Chemical constituents of Tolpis species

Triana, Jorge; López, Mariana; Pérez, Francisco J.; Platas, Javier González; Estévez, Francisco; León, Juan Francisco; Hernández, Juan Carlos; Brouard, Ignacio; Bermejo, Jaime

doi:10.1016/j.fitote.2009.06.001

Cited by 10 publications

(10 citation statements)

References 14 publications

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“…Arnoseris had previously been reported as a close relative of Tolpis on morphological grounds (Stebbins, 1953; Jeffrey, 1966; Blackmoore, 1981). The two genera also share several phytochemical and karyological similarities (Bremer, 1994; Zidorn et al., 2005; Triana et al., 2009). The results of the present investigation corroborate Arnoseris as the closest relative of Tolpis among the taxa evaluated.…”

Section: Discussionmentioning

confidence: 99%

Phylogenetic analyses of Tolpis Adans. (Asteraceae) reveal patterns of adaptive radiation, multiple colonization and interspecific hybridization

2012

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The plant genus Tolpis (Asteraceae) has been the subject of several investigations on the evolution of oceanic island plants. Its insular species were utilized in studies of artificial hybrid fertility, testing the validity of Baker’s law, the application of DNA barcodes, and the phylogenetic utility of inter‐simple sequence repeat markers. Despite this considerable interest in Tolpis, little is known about its phylogenetic history. Past investigations were unable to resolve most of the interspecific relationships, especially within the Canary Islands, where the genus is particularly diverse. Incomplete taxon sampling, the use of ambiguous outgroups and the limited utility of slowly evolving chloroplast DNA markers precluded detailed reconstructions. The present investigation presents a comprehensive molecular phylogeny of Tolpis. By utilizing highly variable nuclear DNA markers and a comprehensive taxon set, we have resolved the majority of interspecific relationships in the genus. Evaluations of competing tree topologies and ancestral area reconstructions complemented the analyses. Our results highlight the presence of three dominant mechanisms of island plant evolution—island colonization, adaptive radiation and interspecific hybridization—in Tolpis: (i) the extant distribution of the genus is the result of two independent colonization pathways, (ii) Tolpis has colonized at least one archipelago multiple times, (iii) the present insular diversity is the product of adaptive radiation, (iv) potential hybridization was detected between species now inhabiting different islands and archipelagoes, indicating sympatric historical distributions, and (v) several undescribed species await taxonomic recognition.

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Section: Discussionmentioning

confidence: 99%

Phylogenetic analyses of Tolpis Adans. (Asteraceae) reveal patterns of adaptive radiation, multiple colonization and interspecific hybridization

2012

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“…Compound 1 could derive from the known triterpene acetyl-ptiloepoxide 4 [ 8 , 9 ] which was identified by us from T. proustii as an inseparable mixture. Triterpenes containing an epoxide at the Δ 21-22 position are known and have been isolated before from a Tolpis species [ 4 ]. Based on this, we envisioned the formation of compound 1 by chlorination of the double bond, followed by isomerization and β opening of the epoxide, and protonation, maintaining the α-orientation at the C-22 observed in the precursor compound acetyl-ptiloepoxide ( Figure 4 ).…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, from T. proustii 15 known compounds were isolated, including aromatic compounds: scopoletin [ 15 ] aesculetin [ 15 ] and apigenin [ 16 ]; the diterpene phytene-1,2-diol [ 17 ] and the triterpenoids stigmasterol [ 18 ], ergosterol peroxide [ 19 ], ursolic acid [ 20 ], lupan-20(29)-ene-3β,30-diol [ 21 ], 21α-hydroxytaraxasterol [ 22 ], 11-oxo-β-amyrin [ 23 ], 3β-acetoxy-urs-12-ene-1β,11α-diol [ 24 ], 21α,22α-epoxy-20α-hydroxy-20(30)-dihydrotaraxasterol [ 4 ], 3β-acetoxy-21α,22α-epoxytaraxastan-20α-ol [ 25 ], 22-oxo-20-taraxasten-3β-ol [ 9 ], β-amyrin [ 26 ]. From T. lagopoda seven known compounds were isolated, including aromatic compounds: 2,4′-dihydroxy-4-methoxybenzophenone [ 4 ] and triterpenoids: stigmasterol [ 18 ], ergosterol peroxide [ 19 ], a mixture of 7-oxo-β-sitosterol and 7-oxo-stigmasterol [ 26 , 27 ], ursolic acid [ 20 ], and α-amyrin [ 28 ]. Their structures were confirmed by comparison of their spectral data with those reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

