1-Triacontanol

Last updated
1-Triacontanol [1]
Triacontanol.png
Names
Preferred IUPAC name
Triacontan-1-ol
Other names
1-Triacontanol
n-Triacontanol
Melissyl alcohol
Myricyl alcohol
Identifiers
3D model (JSmol)
1711965
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.905 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-794-5
KEGG
PubChem CID
UNII
  • InChI=1S/C30H62O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31/h31H,2-30H2,1H3 Yes check.svgY
    Key: REZQBEBOWJAQKS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C30H62O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31/h31H,2-30H2,1H3
    Key: REZQBEBOWJAQKS-UHFFFAOYAU
  • OCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC
Properties
C30H62O
Molar mass 438.81 g/mol
Density 0.777 g/ml at 95 °C
Melting point 87 °C (189 °F; 360 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

1-Triacontanol (n-triacontanol) is a fatty alcohol of the general formula C30H62O, also known as melissyl alcohol or myricyl alcohol. It is found in plant cuticle waxes and in beeswax. Triacontanol is a growth stimulant for many plants, most notably roses, in which it rapidly increases the number of basal breaks. 1-Triacontanol is a natural plant growth regulator. It has been widely used to enhance the yield of various crops around the world, mainly in Asia. [2] Triacontanol has been reported to increase the growth of plants by enhancing the rates of photosynthesis, protein biosynthesis, the transport of nutrients in a plant and enzyme activity, reducing complex carbohydrates among many other purposes. The fatty alcohol appears to increase the physiological efficiency of plant cells and boost the potential of the cells responsible for the growth and maturity of a plant.

Contents

History

Triacontanol was first isolated in 1933 from alfalfa wax. It was identified as a saturated straight chain primary alcohol. [3] Triacontanol is found in various plant species as a minor component of the epicuticular wax. In wheat, triacontanol is about 3-4% of the leaf wax.[ citation needed ]. [4] The effects of triacontanol may also be seen when a chopped[ clarification needed ] alfafa plant is placed in close proximity to the seedlings and various crop seeds.[ which? ] A substantial increase in yield and growth has been seen in different plants, such as cucumber, tomatoes, wheat, maize, lettuce, and rice. [5]

Characteristics

Triacontanol does not react the same way in all plant species. The effects of triacontanol various in terms of photosynthesis and the yield manipulation in plant species.[ clarification needed ] The effects on C-3 plants and C-4 plants. In tomato plant (C-3 plant), the treatment of triacontanol increases the dry leaf weight and inhibited the photosynthesis by 27% in dry leaves,[ clarification needed ] whereas in the maize plants no change in photosynthesis occurs whether treated by triacontanol or not. [6]

Although, the basic effect of treating seedlings of various plant species is an increase in plant growth, photosynthesis and the yield of the crops, the effects of triacontanol are not the same in every plant species. Some exhibit these symptoms while some show no response to the treatment to triacontanol. Different studies reveal that the effects of triacontanol differs with the amounts of the triacontanol used to treat the plant. A much higher dose of triacontanol could also have adverse effects on the growth of a plant. Triacontanol has been reported to increase productivity of some plants that have some therapeutic properties. [7] In addition, the effects of triacontanol are observed in opium and morphine production. [8]

Functionality

There are numerous corporations[ example needed ] making synthetic triacontanol for enhancing the crop yield and pest resistance in the crops.[ citation needed ] Triacontanol improves the rate of cell division in a plant that produces larger roots and shoots. It has been shown that if triacontanol is applied during the maximized growth period of a plant in an appropriate amount, it enhances the enzymatic activity in the roots and hormone functionality increasing the overall performance of the plant. [9] Triacontanol basically operates by enhancing the basic functionality of the plant like increasing the rate of photosynthesis and producing more sugar such as glucose.[ citation needed ] When photosynthesis operates efficiently, the plant produce more sugars and absorb more sunlight. The plant then send more sugars to the rhizosphere via the root system where the growth, respiration and nutrient exchange take place in the vicinity of the soil. [10] Availability of more sugars lead to more respiration and nutrient exchange between the plants and the microorganisms in the soil. when the microbes receive more sugars from the plant, it increases the microbial activity in the root zone and they perform more efficiently in mining the nutrients like in the case of nitrogen fixation. These microorganisms particularly trace the nutrients essential for the soil. These nutrients are further used by the plants to build more complex nutrients and compounds essential for rapid growth and defence from certain other microbes. These complex compounds[ which? ] maximize the yield of the crop. Overall, despite other benefits from adequate amounts of triacontanol, the effect of enhanced photosynthesis may increase the plant outcomes.[ citation needed ]

