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Tsafack, Ponou, Teponno, Nono, Jenett-Siems, Melzig, Park, and Tapondjou: Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae)
Original Article

Natural Product Sciences 2017;23(2):113-118.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.2.113

Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae)

Borice Tapondjou Tsafack1, Beaudelaire Kemvoufo Ponou1, Rémy Bertrand Teponno1, Raymond Ngansop Nono1, Kristina Jenett-Siems2, Matthias F. Melzig2, Hee Juhn Park3, ∗, Léon Azefack Tapondjou1, ∗

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

2Institut für Pharmazie (Pharmazeutische Biologie), Freie Universität Berlin, Königin-Luise-Str. 2–4, D-14195 Berlin, Germany

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

∗Author for correspondence 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 29 January 2017       Revised 28 February 2017       Accepted 7 March 2017

Copyright © 2017 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

A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-Δ8,9;14,15;24,28-trien-3β,11β,12α-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol 5α,8α-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-β-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2''-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- (1H and13C), 2D-NMR (1H-1H COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.

Keywords: Desmodium uncinatum, Fabaceae, Tetracyclic triterpenoid, Integracide, Isoflavonoids

References

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Fig. 1.
Chemical structures of compounds isolated from Desmodium uncinatum.
nps-23-113f1.tif
Fig. 2.
Selected HMBC correlations of Integracide K (1).
nps-23-113f2.tif
Table 1.
1H-NMR (400 MHz) and 13C-NMR (100 MHz) data of compound 1 (J in Hz)
Position    
δH δc
1 1.54 (2H, m) 34.2
2 2.18 (1H, m), 1.51 (1H, m) 33.3
3 3.62 (1H, d, J = 9.7; 4.2) 82.7
4   38.8
5 1.55 (1H, m) 50.9
6 1.69 (1H, m) 1.60 (1H, m) 18.4
7 2.32 (1H, m), 2.20 (1H, m) 26.8
8   125.5
9   140.3
10   36.7
11 4.10 (1H, brs) 67.3
12 4.96 (1H, d, J = 1.5) 77.5
13   46.8
14   147.3
15 5.50 (1H, brt) 120.3
16 2.31 (1H, m), 2.00 (1H, m) 36.2
17 1.85 (1H, m) 48.6
18 1.03 (3H, s) 24.0
19 0.99 (3H, s) 17.1
20 1.55 (1H, m) 33.6
21 0.84 (3H, d, J = 6.6) 18.3
22 1.51 (2H, m) 33.6
23 2.01 (1H, m), 1.88 (1H, m) 31.2
24   156.4
25 2.18 (1H, m) 34.9
26 0.98 (3H, d, J = 3.1) 22.4
27 1.00 (3H, d, J = 3.1) 22.3
28 4.71 (1H, brs) 4.66 (1H, brs) 107.8
29 0.74 (3H, s) 16.8
30 0.92 (3H, s) 28.7
31   170.4
32 1.96 (3H, s) 21.2
11-OH 5.31 (1H, d)  

The data were measured in DMSO with reference to TMS;

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