Prenylation of Aromatic Secondary Metabolites: A New Frontier for Development of Novel Drugs

Alhassan, Alhassan Muhammad; Abdullahi, M. I.; Uba, A.; Umar, Abdulrashid

doi:10.4314/tjpr.v13i2.22

Cited by 58 publications

(53 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Prenylation consists of the addition of an isoprenoid side chain to another molecule (Alhassan et al, 2014). A wide range of pharmacological activities have been reported for prenylated benzoic acids' derivatives of secondary metabolites (Chen et al, 2000;Flores et al, 2009;Malami, 2012;Seeram et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Structural and physicochemical characterization and purity assessment of myrsinoic acids A and B, active compounds isolated from Rapanea ferruginea barks

Zermiani

Malheiros

Silva

et al. 2016

Arabian Journal of Chemistry

View full text Add to dashboard Cite

The present study provided a chemical, physical and physicochemical characterization of myrsinoic acids A (MAA) and B (MAB) isolated from stem bark of Rapanea ferruginea Mez (Myrsinaceae). In previous pre-clinical studies these compounds have shown important antiinflammatory, anticholinesterasic and antimicrobial activities. A gradient stability-indicating LC-UV method was developed, and a forced degradation study was carried out. Purity, log P, solubility, and pK a were determined. Thermal analysis (DSC/TG) was conducted for both compounds. MAB was characterized by X ray powder diffraction (XRPD) and scanning electron microscopy (SEM). When submitted to stress conditions, both markers showed degradation, with MAA presenting higher lability. The purity of MAA (oil) was 76.20%, while that of MAB (powder) was 98.90%. MAA and MAB exhibited log P values of 3.30 and 3.22, respectively. MAA was very slightly soluble in methanol and acetonitrile, while MAB was slightly soluble in both solvents. Both were practically insoluble in water. MAA and MAB showed pK a of 4.5 and 4.8, respectively. In the SEM analysis, MAB showed a semi-crystalline morphology and high purity when analyzed by XRPD and DSC. This data will contribute to the development, quality control and standardization of pharmaceuticals using MAA and MAB. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

show abstract

Section: Introductionmentioning

confidence: 99%

Structural and physicochemical characterization and purity assessment of myrsinoic acids A and B, active compounds isolated from Rapanea ferruginea barks

Zermiani

Malheiros

Silva

et al. 2016

Arabian Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Oxyprenylated compounds (isopentenyloxy, geranyloxy, farnesyloxy compounds, and their biosynthetic derivatives) have attracted the scientific interest only in the last decade, while for years, they were considered just as biosynthetic intermediates of C‐prenylated products (Alhassan, Abdullahi, Uba, & Umar, ). Therefore, their biological activities have recently started to be explored.…”

Section: Introductionmentioning

confidence: 99%

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Kavetsou

Katopodi

Argyri

et al. 2020

Drug Development Research

View full text Add to dashboard Cite

Eighteen 3-aryl-5-substituted-coumarins-six 5-acetyloxy-derivatives, six 5-hydroxyderivatives, and six 5-geranyloxy-derivatives-were synthesized, structurally characterized and their antioxidant activity, lipoxygenase inhibitory ability, as well as their cytotoxic activity against human neuroblastoma SK-N-SH and HeLa adenocarcinoma cell lines were evaluated. The 5-acetyloxy-compounds 3a-3f were found to be the best cytotoxic agents among all the compounds studied. The bromo-substituted coumarins 3a and 3b were remarkably active against HeLa cell line showing IC 50 1.8 and 6.1 μM, respectively. Coumarin 5e possessing a geranyloxy-chain on position 5 of the coumarin scaffold presented dual bioactivity, while 5-geranyloxy-coumarin 5f was the most competent soybean lipoxygenase inhibitor of this series (IC 50 10 μM). As shown by in silico docking studies, the studied molecules present allosteric interactions with soybean lipoxygenases.

show abstract

“…目前报道的异戊烯基化黄酮超过 1000 个. 从药用植物中发现的许多异戊烯基化黄酮具有更为广泛、更强的生理活性, 如抗肿瘤、抗雄激素、抗利什曼虫、抗 NO 的产生等 [53] . 不同存在形式的异戊烯基侧链, 可使黄酮类化合物的亲脂性得到提高, 有助于其在生物体中透过细胞膜, 通过增加与生物膜的结合能力、改善与蛋白的作用, 而导致黄酮显著的生理活性改变 [54] .…”

Section: 而黄酮醇的收率明显下降(Scheme 7)unclassified

Progress in the Synthesis of 3-Hydroxyflavones

Mei¹,

Yuan²,

Wang³

2015

Chin. J. Org. Chem.

View full text Add to dashboard Cite

Prenylation of Aromatic Secondary Metabolites: A New Frontier for Development of Novel Drugs

Cited by 58 publications

References 41 publications

Structural and physicochemical characterization and purity assessment of myrsinoic acids A and B, active compounds isolated from Rapanea ferruginea barks

Structural and physicochemical characterization and purity assessment of myrsinoic acids A and B, active compounds isolated from Rapanea ferruginea barks

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Progress in the Synthesis of 3-Hydroxyflavones

Contact Info

Product

Resources

About