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Molecules 2000, 5(3), 605-607; doi:10.3390/50300605

Article
Phytochemical Study Conyza Sophiaefolia. Antiinflammatory Activity
M. J. Simirgiotis, L. S. Favier, P. C. Rossomando, C. E. Tonn, A. Juarez and O. S. Giordano
INTEQUI-CONICET. Fac. de Qca., Bioqca. y Fcia. UNSL. Chacabuco y Pedernera, San Luis, Argentina
Published: 22 March 2000

Abstract

:
From the aerial parts of Conyza sophiaefolia a new alicyclic furan diterpene was isolated and characterized as an E-isomer in C6 of centipedic acid. In addition, the new clerodane type diterpene 12-epi-bacchotricuneatin A as well as two known related diterpenoids were identified. The flavone apigenine was also isolated. Structures were determined on the basis of spectroscopic evidence.

Introduction

The genus Conyza comprises about 50 species, which are mainly distributed in tropical and subtropical areas. It is well known that this genus produces sesquiterpenes, diterpenes, acetogenic lactones, flavones and cumarines.

Experimental

Plant Material

Conyza sophiaefolia (Asteraceae, Asteroidae, Astereae), was harvested in «El Volcán», February 1998, and identified by Ing. L. A. Del Vitto, E. M. Petenatti & O. S. Giordano. A Voucher specimen is deposited at the Herbario of UNSL N° 6758.

Isolation Procedure

The dried ground aerial parts were extracted with Me2CO, the residue obtained was dissolved with MeOH-H2O 9:1 and partitioned with n-hexane (Extract A) and chloroform (Extract B). These residues were subjected, several times, to a combination of chromatography procedures on Si gel 60 using mixtures of n-hexane-ethyl acetate as eluents and Sephadex LH 20 with methanol as eluent.

Result and Discussion

Hawtriwaic acid [1], 2β hidroxyhardwickiic acid [2], apigenin and the diterpenes 1, 12-epi-bacchotricuneatina A and 2 [3] were isolated from extract B. Structures were determinate by EM, 1H y 13C-RMN (Table 1) and confirmed by bidimentional experiments (COSY, NOESY, ROESY, HMBC, HMQC).
The anti-inflammatory activity of all the extracts has been evaluated by paw edema test [4] (Table 2).

References and Notes

  1. Bohlmann, F.; Grenz, M.; Wegner, P.; Jakupovic. Liebigs Ann. Chem. 1983, 2008.
  2. Jolad, D. S.; Timmermann, B. N.; Hoffmann, J. J.; Bates, R. B.; Camou, F. A. Phytochemistry 1988, 27, 1211.
  3. Wagner, H.; Seitz, R.; Lotter, H.; Herz, W. J. Org. Chem. 1978, 43, 3339.
  4. Favier, L.S.; Tonn, C.E.; Guerreiro, E.; Rotelli, A.; Peltzer, L. Planta Medica 1998, 64, 587.
Table 1.
Table 1.
Molecules 05 00605 i001
H/CδH (Compound 1)δC
11.68 br s25.7 q
2 132.1 s
35.19 br t (6.0)124.1 d
42.10 br t (4.0)28.0 t
52.25 m28.7 t
6 131.7 s
76.72 t (7.3)145.6 d
82.35 m27.0 t
92.30 m38.5 t
10 134.4 s
115.20 br t (6.8)125.1 d
122.23 m27.4 t
132.45 br q (7.5)25.1 t
14 128.2 s
156.28 br s111.2 d
167.31 br s142.8 d
177.20 br s139.2 d
181.60 br s15.8 q
19 174.3 s
201.60 br s17.6 q
*200 MHz, C6D6.
*Mass fragments: [M+] m/z=316; -Me=301; -C6H5=247; pirilio+=81; C5H9 +=69
Table 2.
Table 2.
ProductAcute inflammation inhibit %Dunnet’s Test
Acetonic extract1H3Hs.5Hs.7Hs.(a) p<0.02
-3745(b)49(a)
Chloroformic extract A142245(b)35(b) p<0.04
n-hexane extract B-123626(c) p<0.002
Phenylbutazone5565(d)65(c)52(a)(d) p<0.0003
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
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