Structures and inhibitory activity against breast cancer cells of new bufadienolides from the eggs of toad Bufo bufo gargarizans

Abstract

New bufadienolides with inhibitory activity against breast cancer cells were isolated from the eggs of toad Bufo bufo gargarizans.

Bufadienolides from the Eggs of the Toad Bufo bufo gargarizans and Their Antimelanoma Activities

“…The known compounds (3β,5β,14β,16β)-3,5,14,16-tetrahydroxybufa-20,22-dienolide ( 4 ), (3β,5β,14β)-3,5,10,14-tetrahydroxy-19-norbufa-20,22-dienolide ( 5 ), hellebrigenin ( 6 ), (3β,5β,14β)-3,5,14-trihydroxy-19-norbufa-20,22-dienolide ( 7 ), telocinobufagin ( 8 ), and (3β,5β,10β)-3,5-dihydroxy-14,15-epoxy-19-norbufa-20,22-dienolide ( 9 ) were identified by comparison with literature spectroscopic data (Figures S43–S69).…”

“…In our previous investigations of toad toxins, a series of new bufadienolides were isolated from toad venom and skins, some of which possessed potent hepatocellular carcinoma inhibitory effects . Motivated by previous reports that the early morphology of toads, the eggs, harbor more diverse and toxic bufadienolides than the adults, as they cannot move freely and might need more powerful chemical defenses to fight against natural enemies, we have carried out a systematic chemical investigation on toad eggs in recent years, leading to the isolation of a series of unique bufadienolides conjugated with either a terminal hydroxy fatty acid or d / l -lactic acid. ,, As part of our continuing search for structurally intriguing and biologically active compounds from toad eggs, nine bufadienolides ( 1 – 9 ) including two new compounds ( 1 and 3 ) were obtained. Because compound 2 was only synthesized in a Chinese patent and no relevant spectroscopic data were published, we report the isolation and structure elucidation of 2 along with the new compounds 1 and 3 .…”

Bufadienolides originated from toad source and their anti-inflammatory activity

“…Eight conjugated bufadienolides that C-3 position esterized with fatty acid from the egg of Bufo bufo gargarizans were isolated and identified by Zhang et al ( 96–103 ) ( Zhang et al, 2016 ). Besides, three unusual conjugated bufadienolides were separated from the ovaries of Bufo marinus ( 104–106 ) ( Matsukawa et al, 1998 ).…”

Natural Products Research in China From 2015 to 2016

“…The eggs of toad Bufo bufo gargarizans afforded two novel 19-norbufadienolides, a new 14,15-epoxy bufadienolide as well as eight rare bufadienolide-fatty acid conjugates, among which compounds 722 - 729 displayed cytotoxic activities against MCF-7 and MDA-MB-231 cells with IC 50 ranges of 0.027–0.315 and 0.05–1.96 μM, respectively (Zhang et al, 2016g ). Twelve new sesquiterpenoid dimmers, fortunilides A–L, were isolated from the malaria parasite Plasmodium falciparum (Guangxi, China).…”