stygium in leaves of Anoectochilus roxburghii (Wall.) Lindl. has been performed. Sixteen compounds were isolated and their structures were identified as (−)‐notoamide A, (−)‐notoamide B, (+)‐versicolamide B, notoamide C, notoamide D, stephacidin A, sterigmatocystin, dihydrosterigmatocystin, secosterigmatocystin, versiconol, averufanin, kipukasin D, kipukasin E, diorcinal, palmarumycin CP2 and (−)‐(3R)‐mellein methyl ether, respectively, by spectroscopic analysis and comparison with literature data. All the compounds were isolated from Annulohypoxylon genus for the first time. Sterigmatocystin and palmarumycin CP2 showed selective cytotoxic activities against HepG2, HeLa, MCF‐7 and HT‐29.

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The biosynthesis of phenols—XVII

Cited by 19 publications

References 9 publications

New Diphenyl Ethers from the Insect Pathogenic Fungus Cordyceps sp. BCC 1861

New Diphenyl Ethers from the Insect Pathogenic Fungus Cordyceps sp. BCC 1861

Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

Chemical Constituents from Endophytic Fungus Annulohypoxylon cf. stygium in Leaves of Anoectochilus roxburghii

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