# Opine > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Opine > Markdown URL: https://mediated.wiki/source/Opine.md > Source: https://en.wikipedia.org/wiki/Opine > Source revision: 1338517077 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{Short description|Low molecular weight compound}} {{Wiktionary}} {{for|the verb meaning to express an opinion|Opinion}} '''Opines''' are low molecular weight compounds found in plant [crown gall](/source/Crown_Gall) tumors or [hairy root tumors](/source/Hairy_root_culture) produced by pathogenic bacteria of the genus ''[Agrobacterium](/source/Agrobacterium)'' and ''[Rhizobium](/source/Rhizobium)''.{{cite journal | title = Diversity of opines and opine-catabolizing bacteria isolated from naturally occurring crown gall tumors |author1=Moore, Larry W. |author2=Chilton, William Scott |author3=Canfield, Marilyn L. | journal = Applied and Environmental Microbiology | year = 1997 | volume = 63 | issue = 1 | pages = 201–207|doi=10.1128/AEM.63.1.201-207.1997 |pmid=16535484 |pmc=1389099 |bibcode=1997ApEnM..63..201M }} Opine biosynthesis is catalyzed by specific enzymes encoded by genes contained in a small segment of [DNA](/source/DNA) (known as the T-DNA, for 'transfer DNA'), which is part of the [Ti plasmid](/source/Ti_plasmid) (in ''Agrobacterium'') or [Ri plasmid](/source/Ri_plasmid) (in ''Rhizobium''), inserted by the bacterium into the plant [genome](/source/genome). The opines are used by the bacterium as an important energy, [carbon](/source/carbon) and [nitrogen](/source/nitrogen) source. Each strain of ''[Agrobacterium](/source/Agrobacterium)'' and ''[Rhizobium](/source/Rhizobium)'' induces and catabolizes a specific set of opines, this set typifying the [Ti plasmid](/source/Ti_plasmid) and [Ri plasmid](/source/Ri_plasmid). There are some 30 different opines described so far. thumb|none|600px|General overview of opine-synthesis ==Chemical structure== Chemically, opines fall into two major structural classes: [[File:nopaline.svg|thumb|right|Chemical structure of [nopaline](/source/nopaline)]] [[File:octopine structure.svg|thumb|right|Chemical structure of [octopine](/source/octopine)]] 1. The vast majority are secondary [amine](/source/amine) derivatives resulting from the reduction of the [imine](/source/imine) formed by condensation of an [amino acid](/source/amino_acid), either with a [keto acid](/source/keto_acid) or a [sugar](/source/sugar). The first subcategory includes the opines from the [nopaline](/source/nopaline) and [octopine](/source/octopine) families. The nopaline family (nopaline, nopalinic acid, leucinopine, glutaminopine, succinamopine) is formed when [alpha-ketoglutarate](/source/alpha-ketoglutarate) serves as the keto substrate in the condensation reaction. The octopine family (octopine, octopinic acid, lysopine, histopine) is formed when [pyruvate](/source/pyruvate) is involved in the condensation reaction. [[File:mannopine.svg|thumb|right|Chemical structure of [mannopine](/source/mannopine)]] The second subcategory includes the mannityl family (mannopine, mannopinic acid, agropine, agropinic acid) and the chrysopine family (deoxy-fructosyl glutamate, deoxy-fructosyl glutamine, deoxy-fructosyl oxoproline and chrysopine) formed by the condensation of an amino-acid with [mannose](/source/mannose). 