www.elsevier.com/locate/biochemsysecoBiochemical Systematics and Ecology 34 (2006) 177e179

Chemical constituents of Abrus mollis Hance

Jing Wen, Hai-Ming Shi, Peng-Fei Tu*

School of Pharmaceutical Sciences, Peking University Health Science Center, Department of Natural Medicine, No. 38,

Xueyuan Road, Beijing 100083, China

Received 22 March 2005; accepted 6 August 2005

Keywords: Abrus mollis; Leguminosae; Flavone; Chromone C-glycoside; Flavone C-glycoside; Alkaloid

1. Subject and source

The genus Abrus Adans. (Leguminosae) includes 17 species, mainly distributed in the pantropics. Four species,Abrus precatorius Linn., Abrus pulchellus Wall., Abrus mollis Hance, and Abrus cantoniensis Hance, grow in China(Zhu, 2004). The aerial parts of A. mollis Hance were collected in Yulin, Guangxi province, China, in July 2004. Theplant materials were identified by one of us (Prof. P.-F. Tu). A voucher specimen (No. 20040707) is deposited in theherbarium of Peking University Modern Research Center for Traditional Chinese Medicine.

2. Previous work

A. mollis is widely distributed in the region of Southern China. Previous phytochemical investigations of this planthave yielded ethyl tetracosanoate, melissic acid, palmitic acid, stearic acid, lupeol, stigmasterol, oleanolic acid, ur-solic acid, 8-methylretusin-7-O-b-D-glucopyranoside, retusin 8-methyl ether, 4#,7,8-trimethoxyisoflavone and afror-mosin (Lu et al., 2003, 2004).

3. Present study

Dried aerial plant material (20 kg) was extracted three times with 70% EtOH for 2 h each time. Removal of thesolvent under reduced pressure gave a residue (1 kg), which was suspended subsequently in water. The aqueous sus-pension was partitioned successively with petroleum ether, EtOAc and n-BuOH. The petroleum ether-soluble fractionwas concentrated and subjected to Si gel column chromatography eluting with petroleum ethereMe2CO (10:1/ 1:1)to afford compound 1 (15 mg). The EtOAc-soluble fraction was concentrated and subjected to Si gel column chroma-tography eluting with CHCl3eMeOH (1:0/ 2:1) to yield six fractions. Fraction 2 was purified by repeated SephadexLH-20 column chromatography eluting with MeOH to afford compounds 2 (8.1 mg), 3 (4.2 mg) and 4 (12.5 mg).

* Corresponding author. Tel./fax: þ86 10 82802750.

E-mail address: pengfeitu@bjmu.edu.cn (P.-F. Tu).

0305-1978/$ - see front matter � 2005 Published by Elsevier Ltd.

doi:10.1016/j.bse.2005.08.007

178 J. Wen et al. / Biochemical Systematics and Ecology 34 (2006) 177e179

Fraction 4 was purified by repeated Sephadex LH-20 column chromatography eluting with MeOH and HPLC to affordcompounds 5 (20.5 mg), 6 (5.0 mg), 7 (11.1 mg) and 8 (5.2 mg). The n-BuOH-soluble fraction was concentrated andsubjected to Si gel column chromatography eluting with CHCl3eMeOH (1:0/ 1:1) to yield six fractions. Fraction 2was purified by HPLC to afford compounds 9 (35.2 mg), and 10 (22.0 mg). Fraction 3 was purified by Sephadex LH-20 column chromatography eluting withMeOH to afford compound 11 (12.5 mg). Fraction 4 was purified by HPLC toafford compounds 12 (45.0 mg), 13 (85.3 mg), and 14 (60.2 mg). Fraction 5 was purified by Sephadex LH-20 columnchromatography eluting with MeOHeH2O (1:1) to afford compound 15 (102.3 mg). Fraction 6 was purified by Se-phadex LH-20 column chromatography eluting with MeOHeH2O (1:1) to afford compound 16 (25.8 mg).

The structures of the 16 isolates, including seven flavones, one isoflavone, two chromone C-glycosides, three fla-vone C-glycosides, one isoflavone O-glycoside and two alkaloids, were identified by a combination of spectroscopicmethods (UV, IR, MS, 1H and 13C NMR) and comparisons with the literature data. They are wogonin (1) (Huang et al.,2003), apigenin (2) (Nakasugi et al., 2000), 7,4#-dihydroxyflavone (3) (Wang et al., 1996), isoscutellarein-8-methylether (4) (Stevens et al., 1999), liquiritigenin (5) (Yahara et al., 1989), isoliquiritigenin (6) (Yahara et al., 1989), 7,8-dihydroxy-4#-methoxy-isoflavone (7) (Tolleson et al., 2002), 3#,4#-dihydroxy-7-methoxyflavone (8) (van Acker et al.,2000), isobiflorin (9) (Zhang and Chen, 1997), biflorin (10) (Zhang and Chen, 1997), 8,4#-dimethoxy-isoflavone-7-O-b-D-glucopyranoside (11) (Lu et al., 2004), apigenin 6,8-di-C-b-D-glucopyranoside (12) (Xie et al., 2003), apigenin6-C-a-L-arabinopyranosyl-8-C-b-D-glucopyranoside (13) (Xie et al., 2003), apigenin 6-C-b-D-glucopyranosyl-8-C-a-L-arabinopyranoside (14) (Xie et al., 2003), abrine (15) (Ma et al., 1998), and N,N,N-trimethyl tryptophan (16) (Maet al., 1998), respectively.

4. Chemotaxonomic significance

Except for 8,4#-dimethoxy-isoflavone-7-O-b-D-glucopyranoside (11), none of isolates had previously been re-ported to be present in A. mollis. The results of the present study support the conclusions of Wollenweber and Dietz(1981) that liquiritigenin (5) and isoliquiritigenin (6) are characteristic flavonoid constituents of the Leguminosaefamily. Isobiflorin (9) and biflorin (10) are relatively rare in nature. Isobiflorin (9) has only been isolated from Eugeniacaryophyllata (Myrtaceae) (Zhang and Chen, 1997; Kim et al., 2001), Syzygium aromaticum (Myrtaceae) (Oya et al.,1997), Eucalyptus cypellocarpa (Myrtaceae) (Ito et al., 2000) and Aloe vera (Liliaceae) (Okamura et al., 1998). Bi-florin (10) has only been found in E. caryophyllata (Myrtaceae) (Zhang and Chen, 1997; Kim et al., 2001), S. aroma-ticum (Myrtaceae) (Tanaka et al., 1993; Oya et al., 1997), Baeckea frutescens (Myrtaceae) (Satake et al., 1999),Capraria biflora (Scrophulariaceae) (Fonseca et al., 2003) and Pancratium biflorum (Amaryllidaceae) (Ghosalet al., 1983). Compounds 12, 13 and 14 are widespread in the plant kingdom but so far they have not been reportedfrom the genus Abrus. Abrine (15) has been reported from A. cantoniensis (Yu et al., 1962) and A. precatorius (Kinjoet al., 1991; Ma et al., 1998), and Gastrolobium callistachys (Leguminosae) (Cannon and Williams, 1982). Thus,abrine (15) may be a useful taxonomic marker for this genus.

Acknowledgements

This work was financed in part by the Ministry of Science and Technology of China (No. 2004AA2Z3730).

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