Highly selective transformation by plant catalysts.pdf

Journal of Molecular Catalysis B: Enzymatic 5

1998

187–189

Highly selective transformation by plant catalysts

Hiroki Hamada

a,) , Yuka Miyamoto

a , Nobuyoshi Nakajima

b , Tsutomu Furuya

Dept. of Applied Science, Okayama Uni Í . of Sci., 1-1 Ridai-cho, Okayama 700, Japan

Dept. of Nutritional Sci., Okayama Prefectural Uni Í ., Soja, Okayama 719-11, Japan

Received 26 September 1997; accepted 29 November 1997

Abstract

This review outlines the recent progress in the biotransformation of foreign substrate by plant cultured suspension cells.

The reaction types and stereochemistry involved in the biotransformations are described. q 1998 Elsevier Science B.V. All

rights reserved.

Keywords: Biotransformation; Plant catalyst; Asymmetric reduction; Hydroxylation

1. Introduction

plant cultured suspension cells. These cells have

the ability to specifically convert cheap and

plentiful substrates into more useful com-

pounds. More recently, many studies have fo-

cused on the ability of plant cultured suspension

cells to transform foreign substrates. This paper

summarizes the selectivity in the biotransforma-

tion of foreign substrate by plant cultured sus-

pension cells.

It is well known that plants are the source of

valuable products and some useful basic materi-

als such as cellulose, wood and rubber. In addi-

tion, secondary products such as terpenoids,

cardenolides, coumarins, anthraquinones,

flavonoids, glucosinolates and alkaloids are also

produced

plants

and

are

used

drugs,

flavours, pigments food ingredient and agro-

chemicals. Hitherto, some secondary metabo-

lites from plant cultured suspension cells have

[]

2. Biotransformation of b -keto ester

been produced 1,2 . However the formation and

accumulation of several secondary metabolites

does not normally occur in the plant cultured

suspension cells and it has proven difficult to

harness this potential to industrial processes.

To overcome these problems we have studied

the biotransformation of foreign substrates by

In the biotransformation of ethyl 2-methyl-

3-oxobutanoate by the cultured suspension cells

of Marchantia polymorpha and Glycine max ,

ethyl 2-methyl-3-oxobutanoate was reduced di-

astereo-

and

enantio-selectively to

the

corre-

sponding anti - and syn - S -hydroxyester by the

cultured suspension cells of M. polymorpha and

G. max , respectively

Fig. 1 .

)

Corresponding author. E-mail: hamada@das.ous.ac.jp

1381-1177r98r$19.00 q

PII: S 1 3 8 1 - 1 1 7 7 9 8 0 0 0 3 2 - 0

188

H. Hamada et al. r Journal of Molecular Catalysis B: Enzymatic 5

(

1998

)

187–189

3. Biotransformation of terpenoids

We studied the biotransformation of carvones

and geraniol by the cultured suspension cells of

Catharanthus roseus and we found that they

. .

hydroxylate allylic positions of y -, q -

carvones and geraniol and reduce double bonds

and ketones 4 . The main product of geraniol is

10-hydroxygeraniol and the main products of

Fig. 1. Biotransformation of ethyl 2-methyl-3-oxobutanoate.

y - and q -carvones are 5b-hydroxyneodi-

hydrocarveol and 5a-hydroxycarvone, respec-

tively Fig. 2 . From the study of biotransforma-

tion of monoterpenoids by the cultured suspen-

sion cells of C. roseus periwinkle it was found

that the cultured suspension cells of C. roseus

have the ability to hydroxylate regioselectively

10-position

geraniol

and

C-4

and

C-5

positions of carvones.

Furthermore

investigated

the

biotrans-

formation of menthols and b-thujaplicin

hino-

kitiol

by the cultured suspension cells of Euca -

. w

lyptus perriniana

eucalyptus

5–7 . In the bio-

Fig. 2. Biotransformation of geraniol and

y -carvone.

Fig. 3. Biotransformation of

y -menthol and b-thujaplicin.

Fig. 4. Biotransformation of taxol.

H. Hamada et al. r Journal of Molecular Catalysis B: Enzymatic 5

(

1998

)

187–189

189

transformation of menthols the main products of

III. On the other hand, the cells regioselectively

hydrolyze the benzoyl group at C-2 of taxol.

The reaction types and stereoselectivity in

biotransformation depends on the functional

group in the foreign substrates. Therefore, bio-

transformation by plant cultured suspension cells

y - and q -menthols are y - and q -

menthol 3- O -b- D -gentiobiosides, respectively. In

the case of b-thujaplicin, the cultured cells of

E. perriniana glycosylate the hydroxyl group of

b-thujaplicin. From these results it was found

that eucalyptus cultured suspension cells per-

form

plant catalysts can be considered as an impor-

tant tool for commercial andror large scale

production of secondary products and food in-

gredients.

regioselective

glycosylation,

terpenoids,

e.g.,

-menthols and b-thujaplicin

see

Fig. 3 .

References

4. Biotransformation of taxol

T. Furuya, Yakugaku Zasshi 108

1988

675.

Taxol,

highly

functionalized

diterpenoid

T. Furuya, in: T. Uozumi, T. Kodama Eds. , The Production

of Useful Compounds by Plant Cell Cultures, Maruzen Ad-

vanced Technology, Tokyo, 1993, p. 1.

secondary

product

derived

from

yew

taxus

species which is now recognizing as the best

anticancer drug against human breast cancer.

More recently we studied biotransformation of

taxol by E. perriniana cell suspension cultures.

As shown in Fig. 4, taxol was converted to

baccatin III, 10-deacetylbaccatin III and 2-de-

K. Nakamura, H. Miyoshi, T. Sugiyama, H. Hamada, Phyto-

chemistry 40

1995

1419.

w 4

H. Hamada, H. Yasumune, Y. Fuchukami, T. Hirata, I. Sattler,

H.J. Williams, A.I. Scott, Phytochemistry 44

1997

615.

w 5

T. Furuya, Y. Orihara, H. Miyatake, J. Chem. Soc., Perkin

Trans. 1

1989

1711.

Y. Orihara, H. Miyatake, T. Yuruya, Phytochemistry 30 1991

1843.

benzoyltaxol 8 . From this result, it is found

that E. perriniana cultured suspension cells hy-

drolyze the ester group at C-13 and then the

acetyl group at C-10 of the produced baccatin

w 7

T. Furuya, Y. Asada, Y. Matsuura, S. Mizobata, H. Hamada,

Phytochemistry 46

1997

1355.

w 8

H. Hamada, K. Sanada, T. Furuya, S. Kawabe, M. Jaziri, Nat.

Product Lett. 9

1996

47.

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