Gibberellins

• The gibberellins are a large

group of related compounds
(more than 125 are known) that,
unlike the auxins, are defined by
their chemical structure rather
than by their biological activity.

• All gibberellins are based on the

ent-gibberellane skeleton
 Gibberellins discovery
First known by Japanese farmer Konishi (1898)
• In 1926 Ewiti Kurosawa and colleagues were studying
plants suffering from bakanae, or "foolish seedling"
disease in rice.
• He succeeded in obtaining a filtered extract of this
fungus which could cause symptoms of the Backanae
disease in healthy rice seedlings.

• Disease caused by fungus called, Gibberella

fujikuroi(asexual stage Fusarium monoliforme)) which
was stimulating cell elongation and division.

• Plants were taller, thin and pale in colour

• 1935: Yabuta, Hayashi and Kahnbe first isolated active

principle toxin from the fungal pathogen Gibberella and
named it Gibberellin
 In 1938 Yabuta and Sumuki isolated gibberelins A and B in crystal form from this
fungus
 Not until the mid-1950s did two groups—one at the Imperial Chemical Industries
(ICI) research station at Welyn in Britain, the other at the U.S. Department of
Agriculture (USDA) in Peoria, Illinois—succeed in elucidating the structure of the
material that they had purified from fungal culture filtrates, which they named
gibberellic acid
 MacMillan and Suter (1958) a gibberellin (gibberellin A1) was conclusively
identified from a higher plant (runner bean seeds, Phaseolus coccineus)
 More than 125 compounds belonging to the class of Gibberellins have been
isolated from a wide variety of plants (25 occur in Gibberella fujikuroi and 100 in
other higher plants)
 numbered as gibberellin AX (or GAX), where X is a number, in the order of their
discovery. This scheme was adopted for all gibberellins in 1968.
 They are found in all parts of the plant body but the highest concentrations of
gibberellins are found in developing seeds
 These are cyclic terpenes. Different gibberellins differ in structure and biological
activity
GA 12 has 20 C. Others have only 19 (C19-
GAs), having lost one carbon to
metabolism.There are other variations in
the basic structure, especially the
oxidation state of carbon 20 (in C20-GAs)
and the number and position of hydroxyl
groups on the molecule
 Terpenes

• The terpenes, or terpenoids, constitute the largest class of secondary products. The
diverse substances of this class are generally insoluble in water. They are biosynthesized
from acetyl-CoA or glycolytic intermediates.
• Terpenes Are Formed by the Fusion of Five- Carbon Isoprene Units
• All terpenes are derived from the union of five-carbon elements that have the branched
carbon skeleton of isopentane
• basic structural elements of terpenes are sometimes called isoprene units because
terpenes can decompose at high temperatures isoprene
to give isoprene
• Thus all terpenes are occasionally referred to as isoprenoids.
• Terpenes are classified by the number of five-carbon units they contain, although
extensive metabolic modifications can sometimes make it difficult to pick out the
original five-carbon residues.
• Ten-carbon terpenes, which contain two C5 units, are called monoterpenes;
• 15-carbon terpenes (three C5 units) are sesquiterpenes;
• and 20-carbon terpenes (four C5 units) are diterpenes.
• Larger terpenes include triterpenes (30 carbons), tetraterpenes (40 carbons), and polyterpenoids
([C5]n carbons, where n > 8).
Terpenoids biosynthesis
• Terpenes are biosynthesized from primary metabolites in
at least two different ways.
• In the well-studied mevalonic acid pathway, three
molecules of acetyl-CoA are joined together stepwise to
form mevalonic acid
• This key six-carbon intermediate is then
pyrophosphorylated, decarboxylated, and dehydrated to
yield isopentenyldiphosphate (IPP)-activated five-carbon
building block of terpenes.
• IPP also can be formed from intermediates of glycolysis
or the photosynthetic carbon reduction cycle via a
separate set of reactions
• called the methylerythritol phosphate (MEP) pathway
• that operates in chloroplasts and other plastids
(Lichtenthaler 1999)
• glyceraldehyde-3-phosphate and two carbon atoms
derived from pyruvate appear to combine to generate an
intermediate that is eventually converted to IPP.
Terpenes in growth and development

• Certain terpenes have a well-characterized function in plant growth or development and so can
be considered primary rather than secondary metabolites. For example,
• Gibberellins, an important group of plant hormones, are diterpenes
• Sterols are triterpene derivatives that are essential components of cell membranes, which they
stabilize by interacting with phospholipids
• The red, orange, and yellow carotenoids are tetraterpenes that function as accessory pigments
in photosynthesis and protect photosynthetic tissues from photooxidation
• The hormone abscisic acid is a C15 terpene produced by degradation of a carotenoid precursor.
• Long-chain polyterpene alcohols known as dolichols function as carriers of sugars in cell wall and
glycoprotein synthesis
• Terpene-derived side chains, such as the phytol side chain of chlorophyll help anchor certain
molecules in membranes.
• Thus various terpenes have important primary roles in plants. However, the vast majority of the
different terpene structures produced by plants are secondary metabolites that are presumed to
be involved in defense.
GA biosynthesis

• Step-I :Production of terpenoid precursors and ent-kaurene in plastids.

