![Cucurbitacin-E-from-xtal-3D-st](https://upload.wikimedia.org/wikipedia/commons/d/de/Cucurbitacin-E-from-xtal-3D-st.png)
Cucurbitacin is 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 an ...
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 use ...
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 earli ...
family,
Cucurbitaceae
The Cucurbitaceae, also called cucurbits or the gourd family, are a plant family consisting of about 965 species in around 95 genera, of which the most important to humans are:
*''Cucurbita'' – squash, pumpkin, zucchini, some gourds
*''Lagena ...
– produce and which function as a defence against
herbivore
A herbivore is an animal anatomically and physiologically adapted to eating plant material, for example foliage or marine algae, for the main component of its diet. As a result of their plant diet, herbivorous animals typically have mouthpart ...
s. Cucurbitacins are chemically classified as
triterpene
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squale ...
s, formally derived from
cucurbitane
Cucurbitane is a class of chemical compounds with formula ( CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by ...
, a
triterpene
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squale ...
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 ex ...
– 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.
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 le ...
,
Cucurbitaceae
The Cucurbitaceae, also called cucurbits or the gourd family, are a plant family consisting of about 965 species in around 95 genera, of which the most important to humans are:
*''Cucurbita'' – squash, pumpkin, zucchini, some gourds
*''Lagena ...
,
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 d ...
,
Elaeocarpaceae
Elaeaocarpaceae 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: Be ...
,
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 Fr ...
,
Polemoniaceae
The Polemoniaceae (Jacob's-ladder or phlox family) are a family of flowering plants consisting of about 25 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 plants ...
,
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 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 Sterculioideae.
A ...
,
Rosaceae
Rosaceae (), the rose family, is a medium-sized family of flowering plants that includes 4,828 known species in 91 genera.
The name is derived from the type genus ''Rosa''. Among the most species-rich genera are ''Alchemilla'' (270), ''Sorbus ...
, and
Thymelaeaceae
The Thymelaeaceae are a cosmopolitan 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 Website, St. Louis. It ...
), 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 t ...
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 Vine#Horticultural climbing plants, creeping vine plant in the Cucurbitaceae family that bears usually cylindrical Fruit, fruits, which are used as culinary vegetables. s and
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 stil ...
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 cells ...
properties and are under study for their potential biological activity.
Biosynthesis
The biosynthesis of cucurbitacin C has been described. Zhang et al. (2014) identified nine
cucumber
Cucumber (''Cucumis sativus'') is a widely-cultivated Vine#Horticultural climbing plants, creeping vine plant in the Cucurbitaceae family that bears usually cylindrical Fruit, fruits, which are used as culinary vegetables. genes in the pathway for biosynthesis of cucurbitacin C and elucidated four catalytic steps.
These authors also discovered the
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 func ...
''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 organi ...
''. 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 spec ...
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](https://upload.wikimedia.org/wikipedia/commons/d/d4/Cucurbitacin_A.svg)
*
Cucurbitacin A found in some species of ''
Cucumis
__NOTOC__
''Cucumis'' is a genus of twining, tendril-bearing plants in the family Cucurbitaceae which includes the cucumber (''Cucumis sativus''), muskmelons (''Cucumis melo'', including cantaloupe and honeydew), the horned melon ('' Cucumis ...
''
[
** Pentanorcucurbitacin A, or 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one , white powder][
]
Cucurbitacin B
* Cucurbitacin B from ''Hemsleya endecaphylla
''Hemsleya'' is a genus of flowering plants belonging to the family Cucurbitaceae.
Its native range is Eastern Himalayas to southern China and Papuasia. It is native to the countries of Assam (in India), Bismarck Archipelago (island group, part ...
'' (62 mg/72 g)[ and other plants (e.g. '']Cucurbita andreana
''Cucurbita maxima'', one of at least five species of cultivated squash, is one of the most diverse domesticated species. This species originated in South America from the wild subspecies ''Cucurbita maxima subsp. andreana'' over 4,000 years ago ...
''); 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''][
** Deacetoxycucurbitacin B 2-O-glucoside from roots of '' Picrorhiza kurrooa''][
** Isocucurbitacin B, from '' Echinocystis fabacea''][
** 23,24-Dihydroisocucurbitacin B 3-glucoside from '']Wilbrandia ebracteata
''Wilbrandia'' is a genus of flowering plants belonging to the family Cucurbitaceae. It is also in Tribe Coniandreae.
It is native to Brazil, Paraguay and north-eastern Argentina.
Known species
As accepted by Plants of the World Online:
The g ...
''[
** 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
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 sativus'' (cucumber
Cucumber (''Cucumis sativus'') is a widely-cultivated Vine#Horticultural climbing plants, creeping vine plant in the Cucurbitaceae family that bears usually cylindrical Fruit, fruits, which are used as culinary vegetables. )[
]
Cucurbitacin D
* Cucurbitacin D, from ''Trichosanthes kirilowii
''Trichosanthes kirilowii'' is a flowering plant in the family Cucurbitaceae found particularly in Henan, Shandong, Hebei, Shanxi, and Shaanxi. It is one of the 50 fundamental herbs used in traditional Chinese medicine, where it shares the name ...
