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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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    • "This is because the leaf is considered to have most of the active constituents (Orwa et al., 2009). It has been reported to possess antiplasmodial activity (Ajaiyeoba et al., 2006; Goffin et al., 2002) testifying to the presence of sesquiterpene lactones as well as an artemisinin acid analog from T. diversifolia (Kuo and Chen, 1998; Bordoloi et al., 1996); anti-inflammatory and analgesic activities (Owoyele et al., 2004); bile, kidney, urinary and venereal diseases, testicular inflammation, frigidity, sterility, heavy menstruation, rheumatism and arthritis, upper respiratory tract infections, ranging from cough to tuberculosis, intestinal worms and schistosomiasis, cancer chemopreventive activity (Jian-Qiao et al., 2002); cytotoxic properties (Wu et al., 2001; Coyle et al., 1994) and antimicrobial activity (Ogundare, 2007; Singleton, 1999). Aerial parts of Tithonia diversifolia collected in São Paulo State (Brazil) afforded two new heliangolides in addition to the heliangolides tagitinin F and 1, 2-epoxytagitinin C, one known guaianolide and the flavone hispidulin whose structures were established by spectroscopic studies (Paulo et al., 1997). "
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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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    • "Plants were chosen based on their nematocidal/ insecticide potential, scientific originality, availability and wide geographical distribution in Brazil. Moreover, these species belong to botanical families/genera where the presence of phytochemical classes of nematocidal/ insecticidal compounds have been identified, which suggests the plants used in the present study may be considered a potential source of new nematocidal agents (Chang et al., 1995; Kuo & Chen,1998; Begum et al., 2000; Carbonell et al., 2000; Hitmi et al., 2000; Maciel et al., 2000; Do Vale et al., 2002; Saravanan et al., 2004; Qamar et al., 2005). As expected, we confirmed the presence of compounds such as flavanols, tannins, and alkaloids, usually found in several nematocidal plants (Table 1). "
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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.
    Pharmaceutical Biology 02/2009; 47(3):230-235. DOI:10.1080/13880200802434658 · 1.34 Impact Factor
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    • "Previous studies reported the isolation of sesquiterpene lactones, tagitinins A, C, and F, tirotundin, and hispidulin from the aerial parts of T. diversifolia (Baruah, et al., 1979). Two new compounds, 1-acetyltagitinin A and 8b- isobutyryloxycumambronalide (Kuo, et al., 1998), three new heliangolides (Pereira, et al., 1997; Ciccio, et al., 1979), a novel rearranged eudesmane diversifolol (Kuo & Chen, 1997), acetyltagitinin E, and tagitinin F (Wu, et al., 2001), were isolated from the leaves of the plant. Tagitinin F showed a selective cytotoxicity to Hep G2 human cells (Wu, et al., 2001). "
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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.
    Journal of Research in Science Computing and Engineering 01/2007; 4(1):1-7. DOI:10.3860/jrsce.v4i1.437
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