However, the use of earthworms as a source of biocatalysts for
biotransformation is very limited. Nakajima et al. reported that
one of the earthworm serine protease acts on the hydrolysis of
triacylglycerols [15]. They also reported the stereoselective
reduction of carbonyl compounds using the cell-free extract from
earthworms (Lumbricus rubellus) in the presence of NADH or
NADPH as a coenzyme [16]. Recently, Santos et al. describe bcarboline
imine reductions in high yields and enantiomeric
excesses employing the cell-free extract from earthworms (Eisenia
foetida) in the presence of NADPH [17]. Herein, we report that a
crude extract of earthworms is a versatile biocatalyst for the
asymmetric direct aldol and Mannich reactions, Henry and
Biginelli reactions, direct three-component aza-Diels-Alder reactions
for the synthesis of isoquinuclidines, and domino reactions
for the synthesis of coumarins (Fig. 1). The earthworm species we
used is Eisenia foetida (Annelida, Oligochaeta), known as red
worm.