2. Agrocinopines form a small, separate class of opines. Chemically they are sugar-phosphodiesters. For example, agrocinopine A is a phosphodiester of [sucrose](/source/sucrose) and L-[arabinose](/source/arabinose). ==Nomenclature== The name ''opine'' comes from ''octopine'', the first opine discovered in 1927, not in crown galls, but in [octopus](/source/octopus) muscle. ''Nopaline'' comes from the identification of this molecule in tumors that appeared on "nopal", the Spanish and French names of ''[Opuntia](/source/Opuntia)'' spp. cactus. According to ''[Oxford English Dictionary](/source/Oxford_English_Dictionary)'', the word ''opine'' was first used in print in 1977. Usually, the name of newly discovered opines has the ending "-opine". Exceptions are nopaline and strombine. On the other hand, not all molecule names ending in "-opine" are opines. For example, [atropine](/source/atropine), [stylopine](/source/stylopine), [europine](/source/europine), and [lycopine](/source/lycopine) belong to different classes of molecules. ==Other sources of opines== Opines and opine-like substances are not restricted to crown galls tumors. The very first opine discovered, octopine, was initially isolated from octopus muscle. Similar derivatives have been isolated from muscle tissue of certain marine invertebrates: alanopine, strombine, and tauropine. Opines like acetopine and nopaline can also be formed in normal [callus](/source/callus_(cell_biology)) and plant tissue as a result of [arginine](/source/arginine) metabolism. [Saccharopine](/source/Saccharopine) is an intermediate in the metabolism of amino acid [lysine](/source/lysine) and occurs in [fungi](/source/fungus), higher plants and mammals, including humans. The poisonous mushroom ''[Clitocybe acromelalga](/source/Clitocybe_acromelalga)'' is a source of four opine type amino acids: valinopine, epileucinopine, isoleucinopine and phenylalaninopine. ==Biosynthesis== The enzyme [opine dehydrogenase](/source/opine_dehydrogenase) catalyses reactions that make opines by adding a molecule of pyruvic acid or other [keto acid](/source/keto_acid)s to L-amino acids. This includes making derivatives of [L-methionine](/source/Methionine), [L-isoleucine](/source/Isoleucine), [L-valine](/source/Valine), and [L-phenylalanine](/source/Phenylalanine).{{cite journal | vauthors = Kato Y, Yamada H, Asano Y | date = 1996 | title = Stereoselective synthesis of opine-type secondary amine carboxylic acids by a new enzyme opine dehydrogenase. Use of recombinant enzymes | journal = J. Mol. Catal., B Enzym. | volume = 1 | pages = 151–160 | doi = 10.1016/1381-1177(95)00011-9 | issue = 3–6 }} A typical example is the reaction to give (2''S'')-2-[(''R'')-1-carboxyethylamino]pentanoic acid (1):{{KEGG enzyme|1.5.1.28}}{{cite journal | vauthors = Asano Y, Yamaguchi K, Kondo K | date = 1989 | title = A new NAD+-dependent opine dehydrogenase from Arthrobacter sp strain 1C | journal = J. Bacteriol. | volume = 171 | pages = 4466–71 | pmid = 2753861 | issue = 8 | doi = 10.1128/jb.171.8.4466-4471.1989 | pmc = 210226 }} {{chemrxn|width=65%| {{chemrxn/cpd|Norvaline|upright=1.2 }} {{chemrxn/txt|+ [NADH](/source/NADH) + }} {{chemrxn/cpd|Pyruvic acid }} {{chemrxn/arw|direction=reversible|fwd_in={{chem2|H+}}|fwd_out={{chem2|H2O}}|rev_in={{chem2|H2O}}|rev_out={{chem2|H+}} }} {{chemrxn/cpd|qid=Q27121572|caption=(1)|upright=1.2 }} {{chemrxn/txt|+ [NAD+](/source/NAD%2B)}} }} The enzyme uses [nicotinamide adenine dinucleotide](/source/nicotinamide_adenine_dinucleotide) as its [cofactor](/source/Cofactor_(biochemistry)).