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Cucurbitacins are a class of
Cucurbitacins are a class of biochemical
Biochemistry, or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology, ...
compounds that some plants – notably members of the pumpkin
A pumpkin is a cultivar, cultivated winter squash in the genus ''Cucurbita''. The term is most commonly applied to round, orange-colored squash varieties, but does not possess a scientific definition. It may be used in reference to many dif ...
and gourd
Gourds include the fruits of some flowering plant species in the family Cucurbitaceae, particularly '' Cucurbita'' and '' Lagenaria''. The term refers to a number of species and subspecies, many with hard shells, and some without. Many gourds ha ...
family, Cucurbitaceae
The Cucurbitaceae (), also called cucurbits or the gourd family, are a plant family (biology), family consisting of about 965 species in 101 genera.
– produce and which function as a defense against herbivore
A herbivore is an animal anatomically and physiologically evolved to feed on plants, especially upon vascular tissues such as foliage, fruits or seeds, as the main component of its diet. These more broadly also encompass animals that eat ...
s. Cucurbitacins and their derivatives have also been found in many other plant families (including Brassicaceae
Brassicaceae () or (the older but equally valid) Cruciferae () is a medium-sized and economically important Family (biology), family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous pla ...
, Scrophulariaceae
The Scrophulariaceae are a family of flowering plants, commonly known as the figwort family. The plants are annual and perennial herbs, as well as shrubs. Flowers have bilateral (zygomorphic) or rarely radial (actinomorphic) symmetry. The Scr ...
, Begoniaceae
Begoniaceae is a family of flowering plants with two genera and about 2040 species occurring in the subtropics and tropics of both the New World and Old World. All but one of the species are in the genus ''Begonia''. There have been many recent ...
, Elaeocarpaceae
Elaeocarpaceae is a family of flowering plants. The family contains approximately 615 species of trees and shrubs in 12 genera."Elaeocarpaceae" In: Klaus Kubitzki (ed.). ''The Families and Genera of Vascular Plants'' vol. VI. Springer-Verlag: Ber ...
, Datiscaceae
The Datiscaceae are a family of dicotyledonous plants, containing two species of the genus ''Datisca''. Two other genera, ''Octomeles'' and ''Tetrameles'', are now classified in the family Tetramelaceae.
Datiscaceae are large herbaceous plants, ...
, Desfontainiaceae
''Desfontainia'' is a genus of flowering plants in the family Columelliaceae, though it was placed formerly in Loganiaceae, Potaliaceae (later subsumed in Gentianaceae), or a family of its own, Desfontainiaceae.
The genus was named for the F ...
, Polemoniaceae
The Polemoniaceae (Jacob's-ladder or phlox family) are a family of flowering plants consisting of about 27 genera with 270–400 species of annuals and perennials native to the Northern Hemisphere and South America, with the center of diversity ...
, Primulaceae
The Primulaceae ( ), commonly known as the primrose family (but not related to the Onagraceae, evening primrose family), are a family (biology), family of Herbaceous plant, herbaceous and woody flowering plants including some favourite garden pla ...
, Rubiaceae
Rubiaceae () is a family (biology), family of flowering plants, commonly known as the coffee, madder, or bedstraw family. It consists of terrestrial trees, shrubs, lianas, or herbs that are recognizable by simple, opposite leaves with Petiole ( ...
, Sterculiaceae
Sterculiaceae was a family of flowering plant based on the genus '' Sterculia''. Genera formerly included in Sterculiaceae are now placed in the family Malvaceae, in the subfamilies: Byttnerioideae, Dombeyoideae, Helicteroideae and Sterculioide ...
, Rosaceae
Rosaceae (), the rose family, is a family of flowering plants that includes 4,828 known species in 91 genera.
The name is derived from the type genus '' Rosa''. The family includes herbs, shrubs, and trees. Most species are deciduous, but som ...
, and Thymelaeaceae
The Thymelaeaceae are a cosmopolitan family (biology), family of flowering plants composed of 50 genera (listed below) and 898 species.Zachary S. Rogers (2009 onwards)A World Checklist of Thymelaeaceae (version 1) Missouri Botanical Garden Webs ...
), in some mushroom
A mushroom or toadstool is the fleshy, spore-bearing Sporocarp (fungi), fruiting body of a fungus, typically produced above ground on soil or another food source. ''Toadstool'' generally refers to a poisonous mushroom.
The standard for the n ...
s (including ''Russula
''Russula'' is a very large genus composed of around 750 worldwide species of fungi. The genus was described by Christian Hendrik Persoon in 1796.
