Class of biochemical compounds
Cucurbitacins
are a class of
biochemical
compounds that some plants ? notably members of the
pumpkin
and
gourd
family,
Cucurbitaceae
? produce and which function as a defense against
herbivores
. Cucurbitacins and their
derivatives
have also been found in many other plant families (including
Brassicaceae
,
Cucurbitaceae
,
Scrophulariaceae
,
Begoniaceae
,
Elaeocarpaceae
,
Datiscaceae
,
Desfontainiaceae
,
Polemoniaceae
,
Primulaceae
,
Rubiaceae
,
Sterculiaceae
,
Rosaceae
, and
Thymelaeaceae
), in some
mushrooms
(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, such as
cucumbers
and
zucchinis
.
[1]
In
laboratory research
, cucurbitacins have
cytotoxic
properties and are under study for their potential biological activity.
[2]
[3]
Cucurbitacins are chemically classified as
triterpenes
, formally derived from
cucurbitane
, a
triterpene
hydrocarbon
? specifically, from the unsaturated variant
cucurbit-5-ene
, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as
glycosides
.
[4]
Most cucurbitacins are
tetracyclic
except some have an extra ring due to formal
cyclization
between C
16
and C
24
as in
cucurbitacin S
and
cucurbitacin T
.
[5]
[6]
Biosynthesis
[
edit
]
The biosynthesis of cucurbitacin C has been described. Zhang et al. (2014) identified nine
cucumber
genes in the pathway for biosynthesis of cucurbitacin C and elucidated four catalytic steps.
[7]
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
)
[7]
Variants
[
edit
]
The cucurbitacins include:
Cucurbitacin A
[
edit
]
Cucurbitacin B
[
edit
]
- Cucurbitacin B
from
Hemsleya endecaphylla
(62 mg/72 g)
[9]
: 4
and other plants (e.g.
Cucurbita andreana
);
[10]
anti-inflammatory, any-hepatotoxic
[4]
: 2
- Cucurbitacin B 2-O-glucoside
, from
Begonia heracleifolia
[4]
: 3
- 23,24-Dihydrocucurbitacin B
from
Hemsleya endecaphylla
, 49 mg/72 g
[9]
: 5
- 23,24-Dihydrocucurbitacin B 2-O-glucoside
from roots of
Picrorhiza kurrooa
[4]
: 4
- Deacetoxycucurbitacin B 2-O-glucoside
from roots of
Picrorhiza kurrooa
[4]
: 5
- Isocucurbitacin B
, from
Echinocystis fabacea
[4]
: 6
- 23,24-Dihydroisocucurbitacin B 3-glucoside
from
Wilbrandia ebracteata
[4]
: 7
- 23,24-Dihydro-3-epi-isocucurbitacin B
, from
Bryonia verrucosa
[4]
: 8
- Pentanorcucurbitacin B
or 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid,
C
25
H
36
O
4
, white powder
[8]
: 2
Cucurbitacin C
[
edit
]
Cucurbitacin D
[
edit
]
Cucurbitacin E
[
edit
]
Cucurbitacin F
[
edit
]
Cucurbitacin G
[
edit
]
Cucurbitacin H
[
edit
]
Cucurbitacin I
[
edit
]
Cucurbitacin J
[
edit
]
Cucurbitacin K
[
edit
]
Cucurbitacin L
[
edit
]
Cucurbitacin O
[
edit
]
Cucurbitacin P
[
edit
]
Cucurbitacin Q
[
edit
]
Cucurbitacin R
[
edit
]
Cucurbitacin S
[
edit
]
Cucurbitacin T
[
edit
]
28/29 Norcucurbitacins
[
edit
]
| This section
needs expansion
. You can help by
adding to it
.
(
February 2022
)
|
There are several substances that can be seen as deriving from cucurbit-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
.
[4]
: 87?130
Other
[
edit
]
| This section
needs expansion
. You can help by
adding to it
.
(
February 2022
)
|
Several other cucurbitacins have been found in plants.
[4]
: 152?156, 164?165
Occurrence and bitter taste
[
edit
]
Constituents of the
colocynth
fruit and leaves (
Citrullus colocynthis
) include cucurbitacins.
[13]
[14]
[15]
The 2-O-β-D-
glucopyranosides
of cucurbitacins K and L can be extracted with
ethanol
from fruits of
Cucurbita pepo
cv
dayangua
.
[12]
Pentanorcucurbitacins A and B can be extracted with
methanol
from the stems of
Momordica charantia
.
[8]
Cucurbitacins B and I, and derivatives of cucurbitacins B, D and E, can be extracted with methanol from dried tubers of
Hemsleya endecaphylla
.
[9]
Cucurbitacins impart a bitter taste in plant foods such as
cucumber
,
zucchini
,
melon
and
pumpkin
.
[16]
[7]
Research and toxicity
[
edit
]
Cucurbitacins are under
basic research
for their biological properties, including
toxicity
and potential
pharmacological
uses in development of drugs for
inflammation
,
cancer
,
cardiovascular diseases
, and
diabetes
, among others.
[4]
[2]
[3]
[16]
The toxicity associated with consumption of foods high in cucurbitacins is sometimes referred to as "toxic squash syndrome".
