Luteic Acid
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Luteic Acid
Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of ''Terminalia chebula'' and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, abstract References

Aromatic acids Benzochromenes Coumarins Ellagitannins Isocoumarins Pyrogallols Biphenyls {{aromatic-stub ...
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Natural Phenol
In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants. Classification Various classification schemes can be applied. A commonly used scheme is based on the number of carbons and was devised by Jeffrey Harborne and Simmonds in 1964 and published in 1980: C6-C7-C6 Diarylheptanoids are not included in this Harborne classification. They can also be classified on the basis of their number of phenol groups. They can therefore be called ''simple phenols'' or ...
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Fruit
In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering. Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in particular have long propagated using the movements of humans and animals in a symbiotic relationship that is the means for seed dispersal for the one group and nutrition for the other; in fact, humans and many animals have become dependent on fruits as a source of food. Consequently, fruits account for a substantial fraction of the world's agricultural output, and some (such as the apple and the pomegranate) have acquired extensive cultural and symbolic meanings. In common language usage, "fruit" normally means the seed-associated fleshy structures (or produce) of plants that typically are sweet or sour and edible in the raw state, such as apples, bananas, grapes, lemons, oranges, and strawberries. In botanical usage, the term "fruit" also i ...
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Maximilian Nierenstein
Maximilian Nierenstein (also known as Moses Max Nierenstein or Max Nierenstein; 1877–1946) was a professor of biochemistry at the University of Bristol. He is known for the Nierenstein reaction, an organic reaction describing the conversion of an acid chloride into an haloketone with diazomethane. In 1912, Polish biochemist Casimir Funk isolated a complex of micronutrients and proposed the complex be named "vitamine" (a portmanteau of "vital amine"), a name reportedly suggested by friend Max Nierenstein. He also studied natural phenols and tannins found in different plant species. He showed in 1945 that luteic acid, a molecule present in the myrobalanitannin, a tannin found in the fruit of ''Terminalia chebula'', is an intermediary compound in the synthesis of ellagic acid. Working with Arthur George Perkin, he prepared ellagic acid from algarobilla and certain other fruits in 1905. He suggested its formation from galloyl-glycine by ''Penicillium'' in 1915. Tannase is an enz ...
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Terminalia Chebula
''Terminalia chebula'', commonly known as black- or chebulic myrobalan, is a species of ''Terminalia'', native to South Asia from India and Nepal east to southwest China (Yunnan), and south to Sri Lanka, Malaysia, and Vietnam.Flora of China''Terminalia chebula''/ref> In India, it is known as "Harad" in Hindi and Urdu, "Kadukkai" in Tamil, "Hirada" in Marathi, "Hilikha" in Assamese and "Horitoky" in Bengali. Taxonomy Swedish naturalist Anders Jahan Retzius described the species. Many varieties are known, such as: *''T. c.'' var. ''chebula'' – leaves and shoots hairless, or only hairy when very young *''T. c.'' var. ''tomentella'' – leaves and shoots silvery to orange hairy Description ''Terminalia chebula'' is a medium to large deciduous tree growing to tall, with a trunk up to in diameter. The leaves are alternate to subopposite in arrangement, oval, long and broad with a petiole. They have an acute tip, cordate at the base, margins entire, glabrous above with a yel ...
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Ellagic Acid
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid. Name The name comes from the French term ''acide ellagique'', from the word ''galle'' spelled backwards because it can be obtained from ''noix de galle'' ( galls), and to distinguish it from ''acide gallique'' (gallic acid). The molecule structure resembles to that of two gallic acid molecules being assembled "head to tail" and bound together by a C–C bond (as in biphenyl, or in diphenic acid) and two lactone links (cyclic carboxylic esters). Metabolism Biosynthesis Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. Biodegradation Urolithins are gut flora human metabolites of dietary ellagic acid derivatives. Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolintins. History Ellagic acid was first discovered by ...
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Hexahydroxydiphenic Acid
Hexahydroxydiphenic acid is an organic compound with the formula HO)3C6HCO2Hsub>2. It is the oxidatively coupled derivative of gallic acid It is a white solid, although samples are typically brown owing to oxidation. left, 142px, Ellagic acid. Hexahydroxydiphenic acid is a component of some ellagitannins, such as casuarictin. Luteic acid is the monolactone and ellagic acid is the dilactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ... of hexahydroxydiphenic acid. See also * Diphenic acid References Ellagitannins Pyrogallols Biphenyls Hydroxybenzoic acids {{phenol-stub ...
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Alnusiin
Alnusiin is an ellagitannin found in '' Alnus sieboldiana''.Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, abstract The molecules of gallic acid, luteic acid and hexahydroxydiphenic acid are present in the structure of alnusiin, bound to a glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ... residue. References Ellagitannins {{aromatic-stub ...
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Bicornin
Bicornin is an ellagitannin found in the Myrtales ''Trapa bicornis'' (water caltrop) and '' Syzygium aromaticum'' (clove). The molecule contains a luteic acid Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of ''Terminalia ch ... group.Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, abstract References External links Ellagitannins {{aromatic-stub ...
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Aromatic Acids
In chemistry, aromaticity is a chemical property of cyclic (ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-benz ...
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Coumarins
Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. By inhibiting synthesis of vitamin K, a related compound is used as the prescription drug warfarin – an anticoagulant – to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism. Etymology Coumarin is derived from ''coumarou'', the French word for the tonka bean. The word ''tonka'' for the tonka bean is taken from the Galibi (Carib) tongue spoken by natives of French Guia ...
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