Chemical composition and larvicidal activity of the essential oils of Cordia leucomalloides and Cordia curassavica from the Northeast of Brazil

Abstract

Os óleos essenciais das folhas de Cordia leucomalloides e Cordia curassavica foram obtidos por hidrodestilação e suas composições químicas determinadas por uma combinação de CG-EM e CG-DIC. Como resultado, vinte e três componentes foram identificados em ambos os óleos, representando 98,6 e 91,2% da composição volátil. O óleo essencial de C. leucomalloides foi caracterizado por uma alta percentagem de sesquiterpenos (90,6%), sendo δ-cadineno (17,4%), (E)-cariofileno (15,7%), biciclogermacreno (12,5%) e germacreno D (11,2%) os majoritários. Por outro lado, o óleo de C. curassavica mostrou proporções similares de monoterpenos (47,3%) e sesquitepenos (43,9%), entre os quais α-pineno (20,5%), β-pineno (13,1%), (E)-cariofileno (12,4%) e biciclogermacreno (13,8%) foram os compostos predominantes. O potencial larvicida dos dois óleos foi avaliado contra larvas no terceiro estágio do mosquito Aedes aegypti. Os resultados mostraram que ambos os óleos apresentaram atividade biológica significativa, particularmente o óleo essencial de C. leucomalloides, o qual foi capaz de matar 98,7% das larvas numa concentração de 100 ppm.The essential oils obtained from the leaves of Cordia leucomalloides and Cordia curassavica were obtained by hydrodistillation and their chemical compositions determined by a combination of GC-MS and GC-FID. Twenty-three components were tentatively identified in both oils representing 98.6 and 91.2% of the volatile content. The oil of C. leucomalloides was characterized by a large percentage of sesquiterpenes (90.6%), being δ-cadinene (17.4%), (E)-caryophyllene (15.7%), bicyclogermacrene (12.5%) and germacrene D (11.2%) the major ones. On the other hand, the oil of C. curassavica showed similar proportions of monoterpenes (47.3%) and sesquiterpenes (43.9%) among which α-pinene (20.5%), β-pinene (13.1%), (E)-caryophyllene (12.4%) and bicyclogermacrene (13.8%) were the predominant compounds. The larvicidal potential of the two oils were evaluated against the third-instar of Aedes aegypti larvae. The results showed that both oils exhibited significant activity, particularly the oil of C. leucomalloides which was able to kill 98.7% of the larvae in the concentration of 100 ppm. Keywords:Cordia leucomalloides, Cordia curassavica, essential oil, larvicidal activity, terpenoids IntroductionThe pantropical genus Cordia, represented by shrubs and trees, is one of the major and most important genus of the family Boraginaceae. 1 Some of its species yield excellent wood naturally resistent to attack of several organisms, 2,3 while others are widely used in traditional medicine in several parts of the world. 4 13 and C. globosa (Jacq.) H.B.K. 14 have been described. The two later were recently subject of our studies, including their essential oils. A literature survey revealed that the oil of C. leucomalloides has not been reported but C. curassavica has been the subject of several studies, probably due its etnobotanical value. 1,5,6,15 C. curassavica is a medicinal plant with anti-inflammatory and antimicrobial prop...

Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

“…Essential oil a-Pinene C. curassavica [211] C. cylindrostachya [136] C. verbenacea [137,138] Leaves Twigs and Leaves Flower, Leaves a-Humulene C. globosa [51] C. verbenacea [106,139] Leaves a-Cadinol C. trichotoma [62] Wood a-Muurolol C. trichotoma [62] Wood 6a-Hydroxygermacra-1(10) 4-diene C. chacoensis [140] b-Caryophyllene C. boissieri [141,142] C. chacoensis [135,143] C. curassavica [41] C. globosa [144] C. leucocephala [135] C. leucomalloides [145] C. multispicata [138] C. verbenacea [106,139] Flower Leaves Flowers, Stem Aerial parts, Leaves b-Pinene C. curassavica [135] Leaves b-Eudesmol C. curassavica [146] Aerial parts b-Phellandrene C. multispicata [144] Leaves, flowers, Stem d-Cadinene C. leucomalloides [135] C. trichotoma [72] C. verbenacea [138] Leaves Wood Leaves Aromadendrene C. chacoensis [142] Alloaromadendrene C. verbenacea [137] Flower, leaves Bicyclogermacrene C. curassavica [135] C. globosa [41,143] C. leucocephala [135] C. leucomalloides [145] C. verbenacea [138] Leaves Aerial parts, Leaves Cadinene C. chacoensis [142] Camphene C. cylindrostachya [136] Twigs and leaves Elemol C. chacoensis [142] Germacrene D C. leucomalloides [135] C. ver...…”

