P-35 ゴマノハグサ目植物の腺毛分泌物の化学成分研究(ポスター発表の部)
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Constituents of the glandular trichome exudates on the leaves of Paulownia tomentosa (Scrophulariaceae) and the leaves and stems of Ibicella lutea and Proboscidea louisiana (Martyniaceae) have been investigated. P. tomentosa exudates afforded 30 acylglycerols which belonged to the 1,3-diacetyl-2-fattyacylglycerol, 1-acetyl-2-fattyacyl-sn-glycerol, and 2-fattyacylglycerols families, wherein the fattyacyl moiety was either eicosanoyl or octadecanoyl group bearing hydroxy and/or acetoxy groups at the 3-, 3,6-, 3,7-, 3,8- or 3,9-positions. The configurations of the stereogenic centers in the fattyacyl moieties were determined by ^1H NMR analysis of the mono-(R)- and (S)-2-naphtyl-2-methoxyacetate derivatives of the fatty acid methyl esters. The configuration at C-2 of the glycerol moiety of the 1-acetyl-2-fattyacylglycerols was determined to be S by chemical conversion to a stereodefined mono-TBDPS-glycerol. Relatively abundant constituents included 1-acetyl-2-(3R-acetoxy-6S-hydroxyeicosanoyl)-sn-glycerol, 2-(3R,8R-diacetoxyeicosanoyl)glycerol, 2-(3R,9R-diacetoxyeicosanoyl)glycerol, 2-(3R-acetoxy-6S-hydroxyeicosanoyl)glycerol, 2-(3R-acetoxy-8R-hydroxyeicosanoyl)glycerol and 2-(3R-acetoxy-9R-hydroxyeicosanoyl)glycerol. I. lutea exudates yielded glycolipids, 6S-(6-O-acetyl-β-D-glucopyranosyloxy)eicosanoic acid and 6S-(β-D-glucopyranosyloxy)eicosanoic acid and their C_<18> and C_<22> acid analogs, 2-acylglycerols, 2-(3R-acetoxynonadecanoyl)glycerol and 2-(3R,6S-diacetoxynonadecanoyl)glycerol and their C_<17>, C_<18>, C_<20> and C_<21> acid analogs, along with their isomers having iso- and anteiso-fattyacyl structures. In addition, a new dammarane triterpene, betulatriterpene C 3-acetate, was isolated. P. louisiana exudates furnished glycolipids, 8S-(6-O-acetyl-β-D-glucopyranosyl-oxy)eicosanoic acid, 8S-(β-D-glucopyranosyloxy)eicosanoic acid, their C_<22> acid analogs, and 6S-(β-D-glucopyranosyloxy)eicosanoic acid, 2-acylglycerols identical to those found in I. lutea, and 11 new dammarane triterpenes, such as (1β,3α,12β,20S)-dammar-24-ene-1,3,12,20-tetrol and (3α,11α,12β,20S,24R)-24-hydroperoxydammar-25-ene-3,11,12,20-tetrol.
- 天然有機化合物討論会の論文
- 2008-09-01
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