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CAS Number 544-72-9
Molecular formula:C18H30O2
Molecular weight:278.4296
Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid.
Punicic acid is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil.
Punicic acid has also been found in the seed oils of snake gourd.
Punicic acid is a conjugated linolenic acid or CLnA; i.e. Punicic acid it has three conjugated double bonds.
Punicic acid is chemically similar to the conjugated linoleic acids, or CLA, which have two.
Punicic acid has also been classified as an "n-5" or "omega-5" polyunsaturated fatty acid.
Various researchers have reported pomegranate as a functional fruit owing to presence of wide range of phytochemicals in Punicic acid .
Purposely, antioxidative properties of juice, peel and seed have been examined for their therapeutic potential, which has prompted the nutritionists to further explore their nutraceutical and industrial application.
Punicic acid underutilized seed and peel portion, normally known as agro-waste obtained during industrial processing of pomegranate juice, are gaining attention of researchers now a days due to presence of array of nutraceutics in them.
Abundant presence of pomegranate seed is of keen interest to scientist because of rich composition of oil.
Pomegranate seed oil possesses rich polyunsaturated fatty acid composition, predominantly comprising of punicic acid (~55%) as characterized by Melo.
PA is also recognize as “Trichosanic acid” with molecular formula C18H30O2 while its molar mass is 278.43 g/mol with melting point of 44-45oC.
Punicic acid is an isomer of conjugated α-linolenic acid and a ω-5 polyunsaturated fatty acid which have structural resemblance with conjugated α-linolenic and linoleic acid, for instance number of double bonds and atomic arrangement.
Due to health benefits associated with these fatty acids, scientists are showing great interest in exploring functional and nutraceutical properties of punicic acid against various metabolic ailments.
The International Union of Pure and Applied Chemistry (IUPAC) designated its names as 9Z, 11E, 13Z-octadeca-9, 11, 13-trienoic acid on the basis of its three double bonds.
Principally, Punicic acid is an isomer of conjugated linoleic acid having a double bond on its tail side.
Other isomers of lenolic acid are catalpic acid, alpha-eleostearic acid, calendic acid ( and jacaric acid.
PA is named after its principle source pomegranate.
Among all the sources of PA it is most abundantly present in pomegranate seed oil (PSO).
Punicic acid other sources for PA are snake gourd seed oil and Trichosanthes kirilowii Maxim (TK) seeds containing 32 to 40% PA out of total seed weight.
Whereas, fatty acid profile of PSO contains conjugated linoleic acid up to 74–85 % PA and remaining 14-25% are its isomers.
PA could be chemically synthesized by dehydration and isomerization of secondary oxidation products of linoleic and alpha-linolenic acids.
Primarily, PA is reported to be effective against ailments like obesity, diabetics, inflammation, metabolic syndromes in various in vivo experiments that’s why pomegranate seed lipid portion (principal by-product) was studied after juice extraction as lipolytic enzymes deactivate during thermal processing.
Punicic acid was investigated in different studies that uptake rate of CLnA vary in Caco-2 cells when distribution and conversion of CLnA (punicic, α- and β-eleostearic, and catalpic acid) to CLA is premeditated.
Variation in the conversion efficiency is due to the difference in the structure of ∆13 double bond of CLnA.
The CLnA distribute between neutral and phospholipids and this distribution depends upon the number of trans double bonds.
Nevertheless, another theory also exists about the conversion of CLnA to CLA.
Accordingly, another theory explicates the metabolic conversion of CLnA to CLA is due to ∆13 double bond saturation reactions catalyzed by an enzyme i.e. nicotinamide adenine dinucleotide phosphate (NADP) that is known as a unique enzyme for conjugated trienoic acid reorganization.
Considering the side effects associated with usage of synthetic anti-oxidants and increase in oxidative stress disorders, use of anti-oxidants from natural sources are gaining importance.
Numerous studies revealed that PA is biologically active in hampering the hazards associated with oxidative mechanisms.
