Revision of the Structures of 1,5-Dihydroxy-3,8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from Valeriana jatamansi and V. officinalis.
The structures of 1,5-dihydroxy-3,8-epoxyvalechlorine (1a) and volvaltrate B (6a), two new chlorinated iridoids isolated from Valeriana jatamansi and V. officinalis, respectively, were originally assigned on the basis of spectroscopic methods. Reinvestigation using X-ray analysis and chemical transformation revealed that the original assignment of H-7 in 1a and OH-8 in 6a should be inverted and that the structures should be revised to 1 and 6, respectively. Correspondingly, the structure of valeriotetrate C (7a) should be revised to 7. Volvaltrate B (6) showed cytotoxic activity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC-3M), colon cancer (HCT-8), and hepatoma (Bel7402) cell lines, with IC50 values of 8.5, 2.0, 3.2, and 6.1 μM, respectively.
Lin
Sheng
S
Department of Phytochemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China.
Shen
Yun-Heng
YH
Zhang
Zhong-Xiao
ZX
Li
Hui-Liang
HL
Shan
Lei
L
Liu
Run-Hui
RH
Xu
Xi-Ke
XK
Zhang
Wei-Dong
WD
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D003110:Colonic Neoplasms; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D039823:Iridoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D011471:Prostatic Neoplasms / Q000188:drug therapy; D014632:Valerian / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D039823:Iridoids; C000606018:valeriotetrate C; C000606176:volvaltrate B