Sesquiterpene lactones as taxonomic characters in the asteraceae

We reared larvae of three generalist insect species on plants occurring in their habitats. Individuals of each species were kept either on mixed diets, or on each plant species separately. We measured food plant preference in the mixed-diet group and compared insect performance on single plants to the performance on the mixed diet. For all three insect species, food choice within the mixed-diet groups was non-random and delivered the best overall performance, thus ful®lling the criteria for self-selected diets. When a single diet was as good as the mixed diet for one particular aspect of performance (Adenostyles alliariae and Petasites albus for Miramella alpina; A. alliariae for Callimorpha dominula), it was never the most preferred food plant in the mixed-diet treatment. Whether the bene®t achieved by mixing diets is due to nutrient complementation or toxin dilution, we argue that there is no easy way to distinguish between the two hypotheses on the basis of consumption and performance measurements, as has previously been proposed. From the interpretation of utilisation plots, the ANCOVA equivalent of nutritional indices, we were able to gain insight into where in the sequence from ingestion to growth (preingestive, predigestive or postdigestive) single diets caused di erences from mixed diets. The elements of this control system which were in¯uenced by single diets varied considerably, both within and between insect species. No food plant was toxic or deterrent to all experimental insect species; a food plant that caused consumption e ects (preingestive) for one insect species could be dealt with metabolically (postdigestive) by another; di erent food plants could cause behavioural e ects (preingestive), metabolic e ects (postdigestive), or a combination of both e ects, all within the same insect species. However, one generality did emerge: once a food was ingested, further growth-relevant e ects occurred metabolically (postdigestive) rather than via di erential egestion (digestibility).

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“…Sesquiterpenes of furoeremophilane type b Novotny et al (1964);Seaman (1982) Urtica dioica (Urticaceae)…”

Section: Discussionunclassified

Dietary mixing in three generalist herbivores: nutrient complementation or toxin dilution?

1999

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“…The content of volatile oil produced by T. cinerea was low and the major fraction of the constituents identifi ed was composed of sesquiterpenes. Sesquiterpenoids are typical metabolites of Asteraceae species (Seaman 1982) and are used in the chemotaxonomy of the family (Bohlmann et al 1981, Seaman 1982, Zdero and Bohlmann 1990. It is worth to emphasize that some of the constituents identified in this study present therapeutic potential.…”

Section: T Cinerea: Trichomes and Volatile Oil Composition 319mentioning

confidence: 99%

Trichomes and chemical composition of the volatile oil of Trichogonia cinerea (Gardner) R. M. King & H. Rob. (Eupatorieae, Asteraceae)

Fernandes

Trindade

Rezende

et al. 2016

An. Acad. Bras. Ciênc.

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Trichogonia cinerea is endemic to Brazil and occurs in areas of cerrado and campo rupestre. In this study, we characterized the glandular and non-glandular trichomes on the aerial parts of this species, determined the principal events in the development of the former, and identifi ed the main constituents of the volatile oil produced in its aerial organs. Fully expanded leaves, internodes, fl orets, involucral bracts, and stem apices were used for the characterization of trichomes. Leaves, internodes, fl orets, and involucral bracts were examined by light microscopy and scanning electron microscopy, whereas stem apices were examined only by light microscopy. Branches in the reproductive phase were used for the extraction and determination of the composition of the volatile oil. The species has three types of glandular trichomes, biseriate vesicular, biseriate pedunculate, and multicellular uniseriate, which secrete volatile oils and phenolic compounds. The major components identifi ed in the volatile oil were 3,5-muuroladiene (39.56%) and butylated hydroxytoluene (13.07%).Key words: volatile oil, histochemistry, ontogeny, secretory structure.

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“…22,30,31 In this way, SL occurrence has been used as taxonomic support to determine the limits of the tribes and sub-tribes in Asteraceae, including the sub-tribe Lychnophorinae, in which Eremanthus belongs. 1,32,33 Eremanthus seidelii MacLeish & Schumacher has a restricted ocurrence to the "cerrado" surrounding the Furnas reservoir in southwestern Minas Gerais state, in microenvironments that have been seriously damaged by human activity. 1,2 Previous phytochemical investigation of this species afforded SL of goyazensolide and eremantholide types.…”

Section: Introductionmentioning

confidence: 99%

“…Together, these SL can be responsible for up to 7.5% of the weight of the dry leaves (data from plant 6, population A). This remarkable predominance, taken together with the SL utility as chemotaxonomic markers 24,26,29,32,33 and biological activities 3,6-8,10-12 led us to develop the present HPLC method for their quantification. …”