“…Although a wide-ranging study of different species of Tolpis from the Canary Islands and from other Macaronesian archipelagos has been carried out from the botanical point of view [ 2 , 3 ], only one phytochemical report has previously appeared on the isolation and structural elucidation of aromatic compounds, triterpenes, and sterols from T. webbi and T. spp [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

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Secondary Metabolites from Two Species of Tolpis and Their Biological Activities

et al. 2012

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Phytochemical research of two Tolpis species, T. proustii and T. lagopoda, led to the isolation of three new compounds: 30-chloro-3β-acetoxy-22α-hydroxyl-20(21)-taraxastene (1), 3β,22α-diacetoxy-30-ethoxy-20(21)-taraxastene (2) and 3β,28-dihydroxy-11α-hydroperoxy-12-ursene (3). The structures of the new compounds were elucidated by means of extensive IR, NMR, and MS data and by comparison of data reported in the literature. The in vitro antioxidant activities of the extracts were assessed by the DPPH and ABTS scavenging methods. The cytotoxicity of several known compounds and its derivatives was also assessed against human myeloid leukemia K-562 and K-562/ADR cell lines.

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“…It suggested that these two compounds have nearly similar benzophenone core structure, except for the replacement of methoxyl groups at C-4 ( C 165.9) and C-4' ( C 149.4). Compound 17 structure was identified as (2-hydroxy-4,6-dimethoxyphenyl)(3-hydroxy-4methoxyphenyl)methanone by comparison of reported study [27].…”

Section: Structure Elucidation Of Compound 11mentioning

confidence: 96%

Inhibitory activity of metabolites from mangosteen roots Garcinia mangostana L. on hepatocellular carcinoma and colon cancer cell growth

Koopklang¹

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Liver cancer is one of the most common deadliest diseases both worldwide and in Thailand. Because of its rich and dual blood supply, malignant tumors in the liver could grow proliferative and rapidly spread to another organ. This process was called Metastasis, the major cause of human death. Mangosteen (Garcinia mangostana L.) generally known as a queen of fruits, has been widely studied in medicinal applications for many decades, due to plenty of bioactive metabolites such as xanthones as a major component. Nonetheless, reports about bioactivities of minor components were barely known. In this study, metabolites isolated from mangosteen roots were evaluated their cytotoxic property and antiproliferative against hepatocellular carcinoma (HepG2 and Huh-7) and colon (Caco2 and HCT-116) cancer cells. The remarkable compounds were further investigated in molecular biology, including cell migration, apoptosis assessment and western blot analyses. As results, the EtOAc crude extract of mangosteen roots was afforded four new compounds: mangostanone I – IV (compounds 1, 12, 13 and 18) and eighteen known compounds: a-mangostin (2), b-mangostin (3), g-mangostin (4), mangostanaxanthone IV (5), dulxanthone D (6), toxyloxanthone B (7), 1,7-dihydroxy-3-methoxy-2-prenylxanthone (8), euxanthone (9), norathyriol (10), 8-deoxygartanin (11), maclurin (14), 2,3',4,6-tetrahydroxybenzophenone (15), mangaphenone (16), (2-hydroxy-4,6-dimethoxyphenyl)(3-hydroxy-4-methoxyphenyl)methanone (17), garciosine A (19), 4,5-dimethoxy[1,1′-biphenyl]-3-ol (20), 3-hydroxy-4-geranyl-5-methoxybiphenyl (21) and epicatechin (22). It was showed that compound 1, 2, 3, 5, 6, 11 and 21 accommodated potential effects in anticancer properties against investigated cell lines with IC50 less than 50 mM and considerable anti-migration effects against Huh-7. Using Annexin V apoptosis kit, found out that compounds 1, 6 and 11 have an ability to increase apoptosis rate of cell Huh-7 in dose-dependent manner. In addition, western blot analysis revealed that apoptotic activation of 21 in HepG2 was mediated by selective suppression of Bcl-2 expression.

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Chemical constituents of Tolpis species

Cited by 10 publications

References 14 publications

Phylogenetic analyses of Tolpis Adans. (Asteraceae) reveal patterns of adaptive radiation, multiple colonization and interspecific hybridization

Phylogenetic analyses of Tolpis Adans. (Asteraceae) reveal patterns of adaptive radiation, multiple colonization and interspecific hybridization

Secondary Metabolites from Two Species of Tolpis and Their Biological Activities

Inhibitory activity of metabolites from mangosteen roots Garcinia mangostana L. on hepatocellular carcinoma and colon cancer cell growth

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