A New Monoterpene from the Rhizomes of Alpinia galanga and Its Anti‐Vpr Activity

Abstract

A new menthane‐type monoterpene, alpigalanol (1), together with four known terpenes (2–5) were isolated from the ethyl acetate soluble fraction of the 70 % ethanol extract of the Alpinia galanga rhizomes. The structure of 1 was determined by spectroscopic analyses, including 1D‐ and 2D‐NMR. The extract of the A. galanga rhizomes and all isolated compounds (1–5) possessed Vpr inhibitory activities against the TREx‐HeLa‐Vpr cells at a concentration of 1.25 μM without showing any cytotoxicity.

Three <i>neo</i>-Clerodane Diterpenoids from <i>Tinospora cordifolia</i> Stems and Their Arginase Inhibitory Activities

“…ECD Calculation The absolute configurations of 1 and 2 were determined using Time-Dependent Density Functional Theory-Electronic Circular Dichroism (TDDFT-ECD) as described previously, with some modifications. 24) Conformation search using molecular mechanics calculations were performed by Winmostar 10. Merck molecular force field (MMFF) calculations were performed by using Avogadro 1.2.…”

Phytochemical and pharmacological properties of the genus Alpinia from 2016 to 2023

“…122 Monoterpenoids such as 134, 135, and 136 showed dose-dependent anti-Vpr activity in TREx-HeLa-Vpr cells (concentrations: 0.3-5.0 mM) without cytotoxicity. 84…”

“…An undescribed menthane-type monoterpene, alpigalanol (134), was isolated from A. galanga rhizomes, 84 along with (4R)-4-hydroxy-4-(2-methylethyl)cyclohex-2-en-1-one (135) and 2-O-b-D-glucopyranosyl-(+)-angelicoidenol (136) from the EtOAc fraction of the A. galanga extract. 84 In a later study, the monoterpene esters (2 0 E)-2 0methoxy-4 0 -oxo-6 0 -phenylhexenoic acid 4-hydroxy-2-isopropyl-5methylphenyl ester ( 137) and (2 0 E)-2 0 -methoxy-4 0 -oxo-6 0 -phenylhexenoic acid 4-hydroxy-5-isopropyl-2-methylphenyl ester (138) were newly found in A. zerumbet. 85 The compounds were composed of a monoterpene skeleton of 5-acetyl-thymoquinol and a kavalactone moiety (C-1 0 to C-12 0 ) at 2-OH or 5-OH.…”