Identification of the Volatile Compounds of Leaf Oil of<i>Anacardium humile</i>(Anacardiaceae)

Winck, Cristiane R.; Cardoso, Cláudia Andréa Lima; Jeller, Alex Haroldo; Ré-Poppi, Nilva; Coelho, Rosemary Matias; Schleder, Eloty Justina Dias

doi:10.1080/10412905.2010.9700255

Cited by 6 publications

(6 citation statements)

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“…For the oil from leaves of A . humile collected in another region from Brazil [ 20 ], the authors identified the following major constituents: α -bulnesene (8.6%), γ -cadinene (7.5%), selina-3,7(11)-diene (6.7%), α -himachalene (6.1%) and cyperene (5%). It is not uncommon that different chemical compositions are detected for volatile oils extracted from plant species collected in different locations [ 21 , 22 ].…”

Section: Resultsmentioning

confidence: 99%

Exposure to Anacardiaceae Volatile Oils and Their Constituents Induces Lipid Peroxidation within Food-Borne Bacteria Cells

et al. 2012

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The chemical composition of the volatile oils from five Anacardiaceae species and their activities against Gram positive and negative bacteria were assessed. The peroxidative damage within bacterial cell membranes was determined through the breakdown product malondialdehyde (MDA). The major constituents in Anacardium humile leaves oil were (E)-caryophyllene (31.0%) and α-pinene (22.0%), and in Anacardium occidentale oil they were (E)-caryophyllene (15.4%) and germacrene-D (11.5%). Volatile oil from Astronium fraxinifolium leaves were dominated by (E)-β-ocimene (44.1%) and α-terpinolene (15.2%), whilst the oil from Myracrodruon urundeuva contained an abundance of δ-3-carene (78.8%). However, Schinus terebinthifolius leaves oil collected in March and July presented different chemical compositions. The oils from all species, except the one from A. occidentale, exhibited varying levels of antibacterial activity against Staphylococcus aureus, Bacillus cereus and Escherichia coli. Oil extracted in July from S. terebinthifolius was more active against all bacterial strains than the corresponding oil extracted in March. The high antibacterial activity of the M. urundeuva oil could be ascribed to its high δ-3-carene content. The amounts of MDA generated within bacterial cells indicate that the volatile oils induce lipid peroxidation. The results suggest that one putative mechanism of antibacterial action of these volatile oils is pro-oxidant damage within bacterial cell membrane explaining in part their preservative properties.

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Section: Resultsmentioning

confidence: 99%

Exposure to Anacardiaceae Volatile Oils and Their Constituents Induces Lipid Peroxidation within Food-Borne Bacteria Cells

et al. 2012

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“…Palladium-catalyzed oxidation of 6b afforded ketone 7 again in moderate yield, which was subjected to deuterium exchange under basic conditions to furnish the desired d 5 -bulnesone (14) in an excellent yield of 88%. d 5 -2R-Bulnesol ( 16) and d 7 -αbulnesene (15) were successfully synthesized by reduction of 14 in similar fashions as those utilized for the synthesis of the d 5 -rotund-2-ols (11a/b) and d 7 -α-guaiene (10). Deuterium incorporation by hydrogen exchange is an equilibrium and will always yield a mixture of deuterium-labeled compounds with various degrees of deuterium incorporation at different sites of the substrates depending on the ease of exchange of the hydrogen atoms.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Spectroscopic data of 9 including NMR and MS was in accord with those reported in the literature. 14 d 7 -α-Guaiene (10). LiAlD 4 (42 mg, 1 mmol) was suspended in dry ether (1 mL) at room temperature under N 2 .…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…In nature, sesquiterpenes α-guaiene ( 1) and α-bulnesene ( 5 ) may be biosynthesized by the same δ-synthase from the universal sesquiterpene precursor farnesyl pyrophosphate (FPP) . Moreover, the wide occurrence of rotundone in plant products has suggested that its precursor α-guaiene, the isomer α-bulnesene, and other related oxygenated guaiane derivatives might also be common metabolites widely present in plants. ,− The often low natural abundance of these metabolites in nature coupled with the complexity of the plant matrices are the main obstacles in identifying their occurrence and understanding their biotransformations in vivo. We report here the synthesis of a series of deuterium-labeled standards and the use of these as internal standards in GC-MS to compare the evolution of several guaiane derivatives during in vitro aerial oxidation of α-guaiene ( 1 ) and α-bulnesene ( 5 ) over time at ambient temperature and on a submilligram scale.…”