• cyclization reactions that convert GGPP to ent-kaurene represent the first step that is specific
for the gibberellins
• two enzymes that catalyze the reactions are localized in the proplastids of meristematic shoot
tissues, and they are not present in mature chloroplasts
• Thus, leaves lose their ability to synthesize gibberellins from IPP once their chloroplasts mature
• Stage 2: Oxidation reactions on the ER form GA and GA 12 53

• methyl group on ent-kaurene is oxidized to a carboxylic acid, followed by contraction

of the B ring from a six- to a five-carbon ring to give GA12-aldehyde. GA12-aldeh yde
is then oxidized to GA12, the first gibberellin in the pathway in all plants and thus the
precursor of all the other gibberellins
• hydroxylation of carbon 13 occurs next, forming GA53 from GA12
• Enzyme -monooxygenases that utilize cytochrome P450 in their reactions that are
localized on endoplasmic reticulum
• Stage 3: Formation in the cytosol of all other gibberellins from GA12 or
GA53. All subsequent steps in the pathway (see Figure 20.6) are carried out
by a group of soluble dioxygenases in the cytosol.
• These enzymes require 2- oxoglutarate and molecular oxygen as
cosubstrates, and they use Fe2+ and ascorbate as cofactors.
• The specific steps in the modification of GA12 vary from species to species,
and between organs of the same species.
• Two basic chemical changes occur in most plants:
• 1. Hydroxylation at carbon 13 (on the endoplasmic reticulum) or carbon 3, or both.
• 2. A successive oxidation at carbon 20 (CH2 → CH2OH → CHO). The final step of this
oxidation is the loss of carbon 20 as CO2.
• The Enzymes and Genes of the Gibberellin Biosynthetic Pathway Have Been
Characterized
• Most notable from a regulatory standpoint are two biosynthetic enzymes—GA
20-oxidase (GA20ox)3 and GA 3-oxidase (GA3ox)—and an enzyme involved in
gibberellin metabolism, GA 2-oxidase (GA2ox)
• GA 20-oxidase catalyzes all the reactions involving the successive oxidation steps
of carbon 20 between GA53and GA20, including the removal of C-20 as CO2.
• GA 3-oxidase functions as a 3β-hydroxylase, adding a hydroxyl group to C-3 to
form the active gibberellin, GA1.
• GA 2-oxidase inactivates GA1 by catalyzing the addition of a hydroxyl group to C-
2.
 Active and Inactive Gibberellins
• Free GAs
• Gibberellins May Be Covalently Linked to Sugars
• gibberellin glycosides are formed by a covalent linkage
between gibberellin and a sugar (prevalent in seeds) carboxyl
group forming a gibberellin glycoside, or via a hydroxyl group
forming a gibberellin glycosyl ether.

Conversion of GA20 to GA1 by GA 3β-hydroxylase,

which adds a hydroxyl group (OH) to carbon 3 of GA20.
 AMO-1618, Cycocel, and Phosphon
D are specific inhibitors

Paclobutrazol and
other inhibitors of
P450 monooxygenases
specifically inhibit this
stage of gibberellin
biosynthesis before
GA12-aldehyde, and
they are also growth
retardants.

highly hydrophobic ent-kaurene is oxidized by membrane-bound monooxygenases to GA12 aldehyde

MONOOXYGENASES
The highly hydrophobic ent-kaurene is oxidized by membrane-
bound monooxygenases to GA12. The enzymes require NADPH
and oxygen and, on the basis of the early demonstration that
ent-kaurene and ent-kaurenal oxidation are inhibited by carbon
monoxide with reversibility by light at 450 nm are all assumed
to involve cytochrome P450. The involvement of cytochrome
P450 in ent-kaurenoic acid 7b-hydroxylase
 Form of Gibberellins

Inactive Active
• Synthesis
– Starts in Plastids (Carotenoid Pathway)
– Modified in ER
– Completed in Cytoplasm
• Tissue Localization
– Young Leaves, Apical Internodes
– Developing Fruit, Germinating Seed
– Roots
• Transport
– Xylem and Phloem and non polar with similar
velocity as carbohydrate (5 cm/hr)
 Physiological Roles of Gibberellins
 When applied externally, they can reverse the effect of
certain dwarfing mutations

 They have to be converted to a particular form

(gibberellin A1) before they can have any biological
effect

 Gibberellins can substitute for the dormancy breaking

treatments (cold or light)
 Gibberellins promotes in germination and
radicle growth
 Promote development of seedless fruits
(parthenocarpy) in some species (e.g. Currants,
apples cucumbers
 Bolting and flower induction
 Control of sex expression
Gibberellins promote stem elongation and leaf expansion

• They cause these effects by promoting both cell division and cell
elongation
• The mechanism by which GA regulates cell elongation is different
from that of Auxins which involve cell wall acidification but the effect
of GA on wall loosing takes place without acidification
•Bolting of LD plants plus flowering in some cases.

GA1 naturally increases in

Bolting in Spinach long days producing
(Spinacea oleracea) bolting
Gibberellins can cause bolting in Brassicacea members even in the
absence of inducing photoperiod or cold treatment
 Horticultural Uses
1. Seed Germination: 200 ppm in papaya, potato
5ppm for 5 minutes

2. Floweing: lettuce and radish: GA: 100 ppm

3. Fruit elongation: Thompson Seedless Grapes

4. Parthenocarpic Fruit: in guava 1000 ppm

5. Male Flower production

Monoecious & Dioecious Plants
Wild Radish – Rosette & Bolt
A FLOWERING ANNUAL

Year one Year two

6. Fruit setting: 40 ppm in grape

7. Breaking dormancy/Chilling
Requirement: 25 ppm in potato

8. Fruit thinning : 60 ppm in grape

9. Extending shelf life: 100 ppm in

guava