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Molecules 2013, 18(4), 4257-4266; https://doi.org/10.3390/molecules18044257

Two New Monoterpene Glycosides from Qing Shan Lu Shui Tea with Inhibitory Effects on Leukocyte-Type 12-Lipoxygenase Activity

1
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
2
Faculty of Health and Welfare Sciences, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan
3
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 / Revised: 7 April 2013 / Accepted: 8 April 2013 / Published: 11 April 2013
(This article belongs to the Section Natural Products Chemistry)
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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. View Full-Text
Keywords: Qing Shan Lu Shui; Ligustrum robustum; liguroside; monoterpene glycoside; leukocyte-type 12-lipoxygenase; Chinese tea; catechin 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.

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