PARTE UTILIZADA= Used part: Partes aéreas. 

ACCIÓN FARMACOLÓGICA= Pharmacological action: Anticonceptivo. 

COMPOSICIÓN QUÍMICA= Chemical composition: Eupatorium inulaefolium was collectedat Colinia Benítez, Province of Chaco, Argentina, Febrary 1976 and a voucher specimen is deposited in the University Herbarium (Museo de Botánica, Universidad de Buenos Aires, Argentina) Air dried ground material (900g) was extracted (24 hr) at room temp with aq. MeOh. The aq. MeOH were evapd to dryness, redisolved in hot H2O and partitioned with petrol, CHCI3 and Et2O. The petrol extract contained on flavonoids and was discarded. The CHCI3 extract was evapd to dryness and passed twice through a column packed with Sephadex LH20 and eluted with C6H6, CHCI3 and MeOH eluates afforded 5,6,3trihydroxy-7,4`-dimethoxyflavone wich crystalized from MeOH as yellow crystals (mp 245-247 °). The Et2O extract was applied to a polymide column and upon elution with H2O-MeOH(7:3) afforded 5,6,3`, 4`-tetrahydroxy-7-meth-oxyflavone wich crystallized from MeOH (mp 295-297°) (lit. 300-301°) [4]. 5,6,3-7,4-dimehoxyflavone. Purple (UV) to yellow-brown (UV/NH3); Rfs:TBA 0.7, 15% HOAc=0.02: Uvlanda (nm):232sh, 285, 340; NaOMe, 260, 320sh, 367; AICI3, 240sh, 262sh, 302, 372; AICI3/HCI, 242sh, 257sh, 302, 367; NaAOc, 235, 290, 337; NaOAc/H3BO3, 235, 290, 337. NMR (60 MHz), (DMSO-d6) using TMS as internal standard, signals at delta 7.5 (2H, d, J=4 Hz), delta 7.1 (IH. d. J=9 Hz), delta 6.9 (1H, s), delta 6.7 (H, s) and delta 4.0 (6H, 2Me). MS principal peak at 330 (8%) (M+), 312 (2.4%) (M+-17) 283 (3.5%) (M+-49), 268 (3.1%) (M+-64) and 207 m/e (13%) (M+-125). The IR and NMR spectra were identical to those of the synthetic compound, kindly provided to us by Prof. H. Wagner. Methylation with Me2SO4 (4) afforded 5-hydroxy-6.7.3`,4`-tetramethoflanone, yellow crystal from aq. MeOH (mp188-189grados) (lit. 189-190grados) (4). Uvlandamax(nm), MeOH, 242, 275. 339(5). 5,6,3`,4`-tetrahydroxy-7-methoxy flavone (pedalitin). Purple (UV) to yellow-brown (UV/NH3); Rfs TBA=0,66, 15% HOAc=0,02. Positive test with Sr2+/NH3, UV landa (nm): MeOH, 245sh, 285, 345; NaOMe, 264, 385; AICI3: 270, 300, 420; AICI3/HCI, 257sh, 295, 370; 370; NaOAc, 260sh, 290, 360; NaOAc/H3BO3, 360, NMR (60MHz) (DMSO-d6) using TMS as internal standard, signal at delta 7.45 (2H, d, j = 3 Hz), delta 6.95 (1H, d, j = 9 Hz) delta 6.85 (1H,s), delta 6.65 (1H, s) and delta (3H, 1Me). Methylation with Me2SO4 afforded 5-hydroxy-6,7,3`,4-tetramethoxyflavone. 

ZONA GEOGRÁFICA= Geografical zone: Centro de Argentina. 

DIVERSIDAD GENÉTICA Y MEJORAMIENTO DE PLANTAS MEDICINALES= Medicinal plants and improvement of medicinal herbs

Two flavones isolated from 2 different sources: Teucrium nuchense and Eupatorium inulaefolium having different m.ps. and also different spectral data, were given the same constitution as 5,6,3'-trihydroxy-7,4'-dimethoxyflavone (I). In view of this discrepancy and the absence of any synthetic evidence in the literature, I has been now synthesized. Since the synthetic I agreed with the sample isolated from E. inulaefolium but not with that isolated from T. nuchense, the constitution of the flavone isolated from the latter plant needs reversion. 

ÚLTIMOS AVANCES EN LA QUÍMICA Y ACTIVIDADES BACTERIOLÓGICAS EN LAS PLANTAS MEDICINALES= Medicinal plants, last advances on chemistry and bacteria activities on the medicinal herbs

1) Dried stems and leaves of Eupatorium inulaefolium (Austroeupatorium inulaefolium) (Asteraceae) were used to obtain four crude exts. (hexane, dichloromethane, methanol and ethanol).  Two fractions were obtained from the hexane ext. (S1 and S2) and three compds. (neurolenin B, lobatin A and lobatin B) from the dichloromethane ext.  The ethanol, hexane, dichloromethane and methanol exts., two fractions from the hexane ext. (S1 and S2), and neurolenin B were evaluated in vitro against Plasmodium falciparum, FCB-2 strain.  Two exts. (dichloromethane and methanol), the S2 fraction and neurolenin B showed statistically significant antiplasmodial activity.

2) Finding new substances from natural resources is quite important, esp. those possessing medical usage.  This expt. was performed in order to isolate and elucidate the structure of pentacyclic triterpene and sterol substances from Eupatorium inulaefolium H.B.K. leaves.  The structural elucidation of those substances was performed using IR, UV, mass spectrometry, and 1H and 13C NMR.  The results indicate that those compds. were 12,13-dihydro-alpha-amyrin-20,30-ene 3-acetate, 12,13-dihydro-alpha-amyrin-20,30-en-3-ol, and beta-sitostan-20,21-en-3-ol.

3) Exts. of different polarity from 4 Argentine medicinal plants were tested for bioactivity by carrageenan-induced paw edema in rats and TPA-induced ear edema in mice.  A CH2Cl2 ext. from Pluchea sagittalis showed antiinflammatory activity in both tests.  A CH2Cl2 ext. from Ipomoea fistulosa showed activity in the ear edema test while an ext. from Eupatorium inulaefolium and a H2O ext. of Polygonum punctatum exhibited antiinflammatory activity in the carrageenan-induced edema test.

1) TOURSARKISSIAN, Martín. Plantas medicinales de Argentina : sus nombres botánicos, vulgares, usos y distribución geográfica. Buenos Aires : Hemisferio Sur, 1980, p.30.

2) FERRARO, G. E.; MARTINO, V. S.; COUSSIO, J. D. New flavonoids from Eupatorium Inulaefolium. Phytochemistry. 1977, vol.16, nº10, p.1618-1619.
 
3) BHARDWAJ, D. K., et al. Constitution of Teucrium nuchense flavone: a synthetic study. Proceedings of the Indian National Science Academy, Part A: Physical Sciences. 1982, vol.48, nº3, p.253-256.
 
4) BLAIR, S., et al. Antimalarial activity of neurolenin B and derivates of Eupatorium inulaefolium (Asteraceae).   Pharmazie. 2002, vol.57, nº6, p.413-415.
 
5) SRI MULVANI, M.; SARDJOKO; MAKIN, I. H. M.; SOEGIHARDJO, C. J. Structural elucidation of cytotoxic pentacyclic triterpenes and sterols from leaves of Eupatorium inulaefolium H.B.K.  Majalah Farmasi Indonesia. 1996, vol.7, nº3, p.127-138.
 
6) GORZALCZANY, S., et al. Search for antiinflammatory activity in Argentine medicinal plants. Phytomedicine. 1996, vol.3, nº2, p.181-184.