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Cucurbitacin
Cucurbitacin
is any of a class of biochemical compounds that some plants — notably members of the family Cucurbitaceae, which includes the common pumpkins and gourds — produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as steroids, formally derived from cucurbitane, a triterpene hydrocarbon—specifically, from the unsaturated variant cucurbita-5-ene, or 19-(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides.[1] They and their derivatives have been found in many 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, like cucumbers. In laboratory research, cucurbitacins have cytotoxic properties and are under study for their potential biological activities.[2][3]

Contents

1 Biosynthesis 2 Variants

2.1 Cucurbitacin
Cucurbitacin
A 2.2 Cucurbitacin
Cucurbitacin
B 2.3 Cucurbitacin
Cucurbitacin
C 2.4 Cucurbitacin
Cucurbitacin
D 2.5 Cucurbitacin
Cucurbitacin
E 2.6 Cucurbitacin
Cucurbitacin
F 2.7 Cucurbitacin
Cucurbitacin
G 2.8 Cucurbitacin
Cucurbitacin
H 2.9 Cucurbitacin
Cucurbitacin
I 2.10 Cucurbitacin
Cucurbitacin
J 2.11 Cucurbitacin
Cucurbitacin
K 2.12 Cucurbitacin
Cucurbitacin
L 2.13 Cucurbitacin
Cucurbitacin
O 2.14 Cucurbitacin
Cucurbitacin
P 2.15 Cucurbitacin
Cucurbitacin
Q 2.16 Cucurbitacin
Cucurbitacin
R 2.17 Cucurbitacin
Cucurbitacin
S 2.18 Cucurbitacin
Cucurbitacin
T 2.19 28/29 Norcucurbitacins 2.20 Other

3 Occurrence and bitter taste 4 Research and toxicity 5 See also 6 References

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.[4] 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) [4] Variants[edit] The cucurbitacins include: Cucurbitacin
Cucurbitacin
A[edit]

Cucurbitacin
Cucurbitacin
A

Cucurbitacin A
Cucurbitacin A
found in some species of Cucumis
Cucumis
[1]:1

Pentanorcucurbitacin A, or 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one C 25H 40O 2, white powder[5]:1

Cucurbitacin
Cucurbitacin
B[edit]

Cucurbitacin
Cucurbitacin
B

Cucurbitacin B
Cucurbitacin B
from Hemsleya endecaphylla (62 mg/72 g)[6]:4 and other plants (e.g. Cucurbita andreana[7]); anti-inflammatory, any-hepatotoxic [1]:2

Cucurbitacin B
Cucurbitacin B
2-O-glucoside, from Begonia heracleifolia [1]:3 23,24-Dihydrocucurbitacin B from Hemsleya endecaphylla, 49 mg/72 g[6]:5 23,24-Dihydrocucurbitacin B 2-O-glucoside from roots of Picrorhiza kurrooa [1]:4 Deacetoxycucurbitacin B 2-O-glucoside from roots of Picrorhiza kurrooa [1]:5 Isocucurbitacin B, from Echinocystis fabacea [1]:6 23,24-Dihydroisocucurbitacin B 3-glucoside from Wilbrandia ebracteata [1]:7 23,24-Dihydro-3-epi-isocucurbitacin B, from Bryonia verrucosa [1]:8 Pentanorcucurbitacin B or 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid, C 25H 36O 4, white powder[5]:2

Cucurbitacin
Cucurbitacin
C[edit]

Cucurbitacin
Cucurbitacin
C, from Cucumis
Cucumis
sativus (Cucumber) [1]:11

Cucurbitacin
Cucurbitacin
D[edit]

Cucurbitacin
Cucurbitacin
D

Cucurbitacin
Cucurbitacin
D, from Trichosanthes kirilowii
Trichosanthes kirilowii
and many other plants [1] (e.g. Cucurbita andreana[7]):12

3-Epi-isocucurbitacin D, from species of Physocarpus
Physocarpus
[1]:14 and Phormium tenax[8] 22-Deoxocucurbitacin D from Hemsleya endecaphylla, 14 mg/72 g[6]:6 23,24-Dihydrocucurbitacin D from Trichosanthes kirilowii
Trichosanthes kirilowii
[1]:13 also from H. endecaphylla, 80 mg/72 g[6]:3 23,24-Dihydro-epi-isocucurbitacin D, from Acanthosicyos horridus [1]:20 22-Deoxocucurbitacin D from Wilbrandia ebracteata [1]:21 Anhydro-22-deoxo-3-epi-isocucurbitacin D from Ecballium
Ecballium
elaterium [1]:22 25-O-Acetyl-2-deoxycucurbitacin D (amarinin) from Luffa amara [1]:24 2-Deoxycucurbitacin D, from Sloanea zuliaensis [1]:23

