Synthesis and Antifungal Activity of Cinnamic Acid Esters

Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC 50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

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“…Cinnamic Acid Adamantyl Ester (21 Cinnamic Acid Naphthyl Ester (22). Yield 15%; colourless crystalline solid; m.p.…”

Section: Cinnamic Acid Menthyl Estermentioning

confidence: 99%

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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“…Our previous work with the waste obtained from the bromelain manufacturing process has shown that phenolic acids, such as syringic and ferulic, might be responsible for the antioxidant and antimicrobial activities of the water extract (Upadhyay et al, 2011a). We have synthesized potent fungicides from cinnamic, pcoumaric and ferulic acids that were isolated from pineapple stems (Tawata et al, 1996). We have also proposed that phenolic antioxidant from pineapple waste may be converted to more potent compounds by cytochrome P4502C9 isozyme in vitro (Upadhyay et al, 2009).…”

Section: Utilization Of Pineapple Wastementioning

confidence: 99%

Utilization of Pineapple Waste: A Review

Upadhyay

Lama

Tawata

2013

J Food Sci Technol Nepal

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119

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“…Phenolic acid sugar esters have demonstrable antitumoric activity and have the potential to be used to formulate antimicrobial, antiviral and/or anti-inflammatory agents [10][11][12]. The esterification of oligo-and polysaccharides is a typical subject for both chemical and enzymatic synthesis.…”

Section: Introductionmentioning

confidence: 99%