Synthesis of triacontanol

There are several chemical pathways via which triacontanol can be artificially synthesized. One method includes an organic compound succinic anhydride and a carboxylic acid docosanoic acid that have been used to attach the different carbon chains (C4 and C22) on 2 and 5 positions of thiophene, via two acylation sequences. Later, 2-5 substituted thiophene is reacted for desulphurization using Raney Nickel. It produces triacontanoic acid which can be reduced with lithium aluminium hydride (LAH) to produce 1-triacontanol. [11]

Another method of synthesizing triacontanol focuses on the high yield with the easily available and feasible compounds that can form triacontanol through some chemical reactions in laboratory settings. 1-octadecanol or stearyl alcohol and 1,12-dodecanediol. Using the phase transfer system the 1-octadecanol is converted to octadecanal. On the other hand, 1,12-dodecanediol goes through the phase transfer bromination and further reacted with 1-hydroxy-12-triphenylphosphonium bromide. Both the end products of the two compounds undergo Witting reaction to give the product. The resulted mixture is hydrogenated to give triacontanol. [12]

Physiological effects on some plant species

Cacao Seedlings

Cocoa seedlings (Theobroma cacao L.) shows a positive growth in terms of plant length and the leaf size when treated with triacontanol. In a study, the cocoa seedlings when receive an appropriate amount of triacontanol, led to increase in the leaf size, plant length, leaf number as well as the stem diameter of the cocoa plant. [13] which is due to biosynthesis of secondary metabolites which alters the physiology and the biochemistry of the plants. Treating the cocoa plant with excess amount of triacontanol led to inhibition of plant growth and bearing of adverse effects on the plant physiology. [14] The provision of triacontanol rapidly increase the morphogenetic response in the plant during the embryogenesis process. The enhanced response lead to increase in the cell division and cell growth by the growth regulators. Moreover, it also leads to increased shoots and roots of the plant. The whole process results from the formation of new growth and development proteins and new mRNA.

Rhizophora apiculata (Mangrove)

In the hypocotyl treatment of triacontanol in the mangrove plant resulted in increased root and shoot growth. The rise in the number of primary and secondary roots, the length of roots, height and the biomass resulted from triacontanol treatment. Moreover, the reduction of nitrate reductase as well as increase amount of chlorophylls in the photosystem 1 and 2 observed. [15] However, the increase in the concentration of triacontanol resulted in the decrease of the plant growth. hence, the amount of the alcohol treatment is the driving force for the enhanced results.

Cell cultures in vitro

Triacontanol also increases the growth of a cell in vitro by increasing the cell number in the culture. It can be attributed to the increase protein formation and rapid cell division induced by triacontanol. [16]

The growth of cell culture in vitro has been done with various plant species to observe the effects of triacontanol. Similar effects of triacontanol can be seen with a variety of plants like rice, wheat, corn, maize, cucumber, and many more.

Related Research Articles

<span class="mw-page-title-main">Hydroponics</span> Growing plants without soil using nutrients in water

Hydroponics is a type of horticulture and a subset of hydroculture which involves growing plants, usually crops or medicinal plants, without soil, by using water-based mineral nutrient solutions in an artificial environment. Terrestrial or aquatic plants may grow freely with their roots exposed to the nutritious liquid or the roots may be mechanically supported by an inert medium such as perlite, gravel, or other substrates.

