Chemical Variation in Piper aduncum and Biological Properties of Its Dillapiole‐Rich Essential Oil

Abstract

The essential oils of the specimens of Piper aduncum that occur in deforested areas of Brazilian Amazon, North Brazil, are rich in dillapiole (35-90%), a derivative of phenylpropene, to which are attributed biological properties. On the other hand, the oils of the specimens with occurrence in the Atlantic Forest, and Northeastern and Southeastern Brazil, do not contain dillapiole, but only terpene compounds such as (E)-nerolidol and linalool. One specimen existing in the Amazon was hydrodistilled. The obtained oil was fractioned on a silica chromatographic column, resulting in fractions rich in dillapiole (95.0-98.9%) utilized for analyses by GC and GC/MS, structural characterization by NMR, confirmation of their biological properties, and to obtain the isomer isodillapiole. Dillapiole showed a fungicide action against the fungus Clinipellis perniciosa (witches' broom) by inhibition of its basidiospores, in concentrations ranging from 0.6 to 1.0 ppm. The larvicide and insecticide actions of dillapiole were tested against the larvae and the adult insects of Anopheles marajoara and Aedes aegypti (malaria and dengue mosquitoes), resulting in mortality of the larvae (48 h, 100%) at a concentration of 100 ppm, and mortality of the insects (30 min, 100%) at a concentration of 600 ppm. The isomeric isodillapiole showed no significant activity in the same biological tests.

Piper gaudichaudianum Kunth: Seasonal Characterization of the Essential Oil Chemical Composition of Leaves and Reproductive Organs

“…collected in Rondônia and Piper aduncum L. in Pará and Distrito Federal. The dillapiole levels observed in these EOs ranged from 54.7% and 31.5-97.3%, respectively 31,11,32,33 . 36 .…”

Piper aduncum against Haemonchus contortus isolates: cross resistance and the research of natural bioactive compounds

“…This in vitro effect observed with the LDT may be related to the arylpropanoid dillapiole, to which many of the pharmacological activities of the EO extracted from P. aduncum L. have been attributed (MAIA et al, 1998;POHLIT et al, 2006). In fact, dillapiole has been shown to have acaricidal (SILVA et al, 2009;PINO et al, 2011;ARAÚJO et al, 2012), anti-bacterial (LARA-JÚNIOR et al, 2012BRAZÃO et al, 2014), anti-fungal (LARA-JÚNIOR et al, 2012;GUERRINI et al, 2009), leishmanicidal (PARISE-FILHO et al, 2012, anti-inflammatory (PARISE-FILHO et al, 2011) and insecticidal activities (BELZILE et al, 2000;SOUTO, 2006;LING et al, 2009). When 99% pure, this compound has been evaluated and identified as the mediator of many of the biological activities above (ALMEIDA, 2004).…”

“…aduncum -was adopted (GUIMARÃES et al, 2015). The chemical variation observed in the EO of P. aduncum L. may result from the predominance of different biosynthetic pathways in two chemotypes (ALMEIDA et al, 2009). In the Amazon forest the shikimate pathway took precedence, producing the phenylpropanoid dillapiole, whereas in the Atlantic forest chemotype, the mevalonate/acetate pathway was favored, generating the terpenoids (E)-nerolidol and linalool.…”

“…Specifically, Piperaceae family EOs have been tested in many different contexts worldwide (GUPTA, 1995;OVIEDO-RONDON et al, 2006;SRINIVASAN, 2007;SCOTT et al, 2008;GUERRINI et al, 2009;SILVA et al, 2009;SINGH et al, 2009;PINO et al, 2011;ARAUJO et al, 2012). The biological activity of the Piper genus, native to tropical and subtropical regions (JARAMILLO & MANOS, 2001), has been more extensively studied.…”

Active metabolites of the genus Piper against Aedes aegypti: natural alternative sources for dengue vector control

“…In this study, dillapiole rich oil (95.0-98.9%) was tested against A. aegypti larvae and adult insects. The results showed mortality of 100% of larvae after 48 h at a concentration of 100 ppm, and a mortality of 100% of the adult insects after 30 min at a concentration of 600 ppm (Almeida et al 2009). Isomeric isodillapiole showed no significant activity.…”