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Resins Unveiled:

RESINS are a product of plant metabolism. This means that the plant makes the resin within itself. It uses components made by photosynthesis which are broken down to simpler compounds. And from these compounds with the help of enzymes resins are build, or synthesized. By far most of the resins are terpenoids, build from repeting blocks of C5H8, the isoprene units. But there are also some phenolic resins. They are made from R-OH, just like alcohol, but with the R part being an aromatic ring.

Plants can have specialized secretory structures where resin is made in advance and then stored. This preformed resin is also called CONSTITUTIVE resin, formed by Multi purpose enzymes..

An injury can also stimulate the plant to start resin production, right at the spot where the injury is present. This accute formed resin is called INDUCED resin, formed by single purpose enzymes. These two types of resin are made (synthesized) with different types of enzymes.

The metabolistic process to make resin takes part within the plant cell. Plant cells have different parts with different functions. It has a CELLWALL, the outer protective layer of the cell, and a CELL MEMBRANE, a thin layer around the inner parts of a cell, sort of a sack. The interior of the cell is filled with fluid, the CYTOSOL, and in this cytosol the different ‘organs’ or ORGANELLES of the cell are laying around.

Of course there is the DNA, a structure that holds the genetic information of the cel. The MITOCHONDRIA are organelles where aerobic (with oxygen) energy production takes place. In the ENDOPLASMATIC RETICULUM the synthesis of biomolecules takes place. And in the CHLOROPLASTS carbohydrates such as glucose (sugar) are formed by photosynthesis under the influence of sunlight. It is actually the chloroplasts in the plantcells that give plants their green color.

The different stages of RESIN SYNTHESIS take place at different sites, compartments, within the cell. And in each compartment there are different ENZYMES that help with the production of the compounds. So these enzymes catalyse (help) the formation of the basic skeleton of the terpenoids that resin consists of. But there is something special with those enzymes. Some of them are able to make not one but various terpenoid products, and produce them in fixed ratios.

Plants can have specialized secretory structures where resin is made in advance and then stored. This preformed resin is also called CONSTITUTIVE resin, formed by multi purpose enzymes..

An injury can also stimulate the plant to start resin production, right at the spot where the injury is present. This accute formed resin is called INDUCED resin, formed by single purpose enzymes.

So now we have a mixture of compounds, a sort of fixed recipe for the resin. Formed by single- and multipurpose enzymes. The COMPOSITION as well as the complexity of the skeletal structures of the different compounds give different PROPERTIES to all sorts of resins. Some have a nice fragrance, others make good varnishes or can be used as a medicine.

By far most of the resins are terpenoids, build from repeting blocks of C5H8, the isoprene units. But there are also some phenolic resins. they are made from R-OH, just like alcohol, but with the R part being an aromatic ring.

This differentiation also allows us to analyze and compare resin and find out from what species of plants the resin came from. A resin is normally made of 20 to 50 different compounds but only some of them in high concentration. Within the same plant the percentages of these different compounds can vary a little between constitutive and induced resin.

The terpenoid compounds in resin can be split up into two types, the VOLATILE fraction and the NONVOLATILE fraction. The amounts of these fractions give the resin fluidity, viscosity and the given time it takes for the resin to harden. If the product that a plant exudates consists of only volatile fractions we often call them ESSENTIAL OILS ( It is good to bear in mind that these products are not essential to the plant and they are not actual oils. The essential stands for essence, which means fragrance. And the oil refers to the way they feel.) And the nonvolatile fraction is called RESIN.

A plant makes a lot of different compounds in its cells. Most of them are vital for the plant to have a healthy development and growth. We call them primary compounds. But a plant also produces compounds that do not play a significant role in the primary processes of the plant, the secundary compounds. The terpenoids that a plant produces and that form the resin are secondary compounds. So people used to think that these terpenoids where of no use to the plant and considered them waist products. and that resin secretion was a way of the plant to get rid of excess products like acetate.

But resin-terpenoids not being vital to a plants life does not mean that they are not important. Resins play a very significant role in the defense mechanism of plants. They protect the plant against fungi, bacteria and virusses. And can seal off places of injury.

So how is this resin actually produced in a plant?

By terpenoid synthesis. We start with CO2 (carbondioxide) and sunlight. The plants takes in CO2 from the air and by a proces called photosynthesis makes carbohydrates. This happens in the chloroplasts, the little nuggets in plantcells that make the plant look green. And we know carbohydrates as glucose, or sugar. Then a proces starts to make energy out of the glucose. This proces is called the primary carbon metabolism, or glycolysis in short. During this proces not only energy is made but also organic acid called pyruvate.

This pyruvate can be processed with the use of enzymes into IDP (isopentenyl-diphosphate). This can happen in two ways.

Via the mevalonate pathway or MVA pathway
This operates in the cytosol-ER part of the cell . The pyruvate is converted to acetyl-coenzyme A. And three of these acetylCoA are made into IDP. Via the MVA pathway the sesqui- and triterpenes are formed.

Or the nonmevalonic pathway, also called the DXP pathway:
This happens in the chloroplasts of the cell. Two carbon atoms from pyruvate plus 3-PGA(3-phosphoglyceraldehyde) are made into IDP Via the DXP pathway the mono- and diterpenes are formed.

This IDP and its isomer DMADP are the actual five-carbon (C5H8) buildingblocks. They form compounds that are used for the formation of larger terpenoid molecules. To the DMADP part, units of IDP can be connected and form chains. With every added block of C5H8 the terpenoid molecules can get longer and the possibilities for isomers become greater.

The basic combination is 1 DMADP + 1 IDP make up compounds with 10 carbon atoms. From these compounds terpenoids called monoterpenes are made.

DMADP + IDP - > C10 / Monoterpenes • volatile
DMADP + 2 IDP - > C15 / Sesquiterpenes • volatile
DMADP + 3 IDP - > C20 / Diterpenes • nonvolatile
Doubling of C15 - > C30 / Triterpenes • nonvolatile

Doubling of C20 - > C40 / Tetraterpenes
Addition of much more units : Polyterpenes

Tetra- and polyterpenes can occur alongside resin components but are not part of it.

The percentages of the different terpenoids in a resin determine the kind of properties it has. And thus the way in which we can collect the resin and use it to our own advantage.

Langenheim en biochemie boek

For a bibliography of technical Resin terms explained click here


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