Diarylheptanoids and a Monoterpenoid from the Rhizomes of Zingiber officinale: Antioxidant and Cytoprotective Properties

Abstract

Three new diarylheptanoids and one new monoterpenoid were isolated from the rhizomes of Zingiber officinale together with four known diarylheptanoids, 5-8. Their structures were elucidated mainly by spectroscopic methods, and they were deduced as 5-[4-hydroxy-6-(4-hydroxyphenethyl)tetrahydro-2 H-pyran-2-yl]-3-methoxybenzene-1,2-diol (1), sodium (E)-7-hydroxy-1,7-bis(4-hydroxyphenyl)hept-5-ene-3 S-sulfonate (2), sodium (E)-7-hydroxy-1,7-bis(4-hydroxyphenyl)hept-5-ene-3 R-sulfonate (3), and hydroxycineole-10-O-beta-D-glucopyranoside (4), respectively. Among the isolated compounds, compounds 1, 5, and 8 exhibited strong superoxide anion radical scavenging activities in a phenazine methosulfate-NADH system. In a more biological system, these compounds were demonstrated to exhibit potent protection against lipid peroxidation in mouse liver microsomes exposed to oxidative conditions. These compounds were subsequently tested on primary cultures of rat hepatocytes exposed to oxidative damage, and definitive cytoprotective actions were found.

An Impression on Current Developments in the Technology, Chemistry, and Biological Activities of Ginger (Zingiber officinaleRoscoe)

“…The diarylheptanoids were found to possess potent antioxidant properties in all the above assays. On the other hand, these compounds did not possess any appreciable cytotoxiciy on KB cells and on rat liver hepatocytes (Tao et al, 2008). conducted phylogenetic analysis and metabolic profiling along with anti-inflammatory activity to investigate the diversity of plant material within the ginger species and between ginger and closely related species in the genus Zingiber.…”

Growth-inhibiting and apoptosis-inducing activities of Myricanol from the bark of Myrica rubra in human lung adenocarcinoma A549 cells

“…The bark of Myrica rubra contains flavonoids, tannins, triterpenes, and diarylheptanoids . Diarylheptanoids are used not only as food flavoring agents but also as medicines because of their many beneficial properties, including antitumor (Ishida et al, 2000), antiviral (Konno et al, 2011), antioxidant (Tao et al, 2008), and anti-inflammatory (Aguilar et al, 2011). Medicinal chemists and pharmaceutical researchers have recently focused on natural plants.…”

Research Progress on Nidus Vespae, a Traditional Chinese Medicine Derived From Insects

“…[55][56][57] Meanwhile, the free radical scavenging ability is closely related to anti-inflammatory effect of the crude parts of TCM. [58][59] Phenolic compounds are also proved to demonstrate various kinds of biological activities, [60][61] it is obvious more detailed and comprehensive pharmacological mechanism studies of Nidus vespae still await further detailed research.…”