Punicic acid pomegranate seeds considered as the waste product after the processing of fruit into its various products.
Punicic acid pomegranate seed oil and peels were incorporated into ice-cream to enhance the functional properties and significant changes were observed in product pH, acidity and color while milk fat replacement with PSO improved the fatty acid profile by increasing the conjugated fatty acid contents with elevated antioxidant and anti-diabetic properties due to the phenolic contents.
Punicic acid punicalagins and PA from peel and seed provide the health benefits with improvement in functional properties.
Punicic acid pomegranate seed ethanolic extract (PSEE) possessed the anti-proliferative and antioxidant effects against hormone-dependent prostate carcinoma and human breast cancer cell lines and considered as nutraceutical/functional food ingredient to prevent carcinogenic diseases.
Punicic acid pomegranate seed extract useful in replacing artificial antioxidant in meat products to increase the oxidative stability of such products.
Devatkal et al. incorporated the citrus rind powder and pomegranate rind and seed extracts in meat patties.
Highest antioxidant effect was observed in pomegranate seed extract.
Punicic acid according to such studies, it is believed that industrial by-products of fruits and vegetables are potential source of antioxidant.
Punicic acid pomegranate seed extract helps to reduce the formation of heterocyclic aromatic amines in meat products cooked by various methods with different temperatures and heat thus pomegranate seed useful in producing safe product.
Mohagheghi et al. incorporated PSO (PSO-in-water emulsion) as functional ingredient in juice and beverages with varying concentration of gum Arabic and evaluated the effect on emulsion stability index, droplet size distribution, and turbidity loss rate.
The consequences manifested that the beverage emulsions behaved as Newtonian fluids, and this study begins new glimpse to produce relatively stable PSO-in-water emulsions as functional ingredient in beverage industry.
Encapsulation of PSO and its application in skimmed milk powder as encapsulating agent was studied by.
Punicic acid (PA) is a polyunsaturated fatty acid, which is classified as a conjugated linolenic acid.
PA is also referred as a "super CLnA" whose effect is even more potent than that of an ordinary CLnA.
Punicic acid is found mainly in the seeds of pomegranate fruit and Trichoxanthes kirilowii and some other minor sources.
Punicic acidIt possesses a wide array of biological properties including antidiabetic, antiobesity, antiproliferative, and anticarcinogenic activity against various forms of cancer.
Punicic acid (PUA) has demonstrated effectiveness in decreasing gut inflammation and improving digestive health.
PUA is a dietary lipid found in pomegranate seed oil (PSO).
Pomegranate (Punica granatum) is a well‐known fruit used for alternative medicine.
Various pomegranate extracts are utilized as supplements with a wide variety of purported health benefits including anticancer actions.
Punicic acid supplements contain a number of different components that may either activate or inhibit estrogen action.
Additionally Punicic acid factors associated with pomegranate fruit or extracts may lower oxidation of LDL cholesterol, reduced arterial plaques, lower oxidative stress, enhanced wound healing, inhibition of angiogenesis and tumor proliferation and increased tumor apoptosis.
However, Punicic acid have been conducted with fruit, seeds, pericarp or partially purified pomegranate extracts making it hard to determine what the active component(s) may be.
Punicic acid is an omega‐5 long chain polyunsaturated fatty acid found in pomegranate seed oil.
A number of long chain fatty acids have been reported to have cancer preventive actions.
Punicic acid is an unusual 18-carbon fatty acid bearing three conjugated double bonds.
Punicic acid has been shown to exhibit a myriad of beneficial bioactivities including anti-cancer, anti-diabetes, anti-obesity, antioxidant, and anti-inflammatory properties.
Pomegranate (Punica granatum) seed oil contains approximately 80% PuA and is currently the major natural source of this remarkable fatty acid.
While both PuA and pomegranate seed oil have been used as functional ingredients in foods and cosmetics for some time, their value in pharmaceutical/medical and industrial applications are presently under further exploration.
Unfortunately, the availability of PuA is severely limited by the low yield and unstable supply of pomegranate seeds.
