Guaianolides and chromenes from Calea species

Ober, Alfonso G.; Urbatsch, Lowell E.; Fischer, Nikolaus H.

doi:10.1016/s0031-9422(00)84897-9

Cited by 22 publications

(11 citation statements)

References 8 publications

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“…Comparing the spectroscopic data of the compound 1 and 2 and the literature, 18,22,23 it was possible to determine the structure of the second, with some differences between both. In the compound 2, the methoxyl group is bonded directly to aromatic ring C-4, that way, this carbon showed a higher chemical shift, C-4 (d 152.2), affecting the C-3 with d 113.3.…”

Section: -(2-hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one (2)mentioning

confidence: 99%

Topical anti-inflammatory activity of Calea prunifolia HBK (Asteraceae) in the TPA model of mouse ear inflammation

Gómez¹,

Gil²

2011

J. Braz. Chem. Soc.

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produto natural. Apesar dos dois compostos derivados serem estruturalmente semelhantes, a atividade anti-inflamatória da 1-(2-hidroxi-5-metoxifenil)-3-metilbut-2-en-1-ona não foi significativa (2.08%). O ensaio foi realizado em modelo de inflamação induzido por 12-O-tetra-decanoilforbol-13-acetato (TPA) em orelha de ratos. O controle positivo foi testado com indometacina e foram ensaiados controles negativos tratados somente com o veículo. Estes resultados possibilitam a identificação de um grupo farmacóforo que através de estudos de modelagem molecular e síntese orgânica podem resultar em compostos com atividade anti-inflamatória melhorada.Phytochemical study of Calea prunifolia HBK identified two compounds derived from p-hydroxyacetophenone, the 1-(2-hydroxy-5-(1-methoxyethyl)phenyl)-3-methylbut-2-en-1-one showed a satisfactory anti-inflammatory activity (58.33%), when considering that this is a natural product. Although the two derived compounds are structurally similar, the anti-inflammatory activity of 1-(2-hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one was not significant (2.08%). The test was conducted in a model of inflammation induced by topical application of 12-O-tetradecanoylphorbol-13-acetate (TPA) in the ear of mice. The positive control was tested with indomethacin and the negative control was done only with vehicle. These results allow the identification of a pharmacophore group that through molecular modeling studies and organic synthesis can result in compounds with improved anti-inflammatory activity. Keywords:Calea prunifolia HBK, anti-inflammatory activity, mouse edema IntroductionThe inflammatory process is a physiological response to injuries, traumas, bone fracture, hypersensitivity reactions and other diseases, 1,2 and causes an accumulation of fluid, blood cells, cellular and extracellular constituents of connective tissue and produce pain.3 Many current antiinflammatory drugs are synthetic, and their toxicity and reappearance of symptoms after discontinuation are a common problem. 4,5 These untoward effects restrict their long-term use. 6 Hence, there is a constant demand for better therapeutic alternatives. For this reason, the search for new anti-inflammatory drugs is directed to the research of new hit molecules in plants traditionally used as medicinal, 7-12 which can be modified using organic synthesis to improve activity.The genus Calea is part of the Asteraceae family, which is known for its diverse and important pharmacological activities: antimicrobial, vasodilating activity and others. 13In the searching for compounds, non-steroidal antiinflammatory agents/analgesics (NSAIDs) show a promising potential because this activity in several genus of plants of this family have been widely reported.1,14-16 The reason for this property is the secondary metabolites that these plants possess. It has been particularly reported in studies involving the Calea prunifolia HBK the presence of metabolites like as sesquiterpene, acorane, 17 eudesmanolides, guaianolides, 18 flavonoids and other...

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Section: -(2-hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one (2)mentioning

confidence: 99%

Topical anti-inflammatory activity of Calea prunifolia HBK (Asteraceae) in the TPA model of mouse ear inflammation

Gómez¹,

Gil²

2011

J. Braz. Chem. Soc.

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“…Each test was performed in duplicate and repeated twice. 1 and 2), indicated that 1 was based on a typical guaiane-type sesquiterpene lactone skeleton [13,14]. Comparison of the NMR spectra of 1 (l " Tables 1 and 2) with rupicolin B disclosed that they had closely related structures except for a different ester side chain [13][14][15][16].…”

Section: Cytotoxicity Assaymentioning

confidence: 97%

Highly Oxygenated Guaianolides fromArtemisia dubia

et al. 2010

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Investigation of a Chinese folk medicine, Artemisia dubia (syn. Artemisia subdigitata), has resulted in the isolation of eight new guaianolides (artemdubolides A-H, 1-8), and nineteen known sesquiterpene lactones. Their structures were elucidated primarily on the basis of spectroscopic methods, including extensive 2D NMR experiments. The cytotoxic activities of compounds 1-8 were evaluated against A549 (human lung adenocarcinoma), Colo205 (human colon carcinoma), HepG2 (human hepatoma), and MDA-MB-435 (human melanoma) cell lines. Compounds 2 and 5 showed weak cell growth inhibition of Colo205 and MDA-MB-435 cells.

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“…Many reported constituents are sesquiterpene in character (Ober et al, 1985b(Ober et al, , c, d, 1984a(Ober et al, , 1984b(Ober et al, , 1984cOhguchi et al, 2009;Carvalho et al, 2014;Martinez et al, 1987b;Bohlmann et al, 1984Bohlmann et al, , 1982f, e, d, c, b, a, 1981bFischer et al, 1984;Lee et al, 1982aLee et al, , 1982bVichnewski et al, 1982;Quijano et al, 1979;Herz and Kumar, 1980;Bohlmann and Jakupovic, 1979;Bohlmann and Zdero, 1977b). Also documented are essential oils (Carvalho et al, 2014), chromenes, chromanones and flavonoids (Lima et al, 2015a, b;Nascimento and Oliveira, 2014;Nascimento et al, 2007a;Ober et al, 1985b;Steinbeck et al, 1997) (Table 1).…”

Section: Phytochemistrymentioning

confidence: 99%

“…Also documented are essential oils (Carvalho et al, 2014), chromenes, chromanones and flavonoids (Lima et al, 2015a, b;Nascimento and Oliveira, 2014;Nascimento et al, 2007a;Ober et al, 1985b;Steinbeck et al, 1997) (Table 1).…”

Section: Phytochemistrymentioning

confidence: 99%