<span class="mw-page-title-main">Photosynthesis</span> Biological process to convert light into chemical energy

Photosynthesis is a system of biological processes by which photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical energy necessary to fuel their metabolism. Photosynthesis usually refers to oxygenic photosynthesis, a process that produces oxygen.
Photosynthetic organisms store the chemical energy so produced within intracellular organic compounds like sugars, glycogen, cellulose and starches. To use this stored chemical energy, an organism's cells metabolize the organic compounds through cellular respiration. Photosynthesis plays a critical role in producing and maintaining the oxygen content of the Earth's atmosphere, and it supplies most of the biological energy necessary for complex life on Earth.

<span class="mw-page-title-main">Potassium deficiency (plants)</span> Plant disorder

Potassium deficiency, also known as potash deficiency, is a plant disorder that is most common on light, sandy soils, because potassium ions (K+) are highly soluble and will easily leach from soils without colloids. Potassium deficiency is also common in chalky or peaty soils with a low clay content. It is also found on heavy clays with a poor structure.

<span class="mw-page-title-main">Plant hormone</span> Chemical compounds that regulate plant growth and development

Plant hormones are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of organ size, pathogen defense, stress tolerance and reproductive development. Unlike in animals each plant cell is capable of producing hormones. Went and Thimann coined the term "phytohormone" and used it in the title of their 1937 book.

<span class="mw-page-title-main">Plant nutrition</span> Study of the chemical elements and compounds necessary for normal plant life

Plant nutrition is the study of the chemical elements and compounds necessary for plant growth and reproduction, plant metabolism and their external supply. In its absence the plant is unable to complete a normal life cycle, or that the element is part of some essential plant constituent or metabolite. This is in accordance with Justus von Liebig's law of the minimum. The total essential plant nutrients include seventeen different elements: carbon, oxygen and hydrogen which are absorbed from the air, whereas other nutrients including nitrogen are typically obtained from the soil.

<span class="mw-page-title-main">Auxin</span> Plant hormone

Auxins are a class of plant hormones with some morphogen-like characteristics. Auxins play a cardinal role in coordination of many growth and behavioral processes in plant life cycles and are essential for plant body development. The Dutch biologist Frits Warmolt Went first described auxins and their role in plant growth in the 1920s. Kenneth V. Thimann became the first to isolate one of these phytohormones and to determine its chemical structure as indole-3-acetic acid (IAA). Went and Thimann co-authored a book on plant hormones, Phytohormones, in 1937.

Photobiology is the scientific study of the beneficial and harmful interactions of light in living organisms. The field includes the study of photophysics, photochemistry, photosynthesis, photomorphogenesis, visual processing, circadian rhythms, photomovement, bioluminescence, and ultraviolet radiation effects.

<span class="mw-page-title-main">Plant physiology</span> Subdiscipline of botany

Plant physiology is a subdiscipline of botany concerned with the functioning, or physiology, of plants.

<span class="mw-page-title-main">Callus (cell biology)</span> Growing mass of unorganized plant parenchyma cells

Plant callus is a growing mass of unorganized plant parenchyma cells. In living plants, callus cells are those cells that cover a plant wound. In biological research and biotechnology callus formation is induced from plant tissue samples (explants) after surface sterilization and plating onto tissue culture medium in vitro. The culture medium is supplemented with plant growth regulators, such as auxin, cytokinin, and gibberellin, to initiate callus formation or somatic embryogenesis. Callus initiation has been described for all major groups of land plants.

Theoretical production ecology tries to quantitatively study the growth of crops. The plant is treated as a kind of biological factory, which processes light, carbon dioxide, water, and nutrients into harvestable parts. Main parameters kept into consideration are temperature, sunlight, standing crop biomass, plant production distribution, nutrient and water supply.

Ecophysiology, environmental physiology or physiological ecology is a biological discipline that studies the response of an organism's physiology to environmental conditions. It is closely related to comparative physiology and evolutionary physiology. Ernst Haeckel's coinage bionomy is sometimes employed as a synonym.