Punicic acidIn addition, efforts to produce PuA in transgenic crops have been limited by a relatively low content of PuA in the resulting seed oil.
The production of PuA in engineered microorganisms with modern fermentation technology is therefore a promising and emerging method with the potential to resolve this predicament.
Punicic acid, we provide a comprehensive review of this unusual fatty acid, covering topics ranging from its natural sources, biosynthesis, extraction and analysis, bioactivity, health benefits, and industrial applications, to recent efforts and future perspectives on the production of PuA in engineered plants and microorganisms.
Punicic acid, member of the family Punicaceae, are one of the most ancient edible fruits.
They are widely grown in Mediterranean regions (including Iran) and India, but sparsely cultivated in the USA, China, Japan and Russia.
Punicic acid edible parts (corresponding to 55 - 60 % of the whole fruit weight, of which 75 - 85 % consists of juice and 25 - 15 % consists of seeds) are mostly consumed fresh; however, they are also commercially available as processed foods and drinks, such as juices, wines, liqueurs, jams and canned fruit.
Punicic acid , the fruit is widely used in therapeutic formulations, cosmetics and food seasonings.
Sugars, vitamins, polysaccharides, polyphenols and minerals are found in the edible parts of pomegranate; however, their content in the fruit may vary according to several factors, such as cultivars, environmental growth conditions, ripening stage, postharvest handling and storage conditions, which, in turn, may affect the quality of the fruit as well as the extent of its beneficial health effects.
Pomegranate seeds are usually waste products from thefruit processing.
Their content may range from 40 – 100gkgfruit weight and varies according to cultivars.
Punicic acid seeds have significant antioxidant capacity and a rich chemical composition (sugars, polyunsaturated fatty acids, vitamins, polysaccharides, polyphenols and minerals).
On, average, pomegranate seeds grown in Brazil, carbohydrate content was found to account for 43.97 %, followed by moisture content 38.30 % and high lipid content 14.06 %.
Given the fact that great quantities of pomegranate seeds are mostly wasted and that they can be processed to produce an attractive amount of a chemically-rich oil, which may be of great interest to the food industry as food or a nutraceutical ingredient.
Thanks to its novelty appeal, good customer acceptance, availability at low prices and rich phytochemical composition, the oil from pomegranate seeds has attracted increasing attention as a functional ingredient.
PSO represents between 12% and 20% of the seed total weight and consists chiefly of conjugated octadecatrienoic fatty acid.
Punicic acid, an isomer of this fatty acid, is found in high amounts in the oil and is synthesized in situ from linoleic acid, present in lower amounts (about 7%) in PSO.
The unique composition of PSO has encouraged specific studies into its health benefits, including weight control, skin repair and positive alterations in plasma lipid profiles in hyperlipidaemic individuals. According to Koba et al., since pomegranate abounds in punicic acid, their seed oil represents a suitable source for the investigation of the physiological roles of this CLnA isomer.
The chemical formula of punicic acid (PA), an omega-5 long chain polyunsaturated fatty acid and a positional and geometric isomer of α-linolenic acid (LnA; C18:3-9c,12c,15c), is C18:3- 9c,11t,13c.
Both chemical structures are represented.
Theoretically, PA features 66 % cis-type double bonds and 33 %trans-type double bonds .
Also, punicic acid is structurally similar to conjugated linoleic acid (CLA) and α-linolenic acid (LnA), which have been reported to have numerous health benefits.
Therefore, conjugated linolenic acids (CLnAs) have also been investigated for their potential beneficial effects in vivo and in vitro.
Plant extracts and nutraceuticals are the most ancient and widespread form of medication employed by the general population.
Phytochemicals, especially antioxidants from vegetables and fruits, have achieved popularity because many epidemiological studies have demonstrated their prophylactic effects against distinct chronic conditions including cancer and cardiovascular diseases.
Throughout the last decade, there has been a significantly increased use of dietary supplements such as vitamins, herbals and medicinal foods in the general population.
