Year: 2014
Type: article
Abstract: Alpinia oxyphylla Miq.(Zingiberaceae) is widely cultivated and distributed in southern China.The fruits of this plant have been used as a traditional medicine in Korea and other oriental countries for the treatment of gastrointestinal disorders, urosis, diuresis, ulceration, and dementia.The plants in the genus of Alpinia are reported to be rich of diarylheptanoids, sesquiterpenoids, and flavonoids. 1 Previous pharmacological investigations have indicated that the fruits of A. oxyphylla possess various activities, including antioxidative, 2,3 anti-inflammatory, 4 anti-angiogenic, 5 anti-ulcer, 6 and neuroprotective activities.[7][8][9] Recently, diarylheptanoids and sesquiterpenes have been isolated from this plant, and some of which showed the inhibitory effects on nitric oxide production.[10][11][12][13] As part of our continuing search for inhibitors of nitric oxide (NO) production from medicinal plants, we investigated the active constituents of the fruits of A. oxyphylla.As a result, a new noreudesmane-type sesquiterpenoid, 4-methoxy-oxyphyllenone A (1), along with 15 known compounds was isolated and identified.The present paper describes the structure determination of the new compound 1 and the inhibitory effects of the isolated compounds on NO production.The dried fruits of A. oxyphylla were extracted with methanol and fractionated successively with n-hexane, CH 2 Cl 2 , and water.The CH 2 Cl 2 -soluble fraction was subjected to various column chromatography and led to the isolation of the new noreudesmane-type sesquiterpenoid and 15 known compounds (Figure 1).Compound 1 was isolated as a yellow gum.The HR-ESI-MS of compound 1 exhibited a protonated molecular ion peak at m/z 225.1485 [M+H] + (calcd.225.1491) and established the molecular formula of C 13 H 20 O 3 , implying four degrees of unsaturation.The IR spectrum showed absorptions at 3271 and 1647 cm -1 , which indicated the presence of a hydroxyl and α,β-unsaturated ketone.The 1 H NMR spectrum of compound 1 displayed the presence of two tertiary methyls at δ H 1.37 (s, CH 3 -15) and 1.41 (s, CH 3 -14), an oxygenated methine at δ H 3.70 (dd, J = 3.0, 3.0 Hz, H-3), a methoxyl group at δ H 3.06 (s, OCH 3 -4), and an olefinic proton at δ H 5.99 (s, H-6).The 13 C NMR and HMQC spectra of compound 1 revealed 13 carbon signals, including a ketone carbon (δ C 201.2), two olefinic carbons (δ C 166.3 and 127.8), an oxygenated methine carbon (δ C 74.5), an oxygenated quaternary carbon (δ C 78.1), and a methoxy carbon (δ C 48.6).All the above data indicated that compound 1 was a noreudesmane-
Institution: Chungbuk National University
Language: English
Subfield: Pharmacology
Domain: Life Sciences
Open Access status: bronze
Award: G4993951856
OpenAlex ID: W2950705677