Brief Introduction

Synonyms---

Lycopene, ( all-trans )–Lycopene

Chemical Name:ψ,ψ-carotene
Molecular Formula: C40H56

Mol. Wt.: 536.88

Molecular Structure:

The tomato (Solanum lycopersicum, syn. Lycopersicon lycopersicum & Lycopersicon esculentum), native to South America, is a herbaceous, usually sprawling plant in the Solanaceae or nightshade family that is typically cultivated for the purpose of harvesting its fruit for human consumption. Savory in flavor, the fruit of most varieties ripens to a distinctive red color. Tomato plants typically reach to 1–3 metres (3–10 ft) in height, and have a weak, woody stem that often vines over other plants. The leaves are 10–25 centimetres (4–10 in) long, odd pinnate, with 5–9 leaflets on petioles, each leaflet up to 8 centimetres (3 in) long, with a serrated margin; both the stem and leaves are densely glandular-hairy. The flowers are 1–2 centimetres (0.4–0.8 in) across, yellow, with five pointed lobes on the corolla; they are borne in a cyme of 3–12 together. It is a perennial, often grown outdoors in temperate climates as an annual.

Though it is botanically a berry, a subset of fruit, the tomato is nutritionally categorized as a vegetable. Since "vegetable" is not a botanical term, there is no contradiction in a plant part being a fruit botanically while still being considered a vegetable.

Tomatoes are used extensively in Mediterranean cuisine, especially Italian and Middle Eastern cuisines. The tomato is acidic; this acidity makes tomatoes especially easy to preserve in home canning whole, in pieces, as tomato sauce, or paste. Tomato juice is often canned and sold as a beverage; Unripe green tomatoes can also be breaded and fried, used to make salsa, or pickled. The fruit is also preserved by drying, often by sun, and sold either in bags or in jars in oil.

Tomatoes are now eaten freely throughout the world, and their consumption is believed to benefit the heart among other things. They contain lycopene, one of the most powerful natural antioxidants. In some studies lycopene, especially in cooked tomatoes, has been found to help prevent prostate cancer but other research contradicts this claim. Lycopene has also been shown to improve the skin's ability to protect against harmful UV rays. Natural genetic variation in tomatoes and their wild relatives has given a genetic treasure trove of genes that produce lycopene, carotene, anthocyanin, and other antioxidants. Tomato varieties are available with double the normal vitamin C (Doublerich), 40 times normal vitamin A (97L97), high levels of anthocyanin (P20 Blue), and two to four times the normal amount of lycopene (numerous available cultivars with the high crimson gene).

Tomato consumption has been associated with decreased risk of breast cancer, head and neck cancers and might be strongly protective against neurodegenerative diseases.

Lycopeneis a bright red carotene and carotenoid pigment and phytochemical found in tomatoes and other red fruits & vegetables, such as,GAC, red carrots, watermelons and papayas (but not strawberries or cherries). Although lycopene is chemically a carotene, it has no vitamin A activity.

In plants, algae, and other photosynthetic organisms, lycopene is an important intermediate in the biosynthesis of many carotenoids, including beta carotene, responsible for yellow, orange or red pigmentation, photosynthesis, and photo-protection. Structurally, it is a tetraterpene assembled from eight isoprene units, composed entirely of carbon and hydrogen, and is insoluble in water. Lycopene's eleven conjugated double bonds give it its deep red color and are responsible for its antioxidant activity. Due to its strong color and non-toxicity, lycopene is a useful food coloring.

Lycopene is not an essential nutrient for humans, but is commonly found in the diet, mainly from dishes prepared with tomato sauce. When absorbed from the stomach, lycopene is transported in the blood by various lipoproteins and accumulates in the liver, adrenal glands, and testes.

Because preliminary research has shown an inverse correlation between consumption of tomatoes and cancer risk, lycopene has been considered a potential agent for prevention of some types of cancers, particularly prostate cancer. However, this area of research and the relationship with prostate cancer have been deemed insufficient of evidence for health claim approval by the US Food and Drug Administration.

