Cyclopropane- and spirolimonoids and related compounds from Hortia oreadica

Severino, Vanessa Gisele Pasqualotto; Braga, Patrícia Aparecida de Campos; Silva, Maria Fátima das Graças Fernandes da; Fernandes, João B.; Vieira, Paulo C.; Theodoro, Jahyr E.; Ellena, Javier

doi:10.1016/j.phytochem.2011.12.016

Cited by 11 publications

(10 citation statements)

References 19 publications

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“…Dados micro e macromoleculares vêm sugerindo a união destas duas subfamílias, Rutoideae e Toddalioideae. 31,32 Os flavonoides são geralmente encontrados em muitas, se não em todas, as plantas de Angiosperma, 30 principalmente os glicosilados, portanto de pouco valor quimiossistemático na confirmação da classificação de um táxon. Contudo, os flavonoides de Rutaceae são tri-, tetra-e polioxigenados, uma exceção entre as demais angiospermas.…”

Section: -14unclassified

Fitoquímica e quimiossistemática de Euxylophora paraensis (Rutaceae)

Isidoro¹,

Silva²,

Fernandes³

et al. 2012

Quím. Nova

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Recebido em 27/4/12; aceito em 28/8/12; publicado na web em 28/9/12 PHYTOCHEMICAL AND CHEMOSYSTEMATIC STUDIES OF Euxylophora paraensis (Rutaceae). Phytochemical studies of the leaves and stem have led to the identification of the known coumarins isooxypeucedanin, oxypeucedanin hydrate, xanthotoxin, isopimpinellin, 8-methoxymarmesin and marmesin, flavonoids quercetin-3-O-α-L-rhamnopyranoside, myricetin-3-O-α-Lrhamnopyranoside and hesperidin, alkaloids skimmianine and N-methylflindersine and limonoid limonin. The compounds isolated and the chemical profile of Euxylophora obtained from the literature clearly indicate its phytochemical affinities with other Rutoideae species.Keywords: Euxylophora paraensis; Rutaceae; chemosystematics. INTRODUÇÃOA família Rutaceae constitui o maior grupo de plantas da ordem Sapindales, possuindo cerca de 160 gêneros, com 1900 espécies amplamente distribuídas nas regiões tropicais e temperadas do globo terrestre, sendo mais abundante na América tropical, sul da África e Austrália.1,2 No Brasil existem cerca de 200 espécies já descritas. 2As plantas desta família são muito conhecidas pela presença de uma ampla diversidade de metabólitos secundários, destacando-se os alcaloides, especialmente aqueles derivados do ácido antranílico, as cumarinas, as lignanas, os flavonoides e os limonoides. 1,3,4 Existem relatos de largo espectro de atividades biológicas associadas a estas classes de metabólitos. 1,3 O gênero Euxylophora é monotípico, apresentando somente a espécie Euxylophora paraensis de ocorrência no norte do Brasil. 5Ela é conhecida popularmente como pau-amarelo devido à cor de sua madeira, a qual é de excelente qualidade, encontrando aplicação na confecção de diversos móveis. Suas árvores de grande porte constam na lista de espécies da flora brasileira ameaçadas de extinção desde 1993.6 Segundo a literatura, foram isolados de E. paraensis somente alcaloides do tipo 2(1H)-quinolinona, 4(1H)-quinolinona, 7-9 indolopiridoquinazolínico e bis-2(1H)-quinolinona. [8][9][10][11][12][13][14][15][16] Estas substâncias resultaram do estudo químico da casca do caule e do cerne, não havendo, até o momento, citação sobre fitoquímica das folhas de E. paraensis. As cumarinas são de ocorrência ampla nos gêneros de Rutaceae, ou seja, são marcadores químicos da família. A ausência de citações destes compostos para este gênero despertou o interesse no estudo de outros órgãos na tentativa de se buscar as cumarinas. A análise preliminar via cromatografia liquida de alta eficiência (CLAE-UV) de extratos das folhas de E. paraensis indicou a presença das cumarinas, o que levou ao presente estudo. Assim, este trabalho relata o primeiro estudo químico das folhas de E. paraensis que levou ao isolamento das cumarinas iso-oxipeucedanina, oxipeucedanina hidratada, xantotoxina, isopimpenilina, dos flavonoides quercetina-3-O-α-L-ramnopiranosídeo, miricetina-3-O-α-L-ramnopiranosídeo e hesperidina e do alcaloide esquimmianina. O caule foi reestudado, mas foram analisadas somente as frações que em análise de RMN 1 H m...

