Ambrosanolides and secoambrosanolides from Ambrosia tenuifolia

Oberti, Juan C.; Silva, Gloria L.; Sosa, Virginia E.; Kulanthaivel, Palaniappan; Herz, Werner

doi:10.1016/s0031-9422(00)81289-3

Cited by 30 publications

(24 citation statements)

References 14 publications

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“…Most of the isolated compounds (1-3, 7, 8, apigenin and luteolin) are known metabolites of A. millefolium s.l., but paulitin (4), isopaulitin (5) and psilostachyin C (6) were isolated for the first time from the Achillea genus. These secopseudoguaianolide-type sesquiterpene lactones were described earlier only from different Ambrosia species (Borges del Castillo et al, 1981;Oberti et al, 1986;David et al, 1999). Considering that in our experiment the compounds were isolated from a commercial sample raises the question whether these substances are secondary metabolites of Achillea millefolium itself or whether they arise from the impurity of the plant material.…”

Section: Resultsmentioning

confidence: 73%

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

Csupor-Löffler

Hajdú

Zupkó

et al. 2008

Phytotherapy Research

108

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The antiproliferative activities of n-hexane, chloroform, aqueous-methanol and aqueous extracts of the aerial parts of the Achillea millefolium aggregate on three human tumour cell lines were investigated by means of MTT assays. The chloroform-soluble extract exerted high tumour cell proliferation inhibitory activities on HeLa and MCF-7 cells, and a moderate effect on A431 cells; accordingly, it was subjected to detailed bioactivity-guided fractionation. As a result of the multistep chromatographic purifications (VLC, CPC, PLC, gel filtration), five flavonoids (apigenin, luteolin, centaureidin, casticin and artemetin) and five sesquiterpenoids (paulitin, isopaulitin, psilostachyin C, desacetylmatricarin and sintenin) were isolated and identified by spectroscopic methods. The antiproliferative assay demonstrated that centaureidin is the most effective constituent of the aerial parts of yarrow: high cell growth inhibitory activities were observed especially on HeLa (IC(50) 0.0819 microm) and MCF-7 (IC(50) 0.1250 microm) cells. Casticin and paulitin were also highly effective against all three tumour cell lines (IC(50) 1.286-4.76 microm), while apigenin, luteolin and isopaulitin proved to be moderately active (IC(50) 6.95-32.88 microm). Artemetin, psilostachyin C, desacetylmatricarin and sintenin did not display antiproliferative effects against these cell lines. This is the first report on the occurrence of seco-pseudoguaianolides (paulitin, isopaulitin and psilostachyin C) in the Achillea genus.

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Section: Resultsmentioning

confidence: 73%

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

Csupor-Löffler

Hajdú

Zupkó

et al. 2008

Phytotherapy Research

108

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“…Thus, several sesquiterpene lactones were isolated from A. tenuifolia (Oberti et al 1986;Silva et al 1992). Compounds of this type, isolated from genus Lychnophora, showed trypanocidal activities.…”

Section: Resultsmentioning

confidence: 99%

In vitro evaluation of trypanocidal activity in plants used in Argentine traditional medicine

et al. 2005

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Thirty-two organic and aqueous extracts, belonging to 12 Argentine medicinal plants were tested for their in vitro trypanocidal activity on epimastigote forms of Trypanosoma cruzi. Among the selected species, the organic extracts of Ambrosia scabra, Ambrosia tenuifolia, Baccharis spicata, Eupatorium buniifolium, Lippia integrifolia, Mulinum spinosum and Satureja parvifolia, and the aqueous extracts of E. buniifolium, L. integrifolia, M. spinosum and S. parvifolia showed trypanocidal activity with a percentage of growth inhibition higher than 70% at a concentration of 100 microg/ml.

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“…As selectivity is a relevant characteristic for defining lead molecules (31), the cytotoxicities of the purified compounds (22) and from other species of Ambrosia (15,20). Psilostachyin has demonstrated molluscicidal activity (35), inhibition of nitrite accumulation in cell cultures, and inhibition of the G 2 DNA damage checkpoint (9,28).…”

Section: Discussionmentioning

confidence: 99%

Trypanocidal and Leishmanicidal Activities of Sesquiterpene Lactones from Ambrosia tenuifolia Sprengel (Asteraceae)

Sülsen

Frank

Cazorla

et al. 2008

Antimicrob Agents Chemother

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Bioassay-guided fractionation of the organic extract of Ambrosia tenuifolia Sprengel (Asteraceae) led to the isolation of two bioactive sesquiterpene lactones with significant trypanocidal and leishmanicidal activities. By spectroscopic methods ( 1 H-and 13 C-nuclear magnetic resonance, distortionless enhancement by polarization transfer, correlated spectroscopy, heteronuclear multiple-quantum coherence, electron impact-mass spectrometry, and infrared spectroscopy), these compounds were identified as psilostachyin and peruvin. Both compounds showed a marked in vitro trypanocidal activity against Trypanosoma cruzi epimastigotes with 50% inhibitory concentration (IC 50 ) values of less than 2 g/ml. Psilostachyin exerted a significant in vitro activity against the trypomastigote forms of T. cruzi (IC 50 , 0.76 g/ml) and was selected for in vivo testing. Psilostachyin-treated mice had a survival of 100% and lower parasitemia values than control mice. Both compounds were also tested on Leishmania sp. promastigotes: psilostachyin (IC 50 , 0.12 g/ml) and peruvin (IC 50 , 0.39 g/ml) exerted significant leishmanicidal activities. This is the first time that the trypanocidal and leishmanicidal activities of these compounds have been reported. The selectivity index (SI) was employed to evaluate the cytotoxic effect of lactones on T lymphocytes. Although the SIs of both compounds were high for T. cruzi epimastigotes, psilostachyin was more selective against trypomastigotes (SI, 33.8) while peruvin showed no specificity for this parasite. Both compounds presented high selectivity for Leishmania spp. The results shown herein suggest that psilostachyin and peruvin could be considered potential candidates for the development of new antiprotozoal agents against Chagas' disease and leishmaniasis.Trypanosomiasis and leishmaniasis are widespread protozoal diseases that affect mostly poor and marginal populations in Latin America, Africa, and Asia and have been neglected by the pharmaceutical industry and governments. Under normal circumstances (efficient epidemiological surveillance programs and sanitary education) the control of these diseases could be achieved.

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Ambrosanolides and secoambrosanolides from Ambrosia tenuifolia

Cited by 30 publications

References 14 publications

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

In vitro evaluation of trypanocidal activity in plants used in Argentine traditional medicine

Trypanocidal and Leishmanicidal Activities of Sesquiterpene Lactones from Ambrosia tenuifolia Sprengel (Asteraceae)

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