Sesquiterpenes from the leaves of Tithonia diversifolia

Department of Chemistry, National Taiwan University, Taipei, Taiwan, Republic of China.
Journal of Natural Products (Impact Factor: 3.95). 07/1998; 61(6):827-8. DOI: 10.1021/np970530h
Source: PubMed

ABSTRACT Two new compounds, a germacrane sesquiterpene, 1-acetyltagitinin A (1), and a guaianane sesquiterpene, 8beta-isobutyryloxycumambranolide (2), were isolated from leaves of Tithonia diversifolia, together with two known compounds, methyl 3alpha-acetoxy-4alpha-hydroxy-11(13)-eudesmen-12-oa te and tagitinin A. The structures of compounds 1 and 2 were elucidated on the basis of spectral and chemical evidence.

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    ABSTRACT: Tithonia diversifolia (family-Asteraceae), a wildly growing plant has been reported to possess a number of medicinal properties being used traditionally in tropics especially Kenya and Nigeria. This study evaluated the phytochemicals, acute toxicity (100-10,000 mg/kg) and anti-diarrhoeal effect of Tithonia diversifolia on group of Wistar rats. The anti-diarrhoeal effect of aqueous extract of Tithonia diversifolia leaves (200, 400 and 800 mg/kg doses) was studied using castor-oil-induced-diarrhoea model (dropping test), castor-oil-induced enteropooling (secretory test) and gastrointestinal transit test (charcoal transit) in rats. In castor-oil-induced diarrhoea test, the rats' droppings were observed and noted as wet or dry with wet signifying characteristic diarrhoea. The castor-oil-induced enteropooling was done to determine the volume of intestinal content induced by castor oil while in gastrointestinal transit, the speed and percentage distance travelled by charcoal meal were noted to determine the anti-motility properties of the extract. The results showed that Tithonia diversifolia leaves' aqueous extract reduced wet faecal output in castor-oil-induced diarrhoea but with slightly greater frequencies in comparison with loperamide treated animals and had less volume of intestinal contents as compared with the negative control (distilled water treated animals). It also had a significant (p<0.05) non-dose dependent reduction in speed and distance travelled by charcoal in gastrointestinal tract but slightly higher speed and longer distance than the atropine treated rats. Therefore, Tithonia diversifolia leaves' aqueous extract has a remarkable anti-diarrhoeal effect in castor-oil-induced diarrhoea, enteropooling and gastrointestinal motility models attesting to its utility in a wide range of diarrhoeal states traditionally.
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    ABSTRACT: Synthetic nematicides have been used broadly in past decades for the control of plant parasitic nematodes. Despite their relevant effectiveness, these compounds can cause great damage to the environment, and have a relevant impact on human and animal health. The growing search for new nematicides, particularly natural ones, may lead to higher safety and efficiency in nematode control. In this work, the in vitro nematocidal effect of ethanol extracts obtained from the following plant species was evaluated: Tithonia diversifolia (Hemsl.) A.Gray; Ecilpta alba (L.) Hassk; Mikania glomerata Sprengel (Asteraceae); Tabernaemontana catharinensis A. DC; Mandevilla velutina (Mart.) Woodson (Apocynaceae); Casearia sylvestris Sw. (Salicaceae); Zeyheria montana Mart. (Bignoniaceae); Lippia alba (Mill.) (Verbenaceae); Croton antisyphiliticus Mart. (Euphorbiaceae) and Serjania erecta Radlk. (Sapindaceae). The plant parasitic nematodes Pratylenchus zeae (Graham) (Nematoda: Pratylenchidae) and Pratylenchus jaehni (Inserra) (Nematoda: Pratylenchidae) were used for tests. Moreover, a preliminary phytochemical characterization of these plant extracts was performed in order to associate these data with those observed in nematocidal assays. Our results indicated a significant nematocidal activity of the analyzed extracts, especially those demonstrated by E. alba (DL50 (ppm) = 304.08; 55.32 – P. zeae and DL50 (ppm) =>1000; 212.82 – P. jaehni; 12 and 24 h, respectively), T. catharinensis (DL50 (ppm) = 215.26; 60.04 – P. zeae and DL50 (ppm) = 825.44; 376.60 – P. jaehni; 12 and 24 h, respectively), C. sylvestris (DL50 (ppm) = 198.05; 56.94 – P. zeae and DL50 (ppm) = 747.98; 322.98 – P. jaehni; 12 and 24 h, respectively), Z. montana (DL50 (ppm) = 166.43; 34.08 – P. zeae and DL50 (ppm) =>1000; 427.34 – P. jaehni; 12 and 24 h, respectively) and S. erecta (DL50 (ppm) = 178.74; 74.12 – P. zeae e DL50 (ppm) = 689.24; 249.50 – P. jaehni; 12 and 24 h, respectively). Thus, these data show that the evaluated plants present significant nematocidal effects, which are of high economic or environmental interest and may be useful for the growth of agricultural activities worldwide.
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    ABSTRACT: The air-dried flowers of Tithonia diversifolia, commonly known as native sunflower, afforded tagitinin C (1), fatty acid esters of faradiol (2), squalene (3), and a mixture (1:2) of stigmasterol (4) and sitosterol (5). The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy, while the structures of 2 to 5 were elucidated by a comparison of their 1H and 13C NMR spectral data with those found in the literature. Antimicrobial tests on 1 indicated theat it was moderately active against S. aureus and C. albicans; slightly active against E. coli, P. aeruginosa and T. mentagrophytes; and inactive against B. subtilis and A. niger.
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