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Journal of Natural Medicines

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01.01.2008 | Note

Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.

verfasst von: Haizhou Li, Tatsuya Nakashima, Takashi Tanaka, Ying-Jun Zhang, Chong-Ren Yang, Isao Kouno

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2008

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Abstract

Two new maltol glycosides, maltol 6′-O-β-d-apiofuranosyl-β-d-glucopyranoside and maltol 6′-O-(5-O-p-coumaroyl)-β-d-apiofuranosyl-β-d-glucopyranoside, were isolated from Elsholtzia rugulosa Hemsl. along with 11 known compounds including prunasin and amygdalin. The structures were determined on the basis of spectroscopic and chemical evidence. This is the second example of isolation of cyanogenic glycosides from Lamiaceous plants.

Jiangshu New College of Medicine (1985) The dictionary of Chinese Medicine, Shanghai Press of Science and Technology, Shanghai, p 2132

Tanaka N, Sakai H, Murakami T, Saiki Y, Chen CM, Iitaka Y (1986) Chemical and chemotaxonomic studies on pterophyten. LXII. Chemical studies on the substance from Arachniodes maximowiczii Ohwi. Chem Pharm Bull 34:1015–1022

Ulubelen A, Doguc T (1974) Flavonoid compounds from the flowers of Genista lydia. Planta Med 25:39–42PubMedCrossRef

Kikuchi M, Yamauchi Y (1985) Studies on the constituents of Osmanthus species. IV. On the components of the leaves of Osmanthus fortunei Carr. Yakugaku Zasshi 105:542–546

Ulubelen A, Miski M, Neuman P, Mabry TJ (1979) Flavonoids of Salvia tomentosa (Labiatae). J Nat Prod 42:261–263CrossRef

Markham KR, Ternai B, Stanley R, Geiger H, Mabry TJ (1978) Carbon-13 NMR studies of flavonoids—III: naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron 34:1389–1397CrossRef

Ueda M, Okazaki M, Ueda K, Yamamura S (2000) Leaf-closing substance of Albizzia julibrissin Durazz. Tetrahedron 56:8101–8105CrossRef

Miyase T, Ueno A, Takizawa N (1987) Studies on the glycosides of Epimedium grandiflorum Morr. var. thunbergianum (Miq.) Nakai I Chem Pharm Bull 35:1109–1117

Ling SK, Tanaka T, Kouno I (2002) New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia. J Nat Prod 65:131–135PubMedCrossRef

10.

Tanaka T, Zhang H, Jiang ZH, Kouno I (1997) Relationship between hydrophobicity and structure of hydrolysable tannins, and association of tannins with crude drug constituents in aqueous solution. Chem Pharm Bull 45:1891–1897PubMed

11.

Jiang ZH, Hirose Y, Iwata H, Sakamoto S, Tanaka T, Kouno I (2001) Caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl glucoses from Balanophora japonica. Chem Pharm Bull 49:887–892PubMedCrossRef

12.

Tanaka T, Morimoto S, Nonaka G, Nishioka I, Yokozawa T, Chung HY, Oura H (1989) Magnesium and ammonium–potassium lithospermates B, the active principles having a uremia-preventive effect from Salvia miltiorrhiza. Chem Pharm Bull 37:340–344

13.

Miller RE, McConville MJ, Woodrow IE (2006) Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (× Lamiaceae). Phytochemistry 67:43–51PubMedCrossRef

14.

Jiang ZH, Tanaka T, Kouno I (1999) New phenylpropanoid glycosides from the fruits of Illicium anisatum. Chem Pharm Bull 47:421–422

15.

Tanaka T, Nakashima T, Ueda T, Tomii T, Kouno I (2007) Chem Pharm Bull 55:899–901

16.

Gutierrez-Venegas G, Kawasaki-Cardenas P, Rita Arroyo-Cruz S, Maldonado-Frias S (2006) Luteolin inhibits lipopolysaccharide actions on human gingival fibroblasts. Eur J Pharmacol 541:95–105PubMedCrossRef

17.

Kim JS, Lee HJ, Lee MH, Kim J, Jin C, Ryu JH (2006) Luteolin inhibits LPS-stimulated inducible nitric oxide synthase expression in BV-2 microglial cells. Planta Med 72:65–68PubMedCrossRef

18.

Odontuya G, Hoult JRS, Houghton PJ (2005) Structure-activity relationship for antiinflammatory effect of luteolin and its derived glycosides. Phytother Res 19:782–786PubMedCrossRef

19.

Hougee S, Sanders A, Faber J, Graus YMF, van den Berg WB, Garssen J, Smit HF, Hoijer MA (2005) Decreased pro-inflammatory cytokine production by LPS-stimulated PBMC upon in vitro incubation with the flavonoids apigenin, luteolin or chrysin, due to selective elimination of monocytes/macrophages. Biochem Pharmacol 69:241–248PubMedCrossRef

20.

Englberger W, Hadding U, Etschenberg E, Graf E, Leyck S, Winkelmann J, Parnham MJ (1988) Rosmarinic acid: a new inhibitor of complement C3-convertase with anti-inflammatory activity. Int J Immunopharm 10:729–737CrossRef

21.

Osakabe N, Yasuda A, Natsume M, Yoshikawa T (2004) Rosmarinic acid inhibits epidermal inflammatory responses: anticarcinogenic effect of Perilla frutescens extract in the murine two-stage skin model. Carcinogenesis 25:549–557PubMedCrossRef

22.

Osakabe N, Takano H, Sanbongi C, Yasuda A, Yanagisawa R, Inoue K, Yoshikawa T (2004) Anti-inflammatory and anti-allergic effect of rosmarinic acid (RA); inhibition of seasonal allergic rhinoconjunctivitis (SAR) and its mechanism. BioFactors 21:127–131PubMed

23.

Yun M, Moon HR, Kim HO, Choi WJ, Kim Y, Park CS, Jeong LS (2005) A highly efficient synthesis of unnatural l-sugars from d-ribose. Tetrahedron Lett 46:5903–5905CrossRef

Titel: Two new maltol glycosides and cyanogenic glycosides from Elsholtzia rugulosa Hemsl.
verfasst von: Haizhou Li
Tatsuya Nakashima
Takashi Tanaka
Ying-Jun Zhang
Chong-Ren Yang
Isao Kouno
Publikationsdatum: 01.01.2008
Verlag: Springer-Verlag
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2008
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-007-0188-x

Springer Medizin

Abstract

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