[17]
[18]
In France in 2018, two women who ate soup made from bitter pumpkins became
sick
, involving
nausea
,
vomiting
, and
diarrhea
, and had hair loss weeks later.
[19]
Another French study of poisoning from bitter
squash
consumption found similar acute illnesses and no deaths.
[20]
The high concentration of toxin in the plants could result from
cross-pollination
[21]
with wild cucurbitaceae species, or from plant growth stress due to high temperature and
drought
.
[22]
See also
[
edit
]
References
[
edit
]
- ^
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.
Suddeutsche.de
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. Retrieved
2020-08-21
.
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b
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.
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.
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.
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:
10.1016/0031-9422(88)80031-1
.
ISSN
0031-9422
.
- ^
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.
Pharmacognosy Reviews
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9
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.
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4441156
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b
c
Shang Y, Ma Y, Zhou Y, Zhang H, Duan L, Chen H, et al. (November 2014). "Plant science. Biosynthesis, regulation, and domestication of bitterness in cucumber".
Science
.
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:
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.
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.
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25430763
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206561241
.
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a
b
c
Chen CR, Liao YW, Wang L, Kuo YH, Liu HJ, Shih WL, et al. (December 2010).
"Cucurbitane triterpenoids from Momordica charantia and their cytoprotective activity in tert-butyl hydroperoxide-induced hepatotoxicity of HepG2 cells"
.
Chemical & Pharmaceutical Bulletin
.
58
(12): 1639?42.
doi
:
10.1248/cpb.58.1639
.
PMID
21139270
.
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b
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d
e
f
g
Chen JC, Zhang GH, Zhang ZQ, Qiu MH, Zheng YT, Yang LM, et al. (January 2008). "Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity".
Journal of Natural Products
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71
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10.1021/np0704396
.
PMID
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.
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b
c
d
Halaweish FT, Tallamy DW (June 1993). "A new cucurbitacin profile forCucurbita andreana: A candidate for cucurbitacin tissue culture".
Journal of Chemical Ecology
.
19
(6): 1135?41.
Bibcode
:
1993JCEco..19.1135H
.
doi
:
10.1007/BF00987375
.
PMID
24249132
.
S2CID
23549863
.
- ^
Kupchan S, Meshulam H, Sneden AT (1978). "New cucurbitacins from Phormium tenax and Marah oreganus".
Phytochemistry
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:
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.
doi
:
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.
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a
b
c
Wang DC, Pan HY, Deng XM, Xiang H, Gao HY, Cai H, et al. (2007). "Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua".
Journal of Asian Natural Products Research
.
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.
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.
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.
- ^
Song F, Dai B, Zhang HY, Xie JW, Gu CZ, Zhang J (2015). "Two new cucurbitane-type triterpenoid saponins isolated from ethyl acetate extract of Citrullus colocynthis fruit".
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.
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.
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38269788
.
- ^
Chawech R, Jarraya R, Girardi C, Vansteelandt M, Marti G, Nasri I, et al. (September 2015).
"Cucurbitacins from the Leaves of Citrullus colocynthis (L.) Schrad"
.
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.
20
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doi
:
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.
PMC
6332406
.
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26437392
.
- ^
Kaushik U (January?June 2015).
"Cucurbitacins ? An insight into medicinal leads from nature"
.
Pharmacogn. Rev
.
v.9
(17): 12?18.
doi
:
10.4103/0973-7847.156314
.
PMC
4441156
.
PMID
26009687
.
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a
b
Kaushik U, Aeri V, Mir SR (2015).
"Cucurbitacins - An insight into medicinal leads from nature"
.
Pharmacognosy Reviews
.
9
(17): 12?8.
doi
:
10.4103/0973-7847.156314
.
PMC
4441156
.
PMID
26009687
.
- ^
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.
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- ^
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.
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. March 28, 2018.
- ^
Assouly P (May 2018). "Hair Loss Associated With Cucurbit Poisoning".
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.
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.
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.
|
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Chemokine
| |
---|
CSF
| |
---|
Interferon
| IFNAR (α/β, I)
|
- Agonists:
Albinterferon
- Interferon alpha (interferon alfa, IFN-α)
- Interferon alfa
(
IFNA1
,
IFNA2
,
IFNA4
,
IFNA5
,
IFNA6
,
IFNA7
,
IFNA8
,
IFNA10
,
IFNA13
,
IFNA14
,
IFNA16
,
IFNA17
,
IFNA21
)
- Interferon alfa 2a
- Interferon alfa 2b
- Interferon alfa n1
- Interferon alfacon-1
- Interferon alpha-n3
- Interferon beta (IFN-β)
(
IFNB1
,
IFNB3
)
- Interferon beta 1a
- Interferon beta 1b
- Interferon kappa (IFN-ε/κ/τ/ζ, IFNK)
- Interferon omega (IFN-ω, IFNW1)
- Peginterferon alfa-2a
- Peginterferon alfa-2b
|
---|
IFNGR (γ, II)
| |
---|
IFNLR (λ, III)
|
- See IL-28R (IFNLR)
here
instead.
|
---|
|
---|
Interleukin
| |
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TGFβ
| |
---|
TNF
| |
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Others
| |
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