Trypanocidal and antifungal activities of <i>p</i>-hydroxyacetophenone derivatives from <i>Calea uniflora</i> (Heliantheae, Asteraceae)

Nascimento, A. M.; Salvador, Marcos José; Candido, Renato; Albuquerque, Sérgio de; Oliveira, Dionéia Camilo Rodrigues de

doi:10.1211/0022357023231

Cited by 23 publications

(13 citation statements)

References 30 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%

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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%

“…The results were expressed as edema and as percentage of inhibition versus the control group. 3,12,19,22 …”

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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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“…From another species, Calea uniflora Less. actives chromanones against promastigotes of Leishmania major and acetophenones with weak trypanocidal activity have been isolated (do Nascimento et al, 2004(do Nascimento et al, , 2007. Therefore, it should be interesting to verify if the same products are also present in Calea montana, and also to check if these products are also active on Leishmania.…”

Section: Leishmaniasismentioning

confidence: 99%

Medicinal plants from the Yanesha (Peru): Evaluation of the leishmanicidal and antimalarial activity of selected extracts

Valadeau

Pabón

Deharo

et al. 2009

Journal of Ethnopharmacology

127

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“…So far, 20 compounds (210–229) belonging to this chemical class have been found in Calea genus. Occurrence of acetophenones has been observed in different Calea species, including C. clausseniana , C. uniflora , C. cuneifolia , C. peckii , and C. prunifolia (Castro et al, ; Do Nascimento & de Oliveira, ; Do Nascimento, Salvador, Candido, De Albuquerque, & De Oliveira, ; Gómez & Gil, ; Lourenço et al, ).…”

Section: Chemical Constituentsmentioning

confidence: 99%

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

Lima

Souza

Silva

et al. 2018

Phytotherapy Research

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Calea L. is a genus of shrubs and perennial herbs belonging to Asteraceae family. It is a very well‐known genus, consisting of approximately 125 neotropical species. Calea genus is a rich source of phytochemicals, and some of its species have been used in folk medicine to treat several health problems such as diabetes, arterial hypertension, respiratory and gastrointestinal disorders, gastric ulcers, and inflammation. Many studies have demonstrated the pharmacological potential of this genus, including antinociceptive, antihypertensive, antidiarrheal, antimicrobial, anti‐inflammatory, antidiabetic, antiproliferative, and cytotoxic activities. Moreover, bioactive constituents related to these properties are mainly sesquiterpene lactones and phenolic derivatives. In this review, we compiled the literature data up to December 2016, furnishing a comprehensive survey about medicinal uses, chemistry, and biological activities from Calea species. Bibliographic search was performed in several search engines using “Calea” as search keyword. Further, a manual literature search of references found in the selected studies was also conducted. There was no initial time limit.

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Trypanocidal and antifungal activities of p-hydroxyacetophenone derivatives from Calea uniflora (Heliantheae, Asteraceae)

Cited by 23 publications

References 30 publications

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

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

Medicinal plants from the Yanesha (Peru): Evaluation of the leishmanicidal and antimalarial activity of selected extracts

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

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