Punicic acid pomegranate is a prehistoric, mystical and highly different fruit.
Moreover pomegranate is found in some medicinal systems as a cure for a variety of ailments and has been used for a long time for nutraceutical purposes.
Current researches seem to demonstrate that the most medicinal useful pomegranate components are ellagitannins, anthocyanins, anthocyanidins, flavonoids, estrogenic flavonols and flavones.
Studies on pomegranate’s benefits have risen remarkably in the previous decade.
A PubMed search in Dec 2016 retrieved 1468 studies about pomegranate, 879 of which have been published within the last 5 y.
The number of publications concerning punicic acid (PA) was found to be 68.
Pomegranate seeds contain different components in addition to polyphenols, which may contribute to pomegranate’s useful effects.
Pomegranate seed oil (PSO) contains 12-20% of whole seed mass.
Recently, PSO has received significant dietary attention.
The oil’s possible useful effects have been attributed to its major bioactive constituent, PA, a conjugated linolenic acid (CLA), which constituted 64-83% of PSO.
Conjugated fatty acid (CFA) is the general term of positional and geometric isomers of polyunsaturated fatty acids with conjugated double bonds.
Punicic acid has been reported that CLA exhibited antiinflammatory, antiatherosclerotic, antiobesity, antitumor and antihypertensive effects.
Pomegranate (Punica granatum) is an ancient and adaptable fruit original from Western Asia that belongs to the Punicaceae family.
Punicic acid is cultivated throughout the world, including Middle Eastern, Asian, European, and American countries, mainly in subtropical and tropical areas under variable climatic conditions.
Approximately 50% of the total weight of the fruit corresponds to the peel, which is an important source of phenolic compounds, minerals, and complex polysaccharides.
Meanwhile, the edible part of the pomegranate fruit consists of arils (40%) rich in water, sugars, pectin, and seeds (10%).
Pomegranate seeds contain many components such as polyphenols and fatty acids that contribute to their beneficial effects.
Pomegranate Seed Oil (PSO) represents around 12% and 20% of the total seed weight.
PSO contains 14 fatty acids, the most abundant of which is punicic acid 50–80%, followed by linoleic acid, palmitic acid, stearic acid, oleic acid, linolenic acid, and arachidic acid.
Punicic acid, PSO’s main bioactive component, was shown to achieve a potent anti-oxidative effect that contributes towards its positive effect against a wide arrange of diseases such as osteoporosis, has anti-obesity properties, increases the expression of antioxidant and lipid metabolism-related genes, and modifies the composition and function of high-density lipoprotein.
Punicic acid is an omega-5 isomer of conjugated α-linolenic acid (CLnA) and exhibits structural similarities to conjugated linoleic acid (CLA).
By itself, punicic acid possesses a wide spectrum of biological effects such as anti-inflammatory, anti-diabetic, anti-obesity, anti-proliferative, and anti-carcinogenic properties.
Punicic acid main biological mechanism described for punicic acid involves the modulation of the differential expression of peroxisome proliferator-activated receptors (PPARs), which control the expression of genes involved in cell differentiation and proliferation, regulate enzymes involved in lipids metabolism, and glucose homeostasis.
In addition, Punicic acid are closely related to the activation and production of pro-inflammatory biomarkers.
While the antioxidant and anti-inflammatory properties of punicic acid may provide beneficial effects on the treatment of NDs, the way it interacts in different pathways related to the progression of NDs may give Punicic acid advantages over other anti-oxidative nutraceuticals.
In nature, the most abundant source of punicic acid (PuA) is pomegranate (Punica granatum), with the final amount depending on the fruit genotype.
However, other sources include Momordica balsamina, Ecballium elaterium, Fevillea trilobata, and some species from the Trichosanthes genus, such as T. kirilowii, T. anguina, T. bracteata, T. nervifolia.
Punicic acid, also known as octadecatrienoic acid or trichosanic acid (C18H30O2), possesses a molecular weight of 278.43 g/moL, a melting point of 44–45 °C, and an octanol–water partition coefficient (X LogP) of 6.4.
