Skip to main content
Erschienen in: Journal of Natural Medicines 1/2012

01.01.2012 | Note

New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.

verfasst von: Yoshiki Kashiwada, Fakhruddin Ali Ahmed, Shin-ichiro Kurimoto, Sang-Yong Kim, Hirofumi Shibata, Toshihiro Fujioka, Yoshihisa Takaishi

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2012

Einloggen, um Zugang zu erhalten

Abstract

Two new caffeoyl quinic acid α-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4′-O-α-d-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3′-O-α-d-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses.
Literatur
1.
Zurück zum Zitat Sastri BN (1962) The wealth of India. Council of Scientific and Industrial Research, New Delhi Sastri BN (1962) The wealth of India. Council of Scientific and Industrial Research, New Delhi
2.
Zurück zum Zitat Basu BD, Kirtikar KR (1980) Indian medicinal plants, vol. 1. International Book Distributors, Dehradun, pp 676–83 Basu BD, Kirtikar KR (1980) Indian medicinal plants, vol. 1. International Book Distributors, Dehradun, pp 676–83
3.
Zurück zum Zitat Vaidyaratnam PSV (1994) Indian medicinal plants: a compendium of 500 species, vol. 4. Orient Longman, Madras, pp 59–64 Vaidyaratnam PSV (1994) Indian medicinal plants: a compendium of 500 species, vol. 4. Orient Longman, Madras, pp 59–64
4.
Zurück zum Zitat Anwar F, Bhanger MI (2003) Analytical characterization of Moringa oleifera seed oil grown in temperate regions of Pakistan. J Agric Food Chem 51:6558–6563PubMedCrossRef Anwar F, Bhanger MI (2003) Analytical characterization of Moringa oleifera seed oil grown in temperate regions of Pakistan. J Agric Food Chem 51:6558–6563PubMedCrossRef
5.
Zurück zum Zitat Anwar F, Ashraf M, Bhanger MI (2005) Interprovenance variation in the composition of Moringa oleifera oilseeds from Pakistan. J Am Oil Chem Soc 82:45–51CrossRef Anwar F, Ashraf M, Bhanger MI (2005) Interprovenance variation in the composition of Moringa oleifera oilseeds from Pakistan. J Am Oil Chem Soc 82:45–51CrossRef
6.
Zurück zum Zitat Eilert U, Wolters B, Nahrstedt A (1981) Moringa oleifera and Moringa stenopetala. Planta Med 42:55–61PubMedCrossRef Eilert U, Wolters B, Nahrstedt A (1981) Moringa oleifera and Moringa stenopetala. Planta Med 42:55–61PubMedCrossRef
7.
Zurück zum Zitat Faizi S, Siddiqui BS, Saleem R, Siddiqui S, Aftab K, Gilani AH (1994) Novel hypotensive agents, niazimin A, niazimin B, niazicin A and niazicin B from Moringa oleifera: isolation of first naturally occurring carbamates. J Chem Soc Perkin Trans 1:3035–3040CrossRef Faizi S, Siddiqui BS, Saleem R, Siddiqui S, Aftab K, Gilani AH (1994) Novel hypotensive agents, niazimin A, niazimin B, niazicin A and niazicin B from Moringa oleifera: isolation of first naturally occurring carbamates. J Chem Soc Perkin Trans 1:3035–3040CrossRef
8.
Zurück zum Zitat Faizi S, Siddiqui BS, Saleem R, Aftab K, Shaheen F, Gilani AH (1998) Hypotensive constituents from the pods of Moringa oleifera. Planta Med 64:225–228PubMedCrossRef Faizi S, Siddiqui BS, Saleem R, Aftab K, Shaheen F, Gilani AH (1998) Hypotensive constituents from the pods of Moringa oleifera. Planta Med 64:225–228PubMedCrossRef
9.
