Sesquiterpene Lactones from <i>Anthemis melanolepis</i> and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Saroglou, Vasiliki; Karioti, Anastasia; Rancic, Ana; Dimas, Kostas; Koukoulitsa, Catherine; Zervou, Maria; Skaltsa, Helen

doi:10.1021/np9004129

Cited by 32 publications

(17 citation statements)

References 30 publications

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“…The organic phase was concentrated under vacuum to dryness and yielded a lipophilic residue (0.14%). [9]…”

Section: Methodsmentioning

confidence: 99%

“…[7] It is also used for the treatment of cough and cold. [8] The genus Anthemis is characterized mainly by the presence of sesquiterpene lactones, belonging to germacranolides, eudesmanolides, guaianolides[9,10] and flavonoids. [11] The literature survey on A. wiedemanniana revealed the presence of sesquiterpene lactones of germacrane, eudesmane and guaianolide type.…”

Section: Introductionmentioning

confidence: 99%

“…[11] The literature survey on A. wiedemanniana revealed the presence of sesquiterpene lactones of germacrane, eudesmane and guaianolide type. [9,10,11] According to a previous study, linalool, 1,8-cineole, hexadecanoic acid and chrysanthenone were found to be the major compounds characterized in the essential oil of A. wiedemanniana . [6] Fatty acids are known as self defensive agents in organisms and posses various biological activities including anti-inflamation.…”

Section: Introductionmentioning

confidence: 99%

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Fatty acid composition and preclinical resarches on Anthemis wiedemanniana Fisch. & Mey.: Discovery of a new anti-inflammatory agent

et al. 2014

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Background:Anthemis species have been used for the treatment of gastrointestinal disorders, hemorrhoid, stomachache and inflammatory diseases in Turkish folk medicine. Anthemis wiedemanniana Fisch. And Mey. is an endemic plant used as painkiller, antispasmodic, sedative and for the treatment of urinary inflammations.Objective:The objective of the present study is to evaluate the anti-inflamatory activity of the extracts of A. wiedemanniana by using in vivo methods.Materials and Methods:Carrageenan-, PGE2- and serotonin-induced hind paw edema, 12-O-tetradecanoyl-13-acetate (TPA)-induced mouse ear edema and acetic acid-induced increase in capillary permeability models were used for the anti-inflammatory activity assessment. Moreover, the fatty acid composition of A. wiedemanniana was investigated by gas chromatography (GC).Results:n-Hexane, diethyl ether and total sesquiterpene lactone extracts exhibited significant inhibition in carrageenan-induced hind paw edema and acetic acid-induced increase in capillary permeability model. n-Hexane and total sesquiterperne lactone extracts showed anti-inflammatory activity in PGE2- and serotonin-induced hind paw edema model. However none of the extracts displayed significant activity in TPA-induced ear edema model in mice. C4:0 (Buthyric acid), C20:0 (Arachidic acid) and C16:1 (Palmitoleik acid) were found to be the major fatty acids in these species. Saturated fatty acids (SFA) were found in higher amounts than monounsaturated fatty acids and polyunsaturated fatty acids. SFAs were determined as 63.17%, UFAs as 20.89% and PuFAs as 15.95%.Conclusion:This study confirms the traditional usage of A. wiedemanniana for inflammatory diseases.

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“…The organic phase was concentrated under vacuum to dryness and yielded a lipophilic residue (0.14%). [9]…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fatty acid composition and preclinical resarches on Anthemis wiedemanniana Fisch. & Mey.: Discovery of a new anti-inflammatory agent

et al. 2014

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“…桉烷倍半萜类化合物多样化的生物活性尤为引人关注, 例如: 抗艾滋病病毒 [1] , 抑制晶状体醛糖还原酶 (AR, Aldose Reductase)( 糖性白内障相关酶) [2] , 抗肿瘤 [3～4] , 抗菌 [5] , 抗炎 [6] , 抗疟疾, 细胞生长抑制, 植物生长调节和降血糖 [7] 等活性 [8] , 广泛的生物活性使这类化合物成为化学家追求的合成目标靶分子. 我们发现从植物中间锦鸡儿中分离得到的天然产物桉烷-4(15)-烯-1β,7α-二醇(Y019)在 12 μg/mL 水平具有抗稻瘟酶活性 [9] , 是潜在的抗肿瘤, 抗真菌的先导化合物.…”

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Asymmetric Total Synthesis of 4(15)-Eudesmene-1β,7α-diol

Ma¹,

Zhang²,

Liu³

et al. 2012

Chin. J. Org. Chem.

