Inhibitors of Nitric Oxide Production from the Rhizomes of Alpinia galanga: Structures of New 8-9' Linked Neolignans and Sesquineolignan

Abstract

The 80% aqueous acetone extract from the rhizomes of Alpinia galanga showed nitric oxide (NO) production inhibitory activities in mouse peritoneal macrophages. From the aqueous acetone extract, three new 8-9 linked neolignans, galanganal, galanganols A and B, and a sesquineolignan, galanganol C, were isolated together with nine known phenylpropanoids and p-hydroxybenzaldehyde. The structures of new neolignans were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the constituents from the rhizomes of A. galanga on NO production induced by lipopolysaccharide in mouse peritoneal macrophages were examined. Among them, galanganal (IC 50 ‫86؍‬ m mM), galanganols B (88 m mM) and C (33 m mM), 1S-1-acetoxychavicol acetate (2.3 m mM), 1S-1-acetoxyeugenol acetate (11 m mM), trans-p-hydroxycinnamaldehyde (ca. 20 m mM), trans-p-coumaryl alcohol (72 m mM), and trans-p-coumaryl diacetate (19 m mM) were found to show inhibitory activity.

Structures of New Flavonoids, Erycibenins D, E, and F, and NO Production Inhibitors from Erycibe expansa Originating in Thailand

“…As a part of our studies to characterize the bioactive components of natural medicines, we have investigated various NO production inhibitors, i.e., higher unsaturated fatty acids, 27) polyacetylenes, [28][29][30] coumarins, 28,30,31) flavonoids, 29,32) stilbenes, 33,34) lignans, [35][36][37] sesquiterpenes, [38][39][40][41][42][43][44][45] diterpenes, 46,47) triterpenes, [48][49][50][51] diarylheptanoids, [52][53][54] cyclic peptides, 50) alkaloids, 55,56) and phenylpropanoids. 5,6,37) Continuing of these studies, the effects of the principal constituents from E. expansa on NO production from LPS-activated macrophages were examined, and the results were summarized in Table 2. Among them, two isoflavones, clycosin (8, IC 50 ϭ13 mM) and erythrinin B (14, 18 mM), and two rotenoids, deguelin (28, 26 mM) and rotenone (30, 27 mM), were found to show inhibitory activity, whose activities were nearly equivalent to that of caffeic acid phenetyl ester (CAPE), an inhibitor of nuclear factor-kB activation (IC 50 ϭ15 mM).…”

Antibacterial activity of Thai herbal extracts on acne involved microorganism

“…It has been reported that 1′-ACA possesses various biological activities, such as antitumor (Itokawa et al, 1987;Kondo et al, 1993;Moffatt et al, 2000;Zheng et al, 2002;Ito et al, 2005;Azuma et al, 2006;Campbell et al, 2007), anti-inflammation (Nakamura et al, 1998;Morikawa et al, 2005), antifungal (Janssen & Scheffer, 1985), antiviral (Ye & Li, 2006), antioxidative (Kubota et al, 2001), and xanthine oxidase inhibitory activity (Noro et al, 1988). Although it has been reported that the ethanol extract of A. galanga exhibits antibacterial activity against S. aureus (Oonmetta-aree et al, 2006), the antibacterial activity of 1′-ACA has not yet been reported.…”

Immunomodulatory and anti-oxidant potential of Alpinia galanga Linn. rhizomes

“…and were screened for nitric oxide production inhibitory action. [6] A. galanga is used to treat dyspepsia, fevers, urinary incontinence, halitosis, and to reduce hoarseness in throat infections. [7] It is also used as a carminative and is useful in respiratory troubles.…”