Sesquiterpene and Long Chain Ester from Tanacetum longifolium.

Mahmood, Umar; Kaul, Vijay Kumar; Singh, Bikram

doi:10.1002/chin.200317162

Cited by 6 publications

(7 citation statements)

References 1 publication

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“…The 1 H-NMR and 13 C-NMR signals of compound A are similar to the sesquiterpene (tanacetene) reported by Mahmood et al (2002), but the mass spectrum indicates that compound A (M + m/z 410) is a triterpene (tanacetene dimer) with six isoprene units, four of which are joined head to tail, and the fifth tail to tail. This compound is very similar to the triterpene squalene, which has six isoprene units, four of which are joined head to tail and the third tail to tail.…”

Section: Resultssupporting

confidence: 68%

Anti-inflammatory, free radical scavenging and alpha-glucosidase inhibitory activities of Hamelia patens and its chemical constituents

Jiménez-Suárez

Nieto‐Camacho

Manuel

et al. 2016

Pharmaceutical Biology

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Context Hamelia patens Jacq. (Rubiaceae) is traditionally used to treat wounds, inflammation and diabetes. However, there is still a lack of scientific evidence to support these applications. Objective The objective of this study is to evaluate the anti-inflammatory, antioxidant and antidiabetic activities of Hamelia patens, and identify its bioactive compounds. Materials and methods Four extracts were obtained by maceration and liquid-liquid extraction: HEX, DCM-EtOAc, MeOH-EtOAc and MeOH-Aq. The anti-inflammatory effect was evaluated orally on rat paw carrageenan-induced oedema over 6 h (50, 200 and 500 mg/kg), and topically in mouse ear oedema induced by 12-tetradecanoylphorbol-13-acetate (TPA) after 4 h (0.5 and 1 mg/ear). We also evaluated myeloperoxidase levels in ear tissue, 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging ability, and in vitro α-glucosidase inhibition. The chemical compounds were separated by column chromatography and identified by spectroscopic analysis. Results We found that the oral administration of the HEX extract at 500 and 200 mg/kg significantly decreased the carrageenan-induced inflammation after 1 and 3 h, respectively. The MeOH-EtOAc extract significantly inhibited myeloperoxidase activity (83.5%), followed by the DCM-EtOAc extract (76%), β-sitosterol/stigmasterol (72.7%) and the HEX extract (55%), which significantly decreased oedema induced by TPA at both doses, giving a similar effect to indomethacin. We also found that the MeOH-EtOAc, MeOH-Aq and DCM-EtOAc extracts showed good DPPH scavenging activity (IC50 values of 18.6, 93.9 and 158.2 μg/mL, respectively). The HEX extract showed the lowest α-glucosidase inhibition (an IC50 value of 26.07 μg/mL), followed by the MeOH-EtOAc extract (an IC50 value of 30.18 μg/mL), β-sitosterol/stigmasterol (IC50 34.6 μg/mL) and compound A ((6E,10E,14E,18E)-2,6,10,14,18,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene, an IC50 value of 114.6 μg/mL), which were isolated for the first time from Hamelia patens. Discussion and conclusion Hamelia patens possesses anti-inflammatory, antioxidant and α-glucosidase inhibitory activities, which support its traditional use. These effects can be attributed to the identified compounds.

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Section: Resultssupporting

confidence: 68%

Anti-inflammatory, free radical scavenging and alpha-glucosidase inhibitory activities of Hamelia patens and its chemical constituents

Jiménez-Suárez

Nieto‐Camacho

Manuel

et al. 2016

Pharmaceutical Biology

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“…Although these are the most stable of the cadinane sesquiterpenes, these materials are generally found only in small quantities in plant essential oils. Zonarene is, however, the major hydrocarbon component of the brown seaweed Dictyopteris zonarioides [47], and epizonarene is somewhat abundant in Cedrela fissilis leaf oil (2.5%) [48], the hexane extract of Tanacetum longifolium aerial parts (14.7%) [49], and the essential oil of Teucrium leucocladum (4.5%) [50]. …”

Section: Resultsmentioning

confidence: 99%

Germacrene D Cyclization: An Ab Initio Investigation

Setzer

2008

IJMS

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Essential oils that contain large concentrations of germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G*) and post Hartree-Fock (MP2/6-31G**) ab initio methods. The calculated energies are in general agreement with experimentally observed product distributions, both from acid-catalyzed cyclizations as well as distribution of the compounds in essential oils.

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“…Many studies have been reported on the essential oil composition of various Tanacetum species (El-Shazly et al, 2002;Goren et al, 2001;Greche et al, 2000;Judzentiene and Mockute, 2005;Kandemir et al, 2008;MajedJabari et al, 2002;Marongiu et al, 2009;Mockute and Judzentiene, 2004;Monfared et al, 2002;Piras et al, 2014;Polatoglu et al, 2011;Rohloff et al, 2004;Weyerstahl et al, 1999) and camphor, 1,8-cineole, ␣-thujone, carvone, thymol, trans-sabinyl acetate, borneol, caryophyllene oxide, (E)-myroxide, sabinene, bornyl acetate, isopulegone and artemisia ketone were identified as the major constituents. This genus is also found to contain sesquiterpene lactones (Aljancic et al, 2001;Mahmood et al, 2002), a large group of molecules with several biological activities (Chaturvedi, 2011;Ghantous et al, 2010;Kreuger et al, 2012;Lesiak et al, 2010;Merfort, 2011;Wagner et al, 2008;Zhang et al, 2005).…”

Section: Introductionmentioning

confidence: 97%