Dietary sources:Fruits and vegetables that are high in lycopene include gac, tomatoes, watermelon, pink grapefruit, pink guava, papaya, red bell pepper, seabuckthorn, wolfberry (goji, a berry relative of tomato), and rosehip. Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable, up to 70 times more than tomatoes for example, due to gac's rarity outside its native region of SE Asia, tomatoes and tomato based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people. The lycopene content of tomatoes depends on species and increases as the fruit ripens.

Unlike other fruits and vegetables, where nutritional content such as vitamin C is diminished upon cooking, processing of tomatoes increases the concentration of bioavailable lycopene. Lycopene in tomato paste is four times more bioavailable than in fresh tomatoes. For this reason, tomato sauce is a preferable source as opposed to raw tomatoes.

While most green leafy vegetables and other sources of lycopene are low in fats and oils, lycopene is insoluble in water and is tightly bound to vegetable fiber. Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain the highest concentrations of bioavailable lycopene from tomato based sources.

Cooking and crushing tomatoes (as in the canning process) and serving in oil-rich dishes (such as spaghetti sauce or pizza) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac is a notable exception containing high concentrations of lycopene and also saturated and unsaturated fatty acids.

Lycopene may be obtained from vegetables and fruits such as the tomato, but another source of lycopene is the fungus Blakeslea trispora. Gac is a promising commercial source of lycopene for the purposes of extraction and purification.

The cis-lycopene from some varieties of tomato is more bioavailable.

The Tomato Extract (Lycopene: E number 207-949-1) used as a food additive, is derived from the fruits of the plant Solanum lycopersicum L..

^FOD025C The Global Market for Carotenoids, BCC Research

 Benefits

• Most Powerful Natural Anti-oxidants for free radicals quencher

• Anti-Cancer Properties (Prevent Prostate Cancer, Prevent Breast Cancer, Prevent Head and Neck Cancers, Prevent Lung, Stomach

• Protect Lymphocytes from NO2 Damage

• Improve the skin’s ability to protect against harmful UV rays

• Strongly protective against neurodegenerative diseases

• Benefit the heart, cardiovscular

• Improve osteoporosis

• Improve male infertility

•Improve diabets

• Use as cosmetics materials

Mechanism

Structure and physical properties

Lycopene is a symmetrical tetraterpene assembled from 8 isoprene units. It is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also a carotene. Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. In its natural, all-trans form, the molecule is long and straight, constrained by its system of eleven conjugated double bonds. Each double bond in this extended π electron system reduces the energy required for electrons to transition to higher energy states, allowing the molecule to absorb visible light of progressively longer wavelengths. Lycopene absorbs all but the longest wavelengths of visible light, so it appears red.

Plants and photosynthetic bacteria naturally produce all-trans lycopene, but a total of 72 geometric isomers of the molecule are sterically possible. When exposed to light or heat, lycopene can undergo isomerization to any of a number of these cis-isomers, which have a bent rather than linear shape. Different isomeres were shown to have different stabilities due to their molecular energy (highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest). In the human bloodstream, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.

Lycopene is insoluble in water, and can be dissolved only in organic solvents and oils. Because of its non-polarity, lycopene in food preparations will stain any sufficiently porous material, including most plastics. While a tomato stain can be fairly easily removed from fabric (provided the stain is fresh), lycopene diffuses into plastic, making it impossible to remove with hot water or detergent. If lycopene is oxidized (for example, by reacting with bleaches or acids), the double bonds between the carbon atoms will be broken; cleaving the molecule, breaking the conjugated double bond system, and eliminating the chromophore.

Role in photosynthesis

Carotenoids like lycopene are important pigments found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae. They are responsible for the bright colors of fruits and vegetables, perform various functions in photosynthesis, and protect photosynthetic organisms from excessive light damage. Lycopene is a key intermediate in the biosynthesis of many important carotenoids, such as beta-carotene, and xanthophylls.

Biosynthesis

The biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved. Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give the twenty carbon geranylgeranyl pyrophosphate. Two molecules of this product are then condensed in a tail-to-tail configuration to give the forty carbon phytoene, the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta carotene, which can then be transformed into a wide variety of xanthophylls.