Cucurbitacin
Cucurbitacin
E[edit]

Cucurbitacin E
Cucurbitacin E
(aelaterin), from roots of Wilbrandia ebracteata. Strong antifeedant for the flea beetle, inhibits cell adhesion [1] (also in e.g. Cucurbita andreana[7]):27

22,23-Dihydrocucurbitacin E from Hemsleya endecaphylla, 9 mg/72 g,[6]:8 and from roots of Wilbrandia ebracteata [1]:28 22,23-Dihydrocucurbitacin E 2-glucoside from roots of Wilbrandia ebracteata [1]:29 Isocucurbitacin E, from Cucumis
Cucumis
prophetarum [1]:30 23,24-Dihydroisocucurbitacin E, from Cucumis
Cucumis
prophetarum [1]:31

Cucurbitacin
Cucurbitacin
F[edit]

Cucurbitacin
Cucurbitacin
F from Elaeocarpus dolichostylus [1]:33

Cucurbitacin
Cucurbitacin
F 25-acetate from Helmseya graciliflora [1]:34 23,24-Dihydrocucurbitacin F from Helmseya amabilis [1]:35 25-Acetoxy-23,24-dihydrocucurbitacin F from Helmseya amabilis (hemslecin A) [1]:36 23,24-Dihydrocucurbitacin F glucoside from Helmseya amabilis [1]:40 Cucurbitacin
Cucurbitacin
II glucoside from Helmseya amabilis [1]:41 Hexanorcucurbitacin F from Elaeocarpus dolichostylus [1]:43 Perseapicroside A from Persea mexicana [1]:44 Scandenoside R9 from Hemsleya panacis-scandens [1]:45 15-Oxo-cucurbitacin F from Cowania mexicana [1]:46 15-oxo-23,24-dihydrocucurbitacin F from Cowania mexicana [1]:47 Datiscosides B, D, and H, from Datisca glomerata [1]:48–50

Cucurbitacin
Cucurbitacin
G[edit]

Cucurbitacin
Cucurbitacin
G from roots of Wilbrandia ebracteata [1]:52 3-Epi-isocucurbitacin G, from roots of Wilbrandia ebracteata [1]:54

Cucurbitacin
Cucurbitacin
H[edit]

Cucurbitacin
Cucurbitacin
H, stereoisomer of cucurbitacin G, from roots of Wilbrandia ebracteata [1]:53

Cucurbitacin
Cucurbitacin
I[edit]

Cucurbitacin
Cucurbitacin
I

Cucurbitacin I
Cucurbitacin I
(elatericin B) from Hemsleya endecaphylla, 10 mg/72 g,[6]:7 also from Ecballium
Ecballium
elaterium,[1] Citrullus colocynthis,[1] Cucurbita andreana,[7] deters feeding by flea beetle [1]:55

Hexanorcucurbitacin I from Ecballium elaterium
Ecballium elaterium
[1]:56 23,24-Dihydrocucurbitacin I see Cucurbitacin
Cucurbitacin
L Khekadaengosides D and K from the fruits of Trichosanthes tricuspidata [1]:57,58 11-Deoxocucurbitacin I, from Desfontainia spinosa
Desfontainia spinosa
[1]:59 Spinosides A and B, from Desfontainia spinosa
Desfontainia spinosa
[1]:61,62 23,24-dihydro-11-Deoxocucurbitacin I from Desfontainia spinosa
Desfontainia spinosa
[1]:60

Cucurbitacin
Cucurbitacin
J[edit]

Cucurbitacin
Cucurbitacin
J from Iberis amara [1]:69

Cucurbitacin
Cucurbitacin
J 2-O-β-glucopyranoside from Trichosanthes tricuspidata [1]:71

Cucurbitacin
Cucurbitacin
K[edit]

Cucurbitacin
Cucurbitacin
K, stereoisomer of cucurbitacin J,[9]:2 from Iberis amara [1]:70

Cucurbitacin
Cucurbitacin
K 2-O-β-glucopyranoside from Trichosanthes tricuspidata [1]:72

Cucurbitacin
Cucurbitacin
L[edit]

Cucurbitacin
Cucurbitacin
L, or 23,24-dihydrocucurbitacin I,[1]:63 [9]:1

Brydioside A from Bryonia dioica
Bryonia dioica
[1]:64 Bryoamaride
Bryoamaride
from Bryonia dioica
Bryonia dioica
[1]:65 25-O-Acetylbryoamaride from Trichosanthes tricuspidata
Trichosanthes tricuspidata
[1]:66 Khekadaengosides A and B from Trichosanthes tricuspidata
Trichosanthes tricuspidata
[1]:67–68

