3-(Pentadec-10-enyl)-catechol, a New Allergenic Compound from<i>Lithraea caustica</i>(Anacardiaceae)<sup>1</sup>

Gambaro, Vicente; Chamy, Marı́a C.; Brand, Elisabeth von; Garbarino, Juan A.

doi:10.1055/s-2007-969056

Cited by 19 publications

(17 citation statements)

References 4 publications

(7 reference statements)

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“…The DM extract exerted significant antioxidant action by the two methods could be tested. The antioxidant activity could be related to the presence of alkylene resorcinols and catechol derivatives which have been reported previously in the genus Lithraea (Gambaro et al ., 1986; Alé et al ., 1997). Also, the Anacardiaceae family comprises medicinal species from which a number of biologically active compounds, such as phenolic lipids (alkylresorcinols, alkylphenols, alkylcatechols) have been isolated (Kozubeck et al ., 2001).…”

Section: Discussionmentioning

confidence: 99%

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

López

Ferraro

Anesini

2011

Phytotherapy Research

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Lithraea molleoides (Vell.) Engl. (Anacardiaceae), is known in South America for its medicinal properties: antiarthritic, haemostatic, diuretic, tonic and useful for the treatment of respiratory diseases. Previously the isolation of a new cytotoxic 5-alkyl resorcinol derivative, 1,3-dihydroxy-5-(tridec-4',7'-dienyl) benzene, from a dichloromethane extract (DM) was reported. The aim of this work was to determine and to compare the antioxidant activity of DM and the isolated compound, 1,3-dihydroxy-5-(tridec-4',7'-dienyl) benzene. Moreover, the activity of both on the proliferation of tumoral and normal lymphocytes was determined. The compound was isolated and quantified by HPLC. The compound represented 0.036% of DM. The extract and the compound exerted antioxidant activity by DPPH and FTC methods. On tumoral cells, both exerted antiproliferative action but the compound was more active (EC(50) : 17.4 ± 1 µg/mL). On normal lymphocytes, both exerted a stimulatory effect on cell proliferation inversely related to concentration, the extract was more active than the compound (maximum effect: 300 ± 20% of stimulation). Most of the effects observed with the extract were independent of the isolated compound. DM could be an important source of antioxidant and immunomodulatory compounds to be studied on cancer diseases.

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Section: Discussionmentioning

confidence: 99%

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

López

Ferraro

Anesini

2011

Phytotherapy Research

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“…Normalmente são caracterizados pela presença de grupo fenol ligado a uma cadeia alquílica com número ímpar de carbono. Ocorrem como fenóis simples 69 ou derivados catecólicos 70,71 , resorcinólicos 61,72 ou hidroquinônicos 73,74 , sendo os resorcinólicos os mais abundantes na natureza 4,68 . Além da variação em número e posição relativa dos grupos hidroxílicos no anel aromático, os lipídios fenólicos apresentam cadeias alquílicas com diferentes comprimentos, grau de insaturação e posição das ligações duplas 1 .…”

Section: Lipídios Fenólicos E Derivadosunclassified

“…Lithraea molleoides 78,79 Lithraea caustica 70 73 Campnosperma auriculata 4 Lannea edulis 77 Lannea edulis 77 24 bilidade das porções fenólicas nas regiões lipídicas, nas quais é requerida proteção contra degradação biológica ou oxidação quí-mica. A influência da cadeia alquílica no mecanismo de proteção é similar ao efeito que é proposto para a cadeia poliprenílica do tocoferol 75 .…”

