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Plant Biotransformation
3. Sterility: Higher Lower
Definition: 4. Metabolism Rate: Higher Lower
> Defined as a biological process whereby an organic compound is modified plant biotransformation: Main characteristics
into a chemically different product(s) or it is the conversion from one
chemical form to another. (naturally). 1) Substrate specificity:
Types of biotransformation/Bioconversion : A range of substrates that can be converted to product by an enzyme. A few
enzymes exhibit absolute specificity (catalyze only one particular reaction).
1. Plant cell culture biotransformation. Other enzymes will be specific for a particular type of chemical bond or
2. Microbial biotransformation. functional group. e.g hydroxylases.

3. Animal cell culture biotransformation 2) Site specificity (regio-specificity):

Examples of plant biotransformation: Plant cells can carry out regiospecific modifications that are not easily carried
out by chemical synthesis or by microorganisms. If several functional groups
1. Commercially biotransformation of digitoxin to digoxin using D. lanata of one type are present in the molecule, only one specific position may be
cells, since digoxin has a higher demand. affected. It is possible to obtain conversions at centers that are chemically
2. Arbutin (skin depigmentation agent), is produced commercially by unreactive. ex: Regio- and stereoselective hydroxylation at the C-I, C-5,C-
biotransformation of hydroquinone precursor (inexpensive) using 12 and C-16 of digitoxigenin .
Catharanthus roseus cell culture. 3) Stereo-selectivity (cis and trans, R and S isomers):
3. Vinblastin and vincristin (anticancers) produced commercially by Plant cells are able to catalyze the reactions stereo-specifically, resulting in
extraction of Catharanthus roseus plant chirally pure products.
but it is of low yield. so C. roseus cell suspension culture produce If a racemic mixture is used as: hydroxylase only one specific enantiomer is
catharanthin alkaloid which is coupled with the addded vindoline precursor converted. They are well suited to obtain specific conformation. e.g
(as the culture can't produce it) to form vinblastin alkaloid. hydroxylation at C-4 of B-terpineol afforded only trans-isomer .
Comparison of Plant biotransformation with others:
Microbial culture Plant cell culture
1. Surface-volume ratio: Higher lower
2. Growth Rate: Higher lower

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o 1. The culture must have the essential enzymes.

2. The substrate or precursor must not be toxic to the cell culture.
Advantages Disadvantages 3. The substrate must reach the appropriate cellular compartment of the cell.
1. Biotransformation explores the 1. Chemical reactions are easier to
4. The rate of product formation must be faster than its further breakdown.
unique properties of biocatalysts handle and less complicated
(e.g. stereo-and region specificity equipment used. Chemical Pathways (chemical reactions) of biotransformation
and reactions done at no extreme pH 2. Tedious.
values and temperatures). 3. Specific plant cell culture  Hydroxylation.
2. Conditions are usually mild required.
 Oxido-reduction between alcohols and ketones.
(enzymatic reactions do not cause 4. Selection of plant cell culture is a
destruction of sensitive substrates). laborious job.  reduction of the carbon-carbon double bond.
3. The reaction conditions cause less 5. Sometimes process is not
environmental hazard, as they take economical.  glycosyl conjugation.
place chiefly in aqueous media 6. The substrate concentration
 Hydrolysis.
(mainly no organic solvents). added bound by certain limits.
4. Reactions proceed at ambient  Miscellaneou reactions.
(mild) temperature (20-40 "C),
normal pressure and no extreme pH  Hydroxylation.
values.
 Regio- and stereo-selective introduction of oxygenated functions (oh)
5. The number of reaction steps are
at the various positions of the molecule
much less. For example: chemical
transformation of one steroid to Examples
another require many steps and
the process may be costly and low Alpha Beta Gamma Digitoxiginin
yields is obtained. e.g biosynthesis terpenyl Terpenyl Terpenyl
of androsterones via chemical route acetate acetate acetate
involves several steps as compared At 4 give At 1.2 At 4 give Atc1.5.12.16(region&sterioselective)
e steroidal biotransformation. trans give trans trans
6. Plant cells conversions are much copm.
cheaper than chemical synthesis.
7. ##Combination of two or more
reaction can carried out by the same
plant cell culture.
.For successful biotransformation process,
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o 2-Salicyl alcohol precursor is converted to the corresponding

glucoside. A major product of glucosylation with the cultured cells of
2) Oxido-reduction between alcohols and ketones Gardenia jasminoides is salicin although other plant cultures produce iso-
salicin.
Oxidation of the hydroxyl [Link] are converted to the corresponding
ketones by the palnt cell cultures .
Transfomation of (RS)-bormeol and (RS)-isoborneol with the cultured cells
of [Link] gave (IR,4R)-camphor and unchanged substrates, (IS,2R,4S)-
borneol or (IS,2S,4S)-isoberneol. Such enantioselective oxidation is uscful
for the preparation of chiral compounds.
3) Reduction of the carbonyl group:
Reduction of menthan into S-menthol -Hydrolysis
‫المفروض بيتكون ميكتشر ولكن اس فورم هو الي بيتكون بسبب االستريوا سليكتفتي‬ -The ability of cultured cells to hydrolyse the acetoxyl group has been widely
investigatcd.
-The enantiomers with the R-configuration at the carbon atom bearing the
4-hvdrogenation of the carbon-carbon double bond acetoxyl group are preferentially hydrolysed.
Sterio and regioselective

5) Glycosyl-conjugation
Glycosyl conjugation is of special interest, because of converting water-
insoluble substances to water-soluble compounds.
Two types of glycosyl conjugations are listed Biotransformation using plant cells
1-One involves the esterification between carboxylic acids and sugar (Factors influencing biotransformation):
moieties.
1-. SCLECTION OF PLANT SPECIES:
2-The other is ether formation (glycosidation) of alcohols and sugar moietics.
The capacity for biotransformation is diverse among plant species e.g among
e.g Glucosylation of the added substrate, esculetin to 6-0-B-D- seven species of plant cell cullures, only Datura had capacity to biotransform
glucosylesculetin by cultured cells. coumarins flavonoids, phenolie acids and anthraquinones.

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2. IMPROVEMENT OF CELL VIABILITY
-Many substances are harmful to cultured cells. So it is necessary to decrease
the toxicity
-in order to increase the yield of the product. Sugar can increase cell viability
during glycosylation of phenolic compounds. Antioxidants can improve cell
viability and increase product formation in the biotransformation of phenolics
e.g antioxidant, such as gallic acid, ascorbic acid, cystein and tannins could
increase the production of arbutin when hydroquinone was added to the cell
culture.
3. THE SOLUBILITY OF PRECURSORS.
4. THE AMOUNT OF ENZYME ACTIVITY PRESENT .
5. LOCALIZATION OF ENZYMES.
6. PRESENCE OF SIDE REACTIONS PRODUCING UNDESIRED BYPRODUCT .
7. PRESENCE OF ENZYMES DEGRADING THE DESIRED PRODUCT.
8. ELICITATION, PERMEABILIZATION , PH VARIATION AND OSMOTIC
EFFECTS .

Glycosylation ……. Addition of suger

Glucosylation ……..addtion of glucose
g

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