{{cite journal | vauthors = Dairi T, Asano Y | date = 1995 | title = Cloning, nucleotide sequencing, and expression of an opine dehydrogenase gene from Arthrobacter sp. strain 1C | journal = Appl. Environ. Microbiol. | volume = 61 | pages = 3169–71 | pmid = 7487048 | issue = 8 | doi = 10.1128/aem.61.8.3169-3171.1995 | pmc = 167592 | bibcode = 1995ApEnM..61.3169D }} Similarly, [D-nopaline dehydrogenase](/source/D-nopaline_dehydrogenase), also called nopaline synthase, produces or degrades nopaline: {{chemrxn|width=80%| {{chemrxn/cpd|Arginine }} {{chemrxn/txt|+ [NADPH](/source/NADPH) + }} {{chemrxn/cpd|α-Ketoglutaric acid }} {{chemrxn/arw|direction=reversible|fwd_in={{chem2|H+}}|fwd_out={{chem2|H2O}}|rev_in={{chem2|H2O}}|rev_out={{chem2|H+}} }} {{chemrxn/cpd|Nopaline }} {{chemrxn/txt|+ [NADP+](/source/NADP%2B) }} }} Nopaline is a combination of the amino acid L-arginine with α-ketoglutaric acid.{{cite journal | vauthors = Kemp JD, Sutton DW, Hack E | date = 1979 | title = Purification and characterization of the crown gall specific enzyme nopaline synthase | journal = Biochemistry | volume = 18 | pages = 3755–60 | pmid = 476084 | doi = 10.1021/bi00584a017 | issue = 17 }} ==List of opines== This is an alphabetical list of some opines or opine-like compounds. ;Acetopine Acetopine (''N''2-(carboxymethyl)-arginine or demethyl-octopine) was isolated from cotton (''Gossypium hirsutum'') and soybean (''Glycine max'') callus. It wasn't found in plant tissues transformed by ''Agrobacterium'' and therefore it is not considered a "true" opine. ;Agrocinopines Agrocinopines (A-D) are a separate class of opines. They are sugar-phosphodiesters. Agrocinopine A is phosphodiester of sucrose and L-Arabinose. Agrocinopine B is the corresponding phosphodiester, in which the glucose has been hydrolyzed from the sucrose portion of agrocinopine A. ;Agropine Agropine (1'-deoxy-D-mannitol-1'-yl)-L-glutamine,1',2'-lactone) was obtained from crown gall tumors. It is a member of the mannityl family. It is derived from mannopine through the formation of a [lactone](/source/lactone). ;Agropinic acid Agropinic acid (''N''-1-(D-mannityl)-L-glutamic acid lactam) is produced by crown gall tumors. Belongs to the mannityl family. It is formed by [lactamization](/source/lactamization) of agropine. ;Alanopine Beta-alanopine (2,2'-iminodipropionic acid or L-alanine, ''N''-(1-carboxyethyl)-) and ''meso''-alanopine (meso-''N''-(1-carboxyethyl)-alanine) were isolated from marine invertebrates. Structurally it is a member of the octopine family. ;Asparaginopine See ''succinamopine'' ;Chrysopine Chrysopine (d-lactone of ''N''-1-deoxy-D-fructosyl-L-glutamine) was first obtained from [fig tree](/source/fig_tree) and [chrysanthemum](/source/chrysanthemum) crown gall tumors. It is the deoxyfructosyl analog of agropine. ;Cucumopine Cucumopine (4,6-dicarboxy-4,5,6,7-tetrahydro-1''H''-imidazo[4,5-''c'']pyridine-4-propanoic acid) was found in [grapevine](/source/grapevine) crown gall tumours and carrot hairy-root cultures. ;Epileucinopine Epileucinopine (''N''-(1-carboxy-3-methylbutyl)glutamic acid or ''N''2-(1,3-dicarboxypropyl)leucine) was isolated from the poisonous mushroom ''Clitocybe acromelalga''. ;Glutaminopine Glutaminopine (''N''2-(D-1,3-dicarboxypropyl) derivative of glutamine) is a member of the nopaline family isolated from crown gall tumors. ;Heliopine Heliopine (also named vitopine) (''N''2 -(1-carboxyethyl)glutamine) was obtained from crown gall tumors. ;Histopine Histopine (''N''-(D-1-carboxyethyl)histidine) is a member of the octopine family found in crown gall tumors. ;Isoleucinopine Isoleucinopine (''N''-(1-carboxy-2-methylbutyl)glutamic acid or ''N''-(1,3-dicarboxypropyl)isoleucine) was isolated from the poisonous mushroom ''Clitocybe acromelalga''. ;Leucinopine Leucinopine (''N''2-(D-1,3-dicarboxypropyl) derivative of leucine) is a member of the nopaline family isolated