C-Geranyl Compounds from Mimulus clevelandii

Abstract

Fractionation of the MeCOEt extract of Mimulus clevelandii yielded the novel 4-geranyl-5-hydroxy-2(3H)-benzofuranone (1) and the five known 6-geranylflavanones diplacone (2a), 3'-O-methyldiplacone (2b), diplacol (2c), mimulone (2d), and 3'-O-methyldiplacol (2e). 2D-NMR methods required revision of assignments for diplacone and diplacol and resolved the uncertainty in the site of methylation for the methyl ethers.

Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa

“…EIMS data suggested that compounds 2 and 10 have the identical molecular formula, C 26 H 30 O 6 . The major constituent 10 was identified as 6-geranyl-4 0 ,5,7-trihydroxy-3 0 -methoxyflavanone (3 0 -O-methyldiplacone) (Wollenweber et al, 1989;Phillips et al, 1996;Phommart et al, 2005) by comparison of the 1 H and 13 C NMR spectroscopic data with reported values. The minor constituent 2 was an isomer of 10 with regard to the substitution pattern on the B-ring, since the 1 H signals of the 3 0 ,4 0 -substituted B-ring protons [d 7.13 (d, J = 1.9 Hz), 7.02 (dd, 8.1, 1.9 Hz), 6.88 (d, J = 8.1 Hz)] were different from those [d 6.97 (d, J = 1.9 Hz), 6.90 (dd, 8.2, 1.9 Hz), 6.93 (d, J = 8.2 Hz)] of 10.…”

New Cytotoxic Phenolic Derivatives from Matured Fruits ofMagnolia denudata

“…These observations suggested the presence of a meta-disubstituted 2(3H)-benzofuranone. 5) Moreover, the 1 H-NMR data showed signals for three tertiary methyl groups at 1.52, 1.60 and 1.63 ppm, two olefinic protons at 5.01 and 5.21 ppm, and six methylenic protons at 2.0 ppm (4H, m) and 3.25 ppm (2H, d, J ¼ 7:3 Hz). In addition to this data, an analysis of the 13 C-NMR (Table 1) and COSY spectra led to the identification of a geranyl moiety.…”

“…6,7) In addition, two 2(3H)-benzofuranones have been isolated from an extract of the aerial part of Vernonia trichoclada GLEASON (Asteraceae) and respectively characterized as 4-geranyl-5-O--D-glucopyranosyl-2(3H)-benzofuranone and 5-O--D-glucopyranosyl-4-isoprenyl-2(3H)-benzofuranone, 8) and the aglycon of these compounds have been isolated from Mimulus clevelandii BRANDEGEE (Scrophulariaceae). 5) However, denudalide (1) is a new compound, and this is the first isolation of a benzofuranone type of compound from Magnolia species.…”

Three new prenylated flavonoids from Macaranga denticulata and their anticancer effects

“…The known compounds were identified as 5-hydroxy-2-(4-260 hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)chroman-261 4-one (4) [12], sophoraflavanone A (5) [13], bonanniol A (6) [14], 262 diplacol (7) [15], 5,7,3′,4′-tetrahydroxy-6-geranylflavonol (8) [7], 263 5,7,3′,4′-tetrahydroxy-3-methoxy-6-geranylflavone (9) [7], 3β-264 hydroxy-7α-ethoxy-24β-ethylcholest-5-ene (10) [16], (24R)-265 6β-hydroxy-24-ethylcholest-4-en-3-one (11) [17], epitaraxerol 266 (12) [18], α-tocopherolquinone (13) [19] and boehmenan (14) Since prenylated flavonoids are reported to have modest or 271 strong anticancer activities [1,9], the cytotoxicity of compounds …”