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Article

Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea

by
Yuki Kawakami
1,
Akemi Otsuki
1,
Yoshiko Mori
1,2,
Keita Kanzaki
1,3,
Toshiko Suzuki-Yamamoto
1,
Ding Zhi Fang
4,
Hideyuki Ito
1 and
Yoshitaka Takahashi
1,*
1
Department of Nutritional Science, Faculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan
2
Department of Human Nutrition, Faculty of Contemporary Human Life Science, Chugoku Gakuen University, 83 Niwase, Kita-ku, Okayama 701-0197, Japan
3
Department of Clinical Nutrition, Faculty of Health Science and Technology, Kawasaki University of Medical Welfare, 288 Matsushima, Kurashiki, Okayama 701-0193, Japan
4
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.
Molecules 2019, 24(2), 304; https://doi.org/10.3390/molecules24020304
Submission received: 26 December 2018 / Revised: 8 January 2019 / Accepted: 14 January 2019 / Published: 15 January 2019
(This article belongs to the Special Issue Tea Chemistry)
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Abstract

We have previously found two novel monoterpene glycosides, liguroside A and liguroside B, with an inhibitory effect on the catalytic activity of the enzyme leukocyte-type 12-lipoxygenase in the Qing Shan Lu Shui tea. Here, two new monoterpene glycosides, liguroside C and liguroside D which inhibit this enzyme, were isolated from the same tea. The spectral and chemical evidence characterized the structures of these compounds as (5E)-7-hydroperoxy-3,7-dimethyl-1,5-octadienyl-3-O-(α-l-rhamnopyranosyl)-(1′′→3′)-(4′′′-O-trans-p-coumaroyl)-β-d-glucopyranoside and (2E)-6-hydroxy-3,7-dimethyl-2,7-octadienyl-3-O-(α-l-rhamnopyranosyl)-(1′′→3′)-(4′′′-O-trans-p-coumaroyl)-β-d-glucopyranoside, respectively. These ligurosides, which irreversibly inhibited leukocyte-type 12-lipoxygenase, have a hydroperoxy group in the monoterpene moiety. Additionally, monoterpene glycosides had the same backbone structure but did not have a hydroperoxy group, such as kudingoside A and lipedoside B-III, contained in the tea did not inhibit the enzyme. When a hydroperoxy group in liguroside A was reduced by using triphenylphosphine, the resultant compound, kudingoside B, showed a lower inhibitory effect on the enzyme. These results strongly suggest the involvement of the hydroperoxy group in the irreversible inhibition of the catalytic activity of leukocyte-type 12-lipoxygenase by the monoterpene glycosides contained in the Qing Shan Lu Shui tea.
Keywords: Qing Shan Lu Shui; Ligustrum robustum; liguroside; monoterpene glycoside; hydroperoxy group; leukocyte-type 12-lipoxygenase; irreversible inhibition Qing Shan Lu Shui; Ligustrum robustum; liguroside; monoterpene glycoside; hydroperoxy group; leukocyte-type 12-lipoxygenase; irreversible inhibition

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MDPI and ACS Style

Kawakami, Y.; Otsuki, A.; Mori, Y.; Kanzaki, K.; Suzuki-Yamamoto, T.; Fang, D.Z.; Ito, H.; Takahashi, Y. Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea. Molecules 2019, 24, 304. https://doi.org/10.3390/molecules24020304

AMA Style

Kawakami Y, Otsuki A, Mori Y, Kanzaki K, Suzuki-Yamamoto T, Fang DZ, Ito H, Takahashi Y. Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea. Molecules. 2019; 24(2):304. https://doi.org/10.3390/molecules24020304

Chicago/Turabian Style

Kawakami, Yuki, Akemi Otsuki, Yoshiko Mori, Keita Kanzaki, Toshiko Suzuki-Yamamoto, Ding Zhi Fang, Hideyuki Ito, and Yoshitaka Takahashi. 2019. "Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea" Molecules 24, no. 2: 304. https://doi.org/10.3390/molecules24020304

APA Style

Kawakami, Y., Otsuki, A., Mori, Y., Kanzaki, K., Suzuki-Yamamoto, T., Fang, D. Z., Ito, H., & Takahashi, Y. (2019). Involvement of the Hydroperoxy Group in the Irreversible Inhibition of Leukocyte-Type 12-Lipoxygenase by Monoterpene Glycosides Contained in the Qing Shan Lu Shui Tea. Molecules, 24(2), 304. https://doi.org/10.3390/molecules24020304

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