title: Scapiformolactones A-I: germacrane sesquiterpenoids with an unusual Δ3-15,6-lactone moiety from Salvia scapiformis.
abstract: Nine germacrane sesquiterpenoids with an unusual Δ(3)-15,6-lactone moiety, scapiformolactones A-I (1-9), and one known seco-germacrane sesquiterpenoid, 3,7,11-trimethyldodeca-l,6,9-triene-3,11-diol (10), were isolated from whole plants of Salvia scapiformis Hance. Their structures were elucidated by spectroscopic methods including HR-ESIMS, IR, UV, NMR, and CD, as well as by quantum mechanical calculations and chemical transformations. Structures of compounds 1-3 were also confirmed by single-crystal X-ray diffraction analysis. Six germacrane 6,15-diol derivatives (11-16) were obtained by chemical transformation. Compounds 1-9 and 11-16 were evaluated for their in vitro immunomodulatory effects on T and B cells, as well as their in vitro cytotoxicity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480.
authors.affiliation: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China.
authors.forename: Yongji
authors.initials: Y
authors.lastname: Lai
authors.forename: Yongbo
authors.initials: Y
authors.lastname: Xue
authors.forename: Mengke
authors.initials: M
authors.lastname: Zhang
authors.forename: Jinwen
authors.initials: J
authors.lastname: Zhang
authors.forename: Wei
authors.initials: W
authors.lastname: Tang
authors.forename: Junjun
authors.initials: J
authors.lastname: Liu
authors.forename: Liang
authors.initials: L
authors.lastname: Lei
authors.forename: Juming
authors.initials: J
authors.lastname: Yan
authors.forename: Zengwei
authors.initials: Z
authors.lastname: Luo
authors.forename: Jianping
authors.initials: J
authors.lastname: Zuo
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Guangmin
authors.initials: G
authors.lastname: Yao
authors.forename: Yonghui
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001402:B-Lymphocytes / Q000187:drug effects*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D007155:Immunologic Factors / Q000737:chemistry / Q000276:immunology / Q000302:isolation & purification; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D027544:Salvia / Q000737:chemistry; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013601:T-Lymphocytes / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D007155:Immunologic Factors; D007783:Lactones; D045788:Sesquiterpenes, Germacrane
keywords: Chemical transformation; Conformation; Cytotoxicity; Germacrane sesquiterpene; Immunomodulatory activity; Lamiaceae; Quantum mechanical calculation; Salvia scapiformis