Biochemical Systematics and Ecology 30 (2002) 375–377 www.elsevier.com/locate/biochemsyseco
4⬙-Hydroxymaysin and cassiaoccidentalin B, two unusual C-glycosylflavones from Mimosa pudica (Mimosaceae) Annelise Lobstein a, Bernard Weniger a, Byung H. Um a, Marc Steinmetz a, Lieve Declercq b, Robert Anton a,* a
Laboratoire de Pharmacognosie, Faculte´ de Pharmacie, Strasbourg, BP 24, F-67401 Illkirch Cedex, France b Biological Research Department Europe, Estee Lauder Coordination Center, Nijverheidsstraat 15, B-2260 Oevel, Belgium Received 2 January 2001; accepted 10 May 2001
Keywords: Mimosa pudica; Mimosaceae; Flavonoids
1. Subject and source Mimosa pudica L. (Mimosaceae), commonly known as “sensitive plant”, is native to Middle America and is now widely distributed in all tropical areas (Morton, 1981). Aerial parts of this species were collected near Besinkara Ambalafary (Madagascar) in 1995 (batch A) and near Cali (Colombia) in 1997 (batch B). Voucher specimens (LG 2834 No. 61296 for batch A and BW113 for batch B) were deposited in the Herbarium of the Botanical and Zoological Park of Zsimbazaza (Madagascar) and in the Herbarium (CUVC) of the University del Valle (Colombia), respectively. 2. Previous work Previous work on Mimosa pudica has led to the isolation of actin-like turgorins responsible for the typical leaf-folding movement (Fleurat-Bessard et al., 1988), an * Corresponding author. Tel.: +33-3-90-24-42-41; fax: +33-3-90-24-43-11. E-mail address:
[email protected] (R. Anton). 0305-1978/02/$ - see front matter 2002 Published by Elsevier Science Ltd. PII: S 0 3 0 5 - 1 9 7 8 ( 0 1 ) 0 0 0 8 6 - 2
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alkaloid (Southon and Buckingham, 1989), a triterpenoid glycoside (Jiang et al., 1990) and two flavonoid glycosides (Englert et al., 1994).
3. Present study Dried aerial parts from batch A and batch B were ground separately and each sample was exhaustively extracted with ethanol 30%. The corresponding alcoholic residues were directly subjected to reversed-phase preparative HPLC (C18 preparative column) eluted with a gradient of 15–30% acetonitrile in water adjusted to pH 3 with trifluoroacetic acid in 60 min, 15 ml/min, detection 330 nm and finally purified using Sephadex LH-20 with methanol as mobile phase. The phytochemical fractionation of the aerial parts of Mimosa pudica originating from Madagascar (sample A, 50 g) led to the isolation of three O-glycosyl flavonoids: isoquercitrin (3 mg), avicularin (4 mg) and apigenin-7-O-β-d-glucoside (6 mg) and of four C-glycosyl flavonoids: 4⬙-OH-maysin (3 mg), cassiaoccidentalin B (3 mg), orientin (9 mg) and isoorientin (6 mg). Similar fractionation of Mimosa pudica material originated from Colombia (sample B, 50 g) led to the isolation of only four O-glycosyl flavonoids: myricetin (74 mg), hyperin (8 mg), avicularin (52 mg) and quercitrin (17 mg). These compounds were identified on the basis of UV, mono- and bidimensional 1 H NMR and 13C-NMR, and mass spectrometry. All the data were consistent with the literature (Harborne, 1994; Agrawal, 1989).
4. Chemotaxonomic significance The results of our study indicated extensive qualitative and quantitative differences in the flavonoid content of the samples of Mimosa pudica aerial parts from Madagascar (sample A) and Colombia (sample B). The phytochemical evaluation of both samples A and B showed the absence of 2⬙-O-rhamnosylorientin and 2⬙-O-rhamnosylisoorientin, two flavones previously isolated from another sample, originating from Vanuatu (Englert et al., 1994). Moreover, the study of the aerial parts of Mimosa pudica from Madagascar (sample A) led to the isolation of 4⬙-hydroxymaysin and cassiaoccidentalin B, two unusual Cglycosidic flavonoids, the last with an unusual 3-keto sugar. The presence of cassiaoccidentalin B was recently reported from aerial parts of Cassia occidentalis L. (Leguminosae) (Hatano et al., 1999) and the maysin derivative was reported in corn silks (Zea mays L., Poaceae) (Snook et al., 1995). Thus, as 4⬙-hydroxymaysin and cassiaoccidentalin B could only be detected in sample A from Madagascar, the occurence of these closely related flavonoids in Mimosa pudica cannot be explained by chemotaxonomical criteria. As 4⬙-hydroxymaysin from Zea mays has been reported to inhibit insect development (Elliger et al., 1980), the presence or absence of these two unusual C-glycosidic flavonoids in
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Mimosa pudica may be rather related with environmental factors, particulary with insect resistance activity.
Acknowledgements Financial support of the Laboratory Estee Lauder is gratefully acknowledged.
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