Moreover, it was reported that punicic acid has a molar refractivity and polarizability value of 89.64 m³/moL and 35.91 ų, respectively.
PA exhibits a pKa value of 4.99 (strongest acidic), as it is able to act as a donator of one hydrogen.
Punicic acid is a conjugated linolenic acid isomer with structural similarities to α-linolenic and linoleic acids.
Among the main described characteristics of punicic acid is its ability to scavenge hydroxyls, metal chelation, and reduce properties.
Biosynthesis of punicic acid begins with the de novo synthesis of fatty acids inside the plant’s plastid, mostly palmitic (16:0), stearic (18:0), and oleic acids.
Fatty acids are conjugated on phosphatidylcholine (PC) to undergo desaturations and conjugations in the position sn2 of PC.
Oleic acid-PC (OA 18:1Δ9cis) is processed into linoleic acid-PC (LA 18:2Δ9cis,12cis), which in turn is transformed into Punicic Acid-PC by fatty acid desaturase (FAD) 2 and fatty acid desaturases group X (FADXs), respectively.
Newly synthetized fatty acids are then converted into acyl-Coenzyme A by the action of Acyl-CoA synthetase to act as acyl donors in triacylglycerol (TAG) biosynthesis inside the endoplasmic reticulum (ER) before being stored in cytoplasmic lipid droplets.
The main challenges of using PSO or punicic acid for health applications are chemical instability and limited water solubility.
Since fatty acids such as punicic acid are molecules highly unsaturated, they are susceptible to degradation due to oxidation, light, or thermal treatments.
Likewise, because punicic acid is poorly soluble in water and only a small fraction can be slowly absorbed by the body, the bioavailability of this molecule is very low and exhibits a rapid metabolism to conjugated linoleic acid (CLA), limiting its use in commercial or therapeutic.
In order to overcome these challenges, researchers have explored different strategies such as the synthesis of precursor molecules and the design of specific delivery systems to protect the active drug.
Modifications on the chemical structure can protect the molecule’s active sites from biological degradation and therefore improve its stability.
Esterification of punicic acid showed an improvement by 30% in the oxidative stability of monodispersed punicic acid compared to its free form.
Likewise, this chemical modification of punicic acid significantly improved its water solubility and bioaccessibility.
On the other hand, encapsulation is the most used technique to protect drugs from environmental and chemical degradation.
In this sense, spray-drying microencapsulation of pomegranate seed oil using succinylated taro starch demonstrated 61% of encapsulation efficiency with an improvement in the oxidation stability and a significant delivery of PSO in the small intestine.
Likewise, PSO nanoemulsions have shown improved stability under stress conditions such as osmotic stress and extreme pH values.
Mizrahi et al. reported that nanoemulsions of pomegranate seed oil exhibited strong neuroprotective effects by reducing lipid oxidation and neuronal loss.
Recent technological advances allowed the development of novel delivery systems, which not only protect the drug but also exhibit an efficient release in the target site, improving the bioavailability and biological activity of this by the modification of the pharmacokinetics parameters.
Improved physical and peroxidation stability of PSO at different temperatures (4 °C and 25 °C) was achieved by the incorporation of beeswax and propolis wax during the fabrication of PSO nanostructured lipid carriers.
After 40 days of storage time, PSO nanostructured lipid carriers at 4 °C showed peroxidation levels significantly lower than at 25 °C.
Likewise, the antioxidant activity of these systems, measured by DPPH free radical-scavenging activity, showed to be stable throughout the storage period regardless of temperature conditions.
Moreover, the combination of PSO with other therapeutic drugs or nutraceuticals was shown to improve the pharmacokinetic parameters and biodistribution profile of the latter.
The biological benefits of PSO and punicic acid also attracted the food industry’s interest to design and offer consumers more healthy products through the enrichment in polyunsaturated acids of the different food matrices.
