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Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum
Hong-Xin Liu1, Kai Chen, Qian-Yun Sun
1Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
Abstract:
A new complex natural product with a C39 skeleton, named nudibaccatumone, and the known sesquiterpenes (+)-spathulenol, (-)-4β,10α-aromadendranediol, and ent-T-muurolol, as well as the phenylpropanoid hydroxychavicol, were isolated from the aerial parts of Piper nudibaccatum. The structure and absolute configuration of nudibaccatumone were elucidated using spectroscopic methods and ECD calculations. A 1,8-Michael addition reaction and an intermolecular, inverse electron demand Diels-Alder reaction are proposed as the key steps in the biosynthesis of nudibaccatumone.
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