title: Highly Rigid Labdane-Type Diterpenoids from a Chinese Liverwort and Light-Driven Structure Diversification.
abstract: Two unprecedented labdane-type diterpenoids haplomintrins A (1) and B (2) with six rings system were isolated from a Chinese liverwort Haplomitrium mnioides. Light-driven reaction of homologous haplomitrenonolides C (6), A (4), and D (3) afforded haplomintrins A-C (1, 2, and 7), respectively, while 4 was converted to more complex congeners haplomintrins D-G (8-11) through intramolecular cyclization. Formation of 1 and 2 from compounds 6 and 4, respectively, helps us to postulate that a photochemical reaction is involved in the biosynthetic pathway. These structure features can be used as molecular markers of H. mnioides, and their allelopathic effects are also preliminarily tested.
authors.affiliation: †Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China.
authors.forename: Jinchuan
authors.initials: J
authors.lastname: Zhou
authors.affiliation: †Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China.
authors.forename: Jiaozhen
authors.initials: J
authors.lastname: Zhang
authors.affiliation: †Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China.
authors.forename: Aixia
authors.initials: A
authors.lastname: Cheng
authors.affiliation: ‡College of Life Sciences, Guizhou Unversity, Guiyang 550025, P. R. China.
authors.forename: Yuanxin
authors.initials: Y
authors.lastname: Xiong
authors.affiliation: †Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China.
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.affiliation: †Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China.
authors.forename: Hongxiang
authors.initials: H
authors.lastname: Lou
mesh_terms: D002681:China; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification; D035926:Hepatophyta / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D004224:Diterpenes; C000602333:haplomintrin A; C000602334:haplomintrin B