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Secondary metabolite

 

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Secondary metabolite



 
 
Secondary metabolites are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that are not directly involved in the normal growth
Cell growth

The term cell growth is used in the contexts of Cell development and cell division . When used in the context of cell division, it refers to growth of cell populations, where one cell grows and divides to produce two "daughter cells"....
, development or reproduction of organism
Organism

In biology, an organism is any life thing . In at least some form, all organisms are capable of response to stimulus , reproduction, growth and developmental biology, and maintenance of homeostasis as a stable whole....
s. Unlike primary metabolites, absence of secondary metabolities results not in immediate death, but in long-term impairment of the organism's survivability
Survivability

Survivability is the ability to remain alive or continue to exist. The term has more specific meaning in certain contexts....
/fecundity
Fecundity

Fecundity, derived from the word wikt:fecund, generally refers to the ability to reproduce. In biology and demography, fecundity is the potential reproductive capacity of an organism or population, measured by the number of gametes , seed set or asexual propagules....
 or aesthetics, or perhaps in no significant change at all. Secondary metabolites are often restricted to a narrow set of species within a phylogenetic group.

function or importance of these compounds to the organism is usually of an ecological nature as they are used as defenses against predators, parasites and diseases, for interspecies competition, and to facilitate the reproductive processes (coloring agents, attractive smells, etc).






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Secondary metabolites are organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s that are not directly involved in the normal growth
Cell growth

The term cell growth is used in the contexts of Cell development and cell division . When used in the context of cell division, it refers to growth of cell populations, where one cell grows and divides to produce two "daughter cells"....
, development or reproduction of organism
Organism

In biology, an organism is any life thing . In at least some form, all organisms are capable of response to stimulus , reproduction, growth and developmental biology, and maintenance of homeostasis as a stable whole....
s. Unlike primary metabolites, absence of secondary metabolities results not in immediate death, but in long-term impairment of the organism's survivability
Survivability

Survivability is the ability to remain alive or continue to exist. The term has more specific meaning in certain contexts....
/fecundity
Fecundity

Fecundity, derived from the word wikt:fecund, generally refers to the ability to reproduce. In biology and demography, fecundity is the potential reproductive capacity of an organism or population, measured by the number of gametes , seed set or asexual propagules....
 or aesthetics, or perhaps in no significant change at all. Secondary metabolites are often restricted to a narrow set of species within a phylogenetic group.

Function

The function or importance of these compounds to the organism is usually of an ecological nature as they are used as defenses against predators, parasites and diseases, for interspecies competition, and to facilitate the reproductive processes (coloring agents, attractive smells, etc). Since these compounds are usually restricted to a much more limited group of organisms, they have long been of prime importance in taxonomic research.

Secondary metabolites may be likely candidates for drug or other technological development directly, or as an inspiration for unnatural products. This will concern secondary metabolites in plant
Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
s, bacteria, fungi and many marine
Ocean

An ocean is a major body of Seawater, and a principal component of the hydrosphere. Approximately 71% of the Earth's surface is covered by ocean, a World Ocean that is customarily divided into several principal oceans and smaller seas....
 organisms (sponges, tunicates, corals, snails). In some cases, higher organisms will host a microorganism which is the actual producer of the product in question, as part of a symbiotic relationship.

Categories

Most of the secondary metabolites of interest to humankind fit into categories which classify secondary metabolites based on their biosynthetic origin. Since secondary metabolites are often created by modified primary metabolite synthases, or "borrow" substrates of primary metabolite origin, these categories should not be interpreted as saying that all molecules in the category are secondary metabolites (for example the steroid category), but rather that there are secondary metabolites in these categories.

Small "small molecules"

  • Alkaloid
    Alkaloid

    Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
    s
    (usually a small, heavily derivatized amino acid):
    • Hyoscyamine
      Hyoscyamine

      Hyoscyamine, pronounced hi-oh-SYE-uh-meen, is a chemical compound, a tropane alkaloid. It is the levorotary isomer to atropine. It is a secondary metabolite found in certain plants of the Solanaceae family, including henbane, mandrake , jimsonweed , and deadly nightshade ....
      , present in Datura stramonium
      Datura stramonium

      Datura stramonium, known by the common names jimson weed, ditch weed, stink weed, loco weed, Korean morning glory, Jamestown weed, thorn apple, angel's trumpet, devil's trumpet, devil's snare, devil's seed, mad hatter, crazy tea, malpitte, and, along with...
    • Atropine
      Atropine