Zurück zum Zitat Guevara AP, Vargas C, Sakurai H, Fujiwara Y, Hashimoto K, Maoka T, Kozuka M, Ito Y, Tokuda H, Nishino H (1999) An antitumor promoter from Moringa oleifera Lam. Mutat Res Fundam Mol Mech Mutagen 440:181–188 Guevara AP, Vargas C, Sakurai H, Fujiwara Y, Hashimoto K, Maoka T, Kozuka M, Ito Y, Tokuda H, Nishino H (1999) An antitumor promoter from Moringa oleifera Lam. Mutat Res Fundam Mol Mech Mutagen 440:181–188
10.
Zurück zum Zitat Murakami A, Kitazono Y, Jiwajinda S, Koshimizu K, Ohigashi H (1998) Niaziminin, a thiocarbamate from the leaves of Moringa oleifera, holds a strict structural requirement for inhibition of tumor promoter-induced Epstein-Barr virus activation. Planta Med 64:319–323PubMedCrossRef Murakami A, Kitazono Y, Jiwajinda S, Koshimizu K, Ohigashi H (1998) Niaziminin, a thiocarbamate from the leaves of Moringa oleifera, holds a strict structural requirement for inhibition of tumor promoter-induced Epstein-Barr virus activation. Planta Med 64:319–323PubMedCrossRef
11.
Zurück zum Zitat Cheenpracha S, Park EJ, Yoshida WY, Barit C, Wall M, Pezzuto JM, Chang LC (2010) Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits. Bioorg Med Chem 18:6598–6602PubMedCrossRef Cheenpracha S, Park EJ, Yoshida WY, Barit C, Wall M, Pezzuto JM, Chang LC (2010) Potential anti-inflammatory phenolic glycosides from the medicinal plant Moringa oleifera fruits. Bioorg Med Chem 18:6598–6602PubMedCrossRef
12.
Zurück zum Zitat Morishita H, Iwahashi H, Osaka N, Kido R (1984) Chromatographic separation and identification of naturally occurring chlorogenic acids by 1H nuclear magnetic resonance spectroscopy and mass spectrometry. J Chromatogr A 315:253–260CrossRef Morishita H, Iwahashi H, Osaka N, Kido R (1984) Chromatographic separation and identification of naturally occurring chlorogenic acids by 1H nuclear magnetic resonance spectroscopy and mass spectrometry. J Chromatogr A 315:253–260CrossRef
13.
Zurück zum Zitat Jaramillo K, Dawid C, Hofmann T, Fujimoto Y, Osorio C (2011) Identification of antioxidative flavonols and anthocyanins in Sicana odorifera fruit peel. J Agric Food Chem 59:975–983PubMedCrossRef Jaramillo K, Dawid C, Hofmann T, Fujimoto Y, Osorio C (2011) Identification of antioxidative flavonols and anthocyanins in Sicana odorifera fruit peel. J Agric Food Chem 59:975–983PubMedCrossRef
14.
Zurück zum Zitat Burkard W, Victor W, Rudolf G, Karl H (1989) Malonated flavonol glycosides and 3,5-dicaffeoylquinic acid from pears. Phytochemistry 28:663–664CrossRef Burkard W, Victor W, Rudolf G, Karl H (1989) Malonated flavonol glycosides and 3,5-dicaffeoylquinic acid from pears. Phytochemistry 28:663–664CrossRef
15.
Zurück zum Zitat Liu X, Ye W, Yu B, Zhao S, Wu H, Che C (2004) Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata. Carbohydr Res 339:891–895PubMedCrossRef Liu X, Ye W, Yu B, Zhao S, Wu H, Che C (2004) Two new flavonol glycosides from Gymnema sylvestre and Euphorbia ebracteolata. Carbohydr Res 339:891–895PubMedCrossRef
16.
17.
Zurück zum Zitat Christiane Goedl C, Nidetzky B (2009) Sucrose phosphorylase harbouring a redesigned, glycosyltransferase-like active site exhibits retaining glucosyl transfer in the absence of a covalent intermediate. ChemBioChem 10:2333–2337PubMedCrossRef Christiane Goedl C, Nidetzky B (2009) Sucrose phosphorylase harbouring a redesigned, glycosyltransferase-like active site exhibits retaining glucosyl transfer in the absence of a covalent intermediate. ChemBioChem 10:2333–2337PubMedCrossRef
18.