'' and many other plants[ (e.g. '']Cucurbita andreana
''Cucurbita maxima'', one of at least five species of cultivated squash, is one of the most diverse domesticated species. This species originated in South America from the wild subspecies ''Cucurbita maxima subsp. andreana'' over 4,000 years ago ...
'')
** 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 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 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, somewhat ...
''[
** 22-Deoxocucurbitacin D from '']Wilbrandia ebracteata
''Wilbrandia'' is a genus of flowering plants belonging to the family Cucurbitaceae. It is also in Tribe Coniandreae.
It is native to Brazil, Paraguay and north-eastern Argentina.
Known species
As accepted by Plants of the World Online:
The g ...
''[
** 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 or exploding cucumber (not the same plant as ''Cyclanthera brachystachya''). Its u ...
''[
** 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
''Wilbrandia'' is a genus of flowering plants belonging to the family Cucurbitaceae. It is also in Tribe Coniandreae.
It is native to Brazil, Paraguay and north-eastern Argentina.
Known species
As accepted by Plants of the World Online:
The g ...
''. Strong antifeedant
Antifeedants are organic compounds produced by plants to inhibit attack by insects and grazing animals. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but i ...
for the flea beetle
The flea beetle is a small, jumping beetle of the leaf beetle family (Chrysomelidae), that makes up the tribe Alticini which is part of the subfamily Galerucinae. Historically the flea beetles were classified as their own subfamily.
Though m ...
, 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 junctions or indir ...
[ (also in e.g. '']Cucurbita andreana
''Cucurbita maxima'', one of at least five species of cultivated squash, is one of the most diverse domesticated species. This species originated in South America from the wild subspecies ''Cucurbita maxima subsp. andreana'' over 4,000 years ago ...
'')
** 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
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 '' Elaeocarpus dolichostylus''[
** ]Cucurbitacin F 25-acetate
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 '' Helmseya graciliflora''[
** 23,24-Dihydrocucurbitacin F from '' Helmseya amabilis''][
** 25-Acetoxy-23,24-dihydrocucurbitacin F from '' Helmseya amabilis'' ( hemslecin A)][
** 23,24-Dihydrocucurbitacin F glucoside from ''Helmseya amabilis''][
** Cucurbitacin II glucoside from ''Helmseya amabilis''][
** Hexanorcucurbitacin F from '' Elaeocarpus dolichostylus''][
** Perseapicroside A from '']Persea mexicana
''Persea'' is a genus of about 150 species of evergreen trees belonging to the laurel family, Lauraceae. The best-known member of the genus is the avocado, ''P. americana'', widely cultivated in subtropical regions for its large, edible fruit.
O ...
''[
** Scandenoside R9 from '']Hemsleya panacis-scandens
''Hemsleya'' is a genus of flowering plants belonging to the family Cucurbitaceae.
Its native range is Eastern Himalayas to southern China and Papuasia. It is native to the countries of Assam (in India), Bismarck Archipelago (island group, part ...
''[
** 15-Oxo-cucurbitacin F from '']Cowania mexicana
''Purshia mexicana'' is a species of perennial flowering small tree in the rose family known by the common name Mexican cliffrose. It is native to western-northern Mexico, the region of the Sierra Madre Occidental cordillera.
'' Purshia stansbur ...
''[
** 15-oxo-23,24-dihydrocucurbitacin F from ''Cowania mexicana''][
** Datiscosides B, D, and H, from '']Datisca glomerata
''Datisca glomerata'' is a species of plant native to California, Nevada, and Baja California known by the common name Durango root. It is one of only two to four species in the plant family Datiscaceae. It is an erect perennial herb with distin ...
''[
]
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
''Hemsleya'' is a genus of flowering plants belonging to the family Cucurbitaceae.
Its native range is Eastern Himalayas to southern China and Papuasia. It is native to the countries of Assam (in India), Bismarck Archipelago (island group, part ...
'', 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 or exploding cucumber (not the same plant as ''Cyclanthera brachystachya''). Its u ...
''[ '']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 desert viny plant native to the Mediterranean Basin and ...
'',[ '']Cucurbita andreana
''Cucurbita maxima'', one of at least five species of cultivated squash, is one of the most diverse domesticated species. This species originated in South America from the wild subspecies ''Cucurbita maxima subsp. andreana'' over 4,000 years ago ...
'', deters feeding by flea beetle
The flea beetle is a small, jumping beetle of the leaf beetle family (Chrysomelidae), that makes up the tribe Alticini which is part of the subfamily Galerucinae. Historically the flea beetles were classified as their own subfamily.
Though m ...
[
** 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) Cruciferae () is a medium-sized and economically important family of flow ...
''[
** 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) Cruciferae () is a medium-sized and economically important family of flow ...