from crown gall tumors. ;Lysopine Lysopine (''N''2-(D-1-carboxyethyl)-L-lysine) is a member of the octopine family found in crown gall tumors. ;Mannopine Mannopine (''N''-1-(D-mannityl)-L-glutamine) is found in crown gall tumors. It is the head member of the mannityl family of opines. ;Mannopinic acid Mannopinic acid (''N''-1-(D-mannityl)-L-glutamic acid) was isolated from crown gall tumors. Belongs to the mannityl family. ;Methiopine Methiopine (''N''-[1-D-(carboxyl)ethyl]-L-methionine) was found in crown gall tumors. ;Mikimopine Mikimopine (4-epimer of cucumopine) was first isolated from [tobacco](/source/tobacco) crow gall tumors. ;[Nopaline](/source/Nopaline) Nopaline (''N''2-(D-1,3-dicarboxypropyl)-L-arginine) was first isolated from crown gall tumors. It is the head member of the nopaline family of opines. It was also found in certain nontransformed plant tissues as a result of arginine metabolism ;Nopalinic acid Nopalinic acid (also named ornaline) (''N''2-(D-1,3-dicarboxypropyl)-L-ornithine) is a member of the nopaline family found in crown gall tumors. ;[Octopine](/source/Octopine) Octopine (''N''2-(D-1-carboxyethyl)-L-arginine) is the first opine discovered in 1927 in [octopus](/source/octopus) muscle and later in crown gall tumors. It is also found in other cephalopod species and lamellibranchs. It is the head member of the octopine family of opines. ;Octopinic acid Octopinic acid (''N''2-(D-1-carboxyethyl)-L-ornithine) is a member of the octopine family isolated from crown gall tumors. ;Ornaline See ''nopalinic acid'' ;Phenylalaninopine Phenylalaninopine (''N''-(1-carboxy-2-phenylethyl)glutamic acid) was isolated from the poisonous mushroom ''Clitocybe acromelalga''. ;Rideopine Rideopine (''N''-(4'-aminobutyl)-D-glutamic acid) is an opine-like molecule derived from [putrescine](/source/putrescine). It is obtained from crown gall tumors. ;[Saccharopine](/source/Saccharopine) Although not found in crown gall tumors, saccharopine (epsilon-''N''-(L-glutar-2-yl)-L-lysine) is chemically similar to "true" opines. It is formed by condensation of lysine and alpha-ketoglutarate. Saccharopine is an intermediate in the metabolism of amino acid lysine and occurs in fungi, higher plants and mammals, including man. ;Santhopine Santhopine is the deoxyfructosyl analog of mannopine. It is a naturally occurring compound found in rotting fruits and vegetables. It was also isolated from crown gall tumors. ;Strombine Strombine (Methylimidodiacetic acid or ''N''-(D-1-carboxyethyl)-glycine) was first isolated from the [gastropod](/source/gastropod) [mollusk](/source/mollusk) ''Strombus''. It acts as a fish attractant. Structurally it is a member of the octopine family. ;Succinamopine Succinamopine (also named asparaginopine) (''N''-(3-amino-1-carboxy-3-oxopropyl)glutamic acid) is a member of the nopaline family isolated from crown gall tumors. Its structure is analogous to that of nopaline, with asparagine replacing arginine. ;Tauropine Tauropine (''N''-(D-1-carboxyethyl)-taurine) was found in some marine invertebrates. It is also called rhodoic acid. Structurally it is a member of the octopine family. ;Valinopine Valinopine (''N''-(1-carboxy-2-methylpropyl)glutamic acid or ''N''-(1,3-dicarboxypropyl)valine) was isolated from the poisonous mushroom ''Clitocybe acromelalga''. ;Vitopine See ''heliopine'' ==References== {{reflist}} Category:Amino acid derivatives --- Adapted from the Wikipedia article [Opine](https://en.wikipedia.org/wiki/Opine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Opine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.