Characterization of the chemical composition of the essential oils from Annona emarginata (Schltdl.) H. Rainer 'terra-fria' and Annona squamosa L.

Abstract

-The objective of this study was to characterize the chemical composition of the essential oil from the leaves of Annona emarginata (Schltdl.) H. Rainer 'terra-fria' and Annona squamosa L. The species were grown in a greenhouse for 18 months, which nutrient solution was applied weekly; the plants were then harvested and the leaves dried to extract the essential oil. The essential oil was analyzed by gas chromatography and mass spectrometry to study its chemical profiles. Eleven substances were found in the essential oil of A. emarginata, primarily (E)-caryophyllene (29.29%), (Z)-caryophyllene (16.86%), γ-muurolene (7.54%), α-pinene (13.86%), and tricyclene (10.04%). Ten substances were detected in the oil from A. squamosa, primarily (E)-caryophyllene (28.71%), (Z)-caryophyllene (14.46%), α-humulene (4.41%), camphene (18.10%), α-pinene (7.37%), β-pinene (8.71%), and longifolene (5.64%). Six substances were common to both species: (E)-caryophyllene, (Z)-caryophyllene, α-humulene, camphene, α-pinene, and β-pinene. Index terms: Annonaceae, secondary metabolites, terpenes, pharmacological potential. CARACTERIZAÇÃO DO PERFIL QUÍMICO DO ÓLEO ESSENCIAL DE Annona emarginata (Schltdl.) H. Rainer 'terra-fria'e Annona squamosa L.RESUMO-O objetivo do presente estudo foi caracterizar a composição química do óleo essencial das folhas de Annona emarginata (Schltdl.) H. Rainer 'terra-fria' e Annona squamosa L. As espécies foram cultivadas em casa de vegetação, com aplicação semanal de solução nutritiva até completar 18 meses, quando se realizaram a colheita e a secagem das folhas para a extração do óleo essencial, analisado por cromatografia gasosa acoplada à espectrometria de massas, para estudo dos perfis químicos. Onze substâncias majoritárias foram encontradas no óleo essencial de A. emarginata: (E)-cariofileno-29,29%; (Z)-cariofileno-16,86%; γ-muroleno-7,54%; α-pineno-13,86%; tricicleno-10,04%. No óleo de A. squamosa, 10 substâncias foram detectadas, entre elas: (E)-cariofileno-28.71%; (Z)-cariofileno-14,46%; α-humuleno-4,41%; canfeno-18,10%; α-pineno-7,37%, e β-pineno-8,71%; longifoleno-5,64%; majoritárias. (E)-cariofileno; (Z)-cariofileno; α-humuleno; canfeno; α-pineno, e β-pineno foram as seis substâncias comuns às duas espécies. Termos para indexação: Annonaceae, metabólitos secundários, terpenos, potencial farmacológico.

Chemophenetics as a Tool for Distinguishing Morphotypes of Annona emarginata (Schltdl.) H. Rainer

“…The result found for A. emarginata ‘terra‐fria’ – where the major compounds are always sesquiterpenes in the three phenological stages at both harvest sites – is corroborated by Campos et al. [24] . These authors found a majority percentage of sesquiterpenes in young plants of A. emarginata ‘terra‐fria’ – collected in 2012 –, with the major substance being the compound E‐caryophyllene.…”

Characterization of seasonal and chemotypical variability in the essential oil from leaves of Annona neosalicifolia H. Rainer (Annonaceae)

“…Other reports referred (E)-caryophyllene (29.29%), (Z)-caryophyllene (16.86%), γ-muurolene (7.54%), α-pinene (13.86%), and tricyclene (10.04%) as main volatiles in A. emarginata var. 'terra-fria' (Campos et al, 2014) and, in the EO from leaves of the rootstock for grafted A. x atemoya, β-selinene (12.63%), α-selinene (12.21%), β-elemene (9.66%), spathulenol (7.25%), α-pinene (5.55%), (E)-caryophyllene (5.39%) (Campos, Vieira, Baron, et al, 2019b). The volatile chemical profile of the rootstock may influence the success of grafting, probably due to antioxidant, antiradical, and antibiotic activities (Campos, Vieira, Baron, et al, 2019a,b), so it is reasonable to hypothesize that if A. emarginata s.s. and A. neosalicifolia are actually the same species, the chemical composition of A. neosalicifolia chemotype II qualifies it as a new chemotype, different from any reported for A. emarginata s.s. and could be tested as an alternative rootstock for grafting A. x atemoya.…”

“…Volatiles were reported from Annonaceae species, especially from Cananga odorata (Ylang-Ylang) and edible species in the genus Annona (Campos et al, 2014;Felipe G Campos et al, 2019a, Felipe G Campos et al, 2019bJirovetz et al, 1998;Pino, 2000;Thang et al, 2013;Wyllie et al, 1987). The most commonly reported volatiles were terpenic in origin: α-pinene, β-pinene, limonene, β-caryophyllene, p-cymene, and caryophyllene oxide, which are found in many oils and, therefore, have no special taxonomic value.…”

Chemical composition of the volatile oil of Cardiopetalum calophyllum collected in the Cerrado area

“…PONTES et al (2007) evaluated the acaricidal activity of the essential oil obtained from the leaves of Xylopia sericea; ~95% of the oil comprised of a complex mixture of sesquiterpenes. CAMPOS et al (2014) also reported a predominance of sesquiterpenes in the essential oils of Annona emarginata and Annona squamosa.…”

“…Some genera are chemically welldocumented, such as Xylopia, where significant concentrations of caryophyllene oxide, α-pinene, α-terpinene, limonene, spathulenol, germacrene-D, trans-β-guaiene, and β-caryophyllene are present in the essential oils extracted from the leaves and fruits (SANTOS, et al 2004;PONTES et al, 2007;VALTER et al, 2008). Annona genus has also been well-characterized; caryophyllene, camphene, α-pinene, and β-pinene have been identified in the essential oil extracted from the leaves (BANDEIRA et al, 2011;CAMPOS et al, 2014). However, the active substances present in the plants of this family are still investigated (NASCIMENTO et al, 2003;SILVA, 2007;NUNES et al, 2012;ALMEIDA et al, 2014;KRINSKI et al, 2014).…”