Identification of 1 a-hydroxy phaseollone, a phaseollin metabolite produced by Fusarium solani

Denheuvel, J.Van; Etten, H. D. Van; Serum, James W.; Coffen, David L.; Williams, Thomas H.

doi:10.1016/0031-9422(74)80086-5

Cited by 30 publications

(6 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The positive ion mass spectra for each phytoalexin (M þ H) þ were phaseollin at m/z 323 and kievitone at m/z 357. Evaluation of the UV spectra for the peaks corresponding to phytoalexins revealed identical spectra compared with those in earlier papers with UV max for phaseollin at 280 nm and for kievitone at 294 nm (18,27,30,(42)(43)(44). 1 H NMR results for each phytoalexin matched earlier results (30,(42)(43)(44).…”

Section: Resultssupporting

confidence: 78%

Estrogenic and Antiestrogenic Activities of Phytoalexins from Red Kidney Bean (Phaseolus vulgaris L.)

Boué

Burow

Wiese

et al. 2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

Legumes are the predominant source of isoflavones considered to be phytoestrogens that mimic the hormone 17β-estradiol (E2). Due to the risks associated with hormone replacement therapy, there is a growing need for alternative sources of estrogenic formulations for the treatment of menopausal symptoms. Legume phytoalexins (induced isoflavones) are produced under conditions of stress that include insect damage, wounding, or application of elicitors. The estrogenic and antiestrogenic activities of methanolic extracts obtained from red kidney bean treated with the fungus Aspergillus sojae were compared with those of untreated controls using an estrogen responsive element-based (ERE) luciferase reporter assay. A. sojae-treated red kidney bean extracts displayed both estrogenic and antiestrogenic activities. Analysis of elicitor-treated red kidney bean extracts showed that A. sojae treatments achieved maximal levels of kievitone at 1199 ± 101 μg/g and phaseollin at 227.8 ± 44 μg/g. The phytoalexins kievitone and phaseollin were isolated from A. sojae-treated red kidney bean extracts and analyzed for estrogenic activity using ERα and ERβ binding, ERE luciferase assays in MCF-7 and HEK 293 cells, and MCF-7 cell proliferation. Kievitone showed the highest relative binding affinity to ERα with kievitone (0.48%) > phaseollin (0.21%), and phaseollin showed the highest relative binding affinity to ERβ with phaseollin (0.53%) > kievitone (0.42%). In an ERE luciferase assay in MCF-7 cells, kievitone displayed high ER transactivation at 10 μM; phaseollin displayed low ER transactivation. Both kievitone and phaseollin stimulated MCF-7 cell proliferation, with kievitone displaying agonist activity between 0.1 and 10 μM. Cotransfection reporter assays performed in HEK 293 demonstrated that phaseollin selectively increased ERE transcriptional activity of ERβ and kievitone selectively increased ERE transcriptional activity of ERα. Although phaseollin displayed attenuation of ER transactivation in the ERE luciferase assay in MCF-7 cells, both phytoalexins attenuated the effects of E2 in an MCF-7 cell colonial survival assay. This work provides evidence that the red kidney bean phytoalexins kievitone and phaseollin possess both estrogenic and antiestrogenic activities.

show abstract

Section: Resultssupporting

confidence: 78%

Estrogenic and Antiestrogenic Activities of Phytoalexins from Red Kidney Bean (Phaseolus vulgaris L.)

Boué

Burow

Wiese

et al. 2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…These were assigned to H-2 and H-4, respectively. The unusual high field of H-4 was thought to be due to the anisotropic effects of the conjugated carbonyl group, as well as additional ortho shielding by the oxygen of the pyran ring as noted previously in la-hydroxyphaseollone {4} (9). Two apparently aromatic singlets at 6.63 and 6.34 ppm were then assigned to either H-9 or H-12.…”

mentioning

confidence: 65%

“…The co-occurence of 1 and 2 with 7-hydroxy-3-(4-hydroxybenzyl)chromane [8] in D. loureiri suggested that its close relative, 7-hydroxy-3-(3-hydroxy-4-methoxybenzyl) chromane [9], might cyclize by para-para phenolic oxidative coupling to a tetracyclic intermediate which can undergo dienone-phenol rearrangement to the dracaenone skeleton as shown in Scheme 1. Synthetic studies, including the synthesis of 1 and 2 in racemic form, will be reported elsewhere (20).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Traditional Medicinal Plants of Thailand, IX. 10-Hydroxy-11-methoxydracaenone and 7,10-Dihydroxy-11-methoxydracaenone from Dracaena loureiri

Meksuriyen¹,

Cordell²,

Ruangrungsi³

et al. 1987

J. Nat. Prod.

View full text Add to dashboard Cite

“…The compound produced by these fungi proved to be la-hydroxyphaseollone, which, in earlier experiments (Van den Heuvel and VanEtten, 1973;Van den Heuvel et al, 1974), was found to be a detoxification product of phaseollin formed by F. solani f. sp. solani f sp.…”

Section: Identification Of the Metabolic Productsmentioning

confidence: 80%

Comparative abilities of fungi pathogenic and nonpathogenic to bean (Phaseolus vulgaris) to metabolize phaseollin

Heuvel¹,

Glazener²

1975

Netherlands Journal of Plant Pathology

View full text Add to dashboard Cite

The abilities of fungi pathogenic and nonpathogenic to bean (Phaseolus vulgaris) to metabolize the phytoalexin phaseollin were compared when grown in shake cultures containing 12 to 15 [zg phaseollin/ ml. Under these conditions phaseollin was metabolized by five out of seven pathogens and by three out of five nonpathogens.Disappearance of phaseollin was accompanied by the appearance of metabolic products in cultures of Fusarium solani f. sp. phaseoli, Colletotrichurn lindemuthianum, Botrytis cinerea and Cladosporium herbarum. The nonpathogen C. herbarum detoxified phaseollin to la-hydroxyphaseollone as rapidly as the pathogen F. solani f.sp. phaseoB. Phaseollin was converted to 6a-hydroxyphaseollin by the pathogens B. einerea and C. lindemuthianum, and this product was further metabolized by the latter fungus. 6a-Hydroxyphaseollin was less fungitoxic to B. cinerea. C. lindemuthianum was equally sensitive to both compounds.Phaseollin was not metabolized by the pathogens Fusarium oxysporum f. sp. phaseoB and Thielaviopsis basicola.

show abstract

Identification of 1 a-hydroxy phaseollone, a phaseollin metabolite produced by Fusarium solani

Cited by 30 publications

References 7 publications

Estrogenic and Antiestrogenic Activities of Phytoalexins from Red Kidney Bean (Phaseolus vulgaris L.)

Estrogenic and Antiestrogenic Activities of Phytoalexins from Red Kidney Bean (Phaseolus vulgaris L.)

Traditional Medicinal Plants of Thailand, IX. 10-Hydroxy-11-methoxydracaenone and 7,10-Dihydroxy-11-methoxydracaenone from Dracaena loureiri

Comparative abilities of fungi pathogenic and nonpathogenic to bean (Phaseolus vulgaris) to metabolize phaseollin

Contact Info

Product

Resources

About