      Atropine is a tropane alkaloid extracted from deadly nightshade , jimsonweed , Mandrake and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a hard drug with a wide variety of effects....
      , present in Atropa belladonna, Deadly nightshade
      Deadly nightshade

      Atropa belladonna or Atropa bella-donna, commonly known as belladonna or deadly nightshade, is a perennial plant herbaceous plant in the family Solanaceae, native to Europe, North Africa, and Western Asia....
    • Cocaine
      Cocaine

      Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine....
      , present in Erythroxylon coca the Coca
      Coca

      Coca is a plant in the family Erythroxylaceae, native to north-western South America. The plant plays a significant role in traditional Andean culture....
       plant
    • Codeine
      Codeine

      Codeine or methylmorphine is an opiate used for its analgesic, Cough medicine and Antidiarrhoeal properties. It is by far the most widely used opiate in the world and probably the most commonly used drug overall according to numerous reports over the years by organizations such as the World Health Organization and its League of Nations...
       and Morphine
      Morphine

      Morphine is a highly potent opiate analgesic Medication, is the principal active agent in opium, and is considered to be the prototypical opioid....
      , present in Papaver somniferum, the opium poppy
      Opium poppy

      The Opium Poppy, Papaver somniferum, is the type of poppy from which opium and many refined opiates, including morphine, thebaine, codeine, papaverine, and noscapine, are extracted....
    • Tetrodotoxin
      Tetrodotoxin

      Tetrodotoxin is a potent neurotoxin with no known antidote. Tetrodotoxin blocks action potentials in nerves by binding to the pores of the voltage-gated, fast sodium channels in neuron cell membrane....
      , a microbial product in Fugu
      Fugu

      is the Japanese word for pufferfish and is also a Japanese dish prepared from the meat of pufferfish or porcupinefish of the genus Diodon. Because pufferfish is lethally poisonous if prepared incorrectly, fugu has become one of the most celebrated and notorious dishes in Japanese cuisine....
       and some salamanders
    • Vincristine
      Vincristine

      Vincristine , also known as leurocristine, is a vinca alkaloid from the Catharanthus roseus , formerly Vinca rosea and hence its name....
       & Vinblastine
      Vinblastine

      Vinblastine is an mitotic inhibitor medication used to treat certain kinds of cancer, including Hodgkin's lymphoma, non-small cell lung cancer, breast cancer, head and neck cancer, and testicular cancer....
      , mitotic inhibitor
      Mitotic inhibitor

      A mitotic inhibitor is a type of drug derived from natural substances such as plant alkaloids and primarily used in cancer treatment and certain types of cancer research including cytogenetics....
      s found in the Rosy Periwinkle
  • Terpenoid
    Terpenoid

    The terpenoids , sometimes called isoprenoids, are a large and diverse class of naturally-occurring organic compound similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways....
    s
    (come from semiterpene
    Terpene

    Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
     oligomerization):
    • Azadirachtin
      Azadirachtin

      Azadirachtin is a chemical compound belonging to the limonoids. It is a secondary metabolite present in the Neem tree seeds. The molecular formula is C35H44O16....
      , (Neem
      Neem

      Neem is a tree in the mahogany family Meliaceae. It is one of two species in the genus Azadirachta, and is native to India, Myanmar, Bangladesh, and Pakistan growing in tropical and semi-tropical regions....
       tree)
    • Artemisinin
      Artemisinin

      Artemisinin is a medication used to treat multi-drug resistant strains of Plasmodium falciparum malaria. The compound is isolated from the plant Artemisia annua....
      , present in Artemisia annua
      Artemisia annua

      Artemisia annua, also known as Sweet Wormwood, Sweet Annie, Sweet Sagewort or Annual Wormwood , is a common type of Artemisia that is native to temperate Asia, but naturalized throughout the world....
       Chinese wormwood
    • tetrahydrocannabinol
      Tetrahydrocannabinol

      Tetrahydrocannabinol , also known as THC, ?9-THC, ?9-tetrahydrocannabinol, ?1-tetrahydrocannabinol , or dronabinol, is the main psychoactive substance found in the Cannabis plant....
      , present in cannabis sativa
      Cannabis sativa

