15-Hydroxyeremantholide B and derivatives from Eremanthus arboreus

Vichnewski, Walter; Skrochy, C.A; Nasi, Ana Maria T. T.; Lopes, João Luís Callegari; Herz, Werner

doi:10.1016/s0031-9422(98)00524-x

Cited by 12 publications

(6 citation statements)

References 29 publications

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“…It is well know that Lychnophorinae produce metabolites of therapeutic importance, such as terpenoids (mono‐, sesqui‐, di‐ and triterpenes and sesquiterpene lactones) and phenolic compounds (flavonoids and cinnamic acid derivatives) (Vichnewski & Gilbert, ; Vichnewski et al ., ; Herz et al ., ; Dias Barros et al ., ; Oliveira et al ., ; Grael et al ., ; Dos Santos et al ., ; Kanashiro et al ., ; Taleb‐Contini et al ., ; Silvério et al ., ; Keles et al ., ; Dos Santos et al ., ; Baldin et al ., ; De Souza et al ., ; Abreu et al ., ; Silvério et al ., ; Gouvea et al ., ; Saúde‐Guimarães, Raslan & Oliveira, ). In addition, many studies have investigated the chemotaxonomy of Lychnophorinae because of the chemical richness that characterizes the subtribe (Bohlmann et al ., , b; Herz et al ., ; Bohlmann et al ., ; Zdero et al ., ; Bohlmann et al ., ; Bohlmann & Jakupovic, ; Borella et al ., ; Lunardello et al ., ; Borella et al ., ; Vichnewski et al ., ; Sacilotto, Sartori & Vichnewski, ; Sartori et al ., ; Sakamoto et al ., , ; Keles et al ., ; Sakamoto et al ., ; Souza et al ., ; Lusa et al ., ). In regard to the secretory structures of Lychnophorinae, the presence of glandular trichomes has been reported by Luque, Menezes & Semir () in leaves and by Luque & Menezes () in stems of Lychnophora Mart.…”

Section: Introductionmentioning

confidence: 99%

Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae)

2016

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Vernonieae are well represented in South America by subtribe Lychnophorinae, with 104 Brazilian species, some of them rare and endangered. Lychnophorinae are well known for producing metabolites of high pharmaceutical and chemotaxonomic value. Despite the importance of secondary metabolites in Lychnophorinae, there is still little evidence regarding the secretory structures responsible for producing these compounds. Therefore, in this study we investigated 15 species representative of the main lineages of Lychnophorinae, with the following objectives: to identify where the chemotaxonomic markers of Lychnophorinae are secreted and stored and in which developmental stage of the organ these metabolites are found. Samples of stems and leaves were processed according to the usual techniques in plant anatomy. It was found that the main sites of secondary metabolite biosynthesis are glandular trichomes, epidermal cells and parenchyma tissues. Metabolites from glandular trichomes, especially sesquiterpene lactones (STL), are prevalent in the early developmental stages of organs. The metabolite compounds stored in parenchyma tissues are mainly terpenoids, flavonoids and other phenolic compounds; young and expanded leaves are equally rich in metabolites. Thus, the information obtained in this study is essential for conducting chemotaxonomic studies in this group, helping to promote selective collection and conservation of species.

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Section: Introductionmentioning

confidence: 99%

Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae)

2016

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“…Furthermore, the presence of polyacetylenes and phenolics derived from trans ‐cinnamic acids and the recognition of putative synapomorphies presented by some substances in these groups may also effectively contribute to the chemical and evolutionary knowledge of Lychnophorinae, because these compounds were hitherto less recognized as diagnostic for the subtribe (Bohlmann et al ., , b, , ; Herz et al ., ; Zdero et al ., ; Bohlmann & Jakupovic, ; Lunardello et al ., ; Oliveira et al ., ; Vichnewski et al ., ; Sartori et al ., ; Sousa et al ., ).…”

Section: Discussionmentioning

confidence: 99%

“…Due to this chemical richness, many Lychnophorinae have been investigated for the anti‐inflammatory and antiulcerogenic properties of some metabolites and their anthelmintic, antibiotic and antifungal potential (Vichnewski & Gilbert, ; Vichnewski et al ., ; Oliveira et al ., ; Barth et al ., ; Saúde et al ., ; Silvério et al ., ; de Souza et al ., ; Keles et al ., ). Furthermore, chemical studies on Lychnophorinae have gained notoriety in the field of chemotaxonomy and chemosystematics (Bohlmann et al ., , b, , ; Herz et al ., ; Zdero et al ., ; Bohlmann & Jakupovic, ; Lunardello et al ., ; Oliveira et al ., ; Vichnewski et al ., ; Sartori et al ., ; Sousa et al ., ). Flavonoids and STLs are the most representative groups of secondary metabolites of pharmacological interest in Lychnophorinae (Keles et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Characterization and evolution of secondary metabolites in Brazilian Vernonieae (Asteraceae) assessed by LC-MS fingerprinting

et al. 2016

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Tribe Vernonieae are well represented in Brazil, mainly by subtribe Lychnophorinae comprising mostly perennial plants that inhabit arid lands, where species have developed a number of adaptations with recognized ecological protective functions, including secondary metabolite diversification. Recent phylogenetic studies indicate that the subtribe is monophyletic, but questions regarding lineage relationships have yet to be resolved. Phytochemical investigations have also been conducted recently and provide information on the secondary metabolite chemistry of Lychnophorinae. Chemotaxonomic studies have also been carried out. However, these phytochemical investigations are fragmentary and non-standardized. Therefore, in this study, 15 species representing the major lineages of the subtribe were selected for phytochemical investigation and reconstruction of the ancestral states of their secondary metabolites. The main secondary metabolites of these species were detected by UHPLC-UV-MS in different types of extract, showing the presence of trans-cinnamic acid derivatives, flavonoids, polyacetylenes and sesquiterpene lactones. The ancestral states of these secondary metabolites were reconstructed by parsimony and indicate the occurrence of 12 putative chemical synapomorphies. In this study, we present for the first time phytochemical and evolutionary studies based on the reconstruction of the ancestral chemical character states on a phylogenetic tree of Lychnophorinae.

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“…A phylogenetic analysis was carried out in PAUP [20] using 389 chemical characters based on ~7,000 different compounds reported in theliterature from 3,159 species of the Asteraceae, grouped by skeletal types ( Figure 6) [21][22][23][24][25][26][27]. The chemical characters used for the two outgroups, Goodeniaceae and Calyceraceae, were also taken from the literature [28,29].…”

mentioning

confidence: 99%

A Phylogenetic Analysis of Tribes of the Asteraceae Based on Phytochemical Data

Calabria

Emerenciano

Ferreira

et al. 2007

Natural Product Communications

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This work describes the first phylogenetic analysis of the entire Asteraceae based only on chemical data. The data matrix used in this study was based on a large chemical database comprising ~400 skeletal types of terpenes, coumarins, flavonoids, benzofurans and polyacetylenes isolated from the family. Hypotheses about the relationships among tribes are discussed based on the chemical data and compared with relationships inferred from the morphological and macromolecular based classifications.

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15-Hydroxyeremantholide B and derivatives from Eremanthus arboreus

Cited by 12 publications

References 29 publications

Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae)

Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae)

Characterization and evolution of secondary metabolites in Brazilian Vernonieae (Asteraceae) assessed by LC-MS fingerprinting

A Phylogenetic Analysis of Tribes of the Asteraceae Based on Phytochemical Data

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