1. Studies on the Constituents and Biological Activities of Salvia yunnanensis C. H. Wright, S. trijuga Diels and Cryptocarya chinensis Hemsl.; 2. Semisynthesis of Salviamines and Isosalviamines

• Main Authors: Fu-Wen Lin, 林福文
• Other Authors: Tian-Shung Wu
• Format: Others
• Language: zh-TW
• Published: 2002
• Online Access: http://ndltd.ncl.edu.tw/handle/34502009534522578366

博士 === 國立成功大學 === 化學系 === 90 === A systematic chemical investigation of the wood, stem barks and leaves of Cryptocarya chinensis, and root of Salvia yunnanensis, and S. trijuga have resulted in the isolation of 153 compounds. Their structures were characterized by spectral methods and chemical transformation and/or comparison with the literature values. Among 153 compounds, 50 were first isolated from the natural source and the other was known compounds. The new compounds are salviamine-A, -B, -C, -D, -E, -F, -G, isosalviamine-A, -B, -C, -D, -E, salviaflavone-A, -B, butyl caffeate, salviacid-A, -B, -C, -D, 4-methenesalvipisone, nanodecyl 3-(4-hydroxyphenyl)propionate, tanshinlactone, salviatrinone-A, -B, -C, -D, -E, —F, -G, -H, -I, -J, -K, -L, -M, -N, isocryprochine, prooxocryprochine, (+)-eschscholtzidine-N-oxide, (+)-6-hydroxycrychine, (+)-12-hydroxyeschscholtzidine, (-)-N-demethylcrychine, 1-hydroxycryprochine, (-)-isocaryachine-N-oxide B, (+)-caryachine-N-oxide, (-)-caryachine-N-oxide, (-)-isocaryachine-N-oxide A, isoboldine-β-N-oxide, isoamuronine, (+)-8,9-dihydrostepharine, and 6,7-methylenedioxy-N-methylisoquinoline. In our research, we found an interesting structural feature i.e. diterpenes with oxazole ring in salviamine and isosalviamine types for the first time from natural source. The 1H NMR studies of these types were also discussed and the results provided a simple and an elegant method to characterize these types of compounds. The biosynthetic route of salviamines and isosalviamines were also discussed and we predicted that they might be formed through condensation of ortho-quinone diterpenes with relative amino acids. We also found an unusual skeleton of abietane diterpene with 23 carbons from S. trijuga. Many pavine-N-oxide compounds were isolated from C. chinensis and some of them were stereoisomer. We presented an important method to distinguish isomers of pavine alkaloids. The isolated compounds were also subjected to evaluate their bioactivities. The results showed that ortho and para-quinone diterpenes, which were isolated from Salvia yunnanensis and S. trijuga inhibited platelet aggregation induced by AA and collagen. The new compound, salviatrinone-B (717), showed 100% inhibition activity of antiplatelet aggregation induced by collagen. The compounds, antofine and dehydroantofine, isolated from Cryptocarya chinensis, showed significant cytotoxicity against L-1210, P-388, A-549 and HCT-8 at ED50 under 0.1μg/ml and anti-HIV activity, respectively. In this study, we also synthesized salviamine and isosalviamine diterpene alkaloids, which we had isolated from Salvia species.