Section: Introductionmentioning

confidence: 99%

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Comparison of the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions

Huang

Sefton

Taylor

2015

J. Agric. Food Chem.

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Deuterium-labeled guaiane derivatives and their precursors, namely, d5-2R-rotundol (11a), d5-2S-rotundol (11b), d5-bulnesone (14), d5-2R-bulnesol (16), d7-α-guaiene (10), and d7-α-bulnesene (15), were synthesized in good yields as GC-MS internal standards for comparing the behavior of α-guaiene (1) and α-bulnesene (5) under autoxidative conditions. It was found that approximately 99% of α-guaiene coated onto filter paper and exposed to air at ambient temperature was autoxidized after 48 h and up to 7% of rotundone (3) and 0.6% of rotundols (2a/b) were formed during this period. Autoxidation of α-bulnesene (5) was considerably slower, with approximately 80% remaining after 2 days and yielding less than 1.5% of α-bulnesone (7) and 0.3% and 0.9% of bulnesols 6a and 6b, respectively, after 5 days. The results indicate the feasibility of rapid changes of aroma profiles of herbs and other plant materials over time when exposed to air.

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“…The same types of substances are also identified as main components of essential oils in fruits and leaves of both species. However, in these organs, the predominant sesquiterpenes in A. humile are α-bulnesene and γ-cadinene ( Cardoso et al 2010 ; Winck et al 2010 ), and in leaves of M. indica the principal monoterpene is cyperene ( Gebara et al 2011 ).…”

Section: Discussionmentioning

confidence: 99%

Osmophores and floral fragrance inAnacardium humileandMangifera indica(Anacardiaceae): an overlooked secretory structure in Sapindales

et al. 2018

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Flowers of Anacardiaceae and other Sapindales typically produce nectar, but scent, often associated with a reward for pollinators, has surprisingly been mentioned only rarely for members of the family and order. However, flowers of Anacardium humile and Mangifera indica produce a strong sweet scent. The origin and composition of these floral scents is the subject of this study. Screening of potential osmophores on the petals and investigations of their anatomy were carried out by light, scanning and transmission electron microscopy. The composition of the floral fragrance was characterized by gas chromatography–mass spectrometry. In both species, the base of the adaxial side of each petal revealed specialized secretory epidermal cells which are essentially similar in structure and distinct from all other neighbouring cells. These cells also showed evidence of granulocrine secretory mechanisms and slight specific variations in their subcellular apparatus coinciding with the respective composition of the floral fragrance, predominantly composed of sesquiterpenes in A. humile and monoterpenes in M. indica. This study reports the presence of osmophores for the first time in flowers of Anacardiaceae and confirms the link between the ultrastructural features of their secretory cells and the volatiles produced by the flowers. The flowers of most Sapindales, including Anacardiaceae, are nectariferous. However, the presence of osmophores has only been described for very few genera of Rutaceae and Sapindaceae. Both the occurrence of osmophores and fragrance may have largely been overlooked in Anacardiaceae and Sapindales until now. Further studies are needed to better understand the nature and diversity of the interactions of their nectariferous flowers with their pollinators.

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Identification of the Volatile Compounds of Leaf Oil ofAnacardium humile(Anacardiaceae)

Cited by 6 publications

References 1 publication

Exposure to Anacardiaceae Volatile Oils and Their Constituents Induces Lipid Peroxidation within Food-Borne Bacteria Cells

Exposure to Anacardiaceae Volatile Oils and Their Constituents Induces Lipid Peroxidation within Food-Borne Bacteria Cells

Comparison of the Formation of Peppery and Woody Sesquiterpenes Derived from α-Guaiene and α-Bulnesene under Aerial Oxidative Conditions

Osmophores and floral fragrance inAnacardium humileandMangifera indica(Anacardiaceae): an overlooked secretory structure in Sapindales

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