The biosynthesis of fungal metabolites. Part IV. Tajixanthone: 13C nuclear magnetic resonance spectrum and feedings with [1-13C]- and [2-13C]-acetate

Holker, J. S. E.; Lapper, Roy D.; Simpson, Thomas J.

doi:10.1039/p19740002135

Cited by 40 publications

(29 citation statements)

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“…Flash chromatography (methylene chloride/acetone, 8:2) of the residue gave tajixanthone hydrate (20 mg) as a yellow oil, [R] 25 D -97.3°(c 1.66, CHCl3), (lit. 22 [R] 25 D -71.5°, c 2.3, CHCl3); 1 H and 13 C NMR spectra matched those previously described. 21,22 Triacetylvaritriol ( …”

Section: Methodssupporting

confidence: 67%

“…22 [R] 25 D -71.5°, c 2.3, CHCl3); 1 H and 13 C NMR spectra matched those previously described. 21,22 Triacetylvaritriol ( …”

Section: Methodssupporting

confidence: 67%

“…Subsequent hydrolysis of 4 gave tajixanthone hydrate with spectroscopic properties, including optical rotation, in agreement with those previously described. 21,22 Thus, the structure and relative stereochemistry of 4 were confirmed. Furthermore, the absolute configuration (depicted in Chart 1) could be established, H-1′ 2′ 5, 3′ H-2′ 1′, 3′ 6, 3′ 5, 3′, 4′ 3′, 4′ H-3′ 2′, 4′ 1′, 2′, 6′ 1′, 2′, 6′, 2′′ H-4′ 3′, 5′, OH 2′, 5′ 2′, 5′, 3′′ H-5′ 4′, 6′, OH 4′, 7′ 4′, 7′, 3′′ H-6′ 5′, 7′ 3′, 7′ 3′, 7′, 2′′ H 3-7′ 6′ 5′, 6′ OCH3 2 OCH2-C-1 OH 1, 2, 6 H3-2′′ 3′, 6′…”

Section: Resultsmentioning

confidence: 76%

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Bioactive Metabolites from a Marine-Derived Strain of the Fungus Emericella variecolor

et al. 2002

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From a marine-derived strain of the fungus Emericella variecolor, varitriol (1), varioxirane (2), dihydroterrein (3), and varixanthone (4), besides the known mold metabolites ergosterol, terrein, shamixanthone, and tajixanthone hydrate, were identified. The chemical structures of 1-4 were established by means of spectroscopic techniques and some chemical transformations. In the NCI's 60-cell panel, varitriol (1) displayed increased potency toward selected renal, CNS, and breast cancer cell lines. Varixanthone (4) showed antimicrobial activity.Recently, increased interest in the chemistry of fungi isolated from the marine environment has been documented. 1 Marine fungi are interesting organisms from an ecological point of view, because they are serious pathogens in the marine environment. 2 Furthermore, since many can be cultured, they represent an important biomedical resource. During our studies on the chemistry and biology of fungi, 3,4 we have investigated a marine strain 5 (named M75-2) of the fungus Emericella variecolor, isolated from a sponge collected in Venezuelan waters of the Caribbean Sea. 6 E. variecolor Berk and Br. is the perfect state of Aspergillus variecolor (Berk and Br.) Thom and Raper. 7 From different terrestrial strains of A. variecolor terrein, 8 2-methoxy-6-(3,4-dihydroxyhepta-1,5-dienyl)benzyl alcohol, 9 4,7-dimethoxy-5-methylcoumarin, 10 a dihydroisocoumarin, 11 and two sesterterpenoids (variecolin 12 and astellatol 13 ), as well as numerous xanthones 14 and meroterpenoids 15 of mixed polyketide and terpenoid origins, have been isolated. Moreover, in a terrestrial strain of E. variecolor, asteltoxin has been found. 16,17 This report deals with the chemical analysis and biological screening of the metabolites from the first marine strain of E. variecolor. Results and DiscussionFrom a static culture of the fungus the new compounds 1-4 (Chart 1) were identified, in addition to the known mold metabolites ergosterol, 18 terrein, 19 shamixanthone, 20 and tajixanthone hydrate. 21

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Section: Methodssupporting

confidence: 67%

“…22 [R] 25 D -71.5°, c 2.3, CHCl3); 1 H and 13 C NMR spectra matched those previously described. 21,22 Triacetylvaritriol ( …”

Section: Methodssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 76%

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Bioactive Metabolites from a Marine-Derived Strain of the Fungus Emericella variecolor

et al. 2002

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“…Bioi. Chem., 42 (2), 465~466, 1978 and 72 mg per 2 liters of the isotope enriched II was isolated by the method described previously,1l…”

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confidence: 99%

Biosynthesis of Shamixanthone

Ishida

Hamasaki

Hatsuda

1978

Agricultural and Biological Chemistry

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“…Incorporation into the whole carbon skeleton of aflatoxin and an intermediate, sterigmatocystin (194) was demonstratedz00-202. These studies were followed by feeding norsolorinic acid ( 195) (193),whilelabel from l'-''Cand 1'-'H wereretainedin the 13-positi0n~~~~~~~.Feedingof [5, 6-"C]-and [8, ll-'3C]averufin to the same mutant of A. parasiticus further showed that C(S)-C(l 1) of averufin was intactly incorporated into C(2)-C(3) of 193, whereas only C(6) ofaverufin was introduced into C(5) of 193 with loss of C(5) ofaverufin in the process, which is also in accordance with the assumed acetate assembly of 193'',.…”

Section: Aflatoxins and Congenersmentioning

confidence: 99%

Biochemistry of quinones

Inouye

Leistner

The Quinonoid Compounds: Vol. 2 (1988)

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The biosynthesis of fungal metabolites. Part IV. Tajixanthone: 13C nuclear magnetic resonance spectrum and feedings with [1-13C]- and [2-13C]-acetate

Cited by 40 publications

References 0 publications

Bioactive Metabolites from a Marine-Derived Strain of the Fungus Emericella variecolor

Bioactive Metabolites from a Marine-Derived Strain of the Fungus Emericella variecolor

Biosynthesis of Shamixanthone

Biochemistry of quinones

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