''[
** 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
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 trit ...
, from '' Picrorhiza kurrooa''[
** 16-Deoxy-D-16-hexanorcucurbitacin O from ''Ecballium elaterium''][
** Deacetylpicracin from '']Picrorhiza scrophulariaeflora
''Picrorhiza'' is a genus of flowering plants belonging to the family Plantaginaceae.
Its native range is Pakistan to Western Himalaya.
Species:
*''Picrorhiza kurroa
''Picrorhiza kurroa'' is one of the major income generating non-timber fo ...
''[
** Deacetylpicracin 2-O-glucoside from ''Picrorhiza scrophulariaeflora''][
** 22-Deoxocucurbitacin O from '']Wilbrandia ebracteata
''Wilbrandia'' is a genus of flowering plants belonging to the family Cucurbitaceae. It is also in Tribe Coniandreae.
It is native to Brazil, Paraguay and north-eastern Argentina.
Known species
As accepted by Plants of the World Online:
The g ...
''[
]
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
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 trit ...
from ''Cucumis'' species, actually Cucurbitacin F 25-acetate[
]
Cucurbitacin R
* Cucurbitacin R 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 trit ...
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 desert viny plant native to the Mediterranean Basin and ...
''[
]
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
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
groups (28 or 29) attached to carbon 4; often with the adjacent ring (ring A) becoming aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
.[
]
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 desert viny plant native to the Mediterranean Basin and ...
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 desert viny plant native to the Mediterranean Basin and ...
'') 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 (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...
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 and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
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, Afr ...
''. 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 Vine#Horticultural climbing plants, creeping vine plant in the Cucurbitaceae family that bears usually cylindrical Fruit, 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 stil ...
, melon
A melon is any of various plants of the family Cucurbitaceae with sweet, edible, and fleshy fruit. The word "melon" can refer to either the plant or specifically to the fruit. Botanically, a melon is a kind of berry, specifically a "pepo". The ...
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 use ...
.
Research and toxicity
Cucurbitacins are under basic research
Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenomena. In contrast, applied resear ...
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, bacterium, or plant, as well as the effect on a subst ...
and potential pharmacological
Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...
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 b ...
, cardiovascular diseases
Cardiovascular disease (CVD) is a class of diseases that involve the heart or blood vessels. CVD includes coronary artery diseases (CAD) such as angina and myocardial infarction (commonly known as a heart attack). Other CVDs include stroke, ...
, 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 ap ...
, 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
Sick may refer to:
Medical conditions
* Having a disease or infection
* Vomiting (British)
Music
* The Sick, a Swedish band formed by two members of Dozer
Albums
* Sick (Loaded album), ''Sick'' (Loaded album), 2009
* Sick (Massacra album), ' ...
, 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, gastroenteriti ...
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 wi ...
, and had hair loss weeks later. Another French study of poisoning from bitter squash
Squash may refer to:
Sports
* Squash (sport), the high-speed racquet sport also known as squash racquets
* Squash (professional wrestling), an extremely one-sided match in professional wrestling
* Squash tennis, a game similar to squash but pla ...
consumption found similar acute illnesses and no deaths. The high concentration of toxin in the plants could result from cross-pollination
Pollination is the transfer of pollen from an anther of a plant to the stigma of a plant, later enabling fertilisation and the production of seeds, most often by an animal or by wind. Pollinating agents can be animals such as insects, birds, ...
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 Goyaglycoside is any of several related triterpenoid glycosides found in the fruits bitter melon vine (''Momordica charantia''), called ''goya'' in Okinawan language. They include:
* goyaglycoside c.
* goyaglycoside d.
Goyaglycosides c and d can ...
* 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 F.Jian-Chao Chen, Gao ...
* Mogroside
A mogroside is a glycoside of cucurbitane derivatives found in certain plants, such as the fruit of the gourd vine ''Siraitia grosvenorii'' (known as monkfruit or luo han guo).Subhuti Dharmananda (January 2004)"Luo han guo - Sweet fruit used as su ...
* Momordicine A momordicine is any of several compounds found in the bitter melon vine, ''Momordica charantia''. They are glycosides of cucurbitane derivatives.Daniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glu ...
* Momordicoside Momordicoside is any of several related cucurbitane triterpenoid glycosides that can be extracted from the bitter melon vine (''Momordica charantia'').Toshihiro Akihisa, Naoki Higo, Harukuni Tokuda, Motohiko Ukiya, Hiroyuki Akazawa, Yuichi Tochigi, ...
* Neomogroside
Neomogroside is a cucurbitane glycoside isolated from the fruit of ''Siraitia grosvenorii
''Siraitia grosvenorii'', also known as monkfruit or ''luohan guo'', is a herbaceous perennial vine of the gourd family, Cucurbitaceae. It is native to so ...
* Scandenosides R1–R8, R10-R11
* Siamenoside I
References
{{Cytokine receptor modulators
Chemistry set index articles
Laxatives
Plant toxins
Steroidal glycosides
Terpenoid glycosides