10359. Botrydial

Nomenclature

CAS number: 54986-75-3
(1S,3aR,4S,6R,7S,7aS)-4-(Acetyloxy)octahydro-7a-hydroxy-1,3,3,6-tetramethyl-1H-indene-1,7-dicarboxaldehyde.
C17H26O5; mol wt 310.39.
C 65.78%, H 8.44%, O 25.77%.

Description and references

Sesquiterpenoid phytotoxin produced by Botrytis cinerea Pers., Sclerotiniaceae, the pathogenic gray mold fungus of grapevines, tobacco, vegetables, and fruits. Isoln from B. cinerea cultures: H.-W. Fehlhaber et al., Ber. 107, 1720 (1974). Biosynthetic study and 13C-NMR: J. R. Hanson, R. Nyfeler, Chem. Commun. 1976, 72 DOI. Phytotoxic activity: L. Rebordinos et al., Phytochemistry 42, 383 (1996) DOI. Identification in infected plant tissue: N. Deighton et al., ibid. 57, 689 (2001) DOI PubMed. Characterization of biosynthetic gene cluster: C. Pinedo et al., ACS Chem. Biol. 3, 791 (2008) DOI PubMed.

Chemical structure

Properties

Crystals from petroleum ether, mp 108-110°. [α]D20 +34° (c = 0.14 in chloroform).