Chemical constituents and their bioactivities of "Tongling White Ginger" (Zingiber officinale).

Abstract

Gingerols and their corresponding dehydration products shogaols were considered as the active principles of ginger, the rhizome of the plant Zingiber officinale, for its antioxidant, anti-inflammatory, and antitumor activities. Ginger (Z. officinale) has been cultivated for thousands of years as a spice and for medicinal purposes in China. Tongling (Anhui province, China) has traditionally been regarded as an ideal cultivation place. "Tongling White Ginger" enjoys a reputation for being one of the top gingers in China for its thin white peel, tender flesh, rich juice, and flavor. In this study, we have isolated and identified two novel gingerdione dimers, bisgingerdiones A (1) and B (2); two new gingerol derivatives, (5R)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (3) and methyl (Z)-neral acetal-[6]-gingerdiol (4); and 38 known compounds (5-42) from rhizomes of Zingiber officinale collected from Tongling, China. Their structures were elucidated by means of spectroscopic methods. Compounds 1-4 showed weak cytotoxic and anti-HIV-1 activities. Compounds 6, 8, and 26 showed inhibitory activities against human and mouse 11β-HSD1 (11β-hydroxysteroid dehydrogenases) with IC(50) values between 1.09 and 1.30 μM.