The mushrooms are fairly large, and brightly colored – making them one of the most recognizable ...
'' and ''Hebeloma
''Hebeloma'' is a genus of fungi in the family Hymenogastraceae. Found worldwide, it contains the poison pie or fairy cakes ''(Hebeloma crustuliniforme)'' and the ghoul fungus ''(Hebeloma aminophilum, H. aminophilum)'', from Western Australia, wh ...
'') and even in some marine mollusks.
Cucurbitacins may be a taste deterrent in plants foraged by some animals and in some edible plants preferred by humans, such as cucumber
The cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables.zucchini
Zucchini (; : ''zucchini'' or ''zucchinis''), courgette () or ''Cucurbita pepo'' is a summer squash, a Vine, vining herbaceous plant whose fruit are harvested when their immature seeds and Fruit anatomy#Epicarp, epicarp (rind) are still soft a ...
s. In laboratory research, cucurbitacins have cytotoxic
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of dr ...
properties and are under study for their potential biological activity.
Cucurbitacins are chemically classified as triterpene
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...
s, formally derived from cucurbitane
Cucurbitane is a tetracyclic chemical compound with formula . It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of ...
, a triterpene
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...
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 ...
– specifically, from the unsaturated variant cucurbit-5-ene, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
s. Most cucurbitacins are tetracyclic
Tetracyclics are cyclic compound, cyclic chemical compounds that contain four fused ring (chemistry), rings of atoms, for example, Tröger's base.
Some tricyclic compounds having three fused and one tethered ring (connected to main nucleus by ...
except some have an extra ring due to formal cyclization
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where ...
between C16 and C24 as in cucurbitacin S and cucurbitacin T.
Biosynthesis
The biosynthesis of cucurbitacin C has been described. Zhang et al. (2014) identified ninecucumber
The cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables. These authors also discovered the
* Cucurbitacin A found in some species of ''
* Cucurbitacin B from '' Hemsleya endecaphylla'' (62 mg/72 g) and other plants (e.g. '' Cucurbita andreana''); anti-inflammatory, anti-hepatotoxic
** Cucurbitacin B 2-O-glucoside, from '' Begonia heracleifolia''
** 23,24-Dihydrocucurbitacin B from ''Hemsleya endecaphylla'', 49 mg/72 g
** 23,24-Dihydrocucurbitacin B 2-O-glucoside from roots of '' Picrorhiza kurrooa''
** Deacetoxycucurbitacin B 2-O-glucoside from roots of '' Picrorhiza kurrooa''
** Isocucurbitacin B, from '' Echinocystis fabacea''
** 23,24-Dihydroisocucurbitacin B 3-glucoside from '' Wilbrandia ebracteata''
** 23,24-Dihydro-3-epi-isocucurbitacin B, from '' Bryonia verrucosa''
** Pentanorcucurbitacin B or 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid, , white powder
transcription factors
In molecular biology, a transcription factor (TF) (or sequence-specific DNA-binding factor) is a protein that controls the rate of transcription of genetic information from DNA to messenger RNA, by binding to a specific DNA sequence. The fun ...
''Bl'' (Bitter leaf) and ''Bt'' (Bitter fruit) that regulate this pathway in leaves and fruits, respectively. The Bi gene confers bitterness to the entire plant and is genetically associated with an operon
In genetics, an operon is a functioning unit of DNA containing a cluster of genes under the control of a single promoter. The genes are transcribed together into an mRNA strand and either translated together in the cytoplasm, or undergo splic ...
-like gene cluster, similar to the gene cluster involved in thalianol biosynthesis in ''Arabidopsis
''Arabidopsis'' (rockcress) is a genus in the family Brassicaceae. They are small flowering plants related to cabbage and mustard. This genus is of great interest since it contains thale cress (''Arabidopsis thaliana''), one of the model organ ...
''. Fruit bitterness requires both Bi and the dominant Bt (Bitter fruit) gene. Nonbitterness of cultivated cucumber fruit is conferred by bt, an allele selected during domestication. Bi is a member of the oxidosqualene cyclase (OSC) gene family. Phylogenetic analysis showed that Bi is the ortholog
Sequence homology is the biological homology between DNA, RNA, or protein sequences, defined in terms of shared ancestry in the evolutionary history of life. Two segments of DNA can have shared ancestry because of three phenomena: either a speci ...
of cucurbitadienol synthase gene CPQ in squash (''Cucurbita pepo
''Cucurbita pepo'' is a cultivated plant of the genus ''Cucurbita''. It yields varieties of winter squash and pumpkin, but the most widespread varieties belong to the subspecies ''Cucurbita pepo'' subsp. ''pepo'', called summer squash.