Cucurbitacin
Cucurbitacin
O[edit]

Cucurbitacin
Cucurbitacin
O from Brandegea bigelovii
Brandegea bigelovii
[1]:73

Cucurbitacin Q
Cucurbitacin Q
2-O-glucoside, from Picrorhiza kurrooa [1]:76 16-Deoxy-D-16-hexanorcucurbitacin O from Ecballium elaterium
Ecballium elaterium
[1]:77 Deacetylpicracin from Picrorhiza scrophulariaeflora [1]:78 Deacetylpicracin 2-O-glucoside from Picrorhiza scrophulariaeflora [1]:80 22-Deoxocucurbitacin O from Wilbrandia ebracteata [1]:83

Cucurbitacin
Cucurbitacin
P[edit]

Cucurbitacin
Cucurbitacin
P from Brandegea bigelovii
Brandegea bigelovii
[1]:74

Picracin from Picrorhiza scrophulariaeflora [1]:79 Picracin 2-O-glucoside from Picrorhiza scrophulariaeflora [1]:79

Cucurbitacin
Cucurbitacin
Q[edit]

Cucurbitacin
Cucurbitacin
Q

Cucurbitacin Q
Cucurbitacin Q
from Brandegea bigelovii
Brandegea bigelovii
[1]:75

23,24-Dihydrodeacetylpicracin 2-O-glucoside from Picrorhiza kurrooa [1]:82 Cucurbitacin
Cucurbitacin
Q1 from Cucumis
Cucumis
species, actually Cucurbitacin
Cucurbitacin
F 25-acetate [1]

Cucurbitacin
Cucurbitacin
R[edit]

Cucurbitacin
Cucurbitacin
R is actually 23,24-dihydrocucurbitacin D.[1]

Cucurbitacin
Cucurbitacin
S[edit]

Cucurbitacin
Cucurbitacin
S from Bryonia dioica
Bryonia dioica
[1]:84'85

Cucurbitacin
Cucurbitacin
T[edit]

Cucurbitacin
Cucurbitacin
T, from the fruits of Citrullus colocynthis
Citrullus colocynthis
[1]:86

28/29 Norcucurbitacins[edit] There are several substances that can be seen as derving 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.[1]:87–130 Other[edit] Several other cucurbitacins have been found in plants.[1]:152–156,164–165 Occurrence and bitter taste[edit]

Fruit and flower of the Ecballium
Ecballium
elaterium, also called the squirting cucumber or exploding cucumber containing cucurbitacin B

Constituents of the colocynth fruit and leaves (Citrullus colocynthis) include cucurbitacins.[10][11] The 2-O-β-D-glucopyranosides of cucurbitacins K and L can be extracted with ethanol from fruits of Cucurbita pepo
Cucurbita pepo
cv dayangua.[9] Pentanorcucurbitacins A and B can be extracted with methanol from the stems of Momordica charantia.[5] Cucurbitacins B and I, and derivatives of cucurbitacins B, D and E, can be extracted with methanol from dried tubers of Hemsleya endecaphylla.[6] Cucurbitacins impart a bitter taste in plant foods such as cucumber, zucchini, melon and pumpkin.[12][13] 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.[1][2][3][12] Pathologists found cucurbitacin in the stomach of a 79-year-old man who died in Bavaria, Germany, shortly after eating a casserole containing zucchini he had received from a neighbor.[14][15] See also[edit]

Goyaglycoside Hemslecin Mogroside Momordicine Momordicoside Neomogroside Scandenosides R1–R8, R10-R11[1]:172–181 Siamenoside I[1]:182

References[edit]