<i>Crotalaria juncea</i> Species of legume

Crotalaria juncea, known as brown hemp, Indian hemp, Madras hemp, or sunn hemp, is a tropical Asian plant of the legume family (Fabaceae). It is generally considered to have originated in India.

A xerophyte is a species of plant that has adaptations to survive in an environment with little liquid water. Examples of xerophytes include cacti, pineapple and some gymnosperm plants. The morphology and physiology of xerophytes are adapted to conserve water during dry periods. Some species called resurrection plants can survive long periods of extreme dryness or desiccation of their tissues, during which their metabolic activity may effectively shut down. Plants with such morphological and physiological adaptations are said to be xeromorphic. Xerophytes such as cacti are capable of withstanding extended periods of dry conditions as they have deep-spreading roots and capacity to store water. Their waxy, thorny leaves prevent loss of moisture.

Biotic stress is stress that occurs as a result of damage done to an organism by other living organisms, such as bacteria, viruses, fungi, parasites, beneficial and harmful insects, weeds, and cultivated or native plants. It is different from abiotic stress, which is the negative impact of non-living factors on the organisms such as temperature, sunlight, wind, salinity, flooding and drought. The types of biotic stresses imposed on an organism depend the climate where it lives as well as the species' ability to resist particular stresses. Biotic stress remains a broadly defined term and those who study it face many challenges, such as the greater difficulty in controlling biotic stresses in an experimental context compared to abiotic stress.

Soil microbiology is the study of microorganisms in soil, their functions, and how they affect soil properties. It is believed that between two and four billion years ago, the first ancient bacteria and microorganisms came about on Earth's oceans. These bacteria could fix nitrogen, in time multiplied, and as a result released oxygen into the atmosphere. This led to more advanced microorganisms, which are important because they affect soil structure and fertility. Soil microorganisms can be classified as bacteria, actinomycetes, fungi, algae and protozoa. Each of these groups has characteristics that define them and their functions in soil.

Breeding for drought resistance is the process of breeding plants with the goal of reducing the impact of dehydration on plant growth.

Korean natural farming (KNF) is an organic agricultural method that takes advantage of indigenous microorganisms (IMO) to produce rich soil that yields high output without the use of herbicides or pesticides.

CO<sub>2</sub> fertilization effect Fertilization from increased levels of atmospheric carbon dioxide

The CO2 fertilization effect or carbon fertilization effect causes an increased rate of photosynthesis while limiting leaf transpiration in plants. Both processes result from increased levels of atmospheric carbon dioxide (CO2). The carbon fertilization effect varies depending on plant species, air and soil temperature, and availability of water and nutrients. Net primary productivity (NPP) might positively respond to the carbon fertilization effect. Although, evidence shows that enhanced rates of photosynthesis in plants due to CO2 fertilization do not directly enhance all plant growth, and thus carbon storage. The carbon fertilization effect has been reported to be the cause of 44% of gross primary productivity (GPP) increase since the 2000s. Earth System Models, Land System Models and Dynamic Global Vegetation Models are used to investigate and interpret vegetation trends related to increasing levels of atmospheric CO2. However, the ecosystem processes associated with the CO2 fertilization effect remain uncertain and therefore are challenging to model.

Plant root exudates are fluids emitted through the roots of plants. These secretions influence the rhizosphere around the roots to inhibit harmful microbes and promote the growth of self and kin plants.

Plants are constantly exposed to different stresses that result in wounding. Plants have adapted to defend themselves against wounding events, like herbivore attacks or environmental stresses. There are many defense mechanisms that plants rely on to help fight off pathogens and subsequent infections. Wounding responses can be local, like the deposition of callose, and others are systemic, which involve a variety of hormones like jasmonic acid and abscisic acid.

