title: Lithocarpic Acids A-N, 3,4-seco-Cycloartane Derivatives from the Cupules of Lithocarpus polystachyus.
abstract: Fourteen new 3,4-seco-cycloartane-type triterpenes, lithocarpic acids A-N (1-14), together with one known compound, coccinetane E (15), were identified from the cupules of Lithocarpus polystachyus. The structures of 1-14 were determined by spectroscopic data analysis and chemical methods, and the absolute configurations of 1 and 4 were defined unequivocally by X-ray crystallography using Cu Kα radiation. Compounds 1-15 are the first examples of 3,4-seco-cycloartane derivatives isolated from the genus Lithocarpus. Among them, compounds 1 and 2, 9 and 10, and 11 and 12 were found to be three pairs of C-24 epimers, while compounds 7 and 8 represent the first examples of 3,4-seco-norcycloartane-type triterpenes. Compound 1, as the major component of the plant extract, showed potent antibacterial activity against Micrococcus luteus and Bacillus subtilis, with MIC values of 3.1 and 6.3 μg/mL, respectively, as well as inhibitory activity against human and mouse 11β-hydroxysteroid dehydrogenase type 1, with IC50 values of 1.9 and 0.24 μM, respectively.
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Hongmin
authors.initials: H
authors.lastname: Wang
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Ruonan
authors.initials: R
authors.lastname: Ning
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Shen
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Chen
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Jinlong
authors.initials: J
authors.lastname: Li
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Rujun
authors.initials: R
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Leng
authors.affiliation: Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Weimin
authors.initials: W
authors.lastname: Zhao
mesh_terms: D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1 / Q000037:antagonists & inhibitors*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029962:Fagaceae / Q000737:chemistry*; D006801:Humans; D051379:Mice; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D004365:Drugs, Chinese Herbal; D014315:Triterpenes; C085352:cycloartane; D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1