Isolation and structures of O-methyldihydrobotrydial and deacetyl-O-methyldihydrobotrydialone produced by Botrytis squamosa.

Abstract

Recently, we reported the X-ray structural analysis1} of deacetyldihydrobotrydial as a plant growth regulator1)2) produced by Botrytis squamosa. In the course of further studies on the metabolites of this fungus, we isolated two new compounds (1 and 2) named O-methyldihydrobotrydial and deacetyl-O-methyldihydrobotrydialone, respectively. In this paper, we report the isolation, structural elucidation and biological activities of these two compounds.

Secobotrytriendiol and Related Sesquiterpenoids: New Phytotoxic Metabolites from Botrytis cinerea

“…The compound's 1 H NMR spectrum showed signals very similar to those of O -methyldihydrobotrydial ( 8 ), isolated previously from Botrytis squamosa. In fact, the only differences between the 1 H NMR spectra of 1 and 8 were the absence of signals characteristic of H-15 in 1 , as well as the presence of a signal at δ 4.86 (s, 1H, H-15). COSY experiments showed a correlation between this signal and one corresponding to 3H, δ 3.49, indicating that 1 was the 15-methoxy derivative of 8 .…”

“…The fermentation broth was extracted with ethyl acetate as described previously. [1][2][3][4][5][6] Chromatography of the extract on Si gel, followed by final purification by means of HPLC, led to the isolation of 15Rmethoxy-O-methyl dihydrobotrydial (1), methyl botryoloate (2), secobotrytriendiol (3), dihydrobotrydialone (4), dehydrobotrydienol (5), 11-hydroxydehydrobotrydienol (6), and 12-hydroxydehydrobotrydienol (7).…”

“…In addition to known compounds, we have found seven additional metabolites (1)(2)(3)(4)(5)(6)(7). In this paper we describe their isolation, structure elucidation, and phytotoxic activity.…”

“…In the course of investigations of the phytopathogen Botrytis cinerea, and its pathogenic role, we have studied the production kinetics of the phytotoxic metabolites botrydial, dihydrobotrydial, and related compounds. − The biosynthetic pathway of these characteristic metabolites, which are phytotoxic to tobacco and grapes, , has been investigated . The visible phytotoxic effect of botrydial, dihydrobotrydial, and other derivatives in vitro provides circumstantial evidence for their putative role in the pathogenicity of the fungus.…”

Botryane Sesquiterpenoids, Cyclopentadepsipeptides, Xanthones, and Trichothecenes from Trichoderma oligosporum

“…The 1 H, 13 C, and 2D NMR spectra of the new compounds, RP-HPLC-MS chromatogram of the CH 2 Cl 2 extract and compounds 2, 4, and 12, and the CD spectrum of compound 12 are available in the Supporting Information Botryane sesquiterpenoids were reported to have phytotoxic [30], antimicrobial [31], and cytotoxic activities [32]. These compounds have been isolated from various phytopathogens or endophytes, such as Botrytis squamosa [33], Xylaria sp. [32], Daldinia concentrica [34], Hypoxylon rickii [13], and Geniculosporium sp.…”