Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

Abstract

The Hyacinthaceae family ( APGII), with approximately 900 species in around 70 genera, plays a significant role in traditional medicine in Africa as well as across Europe and the Middle and Far East. The dichloromethane extract of the bulbs of (Hyacinthaceae APGII) yielded two known homoisoflavonoids, ()-5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 1: and 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromone 2: and four spirocyclic nortriterpenoids, eucosterol 3: , 28-hydroxyeucosterol 4: and two previously unreported triterpenoid derivatives, ()-17,23-epoxy-3,22,29-trihydroxylanost-8-en-27,23-olide 5: , and ()-17,23-epoxy-28,29-dihydroxylanost-8-en-3-on-27,23-olide 6: . Compounds 1, 2, 3: , and 5: were assessed for cytotoxicity against CaCo-2 cells using a neutral red uptake assay. Compounds 1, 2: , and 5: reduced cell viability by 70% at concentrations of 30, 100, and 100 µM, respectively. yielded three known homoisoflavonoids, ()(4'-hydroxy)-5-hydroxy-7-methoxy-4-chromanone 1: , ()-(4'-hydroxy)-5,7-dihydroxy-4-chromanone 7: and ()(3'-hydroxy-4'-methoxy)-5,7-dihydroxy-4-chromanone 9: , two previously unreported homoisoflavonoids, ()3-benzylidene-(3',4'-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 8: and ()(3',4'-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 10,: and a spirocyclic nortriterpenoid, 15-deoxoeucosterol 11: . Compounds 1, 1AC, 7, 8, 9,: and 10: were screened for antiangiogenic activity against human retinal microvascular endothelial cells. Some compounds showed dose-dependent antiproliferative activity and blocked endothelial tube formation, suggestive of antiangiogenic activity.

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

“…2). In comparison, the R-enantiomer of compound 1, recently isolated from Massonia bifolia and tested for antiproliferative activity against HRECs gave a GI 50 of 93.2 μM (R), > 700-fold less potent than S-enantiomer 1 [18].…”

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

“…HRECs gave a GI 50 of 93.2 µM (R), >700-fold less potent than S-enantiomer 1 (Schwikkard et al, 2018).…”

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

“…Silica gel (CH 2 Cl 2 –EtOAc) and SLH CC (CH 2 Cl 2 –MeOH 1:1) were carried out as separating processes [ 69 ]. Similarly, two formerly identified HIFs could be isolated from the CH 2 Cl 2 extract of M. pustulata bulb by applying silica gel and SLH CC [ 71 ].…”