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BiochemicalSystematicsand Ecology, VoI.25, No. 2, pp.

185-186,1997
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Flavonoids from Buddleja parviflora*

A M I R A ARCINIEGAS, AIDI~ AVENDAI~IO, A N A - L . PISREZ-CASTORENA and


A L F O N S O R O M O DE VIVART
Instituto de Quimica, Universidad Nacional AutOnoma de M6xico, Circuito Exterior, Ciudad Universitaria,
Coyoac~n 04510, M6xico, D.F.

Key Word Index--Buddleja parvif/ora; Loganiaceae; flavanones; phenyl propanoids; iridoids.

S u b j e c t s and S o u r c e
In a previous study of the genus Buddleja (Romo de Vivar et aL, 1995, 1996), we isolated (+) -cyclocolorenone
and 1 -hydroxycyclocolorenone. In the present study, we collected Buddleja parviflora H.B.K. near the border
between Distrito Federal and the State of Mexico along the Mexico-Oaxtepec highway in March 1995. A
voucher specimen has been deposited at Iztacala Herbarium (IZTA 25080).

Previous Work
The leaves of species of Buddleja studied to date contain iridoids, flavones and phenyl propanoids (Houghton,
1984). B. parviflora (Tepozan), which is used in popular medicine as an anti-rheumatic agent, has not been
studied chemically.

Present Study
Dried and ground bark (411.6 g) was extracted with hexane, EtOAc and MeOH. The hexane extract (2.44 g)
chromatographed over Kieselgel G eluting with mixtures of hexane-EtOAc afforded ~-sitosterol and stigma-
sterol as a mixture (162 mg). The EtOAc extract (3.02 g) after successive column chromatography using as
eluent mixtures of hexane-EtOAc, EtOAc-MeOH, CH2CI2-MeOH and CHCI3-MeOH gave 9mg vanilloyl
ajugol (1: Nishimura et al., 1989) and 25mg verbascoside (2a: Miyase et al,, 1982). The MeOH extract
(36.48 g) was purified as described above yielding 1 (104.9 rag), 2a (930 mg), leucoceptoside A (35.8 mg,
2b; Miyase et al., 1982), O-methyl catalpol (37.9 rag, 3; Duff et aL, 1965) and aucubin (16.13 mg, 4; Scarpati
and Esposito, 1967; Bailleul et al., 1977). Dried and ground leaves (630 g) were extracted with hexane, EtOAc
and MeOH. Each extract was purified as described. The EtOAc extract (14.64 g) gave 2a (1.15 g), eriodictyol
(7.4mg, 5a; Mabry et aL, 1970), glucohesperetin (23 mg, 5b; Lewinsohn eta/., 1986) and pyracanthoside
(13 mg, 5c; H6rhammer et al., 1966). The MeOH extract (188 g) yielded glucose (335 rag), 2a (19.793 g), 5b
(2.39g), 5c (1.575g) and linarine (303.9mg, 5d; Baker et al., 1951; Geissman, 1962). Glucose and com-
pounds 2a, 3, 4 and 6d were identified by comparison with authentic samples and spectroscopic data. Com-
pounds 1, 2b and 5a were identified by comparison of their spectroscopic data with those described in the
literature (IR, MS, 1H-NMR and 13C-NMR). Flavanones 5b and 5c were identified by their spectroscopy
features such as 1H-NMR, 13C-NMR, nOe effect and IRHETCOR experiments, and by their acetylation and
hydrolysis products.

Chemotaxonomic Significance
The genus Buddleja consists of about 100species distributed in the tropics of America, Asia and Africa. Most
are used in popular medicine. A chemical examination of B. parviflora, which is widely distributed in Mexico,
revealed the presence of the flavanones eriodictyol (5a), glucohesperetin (5b) and pyracanthoside (5c). In
addition, we found common constituents of Buddleja such as iridoids, phenyl propanoids and flavones.
Though flavanones are not common constituents of Buddleja, positive confirmation that their presence is

*Contribution No. 1473 of the Instituto de Quimica, U.N.A.M.


tCorresponding author.

(Received 3 October 1996; accepted 4 December 1996)


185
186 A. ARCINIEGASETAL.

OH
OH
0
o J----o o -'---x

OGluc
OH OH

2a R=H
2b R=Me

MeO HO

HO f OGluc

3 4

Sa RI=H R2--OH R3=H


o
5b R1--Gluc Rz==OH Rs=Me
5c Rt--Gtuc Rz=OH R3=H
5d Rt--~tinosyl R2=H R3=H A2,3

characteristic of the species is not possible on the basis of one growing state, sprouting alone. Further inves-
tigation of the plant is required, in other stages of growth.

Acknowledgements---We thank Ruben Gavi~o, Isabel Ch~vez, Beatriz Quiroz, Hector Rios, Ma. del Rocio
Patifio, Hugo Ramirez, Javier P~rez and Luis Velasco, for their technical assistance, and DGAPA, U.N.A.M.
(Grant No. IN204794) for partial financial support.

References
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W., Hemming, R. and Ollis, W. D. (1951) J. Chem. Soc. 691; Duff, R. B., Bacon, J. S., Mundie, C.
M. Farmer, V. C., Russell, J. D. and Forrester, A. R. (1965) Biochem. J. 96, 1; Geissman, T. A. (1962)
The Chemistry of Flavonoid Compounds, p. 322. Macmillan, New York; H6rhammer, L., Wagner, H. and
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