References

  1. Merck Index , 11th Edition, 9506.
  2. Naeem, M.; Khan, M. Masroor A.; Moinuddin (2012). "Triacontanol: A potent plant growth regulator in agriculture". Journal of Plant Interactions. 7 (2): 129–142. Bibcode:2012JPlaI...7..129N. doi: 10.1080/17429145.2011.619281 . S2CID   84691493.
  3. Chibnall, A.C.; E.F. Williams; A.L, Latner; S.H. Piper (1933). "The isolation of n-triacontanol from lucerne wax". Biochemical Journal. 27 (6): 1885–1888. doi:10.1042/bj0271885. PMC   1253114 . PMID   16745314.
  4. Tulloch, A.P., and L.L., Hoffman. 1974. Epicuticular wax of Secale cereale and Triticale hexaploide leaves. Phytochemistry 13: 2535-2540.
  5. Ries, S.K., H. Bittenbinder, R. Hangarter, L.Kolker, G. Morris, and V. Wert. 1976. Improved Growth and Yield of crops from organic supplements. Pages 377-384 in W. Lokeretz, ed. Energy and Agriculture. Academic Press, New York.
  6. Eriksen, A. B.; Selldén, G.; Skogen, D.; Nilsen, S. (1981). "Comparative analyses of the effect of triacontanol on photosynthesis, photorespiration and growth of tomato (C3-plant) and maize (C4-plant)". Planta. 152 (1): 44–49. Bibcode:1981Plant.152...44E. doi:10.1007/BF00384983. PMID   24302317. S2CID   9567091.
  7. Srivastava, N.; Khatoon, S.; Rawat, A. K. S.; Rai, V.; Mehrotra, S. (2009). "Chromatographic Estimation of p-Coumaric Acid and Triacontanol in an Ayurvedic Root Drug Patala (Stereospermum suaveolens Roxb.)". Journal of Chromatographic Science. 47 (10): 936–939. doi: 10.1093/chromsci/47.10.936 . PMID   19930809.
  8. M.M.A. Khan; R. Khan; M. Singh; S. Nasir; M. Naeem; M.H. Siddiqui; F. Mohammad (2007). "Gibberellic acid and triacontanol can ameliorate the opium yield and morphine production in opium poppy (Papaver somniferum)". Acta Horticulturae. 756 (756): 289–298. doi:10.17660/ActaHortic.2007.756.30.
  9. Ries, S. and Houtz, R. 1983. Triacontanol as a plant growth regulator. Horticultural Science, 18: 654-662.
  10. Nelson, N. ( 1944 ). A photometric adaptation of the Somogyi's method for the determination of glucose. J. Bioi. Chem. 153:375-380.
  11. Bhalerao, U.T.; Rao, S.Jagadishwar; Tilak, B.D. (1984). "New synthesis of 1-triacontanol". Tetrahedron Letters. 25 (47): 5439–5440. doi:10.1016/S0040-4039(01)91306-1.
  12. Tran-Thi, N. H.; Falk, H. (1995). "An efficient synthesis of the plant growth hormone 1-triacontanol". Monatshefte für Chemie Chemical Monthly. 126 (5): 565–568. doi:10.1007/BF00807430. S2CID   94909176.
  13. Sitinjak, Rama Riana; Pandiangan, Dingse (2014). "THE EFFECT OF PLANT GROWTH REGULATOR TRIACONTANOL TO THE GROWTH OF CACAO SEEDLINGS (Theobroma cacao L.)". Agrivita Journal of Agricultural Science. 36 (3). doi: 10.17503/Agrivita-2014-36-3-260-267 .
  14. Jaybhay, S., P. Chate and A. Ade. 2010. Isolation and identification of crude triacontanol from rice bran wax. Journal of Experimental sciences. 1 (2): 26.
  15. Moorthy, P.; Kathiresan, K. (1993). "Physiological responses of mangrove seedling to triacontanol". Biologia Plantarum. 35 (4). doi:10.1007/BF02928035. S2CID   36478378.
  16. Hangarter, Roger; Ries, Stanley K.; Carlson, Peter (1978). "Effect of Triacontanol on Plant Cell Cultures in Vitro". Plant Physiology. 61 (5): 855–857. doi:10.1104/pp.61.5.855. PMC   1091993 . PMID   16660401.