7198. Phaseolin

Nomenclature

CAS number: 13401-40-6
(6bR-cis)-6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f′]bis[1]benzopyran-10-ol; phaseollin.
C20H18O4; mol wt 322.35.
C 74.52%, H 5.63%, O 19.85%.

Description and references

Antifungal phytoalexin isolated from French bean (Phaseolus vulgaris L., Leguminosae): I. A. M. Cruickshank, D. R. Perrin, Life Sci. 2, 680 (1963). Structure: D. R. Perrin, Tetrahedron Lett. 1964, 29; D. R. Perrin et al., ibid. 1972, 1673. Crystal structure: C. DeMartinis et al., Tetrahedron 34, 1849 (1978). Biosynthesis: S. L. Hess et al., Phytopathology 61, 79 (1971); P. M. Dewick, M. J. Steele, Phytochemistry 21, 1599 (1982). Total synthesis: S. E. N. Mohamed et al., J. Chem. Soc. Perkin Trans. 1 1987, 431. Mode of action: F. D. Van Etten, D. F. Bateman, Phytopathology 61, 1363 (1971). Antifungal properties: I. A. M. Cruickshank, D. R. Perrin, Phytopathol. Z. 70, 209 (1971); M. A. Gordon et al., Antimicrob. Agents Chemother. 17, 120 (1980).

Chemical structure

Properties

Crystals, mp 177-178°. [α]578 -145°. pKa 9.13. uv max (ethanol): 207, 230, 280, 286 nm (log ε 4.68, 4.40, 3.97, 3.90).