Pharmacokinetics

After ingestion, lycopene is incorporated into lipid micelles in the small intestine. These micelles are formed from dietary fats and bile acids, and help to solubilize the hydrophobic lycopene and allow it to permeate the intestinal mucosal cells by a passive transport mechanism. Little is known about the liver metabolism of lycopene, but like other carotenoids, lycopene is incorporated into chylomicrons and released into the lymphatic system. In blood plasma, lycopene is eventually distributed into the very low and low density lipoprotein fractions. Lycopene is mainly distributed to fatty tissues and organs such as the adrenal glands, liver, and testes.

Antioxidant properties and potential health benefits

Lycopene may be the most powerful carotenoid quencher of singlet oxygen, being 100 times more efficient in test tube studies of singlet-oxygen quenching action than vitamin E, which in turn has 125 times the quenching action of glutathione (water soluble). Singlet oxygen produced during exposure to ultraviolet light is a primary cause of skin aging.

Given its antioxidant properties, substantial scientific and clinical research has been devoted to a possible correlation between lycopene consumption and general health. Early research suggested some amelioration of cardiovascular disease, cancer, diabetes, osteoporosis, and even male infertility.

There have been several studies produced that analyze the anti-cancer properties of lycopene, although research has been primary inconclusive. Evidence for lycopene’s benefit was strongest for cancers of the lung, stomach, and prostrate gland. Lycopene is not modified to vitamin A in the body so can be accessible for other benefits such as antioxidation. The absence of the beta-ionone ring structure for lycopene increases its antioxidant action. Lycopene is also the most efficient oxygen and free radicals quencher and is the prime carotenoid in plasma and other tissues. Lycopene is also found in lung tissue and is valuable in protecting lymphocytes from NO2 damage found in lung cancer. Lycopene also may help decrease the impact of oxidative load from pylori infections in the stomach. The tomato-derived carotenoid lycopene may reduce risk of cancer by activating special cancer preventive enzymes such as phase II detoxification enzymes, which remove harmful carcinogens from cells and the body. In one study of lycopene as a inhibitor of human cancer cell proliferation, it was found that unlike cancer cells, human fibroblasts were less sensitive to lycopene, and the cells gradually escaped growth inhibition over time. In addition to its inhibitory effect on basal endometrial cancer cell proliferation, lycopene also was found to suppress insulin-like growth factor-I-stimulated growth. Insulin-like growth factors are major autocrine/paracrine regulators of mammary and endometrial cancer cell growth. Therefore, lycopene interference in this major autocrine/paracrine system may open new avenues for research on the role of lycopene in the regulation of endometrial cancer and other tumors. In different studies however, lycopene was even found to have an inhibitory effect on cataract development and several different kinds of cancer cells including breast and endometrial cancer cells, prostrate carcinoma cells, and colon cancer cells.

The related carotenoid antioxidant, beta-carotene, has been shown to increase the number of prostate cancer cases in a subset of patients, although this area of research remains controversial and ongoing.

Safety

Lycopene is safe. Itis non-toxic and is commonly found in the diet, but cases of excessive carotenoid intake have been reported. In a middle aged woman who had prolonged and excessive consumption of tomato juice, her skin and liver were colored orange-yellow and she had elevated levels of lycopene in her blood. After three weeks on a lycopene-free diet her skin color returned to normal. This discoloration of the skin is known as lycopenodermia and is non-toxic.

Dosage

• Norecommended daily allowance currently exists for Lycopene as for other nutrients, positive effects have been seen at dietary intake levels of 50-100 mg/day.

• Consult physicians for different condition specifics.

GNI’s Tomato Extract (Lycopene) Features and Benefits:

Tomato Extract (Lycopene) is one of GNI's important products, with many advantages as list in the following, produced as our patent-pending process and know-how technology from Solanum lycopersicum L. fruit.

• High purity: over 90%

• NO solvent - residual free

• Pesticide-free

• Crystalline Oleoresin Liquid or Dark Red Powder in appearance

• High anti-bacteria, and longer shelf life

Product Specifications:

1%, 3%, 5%, 6%, 20%, 90% Lycopene HPLC (Powder or Oleoresin Liquid)

10:1, 20:1