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Phytochemical communication
Abstract
An investigation of Agave americana and Agave barbadensis resulted in the isolation of a new
homoisoflavanoid, 7-hydroxy-3-(4-methoxybenzyl)-chroman (3), together with known compounds
7-hydroxy-3-(4-methoxybenzyl)-chroman-4-one (1), 5,7-dihydroxy-3-(4-methoxybenzyl)-chroman-
4-one (2), cantalasaponin-1 (4), and 2-hydroxy-butanedioic acid-1-methyl ester (5).
D 2005 Elsevier B.V. All rights reserved.
1. Plant
We used Agave americana (Agavaceae) aerial parts and Agave barbadensis rhizomes,
collected in 2000 in the parishes of St. Phillip and St. Lucy, respectively, in Barbados. Dr.
Claire Durant identified the plants and voucher specimens (Agave-2 and Agave-1,
respectively) deposited in Tanaud Ireland, Inc., University of the West Indies, Cave Hill
Campus.
* Corresponding author.
E-mail address: wtinto@uwichill.edu.bb (W.F. Tinto).
0367-326X/$ - see front matter D 2005 Elsevier B.V. All rights reserved.
doi:10.1016/j.fitote.2005.04.013
W.F. Tinto et al. / Fitoterapia 76 (2005) 594–597 595
Several Agave spp. have been used in the treatment of scabies, tumors, syphilis, and
dysentery, and as insecticides. They are also a source of fiber and produce steroidal
sapogenins and saponins, the raw materials for steroid hormone synthesis [1].
Previously isolated constituents are steroidal sapogenins and saponins [2,3], chro-
mones, alcohols, and esters [4–6]. No phytochemical study on A. barbadensis has been
reported.
Newly isolated constituents from the EtOAc extract of A. barbadensis rhizomes were:
7-hydroxy-3-(4-methoxybenzyl)-chroman-4-one (1) (yield: 0.0007%) [7,8], 5,7-dihy-
droxy-3-(4-methoxybenzyl)-chroman-4-one (2) (yield: 0.0004%) [9], 7-hydroxy-3-(4-
methoxybenzyl)-chroman (3) (yield: 0.0003%), and cantalasaponin-1 (4) (yield: 0.014%)
[10]. Newly isolated constituent from the EtOAc extract of the aerial part of A. americana
was 2-hydroxy-butanedioic acid-1-methyl ester (5) (yield: 0.025%).
HO 7 O OCH3
2
1'
5 4 9
R R1
R R1
1 H O
2 OH O
3 H H2
21 O 25
3 1
18 COOCH3
ROOC
19 O OH
OH
OH
O 3
HO O
R
6
HO
OH O 5 H
OH
O 6 CH3
HO
HO
OH 4
596 W.F. Tinto et al. / Fitoterapia 76 (2005) 594–597
Acknowledgements
The authors thank Dr. Alex Young of the Department of Chemistry, University of
Toronto, for MS measurements, and Dr. Claire Durant Tanaud Research Unit, a subsidiary
of Shire-Biochem, for assistance with the collection and identification of the plants.
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