These approaches can be really useful in the development of food products with an enhanced nutritional quality or even for the development of food supplements that contribute to preserving human health.
Pomegranate (Punica granatum L.) is a fruit cultivated under diverse climatic conditions, being an edible fruit with great adaptability and flexibility around the world.
Punicic acid consumption has been related to health benefits.
Pomegranate seeds are an interesting component of this fruit due to their oil content (up to 50 wt.%), which have been distinguished for their pharmaceutical applications and nutraceutical properties.
The main fatty acid residue identified in the oil is punicic acid (PuA) (≈ 80%, with respect to the total fatty acid content).
130PuA can exert important bioactivities such as anticancer, hypolipidemic, antidiabetes, antiobesity, antioxidant, anti-inflammatory, among others.
One of the most potent sources of PuA is pomegranate seed, a byproduct obtained during the industrialization of this fruit.
In this sense, one of the strengths in PuA research is the revalorization of this agroindustrial residue for the further recovery of such bioactive fatty acids.
On the other hand, new and novel applications for PuA can be developed.
A kind of method of producing high purity punicic acid:
A kind of method of producing high purity punicic acid is to be raw material with the Semen Granati, uses supercritical CO2 Extraction, control extracting pressure 12～40Mpa, 31.1～60 ℃ of extraction temperature, separating pressure 5～12MPa, 20～80 ℃ of separation temperatures obtain granada seed oil; The granada seed oil hydrolysis is obtained mixed fatty acid; Adopt urea adduct method to separate the mixed fatty acid thing and obtain high purity punicic acid.
Punicic acid is simple that the present invention has technology, Trichosanoic acid purity height, the advantage that yield is high.
Pomegranate is a Punicaceae Punica plant, is machaka or dungarunga fruit tree.
Pomegranate is the very high fruit of nutritive value, and its pericarp is a traditional Chinese medicine, and effects such as puckery intestines, hemostasis, expelling parasite are arranged.
Up-to-date studies show that, pomegranate contains abundant VITMAIN B1, B2 and vitamins C and nicotinic acid, potassium and phytoestrogen, and is very useful to HUMAN HEALTH.
External studies show that in recent years, effects such as that granada seed oil and extract thereof have is anti-oxidant preferably, prevent and treat mammary cancer, hypoglycemic, diarrhea.
Analysis revealed to granada seed oil: six kinds of main lipid acid are arranged: Trichosanoic acid, linolenic acid, linolic acid, oleic acid, palmitinic acid, stearic acid etc. in the granada seed oil.
Wherein, Trichosanoic acid is conjugated triene unsaturated fatty acids, accounts for about about 80% in pomegranate oil.
Polyvalent unsaturated fatty acid has anti-curing hyperlipemia, cardiovascular and cerebrovascular diseases, effect such as antitumor, granada seed oil is because of having good oxidization resistance, can resist the destruction of human body inflammation and oxyradical effectively, the additive that is used for the cosmetics of super quality, have simultaneously delay senility, prevention of arterial is atherosis and slow down the effect of canceration process.
Because its edibility (when eating pomegranate, can connect seed and chew clothes) is nontoxic, in medicines and health protection, food, cosmetic industry, have broad application prospects simultaneously.
Punicic acid is a remarkable anti-inflammatory conjugated linoleic acid (cla) that is prized for its therapeutic abilities.
found in pomegranate oil, punicic acid can help calm skin ailments such as eczema, psoriasis, and acne.
while its skin calming abilities are amazing, it is most famous for its efficacy as a skin cancer chemopreventive.
topical application of punicic-rich pomegranate oil has been shown to slow the development of cancerous skin cells.
Taking Pomegranate Seed Oil Under Microscope
Rich in antioxidants like vitamin C, pomegranate seed oil also contains punicic acid, an anti-inflammatory omega-5 fatty acid, not to mention bundles of bioflavonoids. Bioflavonoids, a natural sunscreen, fight free radicals and delay the visible signs of aging by protecting your skin from sun damage.
