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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2013 Apr 13

PMID 23579993

Citations 6

Authors

Hideyuki Ito

Akemi Otsuki

Hitomi Mori

Peng Li

Mai Kinoshita

Yuki Kawakami

Hideaki Tsuji

Ding Zhi Fang

Yoshitaka Takahashi

Affiliations

Soon will be listed here.

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.

Citing Articles

Monoterpenoid Glycosides from the Leaves of and Their Bioactivities (II).

Lu S, Li X, Zuo H, Li W, Pan J, Huang J Molecules. 2023; 28(21).

PMID: 37959693 PMC: 10647328. DOI: 10.3390/molecules28217274.

A New HPLC-UV Method Using Hydrolyzation with Sodium Hydroxide for Quantitation of --Hydroxycinnamic Acid and Total --Hydroxycinnamic Acid Esters in the Leaves of .

Lu S, Liang X, Nong X, Chen R, Li X Molecules. 2023; 28(14).

PMID: 37513183 PMC: 10383156. DOI: 10.3390/molecules28145309.

Computational Insights and In Silico Characterization of a Novel Mini-Lipoxygenase from Nostoc Sphaeroides and Its Application in the Quality Improvement of Steamed Bread.

Xia B, Chi H, Zhang B, Lu Z, Liu H, Lu F Int J Mol Sci. 2023; 24(9).

PMID: 37175648 PMC: 10177866. DOI: 10.3390/ijms24097941.

Chemical Constituents from the Leaves of and Their Bioactivities.

Lu S, Zuo H, Huang J, Li W, Huang J, Li X Molecules. 2023; 28(1).

PMID: 36615556 PMC: 9822135. DOI: 10.3390/molecules28010362.

Phenylethanoid and Phenylmethanoid Glycosides from the Leaves of and Their Bioactivities.

Lu S, Zuo H, Huang J, Chen R, Pan J, Li X Molecules. 2022; 27(21).

PMID: 36364215 PMC: 9657303. DOI: 10.3390/molecules27217390.

References

Yamamoto S, Katsukawa M, Nakano A, Hiraki E, Nishimura K, Jisaka M . Arachidonate 12-lipoxygenases with reference to their selective inhibitors. Biochem Biophys Res Commun. 2005; 338(1):122-7. DOI: 10.1016/j.bbrc.2005.08.214. View

Trevisanato S, Kim Y . Tea and health. Nutr Rev. 2000; 58(1):1-10. DOI: 10.1111/j.1753-4887.2000.tb01818.x. View

He Z, Lau K, But P, Jiang R, Dong H, Ma S . Antioxidative glycosides from the leaves of Ligustrum robustum. J Nat Prod. 2003; 66(6):851-4. DOI: 10.1021/np020568g. View

Zhu F, Cai Y, Sun M, Ke J, Lu D, Corke H . Comparison of major phenolic constituents and in vitro antioxidant activity of diverse Kudingcha genotypes from Ilex kudingcha, Ilex cornuta, and Ligustrum robustum. J Agric Food Chem. 2009; 57(14):6082-9. DOI: 10.1021/jf901020h. View

Takahashi Y, Zhu H, Yoshimoto T . Essential roles of lipoxygenases in LDL oxidation and development of atherosclerosis. Antioxid Redox Signal. 2005; 7(3-4):425-31. DOI: 10.1089/ars.2005.7.425. View

Sakashita T, Takahashi Y, Kinoshita T, Yoshimoto T . Essential involvement of 12-lipoxygenase in regiospecific andstereospecific oxidation of low density lipoprotein by macrophages. Eur J Biochem. 1999; 265(2):825-31. DOI: 10.1046/j.1432-1327.1999.00803.x. View

Steinberg D, Parthasarathy S, Carew T, Khoo J, Witztum J . Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N Engl J Med. 1989; 320(14):915-24. DOI: 10.1056/NEJM198904063201407. View

Ichiyanagi T, Kashiwada Y, Shida Y, Ikeshiro Y, Kaneyuki T, Konishi T . Nasunin from eggplant consists of cis-trans isomers of delphinidin 3-[4-(p-coumaroyl)-L-rhamnosyl (1-->6)glucopyranoside]-5-glucopyranoside. J Agric Food Chem. 2005; 53(24):9472-7. DOI: 10.1021/jf051841y. View

Kawakami Y, Nakamura T, Hosokawa T, Suzuki-Yamamoto T, Yamashita H, Kimoto M . Antiproliferative activity of guava leaf extract via inhibition of prostaglandin endoperoxide H synthase isoforms. Prostaglandins Leukot Essent Fatty Acids. 2009; 80(5-6):239-45. DOI: 10.1016/j.plefa.2009.04.006. View

10.

Lau K, He Z, Dong H, Fung K, But P . Anti-oxidative, anti-inflammatory and hepato-protective effects of Ligustrum robustum. J Ethnopharmacol. 2002; 83(1-2):63-71. DOI: 10.1016/s0378-8741(02)00192-7. View

11.

Fukuda T, Kitada Y, Chen X, Yang L, Miyase T . Two new monoterpene glycosides from ku-ding-cha. Inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). Chem Pharm Bull (Tokyo). 1996; 44(11):2173-6. DOI: 10.1248/cpb.44.2173. View