Opines
Encyclopedia
Opines are low molecular weight compounds found in plant crown gall tumors or hairy root tumors
produced by parasitic bacteria of the genus Agrobacterium
. Opine biosynthesis is catalyzed by specific enzymes encoded by genes contained in a small segment of DNA
(known as the T-DNA, for 'transfer DNA'), which is part of the Ti plasmid
, inserted by the bacterium into the plant genome
. The opines are used by the bacterium as an important source of nitrogen
and energy. Each strain of Agrobacterium induces and catabolizes a specific set of opines. There are at least 30 different opines described so far.
1. The vast majority are secondary amine
derivatives formed by condensation of an amino acid
, either with a keto acid
or a sugar
.
The first subcategory includes the nopaline
and octopine families. The nopaline family (nopaline, nopalinic acid, leucinopine, glutaminopine, succinamopine) is formed when alpha-ketoglutarate serves as the keto substrate in the condensation reaction. The octopine family (octopine, octopinic acid, lysopine, histopine) is formed when pyruvate is involved in the condensation reaction.
The second subcategory includes the mannityl family (mannopine, mannopinic acid, agropine, agropinic acid) formed by the condensation of an amino-acid with mannose
.
2. Agrocinopines form a small, separate class of opines. Chemically they are sugar-phosphodiesters. For example, agrocinopine A is a phosphodiester of sucrose
and L-arabinose
.
muscle. According to 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
, stylopine, europine, and lycopine belong to different classes of molecules.
and plant tissue as a result of arginine
metabolism. Saccharopine
is an intermediate in the metabolism of amino acid lysine
and occurs in fungi
, higher plants and mammals, including man. The poisonous mushroom Clitocybe acromelalga
is a source of four opine type amino acids: valinopine, epileucinopine, isoleucinopine and phenylalaninopine.
Acetopine
Acetopine (N2-(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
.
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 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 and chrysanthemum
crown gall tumors. It is the deoxyfructosyl analog of agropine.
Cucumopine
Cucumopine (4,6-Dicarboxy-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-4-propanoic acid) was found in grapevine
crown gall tumours and carrot hairy-root cultures.
Epileucinopine
Epileucinopine (N-(1-Carboxy-3-methylbutyl)glutamic acid or N2-(1,3-Dicarboxypropyl)leucine) was isolated from the poisonous mushroom Clitocybe acromelalga.
Glutaminopine
Glutaminopine (N2-(D-1,3-dicarboxypropyl) derivative of glutamine) is a member of the nopaline family isolated from crown gall tumors.
Heliopine
Heliopine (also named vitopine) (N2 -(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 (N2-(D-1,3-dicarboxypropyl) derivative of leucine) is a member of the nopaline family isolated from crown gall tumors.
Lysopine
Lysopine (N2-(D-l-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.
Methopine
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
crow gall tumors.
Nopaline
Nopaline (N2-(~-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) (N2-(~-1,3-dicarboxypropy1)-L-ornithine) is a member of the nopaline family found in crown gall tumors.
Octopine
Octopine (N2-(D-l-carboxyethyl)-L-arginine) is the first opine discovered in 1927 in 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 (N2-(D-l-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. It is obtained from crown gall tumors.
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 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
Hairy root culture
Hairy root culture, also called transformed root culture, is a type of plant tissue culture that is used to study plant metabolic processes or to produce valuable secondary metabolites, often with plant genetic engineering....
produced by parasitic bacteria of the genus Agrobacterium
Agrobacterium
Agrobacterium is a genus of Gram-negative bacteria established by H. J. Conn that uses horizontal gene transfer to cause tumors in plants. Agrobacterium tumefaciens is the most commonly studied species in this genus...
. Opine biosynthesis is catalyzed by specific enzymes encoded by genes contained in a small segment of DNA
DNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
(known as the T-DNA, for 'transfer DNA'), which is part of the Ti plasmid
Ti plasmid
Ti plasmid is a circular plasmid that often, but not always, is a part of the genetic equipment that Agrobacterium tumefaciens and Agrobacterium rhizogenes use to transduce its genetic material to plants. Ti stands for tumor inducing. The Ti plasmid is lost when Agrobacterium is grown above 28°C....
