A synthesis of bikaverin (7,12-dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione) and some related benzoxanthones and quinones

KJAER, D.; Kjær, Anders; Risbjerg, Elisabeth

doi:10.1039/p19830002815

Cited by 12 publications

(3 citation statements)

References 5 publications

(9 reference statements)

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“…Compounds 6 and 7 exhibited very similar NMR spectra except for the absence of an OH group in 7 compared with 6 , as evident from their APCI-MS and 1 H NMR spectra. Spectroscopic data for 6 and 7 were found to be consistent with those reported for bikaverin 22 and 6-deoxybikaverin, respectively. Rhodolamprometrin ( 5 ) has previously been isolated from the feather star, Lamprometra klunzingeri, and a mutant of the deuteromycete Trichoderma viride .…”

Section: Resultssupporting

confidence: 82%

“…6-Deoxybikaverin (7): yellow powder; 1 H NMR (500 MHz, CDCl 3 ) δ 7.61 (1H, s, H-6), 6.75 (2H, d, J = 2.5 Hz, H-2 and H-4), 6.16 (1H, s, H-9), 3.92 (3H, s, 8-OCH 3 ), 3.88 (3H, s, 3-OCH 3 ), 2.85 (3H, s, 1-CH 3 ); APCIMS (+) mode m / z 367 [M + 1] + . These NMR and MS data were consistent with those reported in the literature …”

Section: Methodssupporting

confidence: 92%

“…Bikaverin ( 6 ) has been encountered in a number of microorganisms including several Fusarium species 25 and Mycogone jaapii . 6-Deoxybikaverin ( 7 ) has previously been obtained only as a byproduct in the synthesis of bikaverin ( 6 ), and this constitutes the first report of its natural occurrence.…”

Section: Resultsmentioning

confidence: 98%

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Search for Cell Motility and Angiogenesis Inhibitors with Potential Anticancer Activity: Beauvericin and Other Constituents of Two Endophytic Strains of Fusarium oxysporum

et al. 2007

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Wound-healing assay-guided fractionation of an EtOAc extract of the fungal strain Fusarium oxysporum EPH2RAA endophytic in Ephedra fasciculata afforded beauvericin (1), (-)-oxysporidinone (2), and two new N-methyl-2-pyridones, (-)-4,6'-anhydrooxysporidinone (3) and (-)-6-deoxyoxysporidinone (4). Beauvericin (1) inhibited migration of the metastatic prostate cancer (PC-3M) and breast cancer (MDA-MB-231) cells and showed antiangiogenic activity in HUVEC-2 cells at sublethal concentrations. Cytotoxicity-guided fractionation of an EtOAc extract of F. oxysporum strain CECIS occurring in Cylindropuntia echinocarpus afforded rhodolamprometrin (5), bikaverin (6), and the new natural product 6-deoxybikaverin (7). All compounds were evaluated for cytotoxicity in a panel of four sentinel cancer cell lines, NCI-H460 (non-small-cell lung), MIA Pa Ca-2 (pancreatic), MCF-7 (breast), and SF-268 (CNS glioma), and only beauvericin (1) and bikaverin (6) were active, with 1 and 6 showing selective toxicity toward NCI-H460 and MIA Pa Ca-2, respectively. Interestingly, 6-deoxybikaverin (7) was completely devoid of activity, suggesting the requirement of the C-6 hydroxy group of bikaverin for its cytotoxic activity.

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Section: Resultssupporting

confidence: 82%

Section: Methodssupporting

confidence: 92%