title: Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum.
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.
authors.affiliation: Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
authors.forename: Hong-Xin
authors.initials: HX
authors.lastname: Liu
authors.forename: Kai
authors.initials: K
authors.lastname: Chen
authors.forename: Qian-Yun
authors.initials: QY
authors.lastname: Sun
authors.forename: Fu-Mei
authors.initials: FM
authors.lastname: Yang
authors.forename: Guang-Wan
authors.initials: GW
authors.lastname: Hu
authors.forename: Yue-Hu
authors.initials: YH
authors.lastname: Wang
authors.forename: Chun-Lin
authors.initials: CL
authors.lastname: Long
mesh_terms: D002176:Candida albicans / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010666:Phenylpropionates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031701:Piper / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045789:Sesquiterpenes, Guaiane; D013211:Staphylococcus aureus / Q000187:drug effects; D013729:Terpenes
chemical_list: D004365:Drugs, Chinese Herbal; D010666:Phenylpropionates; D012717:Sesquiterpenes; D045789:Sesquiterpenes, Guaiane; C499351:T-muurolol; D013729:Terpenes; C543650:aromadendranediol; C582696:nudibaccatumone; C013258:spathulenol