Synthesis of Pterocarpans

Jiménez-González, Leticia; Hernandez‐Cervantes, Carmen; Álvarez-Corral, Míriam; Muñoz‐Dorado, Manuel; Rodrı́guez-Garcı́a, Ignacio

doi:10.1177/1934578x1100600414

Cited by 6 publications

(8 citation statements)

References 124 publications

(140 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The second-largest class of natural isoflavonoids is called pterocarpans 74 which is most frequently found in the Fabaceae family 75 . Pterocarpans can lower total and lowdensity lipoprotein cholesterol levels, which lowers the chance of developing a number of ailments, according to scientific research 76 .…”

Section: Discussionmentioning

confidence: 99%

An Insight into the cardioprotective properties of Prisniparni (Desmodium gangeticum (L)DC) through its secondary metabolites.

2023

KJA

View full text Add to dashboard Cite

Prisniparni is a medicinal plant that is often used in the formulation of many Ayurvedic medicines. Even though some controversy exists about the botanical source of the plant, Kerala physicians generally use Desmodium gangeticum (Linn.) DC. of the Leguminosae family as Prisniparni. Specific usage of the drug in hridroga is emphasized in traditional Ayurvedic textbooks and regional books of Kerala. The results of recent preclinical studies support Prisniparni's traditional use in hridroga. However, their clinical and scientific validation is lacking, especially in terms of their mechanism of action. The therapeutic potential of medicinal plants depends on their secondary metabolites. The plant's pharmacological activity may be due to the combined activity of its secondary metabolites. Based on this, a literature search on secondary metabolites of Desmodium gangeticum (Linn.) DC was done by electronic and hand search. Results of this review revealed the richness of alkaloids and polyphenols in Desmodium gangeticum (Linn.) DC which are antioxidant and anti-inflammatory in nature. The findings support the plant's cardioprotective potential and its traditional use since inflammation and oxidative stress are reported to be major contributors to cardiovascular diseases.

show abstract

Section: Discussionmentioning

confidence: 99%

An Insight into the cardioprotective properties of Prisniparni (Desmodium gangeticum (L)DC) through its secondary metabolites.

2023

KJA

View full text Add to dashboard Cite

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%

“…Pterocarpans comprise the second largest group of isoflavonoids after isoflavones. They primarily act as phytoalexins in leguminous plants, and also function as signal molecules in plant-microorganism interactions [7,9]. Leguminous plants are known to produce pterocarpan phytoalexins [10].…”

Section: Introductionmentioning

confidence: 99%

“…Pterocarpans of pisatin, medicarpin, and maackiain are produced in pea (Pisum sativum), peanut (Arachis hypogaea), and Sophora japonica, respectively [10][11][12][13]. Pterocarpans are formed at the last stages of the flavonoid biosynthetic pathway as a part of the isoflavonoid branch [7]. Isoflavonoids are synthesized by a legume-specific branch of the general phenylpropanoid pathway.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

“…Previously, various transition metals have been employed for the hydrofunctionalization of unsaturated bonds via metal vinylidene intermediates, such as the intramolecular nucleophilic addition of hydroxyl or carbonyl groups generating polycyclic oxygen-containing compounds . For instance, the reactions of 4-alkyn-1-ols bearing a terminal alkyne with oxygen nucleophiles afforded tetrahydrofuran and dihydropyran heterocycles via 5- exo and 6- endo cyclization pathways, respectively. , The Michael addition reaction of oxygen or carbon nucleophiles to an enynone (3-alkynyl chromone), triggering an intramolecular 5- exo cyclization pathway, could be an efficient strategy for the construction of substituted pterocarpan scaffolds . Moreover, Utimoto et al reported the Pd-catalyzed synthesis of substituted furans from β,γ-acetylenic ketones via the intramolecular oxypalladation of acetylene, cyclization, and protodemetalation .…”

mentioning

confidence: 99%

Palladium-Catalyzed Chemo- and Regiocontrolled Tandem Cyclization/Cross-Coupling of 2-Benzyl-3-alkynyl Chromones with Aryl Iodides for the Synthesis of 4H-Furo[3,2-c]chromenes and Xanthones

et al. 2022

View full text Add to dashboard Cite

A novel Pd-catalyzed chemo-and regiocontrolled tandem cyclization/cross-coupling reaction of 3-alkynyl chromone with aryl iodide was developed for the synthesis of 4H-furo[3,2c]chromenes and xanthones. The difunctionalization of alkynes through O-attack/5-exo-dig and C-attack/6-endo-dig cyclization was reported by this rare approach, which was selectively controlled by the addition of KF or a bidentate phosphine ligand. A one-pot tandem process was demonstrated directly from γ-alkynyl-1,3-diketone for this method.

show abstract

Synthesis of Pterocarpans

Abstract: The total synthesis of natural pterocarpans and analogs is reviewed.

Cited by 6 publications

References 124 publications

An Insight into the cardioprotective properties of Prisniparni (Desmodium gangeticum (L)DC) through its secondary metabolites.

An Insight into the cardioprotective properties of Prisniparni (Desmodium gangeticum (L)DC) through its secondary metabolites.

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

Palladium-Catalyzed Chemo- and Regiocontrolled Tandem Cyclization/Cross-Coupling of 2-Benzyl-3-alkynyl Chromones with Aryl Iodides for the Synthesis of 4H-Furo[3,2-c]chromenes and Xanthones

Contact Info

Product

Resources

About