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Molecules 2000, 5(3), 605-607; doi:10.3390/50300605
Phytochemical Study Conyza Sophiaefolia. Antiinflammatory Activity
INTEQUI-CONICET. Fac. de Qca., Bioqca. y Fcia. UNSL. Chacabuco y Pedernera, San Luis, Argentina
Published: 22 March 2000
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.
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.
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.
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 , 2β hidroxyhardwickiic acid , apigenin and the diterpenes 1, 12-epi-bacchotricuneatina A and 2  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).
References and Notes
- Bohlmann, F.; Grenz, M.; Wegner, P.; Jakupovic. Liebigs Ann. Chem. 1983, 2008.
- Jolad, D. S.; Timmermann, B. N.; Hoffmann, J. J.; Bates, R. B.; Camou, F. A. Phytochemistry 1988, 27, 1211.
- Wagner, H.; Seitz, R.; Lotter, H.; Herz, W. J. Org. Chem. 1978, 43, 3339.
- Favier, L.S.; Tonn, C.E.; Guerreiro, E.; Rotelli, A.; Peltzer, L. Planta Medica 1998, 64, 587.
|H/C||δH (Compound 1)||δC|
|1||1.68 br s||25.7 q|
|3||5.19 br t (6.0)||124.1 d|
|4||2.10 br t (4.0)||28.0 t|
|5||2.25 m||28.7 t|
|7||6.72 t (7.3)||145.6 d|
|8||2.35 m||27.0 t|
|9||2.30 m||38.5 t|
|11||5.20 br t (6.8)||125.1 d|
|12||2.23 m||27.4 t|
|13||2.45 br q (7.5)||25.1 t|
|15||6.28 br s||111.2 d|
|16||7.31 br s||142.8 d|
|17||7.20 br s||139.2 d|
|18||1.60 br s||15.8 q|
|20||1.60 br s||17.6 q|
*200 MHz, C6D6.
*Mass fragments: [M+] m/z=316; -Me=301; -C6H5=247; pirilio+=81; C5H9 +=69
|Product||Acute inflammation inhibit %||Dunnet’s Test|
|Acetonic extract||1H||3Hs.||5Hs.||7Hs.||(a) p<0.02|
|Chloroformic extract A||14||22||45(b)||35||(b) p<0.04|
|n-hexane extract B||-||12||36||26||(c) p<0.002|