Section: Tabela 3 Lipídios Fenólicos E Derivados Isolados De Espécieunclassified

Metabólitos secundários de espécies de Anacardiaceae

Correia¹,

David²,

David³

2006

Quím. Nova

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Recebido em 18/5/05; aceito em 14/11/05; publicado na web 13/7/06 SECUNDARY METABOLITES FROM SPECIES OF ANACARDIACEAE. This review describes some aspects of the family Anacardiaceae dealing with the presence and distribution of secondary metabolites in the main genera of this family and their biological activities. It reports the occurrence of different natural compounds present in their species with special emphasis on phenolic lipids, flavonoids and triterpenes that are typical metabolites of this family.Keywords: Anacardiaceae; phenolic lipids; flavonoids. INTRODUÇÃOAnacardiaceae é uma família constituída por cerca de 76 gêne-ros e 600 espécies. Seus gêneros são subdivididos em cinco tribos (Anacardieae, Dobineae, Rhoeae, Semecarpeae e Spondiadeae). Cerca de 25% dos gêneros dessa família são conhecidos como tó-xicos e causadores de dermatite de contato severa. De modo geral, as espécies venenosas desta família estão restritas às tribos Anacardieae, Rhoeae e Semecarpeae 1,2 . A dermatite de contato provocada por essas plantas é atribuída principalmente a compostos fenólicos e catecólicos ou a mistura destas substâncias, denominados lipídios fenólicos. Estas substâncias podem estar presentes em diferentes partes do material vegetal, ocorrendo principalmente em espécies do gênero Rhus 3,4 . Nos últimos anos, a origem dos lipídios fenólicos e derivados também foi objeto de investigação; além disso, espécies da família Anacardiaceae têm se mostrado bastante promissoras na busca de substâncias bioativas. Do ponto de vista químico, os gêneros mais estudados nesta família são Mangifera, Rhus (Toxicodendron), Anacardium, Spondias, Lannea, Semecarpus, Schinus, Pistacia, Lithraea, Tapirira e Melanorrhoea. Mangifera, Rhus e Anacardium destacam-se pelo número de investigações relativas à composição química de suas espécies e atividades biológicas de seus extratos e metabólitos. Os estudos destas espécies possibilitaram verificar a ocorrência de flavonóides, terpenos, esteróides, xantonas e, principalmente, dos lipídios fenó-licos e derivados. Destaca-se que entre os flavonóides, os biflavonóides são os mais freqüentes.

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“…The sap, a resinous material containing pentadecyl catechols and heptadecyl catechols (Gambaro et al, 1986;Mitchell, 1990), causes very disagreeable skin irritations to severe dermatitis (Engler, 1892;Magen, 19 12; Barkley, 1957). Barkley (1 962) found that specimens from various tropical regions have been treated as two or three different species, but may actually be variations of a single species.…”

Section: Introductionmentioning

confidence: 99%

The generic position of Lithraea brasiliensis Marchand (Anacardiaceae): evidence from fruit and seed structure

Pienaar

Teichman

1998

Botanical Journal of the Linnean Society

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In Lithraea brasiliaFis Marchand the exocarp is characterized by brachysclereids and the parenchymatous mesocarp by large secretory ducts; inner sclerenchymatous ridges are absent in the mesocarp. The stratified endocarp S.S. comprises a crystal layer, palisade-like brachysclereids, osteosclereids and macrosclereids. The osteosclereids are characterized by a distinct light line or linea lucida, which has hitherto also been recorded in a species of Rhus. In the partially pachychalazal seed, a typical Anacardiaceae-like hypostase typifies the chalazal part of the seed coat, while the integumentary seed coat reveals a well preserved outer epidermis, a compressed endotegmen and well developed inner cuticular layer. Our comparison of the characters of the ovule, fruit and seed of L. brasiZiensiS with those of various species of Rhus and other genera of the tribe Rhoeae (some closely related) presents evidence that L. brasi1iensi.r could be most closely associated with the genus Rhus.

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3-(Pentadec-10-enyl)-catechol, a New Allergenic Compound fromLithraea caustica(Anacardiaceae)¹

Cited by 19 publications

References 4 publications

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

Metabólitos secundários de espécies de Anacardiaceae

The generic position of Lithraea brasiliensis Marchand (Anacardiaceae): evidence from fruit and seed structure

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3-(Pentadec-10-enyl)-catechol, a New Allergenic Compound fromLithraea caustica(Anacardiaceae)1

Cited by 19 publications

References 4 publications

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

Comparative antioxidant activity of an extract of Lithraea molleoides and an isolated 5‐alkyl resorcinol derivative. Effects on the proliferation of normal and tumoral lymphocytes

Metabólitos secundários de espécies de Anacardiaceae

The generic position of Lithraea brasiliensis Marchand (Anacardiaceae): evidence from fruit and seed structure

Contact Info

Product

Resources

About

3-(Pentadec-10-enyl)-catechol, a New Allergenic Compound fromLithraea caustica(Anacardiaceae)¹