Top

Published in:

01-04-2013 | Original Paper

Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta

Authors: Yuya Nomoto, Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka

Published in: Journal of Natural Medicines | Issue 2/2013

Abstract

From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A–C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher’s method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity.

Cai W-H, Matsunami K, Otsuka H (2009) Supinaionosides A and B: megastigmane glucosides and supinanitrilosides A–F: hydroxynitrile glucosides from the whole plants of Euphorbia supine Rafinesque. Chem Pharm Bull 57:840–845PubMedCrossRef

Mizutani K, Yuda M, Tanaka O, Saruwatari Y-I, Fuwa T, Jia M-R, Ling Y-K, Pu X-F (1988) Chemical studies on Chinese traditional medicine, dangshen. I. Isolation of (Z)-3- and (E)-2-hexenyl-β-d-glucosides. Chem Pharm Bull 36:2689–2690PubMedCrossRef

Sawabe A, Obata T, Kochika Y, Morita M, Yamashita N, Matsubusa Y, Okamoto T (1998) Glycosides in African dietary leaves, Hibiscus sabdariffa. J Jpn Oil Chem Soc 47:25–30CrossRef

De Marino S, Festa C, Zollo F, Iorizzi M (2009) Phenolic glycosides from Cucumis melo var. inodorus seeds. Phytochem Lett 2:130–133CrossRef

De Tommasi N, Rastrelli L, Cumanda J, Speranza G, Pizza C (1996) Aryl and triterpenic glycosides from Margyricarpus setosus. Phytochemistry 42:163–167PubMedCrossRef

De Rosa S, De Giulio A, Tommonaro G (1996) Aliphatic and aromatic glycosides from the cell cultures of Lycopersicon esculentum. Phytochemistry 42:1031–1034PubMedCrossRef

Trifunovic S, Vajs V, Macura S, Juranic N, Djarmati Z, Jankov R, Milosavljevic S (1998) Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry 49:1299–1304CrossRef

Ninomiya M, Itoh T, Ishikawa S, Saiki M, Narumiya K, Yasuda M, Koshikawa K, Nozawa Y, Koketsu M (2010) Phenolic constituents isolated from Fragaria ananassa Duch. inhibits antigen-stimulated degranulation through direct inhibition of spleen tyrosine kinase activation. Bioorg Med Chem 18:5932–5937PubMedCrossRef

Matsunami K, Otsuka H, Takeda Y (2010) Structural revisions of blumenol C glucoside and byzantionoside B. Chem Pharm Bull 58:438–441PubMedCrossRef

10.

Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C (1988) Studies on the constituents of leaves of Citrus unshiu MARCOV. Chem Pharm Bull 36:5004–5008CrossRef

11.

Yoshikawa M, Shimada H, Saka M, Yoshizumi S, Yamahara J, Matsuda H (1997) Medicinal food stuffs. V. Moroheiya. (1): absolute stereostructures of corchoionosides A, B and C, histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L. (Tiliaceae). Chem Pharm Bull 45:464–469PubMedCrossRef

12.

Akgul Y, Ferreira D, Abourashed EA, Khan IA (2004) Lotaustralin from Rhodiola rosea roots. Fitoterapia 75:612–614PubMedCrossRef

13.

Otsuka H, Yu Q, Matsunami K (2010) Bumaldosoides A, B and C from the leaves of Staphylea bumalda. Heterocycles 80:339–348CrossRef

14.

Peng J, Fan G, Hong Z, Chai Y, Wu Y (2005) Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss. by High-speed counter-current chromatography. J Chromatogr A 1074:111–115PubMedCrossRef

15.

Chung S-K, Kim Y-C, Takaya Y, Terashima K, Niwa M (2004) Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect. J Agric Food Chem 52:4664–4668PubMedCrossRef

16.

Matsuura H, Yoshihara T, Ichihara A, Kikuta Y, Koda Y (1993) Tuber-forming substance in Jerusalem artichose (Helianthus tuberosus L.). Biosci Biotechnol Biochem 57:1253–1256CrossRef

17.

Tsuboi Y, Doi T, Matsunami K, Otsuka H, Shinzato T, Takeda Y (2011) Gallates of isoorientin and (2S)-1,2-propanediol glucoside from the leaves of Schoepfia jasminodora. J Nat Med 65:617–622PubMedCrossRef

18.

Wei K, Li W, Koike K, Liu L, Fu X, Lin L, Chen Y, Nikaido T (2004) Two new galloylglucosides from the leaves of Mallotus fuaretianus. Chem Pharm Bull 52:776–779PubMedCrossRef

19.

Matsunami K, Otsuka H, Kondo K, Shinzato T, Kawahata M, Yamaguchi K, Takeda Y (2009) Absolute configuration of (+)-pinoresinol 4-O-(6″-O-galloyl)-β-d-glucopyranoside, macarangionosides E and F, isolated from the leaves of Macaranga tanarius. Phytochemistry 70:1277–1285PubMedCrossRef

20.

Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096CrossRef

21.

Kasai R, Suzuno M, Asakawa J, Tanaka O (1977) Carbon-13 chemical shifts of isoprenoid-β-d-glycopyranosides and -β-d-mannopyranosides. Stereochemical influences of aglycone alcohols. Tetrahedron Lett 18:175–178

22.

Fiorentino A, D’Abrosca B, Pacifico S, Mastellone C, Piscopo V, Caputo R, Monaco P (2008) Isolation and structure elucidation of antioxidant polyphenols from quince (Cydonia vulgaris) peels. J Agric Food Chem 56:2660–2667PubMedCrossRef

23.

Nakamura S, Zhang Y, Matsuda H, Ninomiya K, Muraoka O, Yoshikawa M (2011) Chemical structures and hepatoprotective effects of constituents from the leaves of Salacia chinensis. Chem Pharm Bull 59:1020–1028PubMedCrossRef

Title: Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta
Authors: Yuya Nomoto
Sachiko Sugimoto
Katsuyoshi Matsunami
Hideaki Otsuka
Publication date: 01-04-2013
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 2/2013
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-012-0692-5

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Hirtionosides A–C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 2/2013

In vivo toxicity and antitumor activity of mangosteen extract

Marine-derived fungal sesterterpenes, ophiobolins, inhibit biofilm formation of Mycobacterium species

Vasorelaxant effects on rat aortic artery by two types of indole alkaloids, naucline and cadamine

Erratum to: Withania somnifera extract attenuates stem cell factor-stimulated pigmentation in human epidermal equivalents through interruption of ERK phosphorylation within melanocytes

Regular ingestion of cinnamomi cortex pulveratus offers gastroprotective activity in mice

Protein tyrosine phosphatase 1B inhibitory activity of Indonesian herbal medicines and constituents of Cinnamomum burmannii and Zingiber aromaticum