Altogether, these properties activate your "keratinocytes" (cell structures found in your epidermis or outer layer of skin) so they can better balance your skin's pH levels, improve its elasticity and even out skin tone.
And punicic acid has been proven to protect collagen fibers in the skin, accelerate wound healing and reduce the appearance of scars. The anti-inflammatory property of punicic acid has also effectively addressed skin care ailments such as eczema and psoriasis.
Pomegranate seeds are rich in punicic acid, a ω‐5 fatty acid which renders highly beneficial effects on human health.
However, due to very unstable nature of punicic acid, its quantification becomes difficult.
Pomegranate (Punica granatum) is a perennial herb with its long history and has been the symbol of health, fertility and spirituality.
In addition to being consumed as fresh fruit, pomegranate is consumed as pomegranate juice, syrup, pomegranate syrup and many different product groups.
In particular, pomegranate seeds, which are often produced as waste, are evaluated separately in terms of their fatty acid composition and antioxidant capacity.
The pomegranate (Punica granatum L.) belongs to the Punicaceae family and is one of the oldest known edible fruits.
Punicic acid is accepted as a fruit that is a source of health and recovery in many countries in the world.
Therefore, recently scientific studies have concentrated on pomegranate and pomegranate seed oil.
The objective of this study the dispersion of fatty acids in the seed oil of a type of pomegranate called Hicaznar which is widely grown in Turkey.
Punicic acid has been determined that pomegranate seed oil contains palmitic acid (5.30±0.38%), stearic acid (2.78±0.51%), oleic acid (12.34±2.88%), linoleic acid (13.45±2.01%) and punicic acid (64.65±4.51%) using GC.
Pomegranate seed oil contains a high incidence of punicic acid or omega-5.
Punicic acid type of fatty acid is effective in preventing the formation of acidic cancer cells.
Punicic acid also has antioxidant, antitumor, anti-atherosclerotic and serum lipid-lowering properties.
Punicic acid, also known as 9t,11C,13t-CLN or punicate, belongs to the class of organic compounds known as lineolic acids and derivatives.
Punicic acid are derivatives of lineolic acid.
Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
Based on a literature review a significant number of articles have been published on Punicic acid.
Punicic acid is a conjugated linolenic acid (CLnA) that is found in high amounts in several natural oils, including pomegranate and snake guard seed oils.
CLnAs contain 3 or 4 double bonds (which can be any combination of cis or trans) and 9,11,13- and 8,10,12-octadecatrienoic acid positional isomers.
Punicic acid (PA) is a polyunsaturated fatty acid (18:3 n-5), which is classified as a conjugated linolenic acid.
PA is also referred to as a “super CLnA” whose effect is even more potent than that of an ordinary CLnA.
Punicic acid is found mainly in the seeds of the pomegranate fruit (Punica granatum) and Trichoxanthes kirilowii and some other minor sources.
Punicic acid possesses a wide array of biological properties including antidiabetic, antiobesity, antiproliferative, and anticarcinogenic activity against various forms of cancer.
In spite of this, the PA has not been explored as a nutraceutical or as an ingredient of food products which can be aimed at specific consumer target groups
The Pomegranate fruit has cultivated around the world in subtropical and tropical areas like Arizona, Afghanistan, Iraq, Iran, India, Italy, Turkey, Egypt, California, Chile, and Spain.
2010-11, the region under cultivation for pomegranate production in Pakistan was 12,900 hectares, yielding an annual production of approximately 50,000 tons.
Pomegranate production amounts could reach about 65,000 tons, in which the peels (pericarp, rind, or hull) quantity to about 60% of the pomegranate fruit weight.
One pomegranate contains 1 g of fiber (mostly insoluble), 12% of vitamins B6 and C and potassium per day.
On the opposite hand, it’s noticed that about 500g/kg of the entire fruit weight corresponds to the peel, while the remainder is the edible parts of the pomegranate, consisting of 400g/kg arils and 100g/kg seeds.
