New efficient synthesis and bioactivity of homoisoflavonoids

Rao, Vallabhaneni Madhava; Damu, Guri L.V.; Sudhakar, Dega; Siddaiah, Vidavalur; Rao, C. Venkata

doi:10.3998/ark.5550190.0009.b28

Cited by 23 publications

(13 citation statements)

References 11 publications

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“…Among them, compound 2 is a unique homoisoflavanone comprising dihydroxy at the C5 and C6 positions and a methoxy at the C7 position, respectively, with a 3′-hydroxy-4′-methoxybenzyl group at the C3 position of chromanone. This compound has not previously been reported, although syntheses of similar compounds are known [26] – [30] . The substantial challenge associated with the total synthesis of compound 2 was to uncover three phenolic groups on the C5, C6 (in the A ring) and C3′ (in the B ring) positions.…”

Section: Resultsmentioning

confidence: 81%

Synthesis and Mechanistic Studies of a Novel Homoisoflavanone Inhibitor of Endothelial Cell Growth

et al. 2014

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Preventing pathological ocular angiogenesis is key to treating retinopathy of prematurity, diabetic retinopathy and age-related macular degeneration. At present there is no small molecule drug on the market to target this process and hence there is a pressing need for developing novel small molecules that can replace or complement the present surgical and biologic therapies for these neovascular eye diseases. Previously, an antiangiogenic homoisoflavanone was isolated from the bulb of a medicinal orchid, Cremastra appendiculata. In this study, we present the synthesis of a novel homoisoflavanone isomer of this compound. Our compound, SH-11052, has antiproliferative activity against human umbilical vein endothelial cells, and also against more ocular disease-relevant human retinal microvascular endothelial cells (HRECs). Tube formation and cell cycle progression of HRECs were inhibited by SH-11052, but the compound did not induce apoptosis at effective concentrations. SH-11052 also decreased TNF-α induced p38 MAPK phosphorylation in these cells. Intriguingly, SH-11052 blocked TNF-α induced IκB-α degradation, and therefore decreased NF-κB nuclear translocation. It decreased the expression of NF-κB target genes and the pro-angiogenic or pro-inflammatory markers VCAM-1, CCL2, IL8, and PTGS2. In addition SH-11052 inhibited VEGF induced activation of Akt but not VEGF receptor autophosphorylation. Based on these results we propose that SH-11052 inhibits inflammation induced angiogenesis by blocking both TNF-α and VEGF mediated pathways, two major pathways involved in pathological angiogenesis. Synthesis of this novel homoisoflavanone opens the door to structure-activity relationship studies of this class of compound and further evaluation of its mechanism and potential to complement existing antiangiogenic drugs.

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Section: Resultsmentioning

confidence: 81%

Synthesis and Mechanistic Studies of a Novel Homoisoflavanone Inhibitor of Endothelial Cell Growth

et al. 2014

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“…The in vitro antioxidant and antifungal activities of the products were examined using the superoxide (NBT) and agar cup methods, respectively. 306 …”

Section: Orthoester Reactions In Aqueous Mediamentioning

confidence: 99%

Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

Khademi

Nikoofar

2020

RSC Adv.

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“…Homo-isoflavones have antioxidant activity by scavenging free radicals, blocking lipid peroxidation and inhibiting the enzyme xanthine-oxidase [ 12 , 13 ]; moreover, these polyphenols exhibit an anti-bacterial and antifungal activity as they are able both to inhibit the growth of Aspergillus niger and Penicillium chrysogenum and to block the enzymes involved in proliferation of Phytosporaparasitica during infection [ 14 ]. Recent studies show that the homoisoflavanones contained in this plant, interacting with the estrogenic receptors, may have a potential role as hormone substitutes or useful supplements for the treatment of hormone-sensitive tumours [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Muscari comosum L. Bulb Extracts Modulate Oxidative Stress and Redox Signaling in HepG2 Cells

et al. 2021

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Muscari comosum L. bulbs are commonly used as food in South Italy and also in folk medicine. By evaluating in vitro antioxidant activity and biological activities of their aqueous and methanol extracts, we shed light on the potential role, including both the nutraceutical and health benefits, of this plant. Total polyphenol content (TPC) and total flavonoid content (TFC) were evaluated by the Folin–Ciocalteu method and by the aluminum chloride method, respectively. Antioxidant activity was investigated by three in vitro assays and relative antioxidant capacity index (RACI) was calculated to compare results obtained by different tests. The extracts were tested to evaluate their possible involvement in redox homeostasis, using the human hepatoma (HepG2) cell line used as model. The extracts exhibited concentration/solvent dependent radical scavenging activity, as well as dysregulation of some genes involved in redox pathways by promoting Nrf2, SOD-2, GPX1, ABCC6 and ABCG2 expression. NMR metabolomics analysis suggests that HepG2 cells treated with Muscari comosum extracts experience changes in some metabolites involved in various metabolic pathways.

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New efficient synthesis and bioactivity of homoisoflavonoids

Cited by 23 publications

References 11 publications

Synthesis and Mechanistic Studies of a Novel Homoisoflavanone Inhibitor of Endothelial Cell Growth

Synthesis and Mechanistic Studies of a Novel Homoisoflavanone Inhibitor of Endothelial Cell Growth

Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

Muscari comosum L. Bulb Extracts Modulate Oxidative Stress and Redox Signaling in HepG2 Cells

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