, inserted by the bacterium into the plant genome
Genome
In modern molecular biology and genetics, the genome is the entirety of an organism's hereditary information. It is encoded either in DNA or, for many types of virus, in RNA. The genome includes both the genes and the non-coding sequences of the DNA/RNA....
. The opines are used by the bacterium as an important source of nitrogen
Nitrogen
Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
and energy. Each strain of Agrobacterium induces and catabolizes a specific set of opines. There are at least 30 different opines described so far.
Chemical structure
Chemically, opines fall into two major structural classes:1. The vast majority are secondary amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
derivatives formed by condensation of an amino acid
Amino acid
Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...
, either with a keto acid
Keto acid
Keto acids are organic compounds that contain a carboxylic acid group and a ketone group. The alpha-keto acids are especially important in biology as they are involved in the Krebs citric acid cycle and in glycolysis...
or a sugar
Sugar
Sugar is a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor.Sucrose in its refined form primarily comes from sugar cane and sugar beet...
.
The first subcategory includes the nopaline
Nopaline
Nopaline is one of the Opines. Ti plasmids are classified on the basis of the different types of Opines they produce. These may be Nopaline plasmids, Octopine Plasmids and Agropine Plasmids. These Opines are condensation products of amino acids and keto acids or may be from sugar. The Opines are...
and octopine families. The nopaline family (nopaline, nopalinic acid, leucinopine, glutaminopine, succinamopine) is formed when alpha-ketoglutarate serves as the keto substrate in the condensation reaction. The octopine family (octopine, octopinic acid, lysopine, histopine) is formed when pyruvate is involved in the condensation reaction.
The second subcategory includes the mannityl family (mannopine, mannopinic acid, agropine, agropinic acid) formed by the condensation of an amino-acid with mannose
Mannose
Mannose is a sugar monomer of the aldohexose series of carbohydrates. Mannose is a C-2 epimer of glucose. It is not part of human metabolism, but is a component of microbial cell walls, and is therefore a target of the immune system and also of antibiotics....
.
2. Agrocinopines form a small, separate class of opines. Chemically they are sugar-phosphodiesters. For example, agrocinopine A is a phosphodiester of sucrose
Sucrose
Sucrose is the organic compound commonly known as table sugar and sometimes called saccharose. A white, odorless, crystalline powder with a sweet taste, it is best known for its role in human nutrition. The molecule is a disaccharide composed of glucose and fructose with the molecular formula...
and L-arabinose
Arabinose
Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde functional group.For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.For sugars, the D/L...
.
Nomenclature
The name opine comes from octopine, the first opine discovered in 1927, not in crown galls, but in octopusOctopus
The octopus is a cephalopod mollusc of the order Octopoda. Octopuses have two eyes and four pairs of arms, and like other cephalopods they are bilaterally symmetric. An octopus has a hard beak, with its mouth at the center point of the arms...
muscle. According to Oxford English Dictionary
Oxford English Dictionary
The Oxford English Dictionary , published by the Oxford University Press, is the self-styled premier dictionary of the English language. Two fully bound print editions of the OED have been published under its current name, in 1928 and 1989. The first edition was published in twelve volumes , and...
, 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
Atropine
Atropine is a naturally occurring tropane alkaloid extracted from deadly nightshade , Jimson weed , mandrake and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects...