      Cannabis sativa is an annual plant in the Cannabaceae family. It is a herb that has been used throughout recorded history by humans as a source of fiber, for its seed oil, as food , as a drug , as medicine , and for spiritual purposes ....
    • Steroids (Terpenes with a particular ring structure)
      • Saponins (plant steroids, often glycosylated)
  • Glycosides (heavily modified sugar molecules):
    • Nojirimycin
    • Glucosinolate
      Glucosinolate

      The glucosinolates are a class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid. They occur as secondary metabolites of almost all plants of the order Brassicales , but also in the genus Drypetes ....
      s
  • Phenols
    Phenols

    In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl Functional group attached to an aromatic hydrocarbon group....
    :
    • Resveratrol
      Resveratrol

      Resveratrol is a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi. Resveratrol has also been produced by chemical synthesis and is sold as a nutritional supplement derived primarily from Japanese knotweed....
  • Phenazine
    Phenazine

    Phenazine , also called azophenylene, dibenzo-p-diazine, dibenzopyrazine, and acridizine, is a dibenzo annulation pyrazine and the parent substance of many dyestuffs, such as the eurhodines, toluylene red, indulines and safranines....
    s
    :
    • Pyocyanin
    • Phenazine-1-carboxylic acid (and derivatives)


Big "small molecules", produced by large, modular, "molecular factories"

  • Polyketide
    Polyketide

    Polyketides are secondary metabolites from bacterium, fungi, plants, and animals. Polyketides are biosynthesis by the polymerization of acetyl and propionyl subunits in a similar process to fatty acid metabolism#Synthesis ....
    s
    :
    • Erythromycin
      Erythromycin

      Erythromycin is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins....
    • Discodermolide
      Discodermolide

      -Discodermolide is a recently discovered polyketide natural product found to be a potent inhibitor of tumor cell growth. The molecule's carbon skeleton is made up of eight polypropionate and four acetate units with 13 stereocenters....
  • Fatty acid
    Fatty acid

    In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
     synthase products
    :
    • FR-900848
    • U-106305
    • phloroglucinol
      Phloroglucinol

      Phloroglucinol is the organic compound that is used in the organic synthesis. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5--cyclohexanetrione, which has ketone-like character....
      s
  • Nonribosomal peptide
    Nonribosomal peptide

    Nonribosomal peptides are a class of peptide secondary metabolites, usually produced by microorganisms like bacterium and fungi. Nonribosomal peptides are also found in higher organisms, such as nudibranchs, but are thought to be made by bacteria commensurism these organisms....
    s
    :
    • Vancomycin
      Vancomycin

      Vancomycin is a glycopeptide antibiotic used in the prophylaxis and treatment of infections caused by Gram-positive bacterium. It has traditionally been reserved as a drug of last resort, used only after treatment with other antibiotics had failed, although the emergence of vancomycin-resistant organisms means that it is increasingly being...
    • Thiostrepton
      Thiostrepton

      Thiostrepton is a natural cyclic oligopeptide antibiotic, derived from several strains of Streptomyces, such as Streptomyces azureus and Streptomyces laurentii....
    • Ramoplanin
      Ramoplanin

      Ramoplanin is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of Actinoplanes....
    • Teicoplanin
      Teicoplanin

      Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacterium, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis....
    • Gramicidin
      Gramicidin

      Gramicidin is a heterogeneous mixture of six antibiotic compounds, Gramicidins A, B and C, making up 80%, 6%,and 14% respectively, all of which are obtained from the soil bacterial species Bacillus brevis and called collectively Gramicidin D....
    • Bacitracin
      Bacitracin

      Bacitracin is a mixture of related cyclic peptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy, isolation of which was first reported in 1945....
  • Hybrids of the above three:
    • Epothilone
      Epothilone

      The epothilones are a new class of cytotoxic molecules identified as potential chemotherapeutic drugs. , epothilones A to F have been identified and characterised....


Non-"small molecules" - DNA, RNA, ribosome, or polysaccharide "classical" biopolymers

  • Ribosomal peptides
    Ribosome

    Ribosomes are complexes of RNA and protein that are found in all cell s. Ribosomes from bacteria, archaea and eukaryotes, the three domains of life on Earth, have significantly different structure and RNA....
    :
    • Microcin-J25


See also

Secondary metabolism
Secondary metabolism

Secondary metabolism is a term for pathways and small molecule products of metabolism that are not absolutely required for the survival of the organism....