Top

Published in:

01-03-2018 | Original Paper

Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities

Authors: Ayano Sasaki, Yoshi Yamano, Sachiko Sugimoto, Hideaki Otsuka, Katsuyoshi Matsunami, Takakazu Shinzato

Published in: Journal of Natural Medicines | Issue 2/2018

Abstract

From the EtOAc-soluble fraction of a MeOH extract of the leaves of Breynia officinalis, five new compounds (1–5) along with 11 known compounds (6–16) were isolated. The structures of the new compounds were elucidated by spectroscopic methods and compounds 1–3 were found to be acylated hydroquinone apiofuranosylglucopyranosides, while compound 4 was an acylated hydroquinone glucopyranoside. Compound 5 was shown to be butyl p-coumarate and this seems to be its first isolation from a natural source. The tyrosinase inhibitory activity of all of the isolated compounds was assayed, and the activity was significant in p-coumarate derivatives. The most active compound, compound 3, also inhibited melanogenesis in an in vivo whole animal model, zebrafish.

Chang PC, Wu CC (1979) Herbs of Taiwan in color, vol 1. Taipei, Nan Cun (South Villa) Trade, p 99

Morikawa H, Kasai R, Otsuka H, Hirata E, Shinzato T, Aramoto M, Takeda Y (2004) Terpenic and phenolic glycosides from leaves of Breynia officinalis HEMSL. Chem Pharm Bull 52:1086–1090CrossRef

Mizutani K, Yuda M, Tanaka O, Saruwatari Y, Fuwa T, Jia M-R, Ling Y-K, Pu X-F (1998) Chemical studies on Chinese traditional medicine, dangshen. I.: isolation of (Z)-3- and (E)-2-hexenyl β-d-glucosids. Chem Pharm Bull 36:2689–2690CrossRef

Ma S-J, Mizutani M, Hiratake J, Hayashi K, Yagi K, Watanabe N, Sakata K (2001) Substrate specificity of β-primeverosidase, a key enzyme in aroma formation during oolong tea and black tea manufacturing. Biosci Biotechnol Biochem 65:2719–2729CrossRef

He Z-D, Yang C-R (1991) Brandioside, a phenylpropanoid glycoside from Brandisia hancei. Phytochemistry 30:701–702CrossRef

Oyama K, Watanabe N, Yamada T, Suzuki M, Sekiguchi Y, Kondo T, Yoshida K (2015) Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate. Tetrahedron 71:3120–3130CrossRef

Evtushenko EV (2012) Regioselective benzoylation of glycopyranosides by benzoic anhydride in the presence of Cu(CF₃COO)₂. Carbohyd Res 359:111–119CrossRef

Yang R-L, Li N, Ye M, Zong M-H (2010) Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum. J Mol Catalysis B: Enzymatic 67:41–44CrossRef

Verotta L, Orsini F, Pelizzoni F, Torri G, Rogers CB (1999) Polyphenolic glycosides from African Proteaceae. J Nat Prod 62:1526–1531CrossRef

10.

Ahmed AS, Nakamura N, Meselhy MR, Makhboul MA, El-Emary N, Hattori M (1988) Phenolic constituents from Grevillea robusta. Phytochemistry 53:149–154CrossRef

11.

Shimomura H, Sashida Y, Adachi T (1988) Phenylpropanoid glucose esters from Prunus buergeriana. Phytochemistry 27:641–644CrossRef

12.

Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Kuriki T (2003) Syntheses of arbutin-α-glycosides and a comparison of their inhibitory effects with those of α-arbutin and arbutin on human tyrosinase. Chem Pharm Bull 51:798–801CrossRef

13.

Zhong X-N, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y (1998) Hydroquinone glycosides from leaves of Myrsine seguinii. Phytochemistry 49:2149–2153CrossRef

14.

Kiuchi F, Nakamura N, Tsuda Y, Kondo K, Yoshimura H (1988) Studies on crude drugs effective on visceral larva Migrans. II.: larvicidal principles in Kaempferiae rhizoma. Chem Pharm Bull 36:412–415CrossRef

15.

Tawata S, Taira S, Kobamoto N, Zhu J, Ishihara Toyama S (1996) Synthesis and antifungal activity of cinnamic acid esters. Biosci Biotech Biochem 60:909–910CrossRef

16.

Pomerants SH (1963) Separation, purification, and properties of two tyrosinases from hamster melanoma. J Biol Chem 238:2351–2357

17.

Choi T-Y, Kim J-H, Ko DH, Kim C-H, Hwang J-S, Ahn S, Kim SY, Kim C-D, Lee J-H, Yoon T-J (2007) Zebrafish as a new model for phenotype-based screening of melanogenic regulatory compounds. Pigment Cell Res 20:120–127CrossRef

18.

Westerfield M (2007) The zebrafish book: a guide for the laboratory use of zebrafish (Danio rerio), 5th edn. University of Oregon Press, Eugene

Title: Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities
Authors: Ayano Sasaki
Yoshi Yamano
Sachiko Sugimoto
Hideaki Otsuka
Katsuyoshi Matsunami
Takakazu Shinzato
Publication date: 01-03-2018
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 2/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-017-1148-8

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities

Abstract

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 2/2018

Correction to: Comparison of glycyrrhizin content in 25 major kinds of Kampo extracts containing Glycyrrhizae Radix used clinically in Japan

Two new aromatic glycosides, elengiosides A and B, from the flowers of Mimusops elengi

Correction to: Ephedra Herb extract activates/desensitizes transient receptor potential vanilloid 1 and reduces capsaicin-induced pain

Rigenolides D–H, norsecoiridoid and secoiridoids from Gentiana rigescens Franch

Methylquercetins stimulate melanin biosynthesis in a three-dimensional skin model

Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells