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Cucurbitacin is a class of biochemical compounds that some plants – notably members of the
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin
A pumpkin is a vernacular term for mature winter squash of species and varieties in the genus '' Cucurbita'' that has culinary and cultural significance but no agreed upon botanical or scientific meaning. The term ''pumpkin'' is sometimes u ...
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. One of the e ...
family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpene 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 hydrophobic, and their odors are usually weak or ...
– 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 glycoside ...
s. They and their derivatives have been found in many plant families (including Brassicaceae
Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The l ...
, Cucurbitaceae, Scrophulariaceae, Begoniaceae, Elaeocarpaceae, Datiscaceae, Desfontainiaceae, Polemoniaceae, Primulaceae, Rubiaceae
The Rubiaceae are a 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 interpetiolar stipules ...
, Sterculiaceae, Rosaceae, and Thymelaeaceae), in some mushroom
A mushroom or toadstool is the fleshy, spore-bearing fruiting body of a fungus, typically produced above ground, on soil, or on its food source. ''Toadstool'' generally denotes one poisonous to humans.
The standard for the name "mushroom" is ...
s (including Russula and Hebeloma) 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, like cucumber
Cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the Cucurbitaceae family that bears usually cylindrical fruits, which are used as culinary vegetables.zucchini
The zucchini (; plural: zucchini or zucchinis), courgette (; plural: courgettes) or baby marrow ('' Cucurbita pepo'') is a summer squash, a vining herbaceous plant whose fruit are harvested when their immature seeds and epicarp (rind) are s ...
s. In laboratory research, cucurbitacins have cytotoxic
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa'').
Cell physiology
Treating ...
properties and are under study for their potential biological activity.
Biosynthesis
The biosynthesis of cucurbitacin C has been described. Zhang et al. (2014) identified ninecucumber
Cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the Cucurbitaceae family that bears usually cylindrical fruits, which are used as culinary vegetables. These authors also discovered the transcription factors ''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-like gene cluster, similar to the gene cluster involved in thalianol biosynthesis in '' Arabidopsis''. 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 of cucurbitadienol synthase gene CPQ in squash ('' Cucurbita pepo'')
*
*
Variants
The cucurbitacins include:Cucurbitacin A
* Cucurbitacin A
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
found in some species of '' Cucumis''
** Pentanorcucurbitacin A, or 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one , white powder
Cucurbitacin B
* Cucurbitacin B
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from '' Hemsleya endecaphylla'' (62 mg/72 g) and other plants (e.g. '' Cucurbita andreana''); anti-inflammatory, any-hepatotoxic
** Cucurbitacin B 2-O-glucoside, from ''Begonia heracleifolia
''Begonia heracleifolia'', the star begonia, is a species of flowering plant in the family Begoniaceae. It is native to Mexico and northern Central America, and has been introduced to Cuba, Hispaniola
Hispaniola (, also ; es, La Española; ...
''
** 23,24-Dihydrocucurbitacin B from ''Hemsleya endecaphylla'', 49 mg/72 g
** 23,24-Dihydrocucurbitacin B 2-O-glucoside from roots of ''Picrorhiza kurrooa
''Picrorhiza kurroa'' is one of the major income generating non-timber forest products found in the Nepalese Himalayas. It is one of the oldest medicinal plants traded from the Karnali zone. Known as kutki or कुटकी in Nepali, it is a pe ...
''
** Deacetoxycucurbitacin B 2-O-glucoside from roots of ''Picrorhiza kurrooa
''Picrorhiza kurroa'' is one of the major income generating non-timber forest products found in the Nepalese Himalayas. It is one of the oldest medicinal plants traded from the Karnali zone. Known as kutki or कुटकी in Nepali, it is a pe ...
''
** Isocucurbitacin B, from ''Echinocystis fabacea
''Echinocystis'' is a monotypic genus in the gourd family, Cucurbitaceae. The sole species is ''E. lobata'', commonly called wild cucumber, prickly cucumber or bur cucumber. It is an annual, sprawling plant that is native to North America.
Descr ...
''
** 23,24-Dihydroisocucurbitacin B 3-glucoside from '' Wilbrandia ebracteata''
** 23,24-Dihydro-3-epi-isocucurbitacin B, from ''Bryonia verrucosa
''Bryonia'' is a genus of flowering plants in the gourd family. Bryony is its best-known common name. They are native to western Eurasia and adjacent regions, such as North Africa, the Canary Islands and South Asia.
Description and ecology
B ...
''
** 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
Cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the Cucurbitaceae family that bears usually cylindrical fruits, which are used as culinary vegetables.
*
*
*
Constituents of the colocynth fruit and leaves ('' Citrullus colocynthis'') include cucurbitacins. The 2-O-β-D- glucopyranosides of cucurbitacins K and L can be extracted with
Cucurbitacin D
Cucurbitacin D is a plant steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes ...
, from '' Trichosanthes kirilowii'' and many other plants (e.g. '' Cucurbita andreana'')
** 3-Epi-isocucurbitacin D, from species of '' Physocarpus'' and ''Phormium tenax
''Phormium tenax'' (called flax in New Zealand English; in 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 Island that is an ...
''
** 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''
** 22-Deoxocucurbitacin D from '' Wilbrandia ebracteata''
** Anhydro-22-deoxo-3-epi-isocucurbitacin D from '' Ecballium elaterium''
** 25-O-Acetyl-2-deoxycucurbitacin D (amarinin) from '' Luffa amara''
** 2-Deoxycucurbitacin D, from ''Sloanea zuliaensis
''Sloanea'' is a genus of flowering plants in the family Elaeocarpaceae, comprising about 150 species.
Species include:
* ''Sloanea acutiflora'' Uittien
* ''Sloanea assamica'' Rehder & E. Wilson
* '' Sloanea australis'' Benth. & F.Muell., an A ...
''
Cucurbitacin E
* Cucurbitacin E (α-Elaterin), from roots of '' Wilbrandia ebracteata''. Strong antifeedant for the flea beetle, inhibits cell adhesion (also in e.g. '' Cucurbita andreana'') **22,23-Dihydrocucurbitacin E
The comma is a punctuation mark that appears in several variants in different languages. It has the same shape as an apostrophe or single closing quotation mark () in many typefaces, but it differs from them in being placed on the baseline o ...
from ''Hemsleya endecaphylla'', 9 mg/72 g, and from roots of ''Wilbrandia ebracteata''
** 22,23-Dihydrocucurbitacin E 2-glucoside
The comma is a punctuation mark that appears in several variants in different languages. It has the same shape as an apostrophe or single closing quotation mark () in many typefaces, but it differs from them in being placed on the baseline o ...
from roots of ''Wilbrandia ebracteata''
** Isocucurbitacin E, from '' Cucumis prophetarum''
** 23,24-Dihydroisocucurbitacin E, from ''Cucumis prophetarum''
Cucurbitacin F
*Cucurbitacin F
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from ''Elaeocarpus dolichostylus
''Elaeocarpus'' is a genus of nearly five hundred species of flowering plants in the family Elaeocarpaceae native to the Western Indian Ocean, Tropical and Subtropical Asia, and the Pacific. Plants in the genus ''Elaeocarpus'' are trees or shrubs ...
''
** 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, cucurbitacin F.Jian-C ...
)
** 23,24-Dihydrocucurbitacin F glucoside from ''Helmseya amabilis''
** Cucurbitacin II glucoside from ''Helmseya amabilis''
** Hexanorcucurbitacin F from ''Elaeocarpus dolichostylus
''Elaeocarpus'' is a genus of nearly five hundred species of flowering plants in the family Elaeocarpaceae native to the Western Indian Ocean, Tropical and Subtropical Asia, and the Pacific. Plants in the genus ''Elaeocarpus'' are trees or shrubs ...
''
** Perseapicroside A Perseapicroside is any one of several chemical compounds isolated from certain plants, notably '' Persea mexicana''. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane (), more specifically from cucurbitacin F
Cucurbi ...
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
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from roots of ''Wilbrandia ebracteata''
* 3-Epi-isocucurbitacin G, from roots of ''Wilbrandia ebracteata''
Cucurbitacin H
*Cucurbitacin H
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
, stereoisomer of cucurbitacin G, from roots of ''Wilbrandia ebracteata''
Cucurbitacin I
* Cucurbitacin I
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
( elatericin B) from '' Hemsleya endecaphylla'', 10 mg/72 g, also from '' Ecballium elaterium'' '' Citrullus colocynthis'', '' Cucurbita andreana'', deters feeding by flea beetle
** Hexanorcucurbitacin I from ''Ecballium elaterium''
** 23,24-Dihydrocucurbitacin I see Cucurbitacin L
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
** Khekadaengosides D and K from the fruits of '' Trichosanthes tricuspidata''
** 11-Deoxocucurbitacin I, from '' Desfontainia spinosa''
** Spinosides A and B, from ''Desfontainia spinosa''
** 23,24-dihydro-11-Deoxocucurbitacin I from ''Desfontainia spinosa''
Cucurbitacin J
* Cucurbitacin J from '' Iberis amara'' ** Cucurbitacin J 2-O-β-glucopyranoside from ''Trichosanthes tricuspidata''Cucurbitacin K
*Cucurbitacin K
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
, stereoisomer of cucurbitacin J, from '' Iberis amara''
** Cucurbitacin K 2-O-β-glucopyranoside from ''Trichosanthes tricuspidata''
Cucurbitacin L
*Cucurbitacin L
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
, or 23,24-dihydrocucurbitacin I,
** Brydioside A Brydioside is any one of several chemical compounds isolated from certain plants, notably ''Bryonia dioica''. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane (), more specifically from cucurbitacin L
Cucurbitacin is a ...
from '' Bryonia dioica''
** Bryoamaride
Bryoamaride is a chemical compound isolated from certain plants, notably ''Bryonia dioica''. It can be seen as a derivative of the triterpene hydrocarbon cucurbitane (), more specifically from cucurbitacin L
Cucurbitacin is a class of bio ...
from ''Bryonia dioica''
** 25-O-Acetylbryoamaride from ''Trichosanthes tricuspidata''
** Khekadaengosides A and B from ''Trichosanthes tricuspidata''
Cucurbitacin O
*Cucurbitacin O
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from ''Brandegea bigelovii
''Brandegea'' is a monotypic genus containing the single species ''Brandegea bigelovii'', the desert starvine. This sprawling perennial vine in the squash family is native to the deserts of California, Arizona, and northern Mexico. The distincti ...
''
** Cucurbitacin Q 2-O-glucoside, from ''Picrorhiza kurrooa
''Picrorhiza kurroa'' is one of the major income generating non-timber forest products found in the Nepalese Himalayas. It is one of the oldest medicinal plants traded from the Karnali zone. Known as kutki or कुटकी in Nepali, it is a pe ...
''
** 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
''Brandegea'' is a monotypic genus containing the single species ''Brandegea bigelovii'', the desert starvine. This sprawling perennial vine in the squash family is native to the deserts of California, Arizona, and northern Mexico. The distincti ...
''
** Picracin from ''Picrorhiza scrophulariaeflora''
** Picracin 2-O-glucoside from ''Picrorhiza scrophulariaeflora''
Cucurbitacin Q
* Cucurbitacin Q
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
from ''Brandegea bigelovii''
** 23,24-Dihydrodeacetylpicracin 2-O-glucoside from ''Picrorhiza kurrooa''
** Cucurbitacin Q1
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from ''Cucumis'' species, actually Cucurbitacin F 25-acetate
Cucurbitacin R
*Cucurbitacin R
Cucurbitacin is a class of biochemistry, biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically clas ...
is actually 23,24-dihydrocucurbitacin D.
Cucurbitacin S
*Cucurbitacin S
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
from '' Bryonia dioica''
Cucurbitacin T
*Cucurbitacin T
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as t ...
, from the fruits of '' Citrullus colocynthis''
28/29 Norcucurbitacins
There are several substances that can be seen as deriving from cucurbita-5-ene skeleton by loss of one of the methyl groups (28 or 29) attached to carbon 4; often with the adjacent ring (ring A) becoming aromatic.Other
Several other cucurbitacins have been found in plants.Occurrence and bitter taste
Constituents of the colocynth fruit and leaves ('' Citrullus colocynthis'') include cucurbitacins. The 2-O-β-D- glucopyranosides of cucurbitacins K and L can be extracted with ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...
from fruits of '' Cucurbita pepo'' cv ''dayangua''. Pentanorcucurbitacins A and B can be extracted with methanol from the stems of ''Momordica charantia
''Momordica charantia'' (commonly called bitter melon; Goya; bitter apple; bitter gourd; bitter squash; balsam-pear; with many more names listed below) is a tropical and subtropical vine of the family Cucurbitaceae, widely grown in Asia, A ...
''. 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
Cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the Cucurbitaceae family that bears usually cylindrical fruits, which are used as culinary vegetables.zucchini
The zucchini (; plural: zucchini or zucchinis), courgette (; plural: courgettes) or baby marrow ('' Cucurbita pepo'') is a summer squash, a vining herbaceous plant whose fruit are harvested when their immature seeds and epicarp (rind) are s ...
, melon and pumpkin
A pumpkin is a vernacular term for mature winter squash of species and varieties in the genus '' Cucurbita'' that has culinary and cultural significance but no agreed upon botanical or scientific meaning. The term ''pumpkin'' is sometimes u ...
.
Research and toxicity
Cucurbitacins are under basic research for their biological properties, includingtoxicity
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, bacterium, or plant, as well as the effect on a subs ...
and potential pharmacological uses in development of drugs for inflammation
Inflammation (from la, wikt:en:inflammatio#Latin, inflammatio) is part of the complex biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or Irritation, irritants, and is a protective response involving im ...
, cancer
Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal bl ...
, cardiovascular diseases, and diabetes
Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level (hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased ...
, 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. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...
, vomit
Vomiting (also known as emesis and throwing up) is the involuntary, 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, gastroenteri ...
ing, and diarrhea
Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin ...
, 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 with wild cucurbitaceae species, or from plant growth stress due to high temperature and drought
A drought is defined as 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, an ...
.
See also
* Goyaglycoside * Hemslecin * Mogroside * Momordicine * Momordicoside * Neomogroside * Scandenosides R1–R8, R10-R11 * Siamenoside IReferences
{{Cytokine receptor modulators Chemistry set index articles Laxatives Plant toxins Steroidal glycosides Terpenoid glycosides