title: Antibacterial Biphenanthrenes from the Fibrous Roots of Bletilla striata.
abstract: Four new 9',10'-dihydro-biphenanthrenes, including an unprecedented 1,2'-linked biphenanthrene, 4,7,3',5'-tetramethoxy-9',10'-dihydro(1,2'-biphenanthrene)-2,7'-diol (1), a new 1,3'-linked biphenanthrene, 4,7,7'-trimethoxy-9',10'-dihydro(1,3'-biphenanthrene)-2,2',5'-triol (2), and two new 1,1'-linked biphenanthrenes, 4,7,4'-trimethoxy-9',10'-dihydro(1,1'-biphenanthrene)-2,2',7'-triol (3) and 4,7,3',5'-tetramethoxy-9',10'-dihydro(1,1'-biphenanthrene)-2,2',7'-triol (4), as well as two known biphenanthrenes (5, 6), were isolated from a 95% ethanol extract of the fibrous roots of Bletilla striata. Their structures were determined by spectroscopic and spectrometric methods. Atropisomerism of these compounds was considered based on their chiral optical properties and potential energy surface scans at the ab initio HF/3-21G level, which revealed their racemic mixture form. Compounds 2-6 showed potent antibacterial activities against six Gram-positive bacterial strains.
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Chao-Dong
authors.initials: CD
authors.lastname: Qian
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Fu-Sheng
authors.initials: FS
authors.lastname: Jiang
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Hang-Su
authors.initials: HS
authors.lastname: Yu
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Shen
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Yu-Hang
authors.initials: YH
authors.lastname: Fu
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Dong-Qing
authors.initials: DQ
authors.lastname: Cheng
authors.affiliation: ‡College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, People's Republic of China.
authors.forename: Li-She
authors.initials: LS
authors.lastname: Gan
authors.affiliation: †Zhejiang Chinese Medical University, 548 Binwen Road, Hangzhou 310053, People's Republic of China.
authors.forename: Zhi-Shan
authors.initials: ZS
authors.lastname: Ding
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D029595:Orchidaceae / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D027343:Rhizome / Q000737:chemistry
chemical_list: C468327:1,1'-biphenanthrene; D000900:Anti-Bacterial Agents; D004365:Drugs, Chinese Herbal; D010616:Phenanthrenes