enzymatic transesterification of flavonoids

Jazmín Pineda1, Arturo Navarro1, Ernesto Sanchez 2, Liliana Hernández2
1 Faculty of Chemistry, Department of Food and Biotechnology, National Autonomous University of Mexico (UNAM),
[email protected] 2 Department of Biological System, UAM-Xochimilco, [email protected]
Keywords: Flavonoids; Lipase; Esterification
Figure1. TLC of transesterification of naringin with methyl
ester of fatty acids
Has been evidence that flavonoids have beneficial
health properties, however, the use of flavonoids in
several domains is limited by their low stability and
solubility in the fatty phase. One solution to improve
their hydrophobic nature is the esterification; this
chemical reaction leads to a mixture of products (1).
To overcome this problem, enzymatic catalysis is an
option for its regioselectivity. The lipases are
capable of promoting the synthesis of the ester,
when the reaction is carried out in a low water
The aim of this work is to transform flavonoids
(naringin and rutin) by way transesterification
reaction with fatty acids from vegetable oils and their
methyl esters, activated with lipase from C.
Naringin and rutin were enzymatically acylated with
different fatty acids as acyl donors (in this case they
were added as oil)
Table 1.Transesterification of flavonoids with different
acylating agents
Acyl donor
Coconut oil
Nutmeg Oil
Olive oil
Almond oil
Pumpkin oil
Linseed oil
Chia oil
Castor oil
Fatty acid in
the oil
Acyl acceptor
Naringin Rutin
1 .Methyl ester of Coconut oil
2. Methyl ester of Nutmeg Oil
3. Methyl ester of Olive oil
4. Methyl ester of Almond oil
5. Methyl ester of Grapeseed oil
6. Methyl ester of Pumpkin oil
7. Methyl ester of Linseed oil
8. Methyl ester of Chia oil
9. Methyl ester of Castor oil
10. Naringin
The reaction was carried out with all the methyl
esters (Figure 1) and no significant difference was
observed in the rate of conversion reactions with
respect to oils.
With C18 fatty acids, yields are in the same range of
magnitude, between 50 and 60% with naringin, and
between 40 and 50% with rutin. For fatty acids C12C14 yields are between 20-30% for both flavonoids.
Higher conversion yields of naringin and rutin were
obtained with aliphatic acids having high carbon
chain length (C18) as reported by other authors (2).
The fatty acid esters of rutin and naringin were
purified and characterized by C y H NMR. The
results suggest the presence of an ester bond on the
C-6 of the glucose moiety of naringin molecule.
While the acylation of rutin took place precisely on
the secondary OH in the C-4 of the rhamnose
moiety in concordance with other studies (3).
Lipase of C. antarctica is capable of carry out the
esterification reaction of flavonoids naringin and rutin
with fatty acids used. With the purification of the
products and their identification is observed
regioselectivity of the enzyme reaction.
+ Reaction – No reaction
For naringin and rutin was observed that the
transesterification reaction was carried out with all
the acylating agents that were tested (Table 1) to
give a single reaction product in all cases.
The methyl esters were obtained by enzymatic
reaction and then used for the esterification of the
The authors are grateful to the CONACYT-2012CB180128.
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Moussoub, P.; Pauly , G.; Ghoul, M. Effect of acyl donor chain
length and substitutions pattern on the enzymatic acylation of
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[3]. Kontogianni, A.; Skouridou, V.; Sereti, V.; Stamatis, H.;
Kolisis, F.; Lipase-catalyzed esterification of rutin and naringin
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VII Workshop on Biocatalysis and Biotransformations and 1o Simposio Latinoamericano de Biocatalisis y Biotransformaciones