Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile.
A new enantiomeric pair of spirodiketones, (+)- and (-)-denobilone A (1 and 2), three new phenanthrene derivatives (3-5), and three new biphenanthrenes (22-24), along with 11 known phenanthrene derivatives (6-16), five known bibenzyl derivatives (17-21), and four known biphenanthrenes (25-28), were isolated from Dendrobium nobile. The structures of 1-5 and 22-24 were elucidated using comprehensive spectroscopic methods. (+)-Denobilone and (-)-denobilone A (1 and 2) were isolated as a pair of enantiomers by chiral HPLC. The absolute configurations of (+)- and (-)-denobilone A (1 and 2) were determined by comparing their experimental and calculated electronic circular dichroism spectra. The absolute configuration of denobilone B (3) was determined by X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated.
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Xue-Ming
XM
Zhou
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Cai-Juan
CJ
Zheng
College of Pharmaceutical Science, Zhejiang University , Hangzhou 310058, People's Republic of China.
Li-She
LS
Gan
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Guang-Ying
GY
Chen
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Xiao-Peng
XP
Zhang
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Xiao-Ping
XP
Song
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University , Haikou 571158, People's Republic of China.
Gao-Nan
GN
Li
Hainan Boying Orchid Industrial Development Co., LTD , Haikou 570105, People's Republic of China.
Chong-Ge
CG
Sun
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001632:Bibenzyls / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D031667:Dendrobium / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D010616:Phenanthrenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D001632:Bibenzyls; D004365:Drugs, Chinese Herbal; D010616:Phenanthrenes