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Section: -14unclassified

Fitoquímica e quimiossistemática de Euxylophora paraensis (Rutaceae)

Isidoro¹,

Silva²,

Fernandes³

et al. 2012

Quím. Nova

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“…Notes: The spectra of 1 – 3 were run in CDCl3 at 100MHz, and at 75 MHz for 5 ; models 5 , 6 and 7 : [2,9,11,12], respectively; Assignments are based on HSQC and HMBC experiments.…”

Section: Resultsmentioning

confidence: 99%

“…Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids [1,2,3]. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica , H. brasiliana and H. superba .…”

Section: Introductionmentioning

confidence: 98%

New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

et al. 2014

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Abstract:Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*)-acetoxy-7(R*)-hydroxy-7-deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-anglespinning 13 C nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen) was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.

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“…From leaves were identified guyanin, rutaecarpin and dictamnine and dihydrocinnamic acid derivatives, together with the new cinnamic acid derivative, been observed plasmocidal and trypanosomidal activities (Severino et al, 2009b). Moreover, several limonoids were identified in the dichloromethane extracts obtained from taproots and stems (Severino et al, 2012).…”

Section: Introductionmentioning

confidence: 98%

“…Considering the phytochemical and pharmacological aspects, H. brasiliana has been described as a large source of alkaloids, coumarins, flavonoids, and limonoids (Suárez et al, 1998;Severino et al, 2009aSeverino et al, , 2009bSeverino et al, , 2012. Five alkaloids were isolated from wood and identified as flindersine, N-methylflindersine, γ-fagarine, skimmianine and 2,4-dimethoxyquinoline (Suárez et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive and anti-inflammatory activities of the hexane extract from Hortia brasiliana Vand. leaves on experimental animal models

Magalhatilde;es¹

2013

Afr. J. Pharm. Pharmacol.

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Antinociceptive and anti-inflammatory activities of the hexane extract from Hortia brasiliana Vand. leaves were investigated by experimental animal models. Guaiol (9.72%), nonacosane (25.57%) and eicosane (10.80%) were the most abundant components identified by GC/MS. The extract, with LD 50 of 2.40 g/kg, reduced the number of abdominal contortions by 13.86 (100 mg/kg) and 18.51% (200 mg/kg). Doses of 100 and 200 mg/kg inhibited both phases of the time paw licking: First phase (9.44% and 16.32%) and the second phase (11.97 and 23.49%), respectively. The extract increased the reaction time on a hot plate at doses of 100 (24.92%) and 200 mg/kg (55.69%) after 90 min of treatment. The paw edema was reduced by the hexane extract at doses of 100 (10.42 and 8.23%) and 200 mg/kg (15.62 and 17.65%) after 3 to 4 h of application of carrageenan, respectively. At the dose of 200 mg/kg, the extract reduced the exudate volume by 19.44%, while the leucocyte migration was inhibited at the doses of 100 and 200 mg/kg (6.13 and 13.84%, respectively). These results suggest that H. brasiliana can be an active source of substances with antinociceptive and anti-inflammatory activities supporting the use in the Brazilian folk medicine.

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Cyclopropane- and spirolimonoids and related compounds from Hortia oreadica

Cited by 11 publications

References 19 publications

Fitoquímica e quimiossistemática de Euxylophora paraensis (Rutaceae)

Fitoquímica e quimiossistemática de Euxylophora paraensis (Rutaceae)

New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

Antinociceptive and anti-inflammatory activities of the hexane extract from Hortia brasiliana Vand. leaves on experimental animal models

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