CLOVE
CLOVE
Eugenol composes 72–90% of the essential oil extracted from cloves and is the compound most responsible for clove aroma.
Constituents of clove oil include:
acetyl eugenol
beta-caryophyllene
vanillin
crategolic acid
tannins such as bicornin
gallotannic acid
methyl salicylate (painkiller)
flavonoids eugenin, kaempferol, rhamnetin, and eugenitin
triterpenoids such as oleanolic acid, stigmasterol, and campesterol
several sesquiterpenes.
- - -
The individual constituents of clove oil:
Acetyl eugenol
Chemical formula: C10H12O2
Eugenol is toxic in relatively small quantities; for example, a dose of 5–10 ml has been reported as being a near fatal dose for a two-year-old child.
Eugenol is hepatotoxic, meaning it may cause damage to the liver. Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhoea, nausea, unconsciousness, dizziness, or rapid heartbeat. According to a published 1993 report, a 2-year-old boy nearly died after taking between 5 and 10 ml.
Eugenol is used in perfumes, flavorings, and essential oils. It is also used as a local antiseptic and anaesthetic.[7][8] Eugenol can be combined with zinc oxide to form zinc oxide eugenol which has restorative and prosthodontic applications in dentistry. For example, zinc oxide eugenol is used for root canal sealing.[9]
Attempts have been made to develop eugenol derivatives as intravenous anesthetics, as an alternative to propanidid which produces unacceptable side effects around the site of injection in many patients.[10]
It is also used in manufacturing stabilizers and antioxidants for plastics and rubbers.[citation needed]
It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[11] It also attracts female cucumber beetle.[12] It was recently discovered that eugenol and isoeugenol, floral volatile scent compounds, are catalyzed by a single type of enzyme in the genus Gymnadenia and the gene encoding for this enzyme is the first functionally characterized gene in these species so far.[13]
Clove oil is growing in popularity as an anaesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.[14][15] Where readily available, it presents a humane method to euthanise sick and diseased fish either by direct overdose or to induce sleep before an overdose of eugenol.[16]
- - -
beta-caryophyllene (from clove oil)
Chemical formula: C15H24
Caryophyllene /ˌkærioʊfɪˈliːn/, or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves),[3] the essential oil of Cannabis sativa, rosemary,[4] and hops.[5] It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.[6]
Caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper
- - -
vanillin (from clove oil)
Chemical formula: C8H8O3
Vanillin is a phenolic aldehyde, which is an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring agent in foods, beverages, and pharmaceuticals.
Vanillin and ethylvanillin are used by the food industry; ethylvanillin is more expensive, but has a stronger note. It differs from vanillin by having an ethoxy group (–O–CH2CH3) instead of a methoxy group (–O–CH3).
Natural "vanilla extract" is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol (4-allyl-2-methoxyphenol). Today, artificial vanillin is made either from guaiacol or lignin.
Vanillin can trigger allergic reactions, as well as migraine headaches in a small fraction of the people who experience migraines.
- - -
crategolic acid (also called maslinic acid) (from clove oil)
Chemical formula: C30H48O4
Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.
In vitro study shows that maslinic acid inhibits serine proteases, key enzymes necessary for the spread of HIV within an individual's body. It also has in vitro antiproliferative effects on colon cancer cells. Maslinic acid increases EAAT2 (GLT-1) glutamate reuptake and may reduce glutamatergic toxicity in rats.
- - -
bicornin (from clove oil)
Chemical formula: C48H32O30
Bicornin is an ellagitannin found in the Myrtales Trapa bicornis (water caltrop)[1] and Syzygium aromaticum (clove).[2]
The molecule contains a luteic acid group
- - -
gallotannic acid (from clove oil)
Chemical formula: C76H52O46
Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian Sumac leaves (Rhus coriaria).
Tannic acid could cause potential health hazards such as damage to the eye, skin, respiratory tract, and gastrointestinal tract. It may cause irritation, redness, pain, blurred vision, and possible eye damage. When tannic acid is absorbed through the skin in harmful amounts, it may cause irritation, redness, and pain. Nausea, vomiting and diarrhoea are symptoms of tannic acid ingestion and prolonged exposure may cause liver damage. Upon inhalation, tannic acid may cause respiratory tract irritation.
- - -
methyl salicylate (from clove oil)
Chemical formula: C8H8O3
Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C6H4(OH)(CO2CH3). It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet odor. It is produced by many species of plants, particularly wintergreens. It is also synthetically produced, used as a fragrance, in foods and beverages, and in liniments.
Methyl salicylate is potentially deadly, especially in the pediatric population. A single teaspoon (5 ml) of methyl salicylate contains approximately 6 g of salicylate,[21] which is equivalent to almost twenty 300 mg aspirin tablets (5 mL × 1.174 g/mL = 5.87 g). Toxic ingestions of salicylates typically occur with doses of approximately 150 mg/kg body weight. This can be achieved with 1 ml of oil of wintergreen, which equates to 140 mg/kg of salicylates for a 10 kg child (22 lbs).[22] The lowest published lethal dose is 101 mg/kg body weight in adult humans,[23] (or 7.07 grams for a 70 kg adult). It has proven fatal to small children in doses as small as 4 ml.[12] A seventeen-year-old cross-country runner at Notre Dame Academy on Staten Island died in April 2007 after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products.[24]
Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children. Salicylate, the major metabolite of methyl salicylate, may be quantitated in blood, plasma or serum to confirm a diagnosis of poisoning in hospitalized patients or to assist in an autopsy.
- - -
eugenin (from clove oil)
Chemical formula: C11H10)4
Eugenin is a chromone derivative, a phenolic compound found in cloves. It is also one of the compounds responsible for bitterness in carrots.
- - -
kaempferol (from clove oil)
Chemical formula: C15H10O6
Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol acts as an antioxidant by reducing oxidative stress. Many studies suggest that consuming kaempferol may reduce the risk of various cancers, and it is currently under consideration as a possible cancer treatment. It is named for 17th-century German naturalist Engelbert Kaempfer.
In vitro studies along with some animal testing has demonstrated the wide range of potential anti-cancer properties of kaempferol. It has been shown in malignant cancer cells to interrupt cell growth, limit angiogenesis, induce apoptosis, and to reduce their available energy and ability to metastasize. Kaempferol has also been shown to reduce MMP-3 protein activity inferring potential ability to reduce metastasis.
Diabetes
A correlation was found between increased levels of kaempferol in the diet and a reduced relative risk of type 2 diabetes in a cohort study in 2005. Additionally, 6-methoxykaempferol-3-O-β-D-robinobioside was shown to have significant inhibitory activity of aldose reductase, which plays an important role in diabetic complications.
Cardiovascular disorders
A cohort study in men showed that consumption of flavonoid containing food decreased the risk of mortality from coronary heart disease. Another cohort study showed that high intake of tea is inversely associated with myocardial infarction.[2] Kaempferol has also been shown to have a protective effect on the apoptosis induced by the ischemia/reperfusion of cardiac cells. Due to this, it has a promising pharmacological role in preventing cardiovascular disease.
Anti-bacterial activity
In a four-week study, kaempferol and its glycosides decreased the number of Helicobacter pylori colonies in gerbils. It also has been shown to work synergistically with antibiotics.
Anti-viral activity
Kaempferol has been shown to inhibit or decrease the activity of enzymes that partake in viral infection such as reverse transcriptase, viral proteases and neuraminidase.
Antioxidant effects
Kaempferol has been shown to have an array of antioxidant effects in vitro and in vivo. At low concentrations, its acts as a super-oxide scavenger, specifically against the highly reactive hydroxyl radical and peroxynitrite species. At high concentrations it increases the activity or expression of antioxidant enzymes such as superoxide dismutase, catalase, and heme oxygenase-1. Kaempferol can prevent the oxidation of low-density lipid proteins indicating a potential protective role in atherosclerosis.
- - -
rhamnetin (from clove oil)
Chemical formula: C16H12O7
Rhamnetin is an O-methylated flavonol, a type of chemical compound. It can be isolated from cloves.
The structure of the molecule was discovered by Austrian chemist Josef Herzig (1853–1924).
- - -
eugenitin (from clove oil)
Chemical formula: C12H12O4
Eugenitin is a chromone derivative, a type of phenolic compound found in cloves. It has also been isolated from the fungal species Cylindrocarpon sp. C.M.I. 127996.
- - -
oleanolic acid (from clove oil)
Chemical formula: C30H48O3
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.
Oleanolic acid is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.
Oleanolic acid was found to exhibit weak anti-HIV and weak anti-HCV activities in vitro, but more potent synthetic analogs are being investigated as potential drugs.
An extremely potent synthetic triterpenoid analog of oleanolic acid was found in 2005, that is a powerful inhibitor of cellular inflammatory processes. They work by the induction by IFN-γ of inducible nitric oxide synthase (iNOS) and of cyclooxygenase 2 in mouse macrophages. They are extremely potent inducers of the phase 2 response (e.g., elevation of NADH-quinone oxidoreductase and heme oxygenase 1), which is a major protector of cells against oxidative and electrophile stress.
A 2002 study in Wistar rats found that oleanolic acid reduced sperm quality and motility, causing infertility. After withdrawing exposure, male rats regained fertility and successfully impregnated female rats.
- - -
stigmasterol (from clove oil)
Chemical formula: C29H48O
Stigmasterol (also known as Wulzen anti-stiffness factor) is a plant sterol, or phytosterol.
Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast, and colon cancers. Studies have also indicated that a diet high in phytoesterols may inhibit the absorption of cholesterol and lower serum cholesterol levels by competing for intestinal absorption. Studies with laboratory animals fed stigmasterol found that both cholesterol and sitosterol absorption decreased 23% and 30%, respectively, over a 6-week period. It also possesses potent antioxidant, hypoglycemic and thyroid inhibiting properties.
- - -
campesterol (from clove oil)
Chemical formula: C28H48O
Campesterol is a phytosterol whose chemical structure is similar to that of cholesterol.
Being a steroid, campesterol is a precursor of anabolic steroid boldenone. Boldenone undecylenate is commonly used in veterinary medicine to induce growth in cattle, but it is also one of the most commonly abused anabolic steroids in sports. This led to suspicion that some athletes testing positive on boldenone undecylenate did not actually abuse the hormone itself, but consumed food rich in campesterol or similar phytosteroids.
Excessive use of plant sterols has been associated with an increased risk of cardiovascular disease,[10] and genetic conditions that cause extremely elevated levels of some phytosterols, such as sitosterol, are associated with higher risks of cardiovascular disease. However, this is an active area of debate, and no data suggest that modestly elevated levels of campesterol have a negative cardiac impact.[18]
Rare cases of hemolytic anemia have been reported.
- - -
sesquiterpenes (from clove oil)
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.
Sesquiterpenes are found naturally in plants and insects, as semiochemicals, e.g. defensive agents or pheromones.
Comments
Post a Comment