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confidence: 98%

“…Therefore, the difference possibly remains in a differential activity of the enzymes that cyclisation 1 to 2. These significant differences in the levels of biosynthetically related SL, taken together with the valuable property of SL as chemotaxonomic markers 24,26,29,32,33 and the fact that 1 and 2 are the main constituents from the secondary chemistry in leaves of E. seidelii, lead us to propose the following quantitative chemotypes: (i) plants in this cluster are the only ones that present 2 in higher concentrations than 1. In fact, individuals in this cluster present the highest concentrations of 2 (more than 2.7% of the dried leaf weight in the plants studied) and the lowest concentrations of 1 (below 1.7% in the plants studied).…”

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confidence: 99%

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Quantitative HPLC analysis of sesquiterpene lactones and determination of chemotypes in Eremanthus seidelii MacLeish & Schumacher (Asteraceae)

Sakamoto¹,

Gobbo‐Neto²,

Cavalheiro³

et al. 2005

J. Braz. Chem. Soc.

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Eremanthus seidelii MacLeish & Schumacher tem ocorrência restrita ao cerrado, em torno do reservatório de Furnas (MG), em habitats que vêm sendo seriamente deteriorados pela ação humana. A presente investigação fitoquímica mostrou, como metabólitos secundários majoritários das folhas de E. seidelii, as lactonas sesquiterpênicas (LS) 4β,5-diidro-2',3'-diidroxi-15-desoxigoiazensolídeo (1) e 4β,5-diidro-1',2'-epoxi-eremantolídeo-C (2); uma metodologia foi desenvolvida em CLAE para sua análise quantitativa. A análise por CLAE mostrou que não há variações sazonais significativas nas concentrações de ambas LS. Não foram encontradas diferenças qualitativas nos perfis de LS nos indivíduos amostrados. Entretanto, há diferenças no perfil quantitativo entre os indivíduos analisados, apontando para a existência de três quimiotipos quantitativos desta espécie, com diferenças possivelmente originadas na atividade enzimática das enzimas que ciclizam uma LS tipo goiazensolídeo (1) em uma LS tipo eremantolídeo (2).Eremanthus seidelii MacLeish & Schumacher has a restricted occurrence to the Brazilian "cerrado" surrounding the Furnas (MG) reservoir, in environments that have been seriously damaged by human activity. The present phytochemical investigation reveals that the sesquiterpene lactones (SL) 4β,5-dihydro-2',3'-dihydroxy-15-desoxy-goyazensolide (1) and 4β,5-dihydro-1',2'-epoxy-eremantholide-C (2) are the major secondary metabolites in E. seidelii leaves, and an HPLC method was developed for their quantitative analysis. HPLC analysis showed no significant seasonal variation in the concentrations of both SL. No qualitative differences were found in the SL patterns of all individuals sampled. However, there is a different SL quantitative pattern among the plants analyzed, pointing to the existence of three quantitative chemotypes of this species, with differences possibly originating from the activity of the enzymes that cyclize the goyazensolide type SL (1) to a eremantholide type SL (2). Keywords: HPLC, sesquiterpene lactones, chemotypes, populational variation, Eremanthus seidelii IntroductionThe genus Eremanthus Less (Asteraceae: Vernonieae) comprises 22 species that are restricted to the Brazilian "cerrado". 1,2 Previous phytochemical investigations with this genus led to the isolation of flavonoids, triterpenes, poliacetylenes and revealed sesquiterpene lactones (SL) as the main secondary metabolites. 3-9 Some of the SL isolated from the Eremanthus genus posses important biological activities, 3,[6][7][8]10 like the antiproliferative effects on some cancer cell lines 11 and the modulation of the inflammatory process in vitro, by inhibiting the NF-κβ transcriptor factor. 12 Seasonal, 13-16 circadian [17][18][19] and populational 20-24 variations in the content of almost all classes of secondary metabolites, including SL, [25][26][27][28][29] were reported. The recognition of variations in secondary metabolite production can be helpful in chemotaxonomic studies, 1397 Quantitative HPLC Analysis of Sesquiterpene Lactones V...

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Sesquiterpene lactones as taxonomic characters in the asteraceae

Cited by 398 publications

References 684 publications

Dietary mixing in three generalist herbivores: nutrient complementation or toxin dilution?

Dietary mixing in three generalist herbivores: nutrient complementation or toxin dilution?

Trichomes and chemical composition of the volatile oil of Trichogonia cinerea (Gardner) R. M. King & H. Rob. (Eupatorieae, Asteraceae)

Quantitative HPLC analysis of sesquiterpene lactones and determination of chemotypes in Eremanthus seidelii MacLeish & Schumacher (Asteraceae)

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