It has b ...
'')
Variants
The cucurbitacins include:Cucurbitacin A
* Cucurbitacin A found in some species of ''Cucumis
__NOTOC__
''Cucumis'' is a genus of vine, twining, tendril-bearing plants in the Family (biology), family Cucurbitaceae which includes the cucumber (''Cucumis sativus''), true melons (''Cucumis melo'', including cantaloupe and Honeydew (melon), ...
''
** Pentanorcucurbitacin A, or 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one , white powder
Cucurbitacin B
* Cucurbitacin B from '' Hemsleya endecaphylla'' (62 mg/72 g) and other plants (e.g. '' Cucurbita andreana''); anti-inflammatory, anti-hepatotoxic
** Cucurbitacin B 2-O-glucoside, from '' Begonia heracleifolia''
** 23,24-Dihydrocucurbitacin B from ''Hemsleya endecaphylla'', 49 mg/72 g
** 23,24-Dihydrocucurbitacin B 2-O-glucoside from roots of '' Picrorhiza kurrooa''
** Deacetoxycucurbitacin B 2-O-glucoside from roots of '' Picrorhiza kurrooa''
** Isocucurbitacin B, from '' Echinocystis fabacea''
** 23,24-Dihydroisocucurbitacin B 3-glucoside from '' Wilbrandia ebracteata''
** 23,24-Dihydro-3-epi-isocucurbitacin B, from '' Bryonia verrucosa''
** Pentanorcucurbitacin B or 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid, , white powder
Cucurbitacin C
* Cucurbitacin C, from ''Cucumis sativus'' (cucumber
The cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables.
* Cucurbitacin D, from '' Trichosanthes kirilowii'' and many other plants (e.g. '' Cucurbita andreana'')
** 3-Epi-isocucurbitacin D, from species of ''
* Cucurbitacin I ( elatericin B) from '' Hemsleya endecaphylla'', 10 mg/72 g, also from ''
* Cucurbitacin Q from ''Brandegea bigelovii''
** 23,24-Dihydrodeacetylpicracin 2-O-glucoside from ''Picrorhiza kurrooa''
** Cucurbitacin Q1 from ''Cucumis'' species, actually Cucurbitacin F 25-acetate
Constituents of the
Physocarpus
''Physocarpus'', commonly called ninebark, is a genus of flowering plants in the family (biology), family Rosaceae, native plant, native to North America (most species) and northeastern Asia (one species).
Description
''Physocarpus'' are decid ...
'' and ''Phormium tenax
''Phormium tenax'' (called flax in New Zealand English; in Māori language, Māori; New Zealand flax outside New Zealand; and New Zealand hemp in historical nautical contexts) is an evergreen perennial plant native to New Zealand and Norfolk I ...
''
** 22-Deoxocucurbitacin D from ''Hemsleya endecaphylla'', 14 mg/72 g
** 23,24-Dihydrocucurbitacin D from ''Trichosanthes kirilowii'' also from ''H. endecaphylla'', 80 mg/72 g
** 23,24-Dihydro-epi-isocucurbitacin D, from ''Acanthosicyos horridus
''Acanthosicyos horridus'' is an unusual melon that is endemic to the Namib, Namib desert. In English it is known as Nara, butter-nuts, or butterpips; in one of the Khoisan languages it is locally called or ("!" is pronounced with a click, so ...
''
** 22-Deoxocucurbitacin D from '' Wilbrandia ebracteata''
** Anhydro-22-deoxo-3-epi-isocucurbitacin D from ''Ecballium elaterium
''Ecballium'' is a genus of flowering plants in the family Cucurbitaceae containing a single species, ''Ecballium elaterium'', also called the squirting cucumber, as well as the noli me tangere and its English translation touch-me-not. Its unus ...
''
** 25-O-Acetyl-2-deoxycucurbitacin D (amarinin) from '' Luffa amara''
** 2-Deoxycucurbitacin D, from '' Sloanea zuliaensis''
Cucurbitacin E
* Cucurbitacin E (α-Elaterin), from roots of '' Wilbrandia ebracteata''. Strongantifeedant
Antifeedants are organic compounds produced by plants to repel herbivores through distaste or toxicity. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but ...
for the flea beetle
The flea beetle is any small, jumping beetle of the leaf beetle family (Chrysomelidae) that is part of the tribe (biology), tribe Alticini, which is part of the subfamily Galerucinae. Historically the flea beetles were classified as their own ...