^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak al am an ao ap aq ar as at au av aw ax ay az ba bb bc bd be bf bg bh bi bj bk bl bm bn bo bp bq br bs bt bu bv bw Jian Chao Chen, Ming Hua Chiu, Rui Lin Nie, Geoffrey A. Cordell and Samuel X. Qiu (2005), "Cucurbitacins and cucurbitane glycosides: structures and biological activities" Natural Product Reports, volume 22, pages 386-399 doi:10.1039/B418841C ^ a b Alghasham, AA (2013). "Cucurbitacins - a promising target for cancer therapy". International Journal of Health Sciences. 7 (1): 77–89. doi:10.12816/0006025. PMC 3612419 . PMID 23559908.  ^ a b Kapoor, S (2013). " Cucurbitacin B
Cucurbitacin B
and Its Rapidly Emerging Role in the Management of Systemic Malignancies Besides Lung Carcinomas". Cancer
Cancer
Biotherapy and Radiopharmaceuticals. 28 (4): 359. doi:10.1089/cbr.2012.1373. PMID 23350897.  ^ a b Zhang, Y.; et al. (2014). "Biosynthesis, regulation, and domestication of bitterness in cucumber". Science. 346 (6213): 1084–1088. Bibcode:2014Sci...346.1084S. doi:10.1126/science.1259215. PMID 25430763.  ^ a b c Chen, Chiy-Rong; Liao, Yun-Wen; Wang, Lai; Kuo, Yueh-Hsiung; Liu, Hung-Jen; Shih, Wen-Ling; Cheng, Hsueh-Ling; Chi-I, Chang (2010). " Cucurbitane
Cucurbitane
Triterpenoids from Momordica charantia
Momordica charantia
and Their Cytoprotective Activity in tert-Butyl Hydroperoxide-Induced Hepatotoxicity of HepG2 Cells". Chemical & Pharmaceutical Bulletin. 58 (12): 1639–1642. doi:10.1248/cpb.58.1639.  ^ a b c d e f g Chen, Jian-Chao; Zhang, Gao-Hong; Zhang, Zhong-Quan; Qiu, Ming-Hua; Zheng, Yong-Tang; Yang, Liu-Meng; Yu, Kai-Bei (2008). "Octanorcucurbitane and Cucurbitane
Cucurbitane
Triterpenoids from the Tubers of Hemsleya endecaphylla with HIV-1 Inhibitory Activity". J. Nat. Prod. 71 (1): 153–155. doi:10.1021/np0704396. PMID 18088099.  ^ a b c d Halaweish, FT; Tallamy, DW (1993). "A new cucurbitacin profile for Cucurbita andreana: A candidate for cucurbitacin tissue culture". Journal of Chemical Ecology. 19 (6): 1135–1141. doi:10.1007/BF00987375. PMID 24249132.  ^ Kupchan, S.Morris; Meshulam, Haim; Sneden, Albert T. (1978). "New cucurbitacins from Phormium tenax
Phormium tenax
and Marah oreganus". Phytochemistry. 17 (4): 767–769. doi:10.1016/S0031-9422(00)94223-7.  ^ a b c Wang, Da-Cheng; Pan, Hong-Yu; Deng, Xu-Ming; Xiang, Hua; Gao, Hui-Yuan; Cai, Hui; Wu, Li-Jun (2007). " Cucurbitane
Cucurbitane
and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo
Cucurbita pepo
cv dayangua"". Journal of Asian Natural Products Research. 9 (6): 525–529. doi:10.1080/10286020600782538.  ^ Song, F; Dai, B; Zhang, H. Y.; Xie, J. W.; Gu, C. Z.; Zhang, J (2015). "Two new cucurbitane-type triterpenoid saponins isolated from ethyl acetate extract of Citrullus colocynthis
Citrullus colocynthis
fruit". Journal of Asian Natural Products Research. 17 (8): 813–8. doi:10.1080/10286020.2015.1015999. PMID 25761128.  ^ Chawech, R; Jarraya, R; Girardi, C; Vansteelandt, M; Marti, G; Nasri, I; Racaud-Sultan, C; Fabre, N (2015). "Cucurbitacins from the Leaves of Citrullus colocynthis
Citrullus colocynthis
(L.) Schrad". Molecules. 20 (10): 18001–15. doi:10.3390/molecules201018001. PMID 26437392.  ^ a b Kaushik, U; Aeri, V; Mir, S. R (2015). "Cucurbitacins – an insight into medicinal leads from nature". Pharmacognosy Reviews. 9 (17): 12–18. doi:10.4103/0973-7847.156314. PMC 4441156 . PMID 26009687.  ^ Shang, Y; Ma, Y; Zhou, Y; Zhang, H; Duan, L; Chen, H; Zeng, J; Zhou, Q; Wang, S; Gu, W; Liu, M; Ren, J; Gu, X; Zhang, S; Wang, Y; Yasukawa, K; Bouwmeester, H. J.; Qi, X; Zhang, Z; Lucas, W. J.; Huang, S (2014). "Plant science. Biosynthesis, regulation, and domestication of bitterness in cucumber". Science. 346 (6213): 1084–8. Bibcode:2014Sci...346.1084S. doi:10.1126/science.1259215. PMID 25430763.  ^ "Mann stirbt an Garten Zucchini". Retrieved 24 August 2015.  ^ "Auf den Geschmack kommt es an". Retrieved 24 August 2015. 

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