Zurück zum Zitat Hu Y, Walker S (2002) Remarkable structural similarities between diverse glycosyltransferases. Chem Biol 9: 1287–1296 Hu Y, Walker S (2002) Remarkable structural similarities between diverse glycosyltransferases. Chem Biol 9: 1287–1296
19.
Zurück zum Zitat Streb S, Egli B, Eicke S, Zeeman CC (2009) The debate on the pathway of starch synthesis: a closer look at low-starch mutants lacking plastidial phosphoglucomutase supports the chloroplast-localized pathway. Plant Physiol 151:1769–1772PubMedCrossRef Streb S, Egli B, Eicke S, Zeeman CC (2009) The debate on the pathway of starch synthesis: a closer look at low-starch mutants lacking plastidial phosphoglucomutase supports the chloroplast-localized pathway. Plant Physiol 151:1769–1772PubMedCrossRef
20.
Zurück zum Zitat Ullah N, Ahmed S, Muhammad P, Ahmed Z, Nawaz HR, Malik A (1999) Coumarinolignoid glycoside from Daphne oleoides. Phytochemistry 51:103–105CrossRef Ullah N, Ahmed S, Muhammad P, Ahmed Z, Nawaz HR, Malik A (1999) Coumarinolignoid glycoside from Daphne oleoides. Phytochemistry 51:103–105CrossRef
21.
Zurück zum Zitat Shi SY, Zhou Q, Peng H, Zhou CX, Hu MH, Tao QF, Hao XJ, Stöckigt J, Zhao Y (2007) Four new constituents from Taraxacum mongolicum. Chin Chem Lett 18:1367–1370 Shi SY, Zhou Q, Peng H, Zhou CX, Hu MH, Tao QF, Hao XJ, Stöckigt J, Zhao Y (2007) Four new constituents from Taraxacum mongolicum. Chin Chem Lett 18:1367–1370
22.
Zurück zum Zitat Cuong NX, Nhiem NX, Thao NP, Nama NH, Dat NT, Anh HLT, Huong LM, Kiem PV, Minh CV, Wonc JH, Chung WY, Kim YH (2010) Inhibitors of osteoclastogenesis from Lawsonia inermis leaves. Bioorg Med Chem Lett 20:4782–4784PubMedCrossRef Cuong NX, Nhiem NX, Thao NP, Nama NH, Dat NT, Anh HLT, Huong LM, Kiem PV, Minh CV, Wonc JH, Chung WY, Kim YH (2010) Inhibitors of osteoclastogenesis from Lawsonia inermis leaves. Bioorg Med Chem Lett 20:4782–4784PubMedCrossRef
23.
Zurück zum Zitat She G, Guo Z, Lv H, She D (2009) New flavonoid glycosides from Elsholtzia rugulosa Hemsl. Molecules 14:4190–4196PubMedCrossRef She G, Guo Z, Lv H, She D (2009) New flavonoid glycosides from Elsholtzia rugulosa Hemsl. Molecules 14:4190–4196PubMedCrossRef
24.
Zurück zum Zitat Myers RW, Lee RT, Lee YC, Thomas GH, Reynolds LW, Uchida Y (1980) The synthesis of 4-methylumbelliferyl α-ketoside of N-acetylneuraminic acid and its use in a fluorometric assay for neuraminidase. Anal Biochem 101:166–174PubMedCrossRef Myers RW, Lee RT, Lee YC, Thomas GH, Reynolds LW, Uchida Y (1980) The synthesis of 4-methylumbelliferyl α-ketoside of N-acetylneuraminic acid and its use in a fluorometric assay for neuraminidase. Anal Biochem 101:166–174PubMedCrossRef
25.
Zurück zum Zitat Reed L, Muench H (1938) A simple method of estimating fifty percent endpoints. Am J Hygiene 27:493–497 Reed L, Muench H (1938) A simple method of estimating fifty percent endpoints. Am J Hygiene 27:493–497
Metadaten
Titel
New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.
verfasst von
Yoshiki Kashiwada
Fakhruddin Ali Ahmed
Shin-ichiro Kurimoto
Sang-Yong Kim
Hirofumi Shibata
Toshihiro Fujioka
Yoshihisa Takaishi
Publikationsdatum
01.01.2012
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2012
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-011-0563-5

Weitere Artikel der Ausgabe 1/2012

Journal of Natural Medicines 1/2012 Zur Ausgabe