, inhibits cell adhesion
Cell adhesion is the process by which cells interact and attach to neighbouring cells through specialised molecules of the cell surface. This process can occur either through direct contact between cell surfaces such as Cell_junction, cell junc ...
(also in e.g. '' Cucurbita andreana'')
** 22,23-Dihydrocucurbitacin E from ''Hemsleya endecaphylla'', 9 mg/72 g, and from roots of ''Wilbrandia ebracteata''
** 22,23-Dihydrocucurbitacin E 2-glucoside from roots of ''Wilbrandia ebracteata''
** Isocucurbitacin E, from '' Cucumis prophetarum''
** 23,24-Dihydroisocucurbitacin E, from ''Cucumis prophetarum''
Cucurbitacin F
* Cucurbitacin F from '' Elaeocarpus dolichostylus'' ** Cucurbitacin F 25-acetate from '' Helmseya graciliflora'' ** 23,24-Dihydrocucurbitacin F from '' Helmseya amabilis'' ** 25-Acetoxy-23,24-dihydrocucurbitacin F from '' Helmseya amabilis'' (hemslecin A Hemslecin is any of several compounds obtained from plants of the genus '' Hemsleya'', which are used in Asian folk medicine. They are triterpene derivatives, specifically with the cucurbitane skeleton, related to cucurbitacin F.Jian-Chao Chen, ...
)
** 23,24-Dihydrocucurbitacin F glucoside from ''Helmseya amabilis''
** Cucurbitacin II glucoside from ''Helmseya amabilis''
** Hexanorcucurbitacin F from '' Elaeocarpus dolichostylus''
** Perseapicroside A from '' Persea mexicana''
** Scandenoside R9 from '' Hemsleya panacis-scandens''
** 15-Oxo-cucurbitacin F from '' Cowania mexicana''
** 15-oxo-23,24-dihydrocucurbitacin F from ''Cowania mexicana''
** Datiscosides B, D, and H, from '' Datisca glomerata''
Cucurbitacin G
* Cucurbitacin G from roots of ''Wilbrandia ebracteata'' * 3-Epi-isocucurbitacin G, from roots of ''Wilbrandia ebracteata''Cucurbitacin H
* Cucurbitacin H,stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
of cucurbitacin G, from roots of ''Wilbrandia ebracteata''
Cucurbitacin I
* Cucurbitacin I ( elatericin B) from '' Hemsleya endecaphylla'', 10 mg/72 g, also from ''Ecballium elaterium
''Ecballium'' is a genus of flowering plants in the family Cucurbitaceae containing a single species, ''Ecballium elaterium'', also called the squirting cucumber, as well as the noli me tangere and its English translation touch-me-not. Its unus ...
'' ''Citrullus colocynthis
''Citrullus colocynthis'', with many common names including Abu Jahl's melon, (native name in Turkey) colocynth, bitter apple, bitter cucumber, egusi, vine of Sodom, or wild gourd, is a poisonous desert viny plant native to the Mediterrane ...
'', '' Cucurbita andreana'', deters feeding by flea beetle
The flea beetle is any small, jumping beetle of the leaf beetle family (Chrysomelidae) that is part of the tribe (biology), tribe Alticini, which is part of the subfamily Galerucinae. Historically the flea beetles were classified as their own ...
** Hexanorcucurbitacin I from ''Ecballium elaterium''
** 23,24-Dihydrocucurbitacin I see Cucurbitacin L
** Khekadaengosides D and K from the fruits of ''Trichosanthes tricuspidata
''Trichosanthes tricuspidata'' is a climbing plant in the family Cucurbitaceae.
Subspecies
The following subspecies are listed in the Catalogue of Life:
* ''T. t. asperifolia''
* ''T. t. seramensis''
* ''T. t. siberutensis''
* ''T. t. javanica ...
''
** 11-Deoxocucurbitacin I, from ''Desfontainia spinosa
''Desfontainia'' is a genus of flowering plants in the family Columelliaceae, though it was placed formerly in Loganiaceae, Potaliaceae (later subsumed in Gentianaceae), or a family of its own, Desfontainiaceae.
The genus was named for the Fr ...
