Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B.
OBJECTIVE
To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B.


RESULTS
Three acylated analogues were produced: quercetin 4'-oleate (C33H42O8), quercetin 3',4'-dioleate (C51H74O9) and quercetin 7,3',4'-trioleate (C69H106O10). Their identities were confirmed with UPLC-ESI-MS and1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4'-oleate was higher than those of quercetin and oleic acid. Quercetin 4'-oleate was also stable over 28 days of storage.


CONCLUSIONS
Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications.
School of Science, Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor, Malaysia.
Amy Yi Hsan
AY
Saik
School of Science, Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor, Malaysia.
Yau Yan
YY
Lim
Pharmacotherapeutics Unit, Department of Medicine, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia (UPM), 43400, Serdang, Selangor, Malaysia.
Johnson
J
Stanslas
School of Science, Monash University Malaysia, Jalan Lagoon Selatan, 47500, Bandar Sunway, Selangor, Malaysia. choo.wee.sim@monash.edu.
Wee Sim
WS
Choo
D004952:Esters / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D019301:Oleic Acid / Q000737:chemistry / Q000378:metabolism*; D011794:Quercetin / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
D004952:Esters; D005656:Fungal Proteins; D019301:Oleic Acid; D011794:Quercetin; D008049:Lipase; C431349:lipase B, Candida antarctica
Acylated quercetin; Lipase; Oleic acid; Quercetin; Quercetin 4′-oleate; Regioselectivity