, stylopine, europine, and 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 callusCallus
A callus is an especially toughened area of skin which has become relatively thick and hard in response to repeated friction, pressure, or other irritation. Rubbing that is too frequent or forceful will cause blisters rather than allow calluses to form. Since repeated contact is required, calluses...
and plant tissue as a result of arginine
Arginine
Arginine is an α-amino acid. The L-form is one of the 20 most common natural amino acids. At the level of molecular genetics, in the structure of the messenger ribonucleic acid mRNA, CGU, CGC, CGA, CGG, AGA, and AGG, are the triplets of nucleotide bases or codons that codify for arginine during...
metabolism. Saccharopine
Saccharopine
Saccharopine is an intermediate in the metabolism of amino acid lysine. It is a precursor of lysine in the alpha-aminoadipate pathway which occurs in a few lower fungi, the higher fungi, and euglenids...
is an intermediate in the metabolism of amino acid lysine
Lysine
Lysine is an α-amino acid with the chemical formula HO2CCH4NH2. It is an essential amino acid, which means that the human body cannot synthesize it. Its codons are AAA and AAG....
and occurs in fungi
Fungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...
, higher plants and mammals, including man. The poisonous mushroom Clitocybe acromelalga
Clitocybe acromelalga
Clitocybe acromelalga is a basidiomycete fungus of the large genus Clitocybe found in Japan. It was discovered to be poisonous in 1918, when symptoms of occurred within 3 days of consumption. It had been mistaken for the edible blewit Lepista inversa.Consumption of a related species, C. amoenolens...
is a source of four opine type amino acids: valinopine, epileucinopine, isoleucinopine and phenylalaninopine.
List of opines
This is an alphabetical list of some opines or opine-like compounds.Acetopine
Acetopine (N2-(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
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
.
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 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 and chrysanthemum
Chrysanthemum
Chrysanthemums, often called mums or chrysanths, are of the genus constituting approximately 30 species of perennial flowering plants in the family Asteraceae which is native to Asia and northeastern Europe.-Etymology:...
crown gall tumors. It is the deoxyfructosyl analog of agropine.
Cucumopine
Cucumopine (4,6-Dicarboxy-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-4-propanoic acid) was found in grapevine
Grapevine
Grapevine is the common name for plants of the genus Vitis. Other meanings include:*Grapevine , a term often used to describe a form of communication by means of gossip or rumor, as in "heard it through the grapevine"...
crown gall tumours and carrot hairy-root cultures.
Epileucinopine
Epileucinopine (N-(1-Carboxy-3-methylbutyl)glutamic acid or N2-(1,3-Dicarboxypropyl)leucine) was isolated from the poisonous mushroom Clitocybe acromelalga.
Glutaminopine
Glutaminopine (N2-(D-1,3-dicarboxypropyl) derivative of glutamine) is a member of the nopaline family isolated from crown gall tumors.
Heliopine
Heliopine (also named vitopine) (N2 -(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 (N2-(D-1,3-dicarboxypropyl) derivative of leucine) is a member of the nopaline family isolated from crown gall tumors.
Lysopine
Lysopine (N2-(D-l-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.
Methopine
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
Tobacco
Tobacco is an agricultural product processed from the leaves of plants in the genus Nicotiana. It can be consumed, used as a pesticide and, in the form of nicotine tartrate, used in some medicines...
crow gall tumors.
Nopaline
Nopaline
Nopaline is one of the Opines. Ti plasmids are classified on the basis of the different types of Opines they produce. These may be Nopaline plasmids, Octopine Plasmids and Agropine Plasmids. These Opines are condensation products of amino acids and keto acids or may be from sugar. The Opines are...
Nopaline (N2-(~-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) (N2-(~-1,3-dicarboxypropy1)-L-ornithine) is a member of the nopaline family found in crown gall tumors.
Octopine
Octopine (N2-(D-l-carboxyethyl)-L-arginine) is the first opine discovered in 1927 in octopus
Octopus
The octopus is a cephalopod mollusc of the order Octopoda. Octopuses have two eyes and four pairs of arms, and like other cephalopods they are bilaterally symmetric. An octopus has a hard beak, with its mouth at the center point of the arms...
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 (N2-(D-l-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. It is obtained from crown gall tumors.
Saccharopine
Saccharopine
Saccharopine is an intermediate in the metabolism of amino acid lysine. It is a precursor of lysine in the alpha-aminoadipate pathway which occurs in a few lower fungi, the higher fungi, and euglenids...
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 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