Bufadienolides and anti-angiogenic homoisoflavonoids from Rhodocodon cryptopodus, Rhodocodon rotundus and Rhodocodon cyathiformis

Abstract

Background: Homoisoflavonoids have been shown to have potent anti-proliferative activities in endothelial cells over other cell types and have demonstrated a strong antiangiogenic potential in vitro and in vivo in animal models of ocular neovascularization. Three species of Rhodocodon (Scilloideaea subfamily of the Asparagaceae family), endemic to Madagascar, R. cryptopodus, R. rotundus and R. cyathiformis, were investigated.Purpose: To isolate and test homoisoflavonoids for their antiangiogenic activity against human retinal microvascular endothelial cells (HRECs), as well as specificity against other ocular cell lines.

Inhibitory mechanism of two homoisoflavonoids from Ophiopogon japonicus on tyrosinase activity: insight from spectroscopic analysis and molecular docking

“…Homoisoavonoids are a small, rare, and unique class of the avonoids, which exist only in few plants such as in the bulbs of Scilla nervosa, 19 Dracaena cinnabari Balf, 20 Ophiopogon japonicas, 21 Portulaca oleraceaetc. 22 and have a wide range of physiological activities, such as inhibition of enzyme activity, 20 anti-angiogenesis, 23,24 antimutagenic, 25 insulin sensitizers, 26 antiviral activity. 27 etc.…”

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

“…Flavonoids and isoflavonoids are promising candidates for the inhibition of ocular angiogenesis ,− but, to our knowledge, the pterocarpan compounds have not been tested previously for the inhibition of ocular angiogenesis, although soybean glyceollins have documented antiangiogenic effects against human umbilical vein endothelial cells . Thus, flavonoids 5 and 6 and pterocarpans 1 – 4 , 9 , 20 , and 22 , isolated in sufficient quantities, were investigated for their antiproliferative activities against human retinal endothelial cells (HRECs), a relevant tissue specific cell type (Figure S1, Supporting Information), as described previously . GI 50 values of the compounds, the concentration at which the growth of cells is reduced by 50% relative to the DMSO control, were determined, and compounds that reduced cell proliferation only at the highest concentration tested (relative to DMSO control) were reported as having a GI 50 > 100 μM (Table ).…”

“…38 Thus, flavonoids 5 and 6 and pterocarpans 1−4, 9, 20, and 22, isolated in sufficient quantities, were investigated for their antiproliferative activities against human retinal endothelial cells (HRECs), a relevant tissue specific cell type (Figure S1, Supporting Information), as described previously. 39 GI 50 values of the compounds, the concentration at which the growth of cells is reduced by 50% relative to the DMSO control, were determined, and compounds that reduced cell proliferation only at the highest concentration tested (relative to DMSO control) were reported as having a GI 50 > 100 μM (Table 3). 39 Seven compounds (1, 2, 4, 5, 6, 20, and 22) showed antiproliferative effects on HREC tubule growth at low micromolar concentrations in a dose-dependent manner and two pterocarpans (3,9) showed a negligible effect on cell proliferation.…”

A Comprehensive Review on Chemotaxonomic and Phytochemical Aspects of Homoisoflavonoids, as Rare Flavonoid Derivatives

“…One novel derivative, (3 S )-5,7-dihydroxy-3 S -(3′-hydroxy-4′-methoxybenzyl)-4-chromanone, was attained from an ethanolic fraction of R. campanulatus bulbs using SLH (CH 2 Cl 2 –MeOH 1:1) and silica gel CC [ 74 ]. Moreover, 2,5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl) chroman-4-one, (3 S )-5,7-dihydroxy-(3′-hydroxy-4′-methoxybenzyl)-4-chromanone, and (3 S )-5,7-dihydroxy-(4′-hydroxy-3′-methoxybenzyl)-4-chromanone were isolated from bulb ethanolic extracts of R. campanulatus [ 75 ], R. cryptopodus , and R. rotundus , respectively [ 76 ].…”