Pomegranate is a crucial source of bioactive compounds and different parts of it are utilized in medicine for several centuries and therefore the edible parts used in pharmaceutical world-wide.
Pomegranate comprises of an upscale kind of flavonoids, which contain roughly 0.2 to 1.0% of the natural product.
About 30% of all anthocyanidins found in pomegranate is contained inside the peel.
These flavonoid-rich pomegranate phenolic divisions are obligated for anticancer action.
Pomegranate peel gives more significant returns of phenolics, flavonoids, and proanthocyanidins than the mash.
Flavonoid content was fundamentally more noteworthy inside the strip than the pulp (59 versus 17mg/g), as were proanthocyanidins (11 versus 5mg/g).
Punicic acid is known to be Paradise fruit because of the therapeutic potential and promising nutraceutical features.
Punicic acid prevents many ailments like blood pressure, diabetes, body stress, joint disorders, anemia, diarrhea and cardiovascular disorders.
Punicic acid seeds also as skin are used for the cure of stomach diseases and improve digestion.
Punicic acid (PuA) is a high-value edible conjugated fatty acid with strong bioactivities and has important potential applications in nutraceutical, pharmaceutical, feeding, and oleochemical industries.
Since the production of PuA is severely limited by the fact that its natural source (pomegranate seed oil) is not readily available on a large scale, there is considerable interest in understanding the biosynthesis and accumulation of this plant-based unusual fatty acid in.
Names
Preferred
IUPAC name
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid
Identifiers
CAS Number 544-72-9
CHEBI:8638
ChemSpider :4444570
PubChem CID : 5281126
UNII : VFQ03H211O
CompTox Dashboard (EPA) : DTXSID10897463
Properties
Chemical formula :C18H30O2
Molar mass :278.43 g/mol
Melting point :44 to 45 °C (111 to 113 °F; 317 to 318 K)
Chemical Formula C18H30O2
Average Molecular Weight 278.4296
Monoisotopic Molecular Weight 278.224580204
IUPAC Name (9E,11Z,13E)-octadeca-9,11,13-trienoic acid
Traditional Name 9t,11c,13t-linolenic acid
CAS Registry Number 544-72-9
SMILES
CCCCC=CC=C/C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7-,10-9+
InChI Key CUXYLFPMQMFGPL-MRZTUZPCSA-N
Synonyms
(9Z,11E,13Z)-9,11,13-Octadecatrienoic acid [ACD/IUPAC Name]
(9Z,11E,13Z)-9,11,13-Octadecatriensäure [German] [ACD/IUPAC Name]
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid
(Z,E,Z)-9,11,13-Octadecatrienoic Acid
(Z,E,Z)-octadeca-9,11,13-trienoic acid
544-72-9 [RN]
9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID
9,11,13-Octadecatrienoic acid, (9Z,11E,13Z)- [ACD/Index Name]
9-cis,11-trans,13-cis-octadecatrienoic acid
9Z,11E,13Z-octadecatrienoic acid
Acide (9Z,11E,13Z)-9,11,13-octadécatriénoïque [French] [ACD/IUPAC Name]
Punicic acid [Wiki]
trichosanic acid
VFQ03H211O
(9Z,11E,13Z)-octadecatrienoic acid
1726550
24022-76-2 [RN]
5534-09-8 [RN]
9(Z),11(E),13(Z)-Octadecatrienoic Acid|9Z,11E,13Z-octadecatrienoic acid
9c,11t,13c-18:3
9c,11t,13c-linolenic acid
9cis,11trans,13cis-octadecatrienoic acid
C18:3 n-5 cis, 7 trans, 9 cis
CHEBI:8638
Cis,trans,cis-octadeca-9,11,13-trienoic acid
cis-9, trans-11, cis-13-octadecatrienoic acid
cis-9,trans-11,cis-13-Octadecatrienoic acid
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8638
octadeca-9c,11t,13c-trienoic acid
Octadeca-9c,11t,13c-triensaeure
UNII:VFQ03H211O
UNII-VFQ03H211O
