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An aliphatic alkene namely pentapentacontene ( 4 ) was isolated for the first time from a natural source,  Gardenia aqualla , along with fourteen other compounds including nonacosanol ( 1 ), tetratriacontanol ( 2 ), octatriacontanol ( 3 ),  β -sitosterol ( 5 ) and stigmasterol ( 6 ), daucosanol ( 7 ), ursolic acid ( 8 ), uvaol ( 9 ), 3 β ,19 α ,23 β ,24 α -tetrahydroxyurs-12-en-28-oic acid ( 10 ), lupenone ( 11 ), oleanolic acid ( 12 ), vanillin ( 13 ), vanillic acid ( 14 ) and D-mannitol ( 15 ).  α -glucosidase inhibitory assay revealed that MeOH and EtOAc extracts of leaves had the best activity with IC 50  of 9.65 and 20.03 µg/ml respectively. All the tested compounds showed dose dependent inhibition of  α -glucosidase and some of them were found to be comparable to acarbose. Compound  10  was the most potent with IC 50  = 1.72 μM. It also showed the most interesting antibacterial activity, against the isolate strain of  S. typhi  and  P. aeruginosa  and also exhibited the most significant antifungal activities against all the tested yeasts.

Antimicrobial and α -glucosidase inhibitory activities of chemical constituents from Gardenia aqualla (Rubiaceae)