Bioassay-directed separation of the methylene chloride extracts from the wood of Liriodendron chinense led to the isolation of six sesquiterpenes, tulipinolide (1), α-liriodenolide (2), β-liriodenolide (3), lipiferolide (4), 11,13-dehydrolanuginolide (5), and tulipinolide diepoxide (6). Compounds 1-6 have not been found previously in L. chinense. The structures of the compounds were established on the basis of NMR spectroscopic data. All the compounds exhibited quinone reductase (QR)- inducing activity in Hepa lclc7 cells.
(a) HuffordCD. (1976) Four new N- acetylnoraporphine alkaloids from Liriodendron tulipifera L. Phytochemistry, 15, 1169–117
2.
(b) DoskotchRW, WiltonJH, HarmFM, FairchildEH, HuangCT, El-FeralyFS. (1983) Six additional sesquiterpene lactones from Liriodendron tulipifera.Journal of Natural Products, 46, 923–929
3.
(c) DoskotchRW, EI-FeralyFS. (1970) The structure of tulipinolide and epitulipinolide, cytotoxic sesquiterpenes from Liriodendron tulipifera L. Journal of Organic Chemistry, 35, 1928–1936
4.
(d) AngyaiSJ, BenderV. (1961) Cyclilols, part XI. The constitution of liriodendritol.Journal of the Chemistry Society, 11, 4718–4720
5.
(e) LiSS, TanNH, ZhouJ, ZhaoSX. (2001) Phytochemical and chemotaxonomic studies on Liriodendron chinense and Paramichelia baillonii (Magnoliaceae). Acta Botanica Yunnanica, 23, 115–120.
6.
(a) DoskotchRW, O'DellTM, GirardL. (1981) Phytochemicals and Feeding Behavior of Gypsy Moth Larvae. In The Gypsy Moth: Research Towards Integrated Pest Management.DoaneCC, McManusML (Eds). US Department of Agriculture, 1584
7.
(b) ProchaskaHJ, TalalayP. (1991) Role of NAD(P)H: quinine reductase in protection against the toxicities of quinines and related agents. In Oxidative Sress. Oxidants and Antioxidants.SiesH (Ed). Academic Press, London, 211–211
8.
(c) ZhangW, GoML. (2007) Quinone reductase induction activity of methoxylated analogues of resveratrol. European Journal of Medicinal Chemistry, 42, 841–850.