''
** Spinosides A and B, from ''Desfontainia spinosa''
** 23,24-dihydro-11-Deoxocucurbitacin I from ''Desfontainia spinosa''
Cucurbitacin J
* Cucurbitacin J from ''Iberis amara
''Iberis amara'', called wild candytuft, rocket candytuft and bitter candytuft, is a species of flowering plant in the family Brassicaceae
Brassicaceae () or (the older but equally valid) Cruciferae () is a medium-sized and economically import ...
''
** Cucurbitacin J 2-O-β-glucopyranoside from ''Trichosanthes tricuspidata''
Cucurbitacin K
* Cucurbitacin K, stereoisomer of cucurbitacin J, from ''Iberis amara
''Iberis amara'', called wild candytuft, rocket candytuft and bitter candytuft, is a species of flowering plant in the family Brassicaceae
Brassicaceae () or (the older but equally valid) Cruciferae () is a medium-sized and economically import ...
''
** Cucurbitacin K 2-O-β-glucopyranoside from ''Trichosanthes tricuspidata''
Cucurbitacin L
* Cucurbitacin L, or 23,24-dihydrocucurbitacin I, ** Brydioside A from ''Bryonia dioica
''Bryonia dioica'', known by the common names red bryony and white bryony, also English mandrake or ladies' seal, is a perennial climbing vine indigenous to Central and Southern Europe. It is a flowering plant in the cucumber family Cucurbitac ...
''
** Bryoamaride from ''Bryonia dioica''
** 25-O-Acetylbryoamaride from ''Trichosanthes tricuspidata''
** Khekadaengosides A and B from ''Trichosanthes tricuspidata''
Cucurbitacin O
* Cucurbitacin O from '' Brandegea bigelovii'' ** Cucurbitacin Q 2-O-glucoside, from '' Picrorhiza kurrooa'' ** 16-Deoxy-D-16-hexanorcucurbitacin O from ''Ecballium elaterium'' ** Deacetylpicracin from '' Picrorhiza scrophulariaeflora'' ** Deacetylpicracin 2-O-glucoside from ''Picrorhiza scrophulariaeflora'' ** 22-Deoxocucurbitacin O from '' Wilbrandia ebracteata''Cucurbitacin P
* Cucurbitacin P from '' Brandegea bigelovii'' ** Picracin from ''Picrorhiza scrophulariaeflora'' ** Picracin 2-O-glucoside from ''Picrorhiza scrophulariaeflora''Cucurbitacin Q
* Cucurbitacin Q from ''Brandegea bigelovii''
** 23,24-Dihydrodeacetylpicracin 2-O-glucoside from ''Picrorhiza kurrooa''
** Cucurbitacin Q1 from ''Cucumis'' species, actually Cucurbitacin F 25-acetate
Cucurbitacin R
* Cucurbitacin R is actually 23,24-dihydrocucurbitacin D.Cucurbitacin S
* Cucurbitacin S from ''Bryonia dioica
''Bryonia dioica'', known by the common names red bryony and white bryony, also English mandrake or ladies' seal, is a perennial climbing vine indigenous to Central and Southern Europe. It is a flowering plant in the cucumber family Cucurbitac ...
''
Cucurbitacin T
* Cucurbitacin T, from the fruits of ''Citrullus colocynthis
''Citrullus colocynthis'', with many common names including Abu Jahl's melon, (native name in Turkey) colocynth, bitter apple, bitter cucumber, egusi, vine of Sodom, or wild gourd, is a poisonous desert viny plant native to the Mediterrane ...
''
28/29 Norcucurbitacins
There are several substances that can be seen as deriving from cucurbit-5-ene skeleton by loss of one of themethyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
groups (28 or 29) attached to carbon 4; often with the adjacent ring (ring A) becoming aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
.
Other
Several other cucurbitacins have been found in plants.Occurrence and bitter taste
Constituents of the colocynth
''Citrullus colocynthis'', with many common names including Abu Jahl's melon, (native name in Turkey) colocynth, bitter apple, bitter cucumber, egusi, vine of Sodom, or wild gourd, is a poisonous desert viny plant native to the Mediterranea ...
fruit and leaves (''Citrullus colocynthis
''Citrullus colocynthis'', with many common names including Abu Jahl's melon, (native name in Turkey) colocynth, bitter apple, bitter cucumber, egusi, vine of Sodom, or wild gourd, is a poisonous desert viny plant native to the Mediterrane ...
'') include cucurbitacins. The 2-O-β-D- glucopyranosides of cucurbitacins K and L can be extracted with ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
from fruits of ''Cucurbita pepo
''Cucurbita pepo'' is a cultivated plant of the genus ''Cucurbita''. It yields varieties of winter squash and pumpkin, but the most widespread varieties belong to the subspecies ''Cucurbita pepo'' subsp. ''pepo'', called summer squash.
