Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties

Selvam, Chelliah; Jordan, Brian C.; Prakash, Sandhya; Mutisya, Daniel; Thilagavathi, Ramasamy

doi:10.1016/j.ejmech.2017.01.023

Cited by 36 publications

(21 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Glyceollins are the major phytoalexins of the soybean. They belong to the pterocarpan subclass of isoflavonoids, which possesses great potential as scaffolds for pharmaceutical development [ 12 ]. Glyceollins are biosynthesized from the isoflavonoid daidzein, which can result from de novo biosynthesis beginning at phenylalanine, or possibly from the hydrolysis of preformed isoflavonoid-glycoside conjugates ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

2017

View full text Add to dashboard Cite

Phytoalexins are metabolites biosynthesized in plants in response to pathogen, environmental, and chemical stresses that often have potent bioactivities, rendering them promising for use as therapeutics or scaffolds for pharmaceutical development. Glyceollin I is an isoflavonoid phytoalexin from soybean that exhibits potent anticancer activities and is not economical to synthesize. Here, we tested a range of source tissues from soybean, in addition to chemical and biotic elicitors, to understand how to enhance the bioproduction of glyceollin I. Combining the inorganic chemical silver nitrate (AgNO3) with the wall glucan elicitor (WGE) from the soybean pathogen Phytophthora sojae had an additive effect on the elicitation of soybean seeds, resulting in a yield of up to 745.1 µg gt−1 glyceollin I. The additive elicitation suggested that the biotic and chemical elicitors acted largely by separate mechanisms. WGE caused a major accumulation of phytoalexin gene transcripts, whereas AgNO3 inhibited and enhanced the degradation of glyceollin I and 6″-O-malonyldaidzin, respectively.

show abstract

Section: Introductionmentioning

confidence: 99%

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

2017

View full text Add to dashboard Cite

show abstract

“…72 Recently, the role of benzofuran and its derivatives present in natural products as emerging framework for antimicrobial agents, 73 antibreast cancer agents 74 and in other natural lead molecules with diverse pharmacological properties have been comprehensively, revealed. 75,76 We are especially interested in heterocyclic chemistry [77][78][79][80][81][82][83][84][85][86][87][88] and heterocyclic compounds showing high biological activity. 89 In recent years, we have highlighted the applications of several name reactions in the total synthesis of biologically active natural products and applications of asymmetric synthesis in total synthesis of natural products.…”

Section: -39mentioning

confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

View full text Add to dashboard Cite

Research on natural products containing benzofuran has remarkably increased during the past few decades.Newly isolated natural products with complex structures are being studied, characterized and screened for possible biological activities. Several of such compounds have exhibited various biological activities, thus their total syntheses have attracted much attention from synthetic organic chemists. In this review, we aim to highlight the origins, structures, biological potencies, and synthetic approaches of those natural products bearing at least one benzofuran in their complex structures. Furthermore, we especially focus on the step in which this key heterocycle is installed during the total synthesis of a natural product as the desired target.

show abstract

“…Among them, pterocarpans-including maackiain, trifolirhizin, and trifolirhizin malonate-are isoflavonoids found in many species of Fabaceae. They have been reported to have various biological activities, such as anti-microbial, anti-cancerous, anti-inflammatory, and anti-malarial activities [7,8]. Pterocarpans comprise the second largest group of isoflavonoids after isoflavones.…”

Section: Introductionmentioning

confidence: 99%

The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures

Kim

Jeong

Park

et al. 2020

IJMS

View full text Add to dashboard Cite

Pterocarpans are derivatives of isoflavonoids, found in many species of the family Fabaceae. Sophora flavescens Aiton is a promising traditional Asian medicinal plant. Plant cell suspension cultures represent an excellent source for the production of valuable secondary metabolites. Herein, we found that methyl jasmonate (MJ) elicited the activation of pterocarpan biosynthetic genes in cell suspension cultures of S. flavescens and enhanced the accumulation of pterocarpans, producing mainly trifolirhizin, trifolirhizin malonate, and maackiain. MJ application stimulated the expression of structural genes (PAL, C4H, 4CL, CHS, CHR, CHI, IFS, I3’H, and IFR) of the pterocarpan biosynthetic pathway. In addition, the co-treatment of MJ and methyl-β-cyclodextrin (MeβCD) as a solubilizer exhibited a synergistic effect on the activation of the pterocarpan biosynthetic genes. The maximum level of total pterocarpan production (37.2 mg/g dry weight (DW)) was obtained on day 17 after the application of 50 μM MJ on cells. We also found that the combined treatment of cells for seven days with MJ and MeβCD synergistically induced the pterocarpan production (trifolirhizin, trifolirhizin malonate, and maackiain) in the cells (58 mg/g DW) and culture medium (222.7 mg/L). Noteworthy, the co-treatment only stimulated the elevated extracellular production of maackiain in the culture medium, indicating its extracellular secretion; however, its glycosides (trifolirhizin and trifolirhizin malonate) were not detected in any significant amounts in the culture medium. This work provides new strategies for the pterocarpan production in plant cell suspension cultures, and shows MeβCD to be an effective solubilizer for the extracellular production of maackiain in the cell cultures of S. flavescens.

show abstract

Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties

Cited by 36 publications

References 75 publications

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

Distinct Mechanisms of Biotic and Chemical Elicitors Enable Additive Elicitation of the Anticancer Phytoalexin Glyceollin I

Total synthesis of natural products containing benzofuran rings

The Synergistic Effect of Co-Treatment of Methyl Jasmonate and Cyclodextrins on Pterocarpan Production in Sophora flavescens Cell Cultures

Contact Info

Product

Resources

About