Antiinflammatory Constituents from Heterotheca inuloides
GUILLERMO DELGADO, MARÍA DEL SOCORRO OLIVARES,† MARÍA ISABEL CHÁVEZ,† TERESA RAMÍREZ-APAN,†
EDELMIRA LINARES,‡ ROBERT BYE,‡ AND FRANCISCO J. ESPINOSA-GARCÍA
Abstract
Three new compounds, cadalen-15-oic acid (1), 3,7-dihydroxy-3(4H)-isocadalen-4-one (2), and dicadalenol (3), were isolated from the aerial parts of Heterotheca inuloides (Mexican arnica), together with the known compounds 7-hydroxycadalene (4), 7-hydroxy-4RH-3,4-dihydrocadalene (5), 1R-hydroxy-1(4H)-isocadalen-4-one (6), 1R-hydroxy-4RH-1,2,3,4-tetrahydrocadalen-15-oic acid (7), 7-(3,3-dimethylallyloxy)coumarin, caryolan-1,9â-diol, and quercetin. The structures of the new compounds were elucidated by spectroscopic methods. The antiinflammatory activities of the extracts and the isolated compounds were evaluated by determining the inhibition of TPA-induced mouse ear edema. The natural products 3, caryolan-1,9â-diol, and quercetin were the most active substances tested and displayed dose-dependent activities.
Antiinflammatory-Constituents-from-Heterotheca-inuloides.pdf
Antioxidative Constituents in Heterotheca inuloides
HIROYUKI HARAGUCHI,",* HARUMI ISHIKAWA," YOLANDA SANCHEZ, B TETSUYA OGURA, B YUMI KUBO ~
AND ISAO KUBO ~
"Faculty of Engineering, Fukuyama University, Gakuen-cho, Fukuyama 729-02, Japan
J'Departamento de Química, Universidad Autónoma de Guadalajara, Guadalajara, México
'Department of Environmental Science, Policy and Management, University of California, Berkeley,
CA 94720-3112, U.S.A.
Abstract
Sesquiterpenoids, 7-hydroxy-3,4-dihydrocadalin and 7-hydroxycadalin, and flavonoids, quercetin, kaempferol and their glycosides, isolated from Heterotheca inuloides (Asteraceae), a Mexican medicinal plant known as "arnica", were evaluated as antioxidants. These compounds showed potent scavenging activity on diphenyl-p-picrylhydrazyl (DPPH) radical. Microsomal lipid peroxidation induced by Fe(III)-ADP/NADPH was inhibited by both terpenoids and flavonoids, though only flavonoids possessed superoxide anion scavenging activity in microsome. Flavonoids also scavenged enzymatically and non-enzymatically generated superoxide anion. On the other hand, mitochondrial lipid peroxidation induced by Fe(III)-ADP/NADH was inhibited only by sesquiterpenoids. Furthermore, these terpenes protected mitochondrial enzyme activity against oxidative stress. These results showed that two types of antioxidants existed in the dried flower of H. inuloMes and would contribute to protection of tissues against various oxidative stresses. :i; 1997 Elsevier Science Ltd.
Antioxidative-Constituents-in-Heterotheca-inuloides.pdf
Heterotheca inuloides: Anti-inflammatory and analgesic effect
ROSA M. GENÉ, LAURA SEGURA, TOMÁS ADZET, ESTHER MARIN, JOSÉ IGLESIAS
UNITAT DE FARMACOLOGIA I FARMACOGNOSIA, FACULTAT DE FARMÁCIA, UNIVERSITAT DE BARCELONA, AVGDA. DIAGONAL 643,
E-08028 -BARCELONA, SPAIN
Abstract
Heterotheca inuloides Cass. (Asteraceae) is used in the traditional medicine of Mexico. The aqueous extract obtained from the flowers of H. inuloides was assessed for anti-inflammatory activity by carrageenan-induced edema test. At 100 mg:kg, i.p, it produced 29% inhibition of inflammation. Ethyl ether (HI-1), butanol (HI-2) and aqueous fraction (HI-3) were obtained from the aqueous extract. The biological assay, by carrageenan-induced edema test, gave the following values (% inhibition): HI-1, 19.9; HI-2, 58.0 and HI-3, 30.0. HI-2 was significantly more effective than HI-1 and HI-3. The dose-effect curve of HI-2 was obtained and the calculated ED50 was 29.7 (22.5–39.2) mg:kg. The peritoneal examination after the treatment with HI-2 showed that the anti-inflammatory action of H. inuloides was not due to an irritating effect at the injection site. At 50–100 mg:kg, i.p., HI-2 inhibited inflammation induced by dextran (38.9–68.1% inhibition) and arachidonic acid (0–33.9 %). No effect was observed at the same doses for zymosan or C16-paf-induced edema. In addition, HI-2 reduced abdominal constrictions in mice following injection of acetic acid: at 50–100 mg:kg, it gave 73.8–78.2% inhibition. The ulcerogenic assay showed that ulcer indices after mHI-2 i.p. treatment were 0.590.5 at 50 mg:kg and 1.290.4 at 100 mg:kg. The results showed related anti-inflammatory activity and the analgesic effect of HI-2. © 1998 Elsevier Science Ireland Ltd. All rights reserved.
Keywords: Heterotheca inuloides; Asteraceae; Anti-inflammatory activity; Analgesic effect
Heterotheca-inuloides-Anti-inflammatory-and-analgesic-effect.pdf