Essential Oils and Diethyl Ether Extracts of Serbian <i>Xeranthemum cylindraceum</i> and <i>X. annum</i>: Chemical Composition, Antimicrobial Activity, and Chemotaxonomic Implications

Dekić, Milan S.; Radulović, Niko S.; Ranđelović, Vladimir; Stojanović-Radić, Zorica; Veljković, Bojana

doi:10.1002/cbdv.201400316

Cited by 11 publications

(6 citation statements)

References 105 publications

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“…9 and Melissa of f icinalis L. 8 Warionea saharae Benth & Coss. (Asteraceae), 42 Xeranthemum cylindraceum and X. annum Astraceae, 43 sweet orange essential oil (Citrus sinensis (L.) Osbeck) 44…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Structure–Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Elsharif

Buettner

2016

J. Agric. Food Chem.

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Despite being isomers having the same citrus-like, floral odor, geraniol, 1, and nerol, 3, show different odor thresholds. To date, no systematic studies are at hand elucidating the structural features required for their specific odor properties. Therefore, starting from these two basic structures and their corresponding esters, namely, geranyl acetate, 2, and neryl acetate, 4, a total of 12 oxygenated compounds were synthesized and characterized regarding retention indices (RI), mass spectrometric (MS), and nuclear magnetic resonance (NMR) data. All compounds were individually tested for their odor qualities and odor thresholds in air (OT). Geraniol, the Z-isomer, with an OT of 14 ng/L, was found to be more potent than its E-isomer, nerol, which has an OT of 60 ng/L. However, 8-oxoneryl acetate was the most potent derivative within this study, exhibiting an OT of 8.8 ng/L, whereas 8-oxonerol was the least potent with an OT of 493 ng/L. Interestingly, the 8-oxo derivatives smell musty and fatty, whereas the 8-hydroxy derivatives show odor impressions similar to those of 1 and 3. 8-Carboxygeraniol was found to be odorless, whereas its E-isomer, 8-carboxynerol, showed fatty, waxy, and greasy impressions. Overall, we observed that oxygenation on C-8 affects mainly the odor quality, whereas the E/ Z position of the functional group on C-1 affects the odor potency.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Structure–Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Elsharif

Buettner

2016

J. Agric. Food Chem.

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“…There are many papers dealing with phytochemical investigations (Valant-Vetschera & Wollenweber, 2007;Zemtsova & Molchanova, 1979;Samek et al, 1977;Powell et al, 1967;Hîbel et al, 1982;Schwind et al, 1990;Skaltsa et al, 2000;Dekić et al, 2015), biological effect (Stanković et al, 2011), flower ontogeny (Dadpour et al, 2012), palynology (Garnatje & Martín, 2007), involucral bracts and petals micromorphology (Gavrilović et al, 2017) and molecular cytogenetics (Garnatje et al, 2004a) of Xeranthemum. Kartal (2016), within the style and ovary cells of X. annuum, found styloid crystals.…”

Section: Introductionmentioning

confidence: 99%

Anatomical characteristics of Xeranthemum L. (Compositae) species: taxonomical insights and evolution of life form

Gavrilović¹,

Rančić²,

Škundrić³

et al. 2019

PAK.J.BOT.

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Comparative anatomical and micromorphological analyses of root, stem, peduncle, leaf and inflorescence have been conducted on two Xeranthemum species, X. annuum and X. cylindraceum, by light microscopy (LM) and scanning electron microscopy (SEM). The main goal of the study was to examine the most important anatomical features and to find new valid taxonomic delimiting characters for the first time in both species. Regarding vegetative organs anatomy, the data obtained in this study indicated that both species possessed secondary tissues in the root, although these plants are annual. Also, stem anatomy was a typical of the Compositae family members, and anomocytic stomata type and dorsiventral leaf structure were present. On the involucral bracts surface crystals were noticeable, while highly developed multilayer sclerenchyma was present in the mesophyll. Palea anatomy was very similar to bract anatomy. Some floral features were as follows: lateral anther dehiscence, corolla composed of uniseriate epidermis and with a homogeneous parenchyma in the mesophyll, inferior ovary and anatropous ovule with basal placentation. The specific quantitative characters that were different between the examined species were emphasized. Some selected, well defined qualitative anatomical characters (e.g. shape of the young stem and peduncle cross-sections, type of glandular trichomes and cortical vascular bundles occurrence), on the basis of which the studied species were distinguishable, strengthen the taxonomy of the Xeranthemum genus and provide features for better identification of the taxa. This is the first study of the anatomy of Xeranthemum species and some of the characters found (secondary growth and dorsiventral leaves) points towards an adaptation of mesophilous ancestors to xeric habitats in Xeranthemum.

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“…There are number of papers dealing with phytochemical investigations (Powell et al, 1967; Samek et al, 1977; Zemtsova & Molchanova, 1979; Hîbel et al, 1982; Skaltsa et al, 2000; Valant-Vetschera & Wollenweber 2007; Dekić et al, 2015), molecular cytogenetics (Garnatje et al, 2004), and biological activity (Stanković et al, 2011) of the genus Xeranthemum . In contrast, there is only one paper which shown presence of styloid crystals in the style and ovary cells in X. annuum (Kartal, 2016).…”

Section: Introductionmentioning

confidence: 99%

Scanning Electron Microscopy Coupled with Energy Dispersive Spectrometric Analysis Reveals for the First Time Weddellite and Sylvite Crystals on the Surface of Involucral Bracts and Petals of two Xeranthemum L. (Compositae) Species

et al. 2017

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In this work, weddellite and sylvite crystals are identified for the first time on the involucral bracts and petals of Xeranthemum annuum and Xeranthemum cylindraceum using scanning electron microscopy coupled with energy dispersive spectrometric (SEM-EDS) analysis. Well-developed crystals of weddellite (CaC2O4·2H2O) occur in the form of a tetragonal bipyramid (hhl), rarely in combination of a bipyramid and tetragonal prism (h00). Indumentum of involucral bracts of X. cylindraceum consists of nonglandular and glandular trichomes. Sylvite (KCl) crystals are observed only on the petal surface of X. cylindraceum. The crystals of sylvite occur in the form of perfect cubes (hexahedrons), but some crystals are deformed, i.e., partially elongated. Taxonomic significance of investigated microcharacters as well as the use of SEM-EDS analysis in taxonomic studies of plants are discussed.

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Essential Oils and Diethyl Ether Extracts of Serbian Xeranthemum cylindraceum and X. annum: Chemical Composition, Antimicrobial Activity, and Chemotaxonomic Implications

Cited by 11 publications

References 105 publications

Structure–Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Structure–Odor Relationship Study on Geraniol, Nerol, and Their Synthesized Oxygenated Derivatives

Anatomical characteristics of Xeranthemum L. (Compositae) species: taxonomical insights and evolution of life form

Scanning Electron Microscopy Coupled with Energy Dispersive Spectrometric Analysis Reveals for the First Time Weddellite and Sylvite Crystals on the Surface of Involucral Bracts and Petals of two Xeranthemum L. (Compositae) Species

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