Front Matter

sources ofc-linolenic acid. Fungal oils containingc-linolenic acid, such as those

fromMortierellaspp. (Hansson and Dosta ́lek, 1988) andMucor ambiguus(Fukuda

and Morikawa, 1987) are now commercially available.c-Linolenic acid has been

enriched from natural resources via urea adduct formation (Traitler et al., 1988),

separation on Y-Zeolite (Arai et al., 1987), and solvent winterization (Yokochi et

al., 1990).

The ability of the lipases from rapeseed,R. miehei, C. rugosa, andG. candidumto

discriminate againstc-linolenic acid has been utilized for the enrichment of this acid

from the mixture of fatty acids derived from evening primrose seed oil or borage seed

oil via lipase-catalyzed selective esterification withn-butanol (Figure 3; Table 2).

Most of the fatty acids from evening primrose oil or borage oil are converted to

butyl esters, with the exception ofc-linolenic acid, which is thus obtained as a con-

centrate in the unesterified fatty acid fraction (Hills et al., 1989; 1990a; Syed Rah-

matullah et al., 1994a). Selective hydrolysis of the triacylglycerols of evening prim-

rose oil or borage oil, catalyzed by lipases from rapeseed (Hills et al., 1989),R.

mieheiandC. rugosa(Syed Rahmatullah et al., 1994b) also leads to enrichment

30 2 Fractionation of Fatty Acids and Other Lipids Using Lipases

Table 2.Enrichment of n-6 unsaturated fatty acids and their derivatives via kinetic resolution catalyzed
by lipases.

Lipase from Reaction Fatty acid enriched Reference

Rapeseed
(Brassica napus),
R. miehei,
G. candidum,
C. rugosa

Selective esterification

of fatty acids of evening

primrose oil or borage

oil withn-butanol

c-Linolenic acid in

unesterified fatty acids

Hills et al., 1989; 1990b;

Syed Rahmatullah et al.,

1994a; Foglia and Sonnet,

1995; Jachmania ́n and

Mukherjee, 1996; Huang et

al., 1997b; Schmitt-Rozie-

res et al., 1999; Van Heer-

den and Litthauer, 1999

Rapeseed,
R. miehei,
C. rugosa

Selective hydrolysis

of evening primrose

oil or borage oil

c-Linolenoyl moieties

in tri-, di- and

monoacylglycerols

Hills et al., 1989; Ergan et

al., 1992; Syed Rahmatul-

lah et al., 1994b; Jachma-

nia ́n and Mukherjee, 1995;

Huang et al., 1997a; 1999;

Shimada et al., 1998d

R. miehei Selective esterification
of fatty acids of fungal
oil fromMortierellasp.
withn-butanol

c-Linolenic acid in

unesterified fatty acids

Mukherjee and Kiewitt,

1991; Carvalho and

Pastore, 1998

C. rugosa Selective hydrolysis of
triacylglycerols of fungal
oil fromMortierellasp.

Arachidonoyl moieties

in tri-, di- and mono-

acylglycerols

Shimada et al., 1995a

R. delemar Selective esterification
of fatty acids of borage
oil with lauryl alcohol

c-Linolenic acid in

unesterified fatty acids

Shimada et al., 1997c;

1998a

C. rugosa Selective esterification
of fatty acids of fungal
oil fromMortierellasp.
with lauryl alcohol

Arachidonic acid in

unesterified fatty acids

Shimada et al., 1998b