Scalable Synthesis and Cancer Cell Cytotoxicity of Rooperol and Analogues

Abstract

Plant polyphenols, such as the African potato (Hypoxis hemerocallidea)-derived bis-catechol rooperol, can display promising anticancer activity yet suffer from rapid metabolism. Embarking upon a program to systematically examine potentially more metabolically stable replacements for the catechol rings in rooperol, we report here a general, scalable synthesis of rooperol and analogues that builds on our previous synthetic approach incorporating a key Pd-catalyzed decarboxylative coupling strategy. Using this approach, we have prepared and evaluated the cancer cell cytotoxicity of rooperol and a series of analogues. While none of the analogues examined here were superior to rooperol in preventing the growth of cancer cells, analogues containing phenol or methylenedioxyphenyl replacements for one or both catechol rings were nearly as effective as rooperol.

Prostate Cancer: Causes and Medicinal Plants Used in Africa for Twenty Years (2001-2021)

“…Hypoxis hemerocallidea called African potato's extract contains hypoxoside and its active derivative called rooperol fight the growth of premalignant cancer cells and in turn used in the treatment of prostate cancer among other activities such as anti-oxidants, anti-inflammatories, anti-diabetic, testicular tumour and in more recent times HIV/AIDS. 59,60 Higher quantity of flavonoids and terpenoids from the ethanolic extract of Plumbago zeylanica Linn. exhibit important anticancer activity which reduces high amount of lipid peroxidation.…”