Enmein-type 6,7-seco-ent-kauranoids from Isodon sculponeatus.
Fourteen enmein-type 6,7-seco-ent-kaurane diterpenoids, seven new ones (sculponins M-S, 1-7) and seven known compounds (8-14), were isolated from the aerial parts of Isodon sculponeatus . Compound 1 is the first example of an ent-kauranoid, possessing a 11,12-epoxy group, and compounds 6 and 7 have a rare 3,6-epoxy group. The structures were established primarily by NMR and MS methods, and the absolute configurations of 1, 3, and 6 were determined by single-crystal X-ray diffraction. Compound 14 showed significant cytotoxic activity against five human tumor lines, with IC50 values ranging from 1.0 to 3.5 μM, and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC50 value of 2.2 μM.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
Hua-Yi
HY
Jiang
Wei-Guang
WG
Wang
Min
M
Zhou
Hai-Yan
HY
Wu
Rui
R
Zhan
Xiao-Nian
XN
Li
Xue
X
Du
Yan
Y
Li
Jian-Xin
JX
Pu
Han-Dong
HD
Sun
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004224:Diterpenes; D045786:Diterpenes, Kaurane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D037602:Isodon / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D008070:Lipopolysaccharides; D009569:Nitric Oxide; C007594:enmein