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Two New Monoterpene Glycosides from Qing Shan Lu Shui Tea with Inhibitory Effects on Leukocyte-Type 12-Lipoxygenase Activity
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
Faculty of Health and Welfare Sciences, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan
Department of Biochemistry and Molecular Biology, West China School of Preclinical and Forensic Medicine, Sichuan University, 17 Section 3, South Renmin Road, Chengdu 610041, China
* Author to whom correspondence should be addressed.
Received: 18 February 2013; in revised form: 7 April 2013 / Accepted: 8 April 2013 / Published: 11 April 2013
Abstract: We evaluated the inhibitory effect of 12 Chinese teas on leukocyte-type 12-lipoxygenase (LOX) activity. Tea catechins such as epigallocatechin gallate have been known to exhibit leukocyte-type 12-LOX inhibition. Qing Shan Lu Shui, which contains lower catechin levels than the other tested teas, suppressed leukocyte-type 12-LOX activity. To characterize the bioactive components of Qing Shan Lu Shui, leukocyte-type 12-LOX inhibitory activity–guided fractionation of the aqueous ethanol extract of the tea was performed, resulting in the isolation of two new monoterpene glycosides: liguroside A (1) and B (2). The structures of compounds 1 and 2 were characterized as (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octadienyl-O-(α-L-rhamnopyranosyl)-(1″→3′)-(4′″-O-trans-p-coumaroyl)-β-D-glucopyranoside and (2E,5E)-7-hydroperoxy-3,7-dimethyl-2,5-octa-dienyl- O-(α-L-rhamnopyranosyl)-(1″→3′)-(4′″-O-cis-p-coumaroyl)-β-D-glucopyranoside, respectively, based on spectral and chemical evidence. Ligurosides A (1) and B (2) showed inhibitory effects on leukocyte-type 12-LOX activity, with IC50 values of 1.7 and 0.7 μM, respectively.
Keywords: Qing Shan Lu Shui; Ligustrum robustum; liguroside; monoterpene glycoside; leukocyte-type 12-lipoxygenase; Chinese tea; catechin
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Ito, H.; Otsuki, A.; Mori, H.; Li, P.; Kinoshita, M.; Kawakami, Y.; Tsuji, H.; Fang, D.Z.; Takahashi, Y. Two New Monoterpene Glycosides from Qing Shan Lu Shui Tea with Inhibitory Effects on Leukocyte-Type 12-Lipoxygenase Activity. Molecules 2013, 18, 4257-4266.
Ito H, Otsuki A, Mori H, Li P, Kinoshita M, Kawakami Y, Tsuji H, Fang DZ, Takahashi Y. Two New Monoterpene Glycosides from Qing Shan Lu Shui Tea with Inhibitory Effects on Leukocyte-Type 12-Lipoxygenase Activity. Molecules. 2013; 18(4):4257-4266.
Ito, Hideyuki; Otsuki, Akemi; Mori, Hitomi; Li, Peng; Kinoshita, Mai; Kawakami, Yuki; Tsuji, Hideaki; Fang, Ding Z.; Takahashi, Yoshitaka. 2013. "Two New Monoterpene Glycosides from Qing Shan Lu Shui Tea with Inhibitory Effects on Leukocyte-Type 12-Lipoxygenase Activity." Molecules 18, no. 4: 4257-4266.