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Kenfack, Ponou, Kühlborn, Teponno, Nono, Fouedjou, Opatz, Park, and Tapondjou: A New Flavonol Glycoside from Tristemma hirtum (Melastomataceae)
Original Article

Natural Product Sciences 2018;24(3):213-218.

Published online: 17 January 2018

DOI: https://doi.org/10.20307/nps.2018.24.3.213

A New Flavonol Glycoside from Tristemma hirtum (Melastomataceae)

Joseph Nandjou Kenfack1, Beaudelaire Kemvoufo Ponou1, Jonas Kühlborn2, Rémy Bertrand Teponno1, Raymond Ngansop Nono1, Romuald Tématio Fouedjou1, Till Opatz2, Hee Juhn Park3, Léon Azefack Tapondjou1

1 Department of Chemistry, Faculty of Science, University of Dschang, Box 67, Dschang, Cameroon

2Johannes Gutenberg University Mainz, Institute of Organic Chemistry, Duesbergweg 10-14, D-55128 Mainz, Germany

3Department of Pharmaceutical Engineering, Sangji University, 26339 Wonju, Korea

∗Author for correspondence Hee Juhn Park, Department of Pharmaceutical Engineering, Sangji University, 26339 Wonju, Korea Tel: +82-33-730-0564; E-mail: hjpark@sangji.ac.kr

Léon Azefack Tapondjou, Department of Chemistry, Faculty of Science, University of Dschang, Box 67, Dschang, Cameroon Tel: +237-675004826; E-mail: tapondjou2001@yahoo.fr

Received 2 May 2018       Revised 8 June 2018       Accepted 11 June 2018

Copyright © 2018 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Chemical investigation of the plant Tristemma hirtum P. Beauv (Melastomataceae) resulted to the isolation of a new flavonol glycoside named quercetin-7-O-α-D-arabinofuranoside (1), together with nine known compounds including 3'-hexadecanoyl-2'-(9aZ)-tetradecanoyl-glycerol 1'-O-[β-D-galactopyranosyl-(1″ → 6″)-α-D-galactopyranoside] (2), arjunolic acid (3), β-sitosterol-3-O-β-D-glucopyranoside (4), terminolic acid (5), quercetin (6), asiatic acid (7), maslinic acid (8), 1β-O-galloylpedunculagin (9) and 6-hydroxyapigenin 7-O-β-D-glucopyranoside (10) from the methanol extract using normal and reversed phase column chromatography. The structures of these compounds were determined by comprehensive interpretation of their spectral data mainly including 1D- 2D-NMR (1H-1H COSY, HSQC, and HMBC) spectroscopic and ESI-TOF-MS mass spectro-metric analysis.

Keywords: Tristemma hirtum, Melastomataceae, flavonol glycoside

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Fig. 1.
Chemical structures of compounds isolated from T. hirtum.
nps-24-213f1.tif
Fig. 2.
Selected HMBC and COSY 1 H-1 H correlations of compound 1.
nps-24-213f2.tif
Table 1.
1 H-NMR (CD3 OD, 500 MHz) and 13 C-NMR (CD3 OD,125 MHz) data of compound 1 (J in Hz)
Position Chemical shift
δ C δ H
2 158.0
3 131.9
4 173.5
5 164.4
6 99.2 6.24 (1H, br s)
7 161.3
8 94.1 6.42 (1H, br s)
9 157.8
10 104.6
1' 121.8
2' 116.1 7.55 (1H, br s)
3' 148.0
4' 158.1
5' 115.2 6.93 (1H, d, J = 8.4 Hz)
6' 121.9 7.52(1H, br s)
1″ 108.2 5.49 (1H, br s)
2″ 82.5 4.35 (1H, br s)
3″ 78.0 3.92 (1H, m)
4″ 84.7 3.87 (1H, m)
5″ 60.7 3.50 (1H, m)3.53(1H, m)
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