Synthesis of Small Combinatorial Libraries of Natural Products: Identification and Quantification of New Long-chain 3-Methyl-2-alkanones from the Root Essential Oil of Inula helenium L. (Asteraceae)

2013 ◽  
Vol 25 (1) ◽  
pp. 75-80 ◽  
Author(s):  
Niko S. Radulović ◽  
Marija S. Denić ◽  
Zorica Z. Stojanović-Radić
Keyword(s):  
Natural Products ◽  
Essential Oil ◽  
Combinatorial Libraries ◽  
Inula Helenium ◽  
Root Essential Oil ◽  
Long Chain ◽  
Identification And Quantification

scholarly journals A note on the biosynthesis of long-chain 3-methyl-2-alkanones from the root essential oil of Inula helenium L. (Asteraceae)

2015 ◽  
Vol 13 (2) ◽  
pp. 83-89
Author(s):  
Marija Gencic ◽  
Niko Radulovic
Keyword(s):  
Essential Oil ◽  
Enzyme System ◽  
Carbon Number ◽  
Plant Tissues ◽  
Biosynthetic Pathways ◽  
Methyl Group ◽  
Inula Helenium ◽  
Related Compounds ◽  
Root Essential Oil ◽  
Long Chain

A predominantly odd-numbered, Gaussian-like distribution of the relative amounts of 3-methyl-2-alkanones, from I. helenium root essential oil, was observed. This distribution pattern indicates that their biosynthesis is related to that of fatty acids and related compounds. Simple (non-branched) 2-alkanones also show an odd carbon number prevalence in plants and other organisms, and it was shown that their biosynthesis indeed proceeds via the acetate pathway. In this paper, we propose three possible biosynthetic pathways by which 3-methyl-2-alkanones could be formed in the plant tissues. The essential distinction between them lies in the way the branching methyl group is introduced. The Gaussian parameter ? for the observed distribution of these ketones could be interpreted as the error introduced by the first elongase enzyme system involved in the biosynthesis of fatty acid-derived compounds.

Anticandidal activity of Inula helenium root essential oil: Synergistic potential, anti-virulence efficacy and mechanism of action

2020 ◽  
Vol 149 ◽  
pp. 112373
Author(s):  
Zorica Stojanović-Radić ◽  
Marina Dimitrijević ◽  
Marija Genčić ◽  
Milica Pejčić ◽  
Niko Radulović
Keyword(s):  
Essential Oil ◽  
Mechanism Of Action ◽  
Inula Helenium ◽  
Anticandidal Activity ◽  
Root Essential Oil

Synthesis of small libraries of natural products: New esters of long-chain alcohols from the essential oil ofScandix pecten-venerisL. (Apiaceae)

2014 ◽  
Vol 29 (4) ◽  
pp. 255-266 ◽  
Author(s):  
Niko S. Radulović ◽  
Marko Z. Mladenović ◽  
Zorica Z. Stojanović-Radić
Keyword(s):  
Natural Products ◽  
Essential Oil ◽  
Long Chain

scholarly journals Conformational Analysis of Antistaphylococcal Sesquiterpene Lactones from Inula helenium Essential Oil

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Polina D. Blagojević ◽  
Niko S. Radulović
Keyword(s):  
Essential Oil ◽  
Molecular Descriptors ◽  
Sesquiterpene Lactones ◽  
Empirical Methods ◽  
Binding Region ◽  
Antistaphylococcal Activity ◽  
Inula Helenium ◽  
Semi Empirical ◽  
2D And 3D ◽  
Root Essential Oil

Isomeric eudesmane-type sesquiterpene lactones: alantolactone (1), isoalantolactone (2) and diplophyllin (3), the main constituents of Inula helenium L. root essential oil, are strong antistaphylococcal agents. Energetically favorable conformations of these were calculated (MM+ and MMFF94 molecular mechanics and AM1 and PM3 semi-empirical methods) and mutually compared. The compounds were additionally described in terms of selected 2D and 3D molecular descriptors. Alantolactone and isoalantolactone mainly adopt “U”-shaped conformations (>99%, calculated at 298 K; “closed” geometries), with the carbonyl moiety being rather sterically hindered by the axial methyl group. In contrast, the cyclohexene and lactone rings of diplophyllin are mutually oriented in such a way to give the overall “S”-shape to the molecule (“open” geometry). These conformational differences, inherently influencing the optimal interaction of lactones 1-3 with the binding region of target biomolecules, could be, at least partially, responsible for the higher observed antistaphylococcal activity of diplophyllin in comparison with the other two isomeric lactones.