It has b ...
'' cv ''dayangua''. Pentanorcucurbitacins A and B can be extracted with methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...
from the stems of ''Momordica charantia
''Momordica charantia'' (commonly called bitter melon, cerassee, goya, bitter apple, bitter gourd, bitter squash, balsam-pear, karela, karavila and many more names listed below) is a tropical and subtropical vine of the family Cucurbitaceae, w ...
''. Cucurbitacins B and I, and derivatives of cucurbitacins B, D and E, can be extracted with methanol from dried tubers of ''Hemsleya endecaphylla''.
Cucurbitacins impart a bitter taste in plant foods such as cucumber
The cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables.zucchini
Zucchini (; : ''zucchini'' or ''zucchinis''), courgette () or ''Cucurbita pepo'' is a summer squash, a Vine, vining herbaceous plant whose fruit are harvested when their immature seeds and Fruit anatomy#Epicarp, epicarp (rind) are still soft a ...
, melon
A melon is any of various plants of the family Cucurbitaceae with sweet, edible, and fleshy fruit. It can also specifically refer to ''Cucumis melo'', commonly known as the "true melon" or simply "melon". The term "melon" can apply to both the p ...
and pumpkin
A pumpkin is a cultivar, cultivated winter squash in the genus ''Cucurbita''. The term is most commonly applied to round, orange-colored squash varieties, but does not possess a scientific definition. It may be used in reference to many dif ...
.
Research and toxicity
Cucurbitacins are underbasic research
Basic research, also called pure research, fundamental research, basic science, or pure science, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenome ...
for their biological properties, including toxicity
Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...
and potential pharmacological
Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...
uses in development of drugs for inflammation
Inflammation (from ) is part of the biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. The five cardinal signs are heat, pain, redness, swelling, and loss of function (Latin ''calor'', '' ...
, cancer
Cancer is a group of diseases involving Cell growth#Disorders, abnormal cell growth with the potential to Invasion (cancer), invade or Metastasis, spread to other parts of the body. These contrast with benign tumors, which do not spread. Po ...
, cardiovascular diseases
Cardiovascular disease (CVD) is any disease involving the heart or blood vessels. CVDs constitute a class of diseases that includes: coronary artery diseases (e.g. angina, heart attack), heart failure, hypertensive heart disease, rheuma ...
, and diabetes
Diabetes mellitus, commonly known as diabetes, is a group of common endocrine diseases characterized by sustained high blood sugar levels. Diabetes is due to either the pancreas not producing enough of the hormone insulin, or the cells of th ...
, among others.
The toxicity associated with consumption of foods high in cucurbitacins is sometimes referred to as "toxic squash syndrome". In France in 2018, two women who ate soup made from bitter pumpkins became sick, involving nausea
Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat.
Over 30 d ...
, vomit
Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose.
Vomiting can be the result of ailments like food poisoning, gastroenteritis, pregna ...
ing, and diarrhea
Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...
, and had hair loss weeks later. Another French study of poisoning from bitter squash consumption found similar acute illnesses and no deaths. The high concentration of toxin in the plants could result from cross-pollination
Xenogamy (Greek ''xenos''=stranger, ''gamos''=marriage) is the transfer of pollen grains from the anther to the stigma of a different plant. This is the only type of cross pollination which during pollination brings genetically different types of ...
with wild cucurbitaceae species, or from plant growth stress due to high temperature and drought
A drought is a period of drier-than-normal conditions.Douville, H., K. Raghavan, J. Renwick, R.P. Allan, P.A. Arias, M. Barlow, R. Cerezo-Mota, A. Cherchi, T.Y. Gan, J. Gergis, D. Jiang, A. Khan, W. Pokam Mba, D. Rosenfeld, J. Tierney, ...
.
See also
* Goyaglycoside *Hemslecin Hemslecin is any of several compounds obtained from plants of the genus ''Hemsleya'', which are used in Asian folk medicine. They are triterpene derivatives, specifically with the cucurbitane skeleton, related to cucurbitacin, cucurbitacin F.Jian-C ...
* Mogroside
* Momordicine
* Momordicoside
* Neomogroside
* Scandenosides R1–R8, R10-R11
* Siamenoside I
References
{{Tetracyclics Set index articles on chemistry Laxatives Plant toxins Steroidal glycosides Terpenoid glycosides