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Antitumor Agents. 261. 20(S)-Protopanaxadiol and 20(S)-Protopanaxatriol as Antiangiogenic Agents and Total Assignment of ¹H NMR Spectra^#

Yoshihide Usami^†^‡, Yi-Nan Liu^†, An-Shen Lin^†^§, Makio Shibano^†^‡, Toshiyuki Akiyama^†, Hideji Itokawa^†, Susan L. Morris-Natschke^†, Kenneth Bastow, Ryoji Kasai and Kuo-Hsiung Lee*^†

Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan, Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China, Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, and Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hiro-koshingai, Kure, Hiroshima, 737-0112 Japan

J. Nat. Prod., 2008, 71 (3), pp 478–481

DOI: 10.1021/np070613q

Publication Date (Web): February 14, 2008

Dedicated to Dr. G. Robert Pettit of Arizona State University for his pioneering work on bioactive natural products.

†

Natural Products Research Laboratories.

‡

Osaka University of Pharmaceutical Sciences.

Kaohsiung Medical University.

Division of Medical Chemistry and Natural Products.

Hiroshima International University.

* Corresponding author. Phone: 919-962-0066 . Fax: 919-966-3893. E-mail: khlee@unc.edu.

This article is part of the

Special Issue in Honor of G. Robert Pettit

special issue.

Abstract

Angiogenesis is a critical step in tumor progression and involves several steps including endothelial cell (EC) proliferation, migration, and matrix remodeling. We investigated the antiangiogenic effects of 20(S)-protopanaxadiol (1) and 20(S)-protopanaxatriol (2), the sapogenins of two major ginseng saponins, in an angiogenesis model of human umbilical vein endothelial cells (HUVECs). These compounds inhibited the proliferative activity of HUVECs in a dose-dependent manner and have potential as anticancer drug candidates. In addition, we report the complete and unambiguous assignment of ¹H NMR spectra of 1 and 2, based on analyses of 2D NMR spectra including COSY, NOESY, HSQC, and HMBC. This report is the first to completely assign the ¹H NMR signals of 2, together with correction of data for 1 from prior reports.

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