Acetogenins
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Acetogenins are a class of
polyketide In organic chemistry, polyketides are a class of natural products derived from a Precursor (chemistry), precursor molecule consisting of a Polymer backbone, chain of alternating ketone (, or Carbonyl reduction, its reduced forms) and Methylene gro ...
natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical s ...
s found in plants of the family
Annonaceae The Annonaceae are a Family (biology), family of flowering plants consisting of trees, shrubs, or rarely lianas commonly known as the custard apple family or soursop family. With 108 accepted genera and about 2400 known species, it is the largest ...
. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including
hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
s,
ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
s,
epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...
s,
tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
s and
tetrahydropyran Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by addin ...
s. They are often terminated with a
lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...
or
butenolide Butenolides are a class of lactones with a four-carbon heterocycle, heterocyclic ring structure.Joule JA, Mills K. (2000). Heterocyclic Chemistry 4th ed. Blackwell Science Publishing: Oxford, UK They are sometimes considered redox, oxidized deri ...
. Over 400 members of this family of compounds have been isolated from 51 different species of plants. Many acetogenins are characterized by
neurotoxicity Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...
. Examples include: *
Annonacin Annonacin is a chemical compound with toxic effects, especially in the nervous system, found in some fruits such as the paw paw, custard apples, soursop, and others from the family ''Annonaceae''. It is a member of the class of compounds known ...
*
Annonin Annonins are a group of chemical compounds classified as acetogenins. They are found in the extracts of ''Annona'' seeds (''Annona squamosa, A. squamosa'' and ''Annona muricata, A. muricata''). Annonin-based Bioinsecticide, bioinsecticides are us ...
s * Bullatacin * Uvaricin


Structure

Structurally, acetogenins are a series of C-35/C-37 compounds usually characterized by a long
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
chain bearing a terminal methyl-substituted α,β-unsaturated γ-lactone ring, as well as one to three tetrahydrofuran (
THF Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...
) rings. These THF rings are located along the
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
chain, along with a number of oxygenated moieties (hydroxyls,
acetoxy In organic chemistry, the acetoxy group (abbr. AcO– or –OAc; IUPAC name: acetyloxy), is a functional group with the formula and the structure . As the ''-oxy'' suffix implies, it differs from the acetyl group () by the presence of an addit ...
ls, ketones, epoxides) and/or double bonds.


Research

Acetogenins have been investigated for their biological properties, but are a concern due to
neurotoxicity Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifical ...
. Purified acetogenins and crude
extract An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered. The aromatic principles of ma ...
s of the common North American pawpaw (''
Asimina triloba ''Asimina triloba'', the American papaw, pawpaw, paw paw, or paw-paw, among many regional names, is a small deciduous tree native to the eastern United States and southern Ontario, Canada, producing a large, yellowish-green to brown fruit. ''As ...
'') or the soursop (''
Annona muricata Soursop (also called graviola, guyabano, and in Latin America ) is the fruit of ''Annona muricata'', a broadleaf, flowering, evergreen tree. It is native to the tropical regions of the Americas and the Caribbean and is widely propagated. It ...
'') remain under laboratory studies.


Mechanism of action

Acetogenins inhibit
NADH dehydrogenase NADH dehydrogenase is an enzyme that converts nicotinamide adenine dinucleotide (NAD) from its reduced form (NADH) to its oxidized form (NAD+). Members of the NADH dehydrogenase family and analogues are commonly systematically named using the f ...
, a key enzyme in energy metabolism.


References


External links

* {{commons category-inline Fatty alcohols Polyketides NADH dehydrogenase inhibitors Plant toxins