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 and ...
compounds that some plants – notably members of the pumpkin and gourd 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
*'' Lagen ...
– 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 mouthp ...
s. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpenehydrocarbon – specifically, from the unsaturated variant cucurbit-5-ene, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides. 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 leav ...
,
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
*'' Lagen ...
,
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 Sc ...
,
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
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 plant ...
,
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 25 genera with 270–400 species of annuals and perennials native to the Northern Hemisphere and South America, with the center of diver ...
,
Primulaceae
The Primulaceae , commonly known as the primrose family (but not related to the evening primrose family), are a family of herbaceous and woody flowering plants including some favourite garden plants and wildflowers. Most are perennial though so ...
,
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 a ...
,
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.
...
,
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 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 sti ...
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 cel ...
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 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
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-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 organis ...
''. 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 spe ...
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 be ...
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 m ...
''
** Pentanorcucurbitacin A, or 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one , white powder
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 ...
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.
* 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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 distinc ...
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 ...
'' ''
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 ...
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 ...
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 Fre ...
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, 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 ...
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 Cucurbita ...
''
**
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
Cucurbitane is a class of chemical compounds with formula ( CAS number 65441 ...
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 Cucurbita ...
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 man ...
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 satu ...
.
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 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 be ...
'' 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, Afri ...
''. 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 sti ...
,
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 ...
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 researc ...
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 subs ...
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 biochemic ...
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, hea ...
, and diabetes, 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,
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, gastroenteritis ...
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, bird ...
with wild cucurbitaceae species, or from plant growth stress due to high temperature and drought.
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, Ga ...
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, ...