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“…They constitute a valuable chemotaxonomic material and might be also decisive for the medicinal value of the raw material, as in Chamomillae anthodium, Cnici benedicti herba, Arnicae anthodium, Millefolii herba, Chrysanthemi partheni herba, Cichorii radix et herba. A recent study has revealed antibacterial and cytotoxic activities of sesquiterpene lactones [1]. These compounds can be detected through visual chromatography and isolated by simple column chromatography, with silica gel as the adsorbent.…”

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TLC of selected sesquiterpenoids of the Asteraceae family

et al. 2011

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IntroductionAmong natural compounds in the species of family Asteraceae, sesquiterpenoids play an important role. They constitute a valuable chemotaxonomic material and might be also decisive for the medicinal value of the raw material, as in Chamomillae anthodium, Cnici benedicti herba, Arnicae anthodium, Millefolii herba, Chrysanthemi partheni herba, Cichorii radix et herba. A recent study has revealed antibacterial and cytotoxic activities of sesquiterpene lactones [1]. These compounds can be detected through visual chromatography and isolated by simple column chromatography, with silica gel as the adsorbent.The possibility of identification of several substituents at guaianolides by TLC with concentrated sulphuric acid as the developer had been mentioned earlier [2,3]. Now, visual chromatography of compounds of four other types of sesquiterpenoids has been presented: germacranolides, germacranes, seco-pseudoguaianolides and pseudoguaianolides.To develop the spots, the sole anisaldehyde reagent, which proved selective enough to rate the colours of the spots of the compounds in question, was used. Material and methods Plant materialThe plant materials used for the studies employed aerial parts of Centaurea bella, C. crocodylium, C. lusitanica, Helenium hoopesii, Santolina pinnata subsp. neapolitana, Stizolophus balsamita, Zoegea baldschuanica, plants cultivated and identified in the garden of Department of Medicinal and Cosmetic Natural Products, University of Medical Sciences in Poznań (Poland), where their voucher specimens are deposited. Isolation and identification of compoundsThe herbs, collected right before blooming (about 450 g each) were extracted with methanol three times. The methanol extracts were inundated with distilled water (ca. 600 cm 3 ), after the evaporation of the solvent. The water phase was extracted with chloroform. The chloroform extracts, in turn, having been dried with anhydrous sodium sulphate, were used for thin layer chromatography and isolation of compounds. Furthermore, some methanol/water/chloroform extracts were prepared from Centaurea crocodylium herb, which had been collected at the same time and from the same plot as the herbs designed to be dried.The extracts were separated by column chromatography on silica gel (Merck art. 7733). The fractions were subjected to repeated column chromatography on silica gel (Merck art. 7729) and eluted by right mobile phases. The structures of the isolated compounds (Fig. 1) were identified on the basis of 1H NMR, IR and EI mass spectroscopy and by comparing the obtained data with those of the reference compounds or reported data [4-8]. AbstractVisual chromatography has been employed for a preliminary identification of natural compound of a group of sesquiterpene lactones -Centaurea bella Trautv., C. crocodylium L., C. lusitanica Boiss. et Reuter, Helenium hoopesii A. Gray = Dugaldia hoopesii (A. Gray) Rydb., Stizolophus balsamita (Lam.) Cass., Zoegea baldschuanica C. Winkl., germacranes -Santolina pinnata Viv. subsp. neapolitana (Jord. et ...

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Sesquiterpene Lactones from Anthemis melanolepis and Their Antibacterial and Cytotoxic Activities. Prediction of Their Pharmacokinetic Profile

Cited by 32 publications

References 30 publications

Fatty acid composition and preclinical resarches on Anthemis wiedemanniana Fisch. & Mey.: Discovery of a new anti-inflammatory agent

Fatty acid composition and preclinical resarches on Anthemis wiedemanniana Fisch. & Mey.: Discovery of a new anti-inflammatory agent

Asymmetric Total Synthesis of 4(15)-Eudesmene-1β,7α-diol

TLC of selected sesquiterpenoids of the Asteraceae family

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