Guaiane Sesquiterpene Lactones and Amino Acid-Sesquiterpene Lactone Conjugates from the Aerial Parts of Saussurea pulchella

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2008-04, Vol.71 (4), p.678-683
• Main Authors: Yang, Min Cheol, Choi, Sang Un, Choi, Wahn Soo, Kim, Sun Yeou, Lee, Kang Ro
• Format: Article
• Language: English
• Subjects: anticarcinogenic activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biological and medical sciences; chemical structure; cultured cells; cytotoxicity; desacylcynaropicrin; dihydrodesacylcynaropicrin; Drug Screening Assays, Antitumor; Female; General pharmacology; guaiane sesquiterpenes; Humans; Korea; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; Medical sciences; medicinal plants; medicinal properties; Molecular Structure; Oriental traditional medicine; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plants, Medicinal - chemistry; pulchellamine; Saussurea; Saussurea - chemistry; Saussurea pulchella; Sesquiterpenes, Guaiane - chemistry; Sesquiterpenes, Guaiane - isolation & purification; Sesquiterpenes, Guaiane - pharmacology; sesquiterpenoid lactones; spectral analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800005r

Two new guaiane sesquiterpene lactones (1 and 2) and seven new amino acid-sesquiterpene lactone conjugates (3−9), together with six known sesquiterpene lactones (10−15), were isolated from the methanol extract of the aerial parts of Saussurea pulchella. Their structures were determined on the basis of spectroscopic and chemical methods to be 8α-O-(3′-hydroxy-3′-methylbutyryl)desacylcynaropicrin (1), 8α-O-(2′, 3′-dihydroxyisobutyryl)11β,13-dihydrodesacylcynaropicrin (2), and pulchellamines A, B, C, D, E, F, and G (3−9). The structures of the new amino acid-sesquiterpene lactone conjugates, pulchellamines A, B, C, D, E, F, and G (3−9), were confirmed by synthesis. The isolated compounds were evaluated for cytotoxic activity against four human tumor cell lines. Compounds 11 and 12 exhibited cytotoxicity against skin melanoma (SK-MEL-2) and ovary malignant ascites (SK-OV-3) human tumor cell lines with ED50 values of 1.53 and 4.07 µM, and 2.49 and 7.42 µM, respectively.