title: Caesalminaxins A-L, cassane diterpenoids from the seeds of Caesalpinia minax.
abstract: Fourteen new cassane diterpenoids, caesalminaxins A-L (1-14), and three known compounds were isolated from the seeds of Caesalpinia minax. Among the new diterpenoids, compounds 3 and 4 possess a rare spiro C/D ring system. The C-16 epimeric mixture 1/2 has an unprecedented carbon skeleton, presumably derived from 3 by cleavage of the C-13-C-14 bond. Compound 5 is the first example of a cassane diterpenoid with a spiro A/B ring system. The structures of the compounds were elucidated on the basis of 1D and 2D NMR analysis, and the absolute configurations of 3, 4, 9, and 11 were determined by single-crystal X-ray crystallography. Biosynthesis pathways for 1/2, 3, and 5 are postulated. Compounds 4, 8, and the known bonducellpin D exhibited moderate activity against four tested human cancer cell lines, HepG-2, K562, HeLa, and Du145.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 501 Haike Road, Zhangjiang Hi-Tech Park, Shanghai 201203, People's Republic of China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Zheng
authors.forename: Shu-Wei
authors.initials: SW
authors.lastname: Zhang
authors.forename: Hai-Jian
authors.initials: HJ
authors.lastname: Cong
authors.forename: Yu-Jie
authors.initials: YJ
authors.lastname: Huang
authors.forename: Li-Jiang
authors.initials: LJ
authors.lastname: Xuan
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029911:Caesalpinia / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D020014:K562 Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012639:Seeds / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D004365:Drugs, Chinese Herbal