Revision of the Structures of 1,5-Dihydroxy-3,8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from Valeriana jatamansi and V. officinalis.

Abstract

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.

• Authors: Sheng Lin, Yun-Heng Shen, Zhong-Xiao Zhang, Hui-Liang Li, Lei Shan, Run-Hui Liu, Xi-Ke Xu, Wei-Dong Zhang
• Journal: Journal of natural products (J Nat Prod) Vol. 73 Issue 10 Pg. 1723-6 (Oct 22 2010) ISSN: 1520-6025 [Electronic] United States
• PMID: 20853876 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Drugs, Chinese Herbal
• Iridoids
• valeriotetrate C
• volvaltrate B

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Colonic Neoplasms
• Drug Screening Assays, Antitumor
• Drugs, Chinese Herbal (chemistry, isolation & purification, pharmacology)
• Humans
• Iridoids (chemistry, isolation & purification, pharmacology)
• Male
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Plant Roots (chemistry)
• Prostatic Neoplasms (drug therapy)
• Valerian (chemistry)