“…Afzal et al Figure 11 Porphyrins and miscellaneous compounds isolated from the genus Cordia. [164] C. americana Antimicrobial Aqueous and hydroalcoholic extract were found to be the most effective against herpes simplex virus type 1 [206] Anti-inflammatory Ethanol extract of leaves showed potent inhibitory effect on 5-lipoxygenase, p38a with IC 50 value of 0.69 and 3.25 lg/ml and moderate inhibition of TNF-a [99] C. boissieri Antimicrobial Methanol extract of the leaves and flowers demonstrated antimicrobial activity against Staphylococcus aureus (MIC 250 lg/ml) and Candida glabrata (MIC 125 lg/ml), respectively [165,166] Antioxidant Methanol extract of the flowers was found to inhibit oxidation of methyl linoleate by 95.8% [169] C. curassavica Antimicrobial The essential oil obtained from aerial parts showed antimicrobial activity against Staphylococcus epidermidis (MIC 0.75-1.00 mg/ml), Sarcina lutea (MIC 0.62 mg/ml), Vibrio cholera (MIC 0.125-0.375 mg/ml) and Rhizoctonia solani (IC 25 0.1300 mg/ml), while hexane extract was active against Trichophyton mentagrophytes (IC 50 = 230 mg/ml) [146,160,161] Larvicidal The essential oil as well as aqueous, acetone and methanol extract of leaves shown potent larvicidal activity against third-instar and 2-3 larval instars of Aedes aegypti, respectively [205,207,211] C. cylindrostachya Antimicrobial The neutral fraction of leaves was found to inhibit growth of Escherichia coli, Staphylococcus aureus, Enterococcus faecalis, Micrococcus spp. and Bacillus subtilis [75] C. dichotoma Antimicrobial The methanol and butanol extract of the bark inhibited the growth of Escherichia coli, and Pseudomonas aeruginosa, Streptococcus pyogenes and Staphylococcus aureus, Aspergillus niger, Aspergillus clavatus and Candida albicans [167] The ethanol extract of the leaves was also demonstrated significant antimicrobial activity against Streptococcus aureus, Streptococcus pyogenes, Vibrio cholera, Streptococcus epidermis, Hafnia and Escherichia coli [188] Antioxidant Methanol and butanol extract of the bark showed significant DPPH radical scavenging activity and also increased ferric reducing power in reducing power assays [170] The methanol extract and taxifolin-enriched methanol fraction of seeds also showed significant antioxidant activity in DPPH radical scavenging assay [174] Antiulcer Oral administration of ethyl acetate, butanol and butanone fraction of fruit at a dose of 300 mg/kg to the rat significantly reduced gastric secretion, free acidity, total acidity and ulcer index in three different models, that is pyloric ligation and indomethacin-and aspirininduced ulcers [184] Analgesic The ethanol extract of ...…”

“…(IC 50 value 75.0 and 129.9 lg/ml, respectively.) [147] Anticholinesterase Essential oil obtained from leaves was also reported to have anticholinesterase activity with IC 50 value of 105.6 lg/ml [147] C. globosa Antioxidant The methanol extract of the aerial parts displayed strong antioxidant activity in DPPH assays and b-carotene bleaching test [210] C. leucomalloides Larvicidal Essential oil obtained from leaves showed larvicidal activity against third-instar of Aedes aegypti larvae [211] C. macleodii Antimicrobial Water, methanol, ethyl acetate and n-hexane extract of leaves and stem were found to show significant antibacterial activity against Gram-positive and Gram-negative bacteria. However water extract displayed excellent activity compared to other extracts [212][213][214] Antioxidant…”

Avaliação da atividade larvicida do óleo essencial do Zingiber officinale Roscoe (gengibre) frente ao mosquito Aedes aegypti

“…Santos et al (2006) reportaram a atividade larvicida de mono e sesquisterpenos extraídos de óleos essenciais da família Boraginaceae frente ao Aedes aegypti. Entre os compostos majoritários os monoterpenos α-e β-pineno foram destacados como responsáveis pela ação larvicida (no presente estudo o primeiro composto apresentou um teor de 1,46%).…”

Efeito fungicida dos óleos essenciais de Schinus molle L. e Schinus terebinthifolius Raddi, Anacardiaceae, do Rio Grande do Sul

“…α-Pineno e sabineno possuem atividade bactericida comprovada por testes com a espécie Lithraea molleoides, conhecida popularmente como aroeira branca (Shimizy et al, 2006). O biciclogermacreno não é citado quanto à atividade bactericida, porém possui potencial larvicida comprovado a partir de testes com as larvas do mosquito Aedes aegypti (Santos et al, 2006). Souza e colaboradores (2005) referenciam a maior ou menor atividade biológica dos óleos essenciais dependente de alguns constituintes químicos em especial (citral, pineno, cineol, cariofileno, elemeno, furanodieno, limoneno, eugenol e carvacrol), porém é importante comentar que devido à complexidade da composição química de um óleo essencial, torna-se difícil relacionar a atividade biológica com as substâncias presentes.…”