The effect of long‐chain alkanes on flavour release and olfactory characteristics of rose essential oil

2021 ◽  
Author(s):  
Yingjie Fu ◽  
Yipeng Zhang ◽  
Shitong Zeng ◽  
Liwen Luo ◽  
Hui Xi ◽  
...  
Keyword(s):  
Essential Oil ◽  
Long Chain ◽  
Flavour Release

Root Essential Oil ofAchillea lingulataWaldst. & Kit. (Asteraceae)

2010 ◽  
Vol 22 (4) ◽  
pp. 336-339 ◽  
Author(s):  
Olga Jovanović ◽  
Niko Radulović ◽  
Radosav Palić ◽  
Bojan Zlatković
Keyword(s):  
Essential Oil ◽  
Root Essential Oil

scholarly journals Chemical Composition and Antimicrobial Activity of Anthriscus nemorosa Root Essential Oil

2011 ◽  
Vol 6 (2) ◽  
pp. 1934578X1100600
Author(s):  
Milica Pavlović ◽  
Silvana Petrović ◽  
Marina Milenković ◽  
Maria Couladis ◽  
Olga Tzakou ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Essential Oil ◽  
Gram Positive Bacteria ◽  
Microdilution Method ◽  
Broth Microdilution Method ◽  
Bacillus Subtilis Atcc ◽  
Germacrene D ◽  
Main Components ◽  
Total Oil ◽  
Root Essential Oil

The essential oil obtained by hydrodistillation from the roots of Anthriscus nemorosa (Bieb.) Sprengel (Umbelliferae) was analyzed by GC and GC-MS. Among sixty-two compounds identified (representing 89.0% of the total oil), the main components were: n-nonane (12.1%), n-hexadecanol (6.9%), δ-cadinene (6.4%), β-pinene (6.0%) and germacrene D (5.4%). Furthermore, the antimicrobial activity of the oil was evaluated against the Gram-positive bacteria Staphylococcus epidermidis (ATCC 12228) and Bacillus subtilis (ATCC 6633), the Gramnegative bacterium Escherichia coli (ATCC 25922), and a yeast Candida albicans (ATCC 10259 and ATCC 24433) using the broth microdilution method.

Composition and antimicrobial activity of root essential oil of Balkan endemic species Eryngium palmatum

2014 ◽  
Vol 49 (6) ◽  
pp. 1140-1142 ◽  
Author(s):  
M. Marcetic ◽  
S. Petrovic ◽  
M. Milenkovic ◽  
Lj. Vujisic ◽  
V. Tesevic ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Essential Oil ◽  
Endemic Species ◽  
Root Essential Oil

New Constituents of the Leaf and Stem Exudate of Ozothamnus hookeri (Asteraceae)

2000 ◽  
Vol 55 (5-6) ◽  
pp. 318-322 ◽  
Author(s):  
Angel Rumbero ◽  
F. J. Arriaga-Giner ◽  
Eckhard Wollenweber
Keyword(s):  
Natural Products ◽  
Fatty Acid ◽  
Chain Fatty Acid ◽  
Long Chain Fatty Acid ◽  
Long Chain

The exudate of Ozothamnus hookeri has been investigated for its non-flavonoid constituents. A new natural C6-C3 ester of a long chain fatty acid and seven structurally related kaurane-diterpenoids were isolated. Three of the latter are new natural products, too. A rare 8-methoxy flavonol was also identified.

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