Total synthesis of two 12-nordrimanes and the pharmacological active sesquiterpene hydroquinone yahazunol

Biological importance of marine algae

“…(+)-Yahazunol 125 (Ochi et al, 1979) and cyckozonarone 126 (Kurata et al, 1996) were showed cytotoxic activity against several human tumor cell lines, while zonarol 127, zonarone 128 and isozonarol 129 (Fenical et al, 1973) isolated from brown alga also displayed cytotoxicity against various human tumour cell lines (Laube et al, 2005).…”

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

“…Interestingly, several simplified analogs of 47 exerted similar complement inhibitory effects, which indicated that the spirobenzofuran unit was a key functional group for the retention of its bioactivity [443]. Smenospongine (402), smenospongidine (403), smenospongiarine (405), and smenorthoquinone (389b) were found to inhibit the proliferative response of lymphocyte, while smenoquinone (384) and smenospondiol (363) showed a stimulatory profile on murine lymphocyte proliferation. Their immunomodulating activity was due to inhibiting or enhancing DNA synthesis of T-lymphocytes [444].…”

“…For example, epoxyphomalin A (221) has been found to show superior cytotoxicity at nano-molar concentrations toward 12 out of 36 human cancer cell lines [161], while stachybotrydial (50) is a potent inhibitor of fucosyltransferase and sialyltransferase, two enzymes correlating with the adhesion and metastasis of cancer cell [383]. Studies revealed that most of SQs showed cytotoxic activities against cancer cells at micromolar concentrations [207,325,382,384]. Quinone is a well-nucleophilic functionality involving the covalent modification of biomolecules such as DNA and proteins to impact related biological events and subsequent process [385,386], which is well consistent with the observed biological activities.…”

Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines

“…Based on these premises, the potential of meroterpenes is of great interest; however, low yields of these compounds have traditionally been obtained from natural sources [ 5 , 6 , 7 , 8 ]. For these reasons, research efforts to chemically synthesize these compounds, their structural analogs, and their derivatives have intensified in recent decades [ 9 , 10 , 11 , 12 ]. However, little has been done on the synthesis and biological evaluation of hybrid molecules combining cyclic monoterpenes and synthetic phenols [ 13 , 14 , 15 ].…”