From Wikipedia, the free encyclopedia
Gedunin
|
Names
|
IUPAC name
Gedunin
|
Systematic IUPAC name
[(1S,2R,4S,7S,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl] acetate
|
Other names
- Gedunine
- (-)-Gedunin
- (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(Furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate
|
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Chemical compound
Gedunin is a
pentacyclic
triterpenoid with the
molecular formula C28H34
O7. It is most notably found in
Azadirachta indica,
[1] but is a constituent of several other plants. Gedunin shows therapeutic potential in the treatment of
leukemia,
[2] and
Parkinson's disease.
[3]
[4]
Natural occurrence
Azadirachta indica
[5] is the most notable source of gedunin, but it has also been found in the following plants:
References
-
^ Hallur, Gurulingappa; Sivramakrishnan, Apoorba; Bhat, Sujata V. (2002-08-01).
"Three New Tetranortriterpenoids from Neem Seed Oil". Journal of Natural Products. 65 (8): 1177–1179.
doi:
10.1021/np0105174.
ISSN
0163-3864.
PMID
12193026.
-
^ Kikuchi, Takashi; Ishii, Koichi; Noto, Taisuke; Takahashi, Akitomo; Tabata, Keiichi; Suzuki, Takashi; Akihisa, Toshihiro (2011-04-25).
"Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem)". Journal of Natural Products. 74 (4): 866–870.
doi:
10.1021/np100783k.
ISSN
1520-6025.
PMID
21381696.
-
^ Rane, Anand; Rajagopalan, Subramanian; Ahuja, Manuj; Thomas, Bobby; Chinta, Shankar J.; Andersen, Julie K. (March 2018).
"Hsp90 Co-chaperone p23 contributes to dopaminergic mitochondrial stress via stabilization of PHD2: Implications for Parkinson's disease". Neurotoxicology. 65: 166–173.
doi:
10.1016/j.neuro.2018.02.012.
ISSN
1872-9711.
PMC
5857252.
PMID
29471019.
-
^ Zhou, Heying; Li, Fengxia; Li, Yanli (November 2022).
"Anti-Cancer Activity of Gedunin by Induction of Apoptosis in Human Gastric Cancer AGS Cells". Applied Biochemistry and Biotechnology. 194 (11): 5322–5332.
doi:
10.1007/s12010-022-04001-8.
ISSN
1559-0291.
PMID
35759172.
S2CID
250065297.
-
^ Chianese, Giuseppina; Yerbanga, Serge R.; Lucantoni, Leonardo; Habluetzel, Annette; Basilico, Nicoletta; Taramelli, Donatella; Fattorusso, Ernesto; Taglialatela-Scafati, Orazio (2010-08-27).
"Antiplasmodial Triterpenoids from the Fruits of Neem, Azadirachta indica". Journal of Natural Products. 73 (8): 1448–1452.
doi:
10.1021/np100325q.
ISSN
0163-3864.
PMID
20669933.
-
^ Leite, Ana; Ambrozin, Alessandra; Fernandes, João; Vieira, Paulo; da Silva, Maria; de Albuquerque, Sérgio (December 2008).
"Trypanocidal Activity of Limonoids and Triterpenes from Cedrela fissilis". Planta Medica. 74 (15): 1795–1799.
doi:
10.1055/s-0028-1088323.
ISSN
0032-0943.
PMID
18991203.
S2CID
260248307.
-
^ Campos, Angela M.; Oliveira, Francisco S.; Machado, Maria Iracema L.; Matos, Francisco J.A.; Braz-Filho, Raimundo (January 1991).
"Triterpenes from Cedrela odorata". Phytochemistry. 30 (4): 1225–1229.
doi:
10.1016/S0031-9422(00)95206-3.
-
^ Carvalho, Paulo S.; Napolitano, Hamilton B.; Camargo, Ademir J.; Silva, Valter H.C.; Ellena, Javier A.; Rocha, Waldireny C.; Vieira, Paulo C. (January 2012).
"X-ray diffraction and theoretical investigation of the Gedunin crystal structure". Journal of Molecular Structure. 1008: 83–87.
doi:
10.1016/j.molstruc.2011.11.028.
-
^ Céspedes, Carlos L.; Calderón, José S.; Lina, Laura; Aranda, Eduardo (2000-05-01).
"Growth Inhibitory Effects on Fall Armyworm Spodoptera frugiperda of Some Limonoids Isolated from Cedrela spp. (Meliaceae)". Journal of Agricultural and Food Chemistry. 48 (5): 1903–1908.
doi:
10.1021/jf990443q.
ISSN
0021-8561.
PMID
10820113.
-
^ Okorie, Domingo A.; Taylor, David A.H. (January 1977).
"Triterpenes from the seed of Entandrophragma species". Phytochemistry. 16 (12): 2029–2030.
doi:
10.1016/0031-9422(77)80123-4.
-
^ Bickii, Jean; Njifutie, Njikam; Ayafor Foyere, Johnson; Basco, Leonardo K; Ringwald, Pascal (January 2000).
"In vitro antimalarial activity of limonoids from Khaya grandifoliola C.D.C. (Meliaceae)". Journal of Ethnopharmacology. 69 (1): 27–33.
doi:
10.1016/S0378-8741(99)00117-8.
PMID
10661881.
-
^ Khalid, Sami A.; Farouk, Asim; Geary, Timothy G.; Jensen, James B. (February 1986).
"Potential antimalarial candidates from African plants: An in vitro approach using Plasmodium falciparum". Journal of Ethnopharmacology. 15 (2): 201–209.
doi:
10.1016/0378-8741(86)90156-X.
PMID
3520157.
-
^ Mitsui, Kumiko; Saito, Hiroaki; Yamamura, Ryota; Fukaya, Haruhiko; Hitotsuyanagi, Yukio; Takeya, Koichi (2007).
"Apotirucallane and Tirucallane Triterpenoids from Cedrela sinensis". Chemical and Pharmaceutical Bulletin. 55 (10): 1442–1447.
doi:
10.1248/cpb.55.1442.
ISSN
0009-2363.
PMID
17917286.
-
^ Mitsui, Kumiko; Saito, Hiroaki; Yamamura, Ryota; Fukaya, Haruhiko; Hitotsuyanagi, Yukio; Takeya, Koichi (2006-09-01).
"Hydroxylated Gedunin Derivatives from Cedrela sinensis". Journal of Natural Products. 69 (9): 1310–1314.
doi:
10.1021/np068021f.
ISSN
0163-3864.
PMID
16989525.
-
^ Uddin, Shaikh J.; Nahar, Lutfun; Shilpi, Jamil A.; Shoeb, Mohammad; Borkowski, Tomasz; Gibbons, Simon; Middleton, Moira; Byres, Maureen; Sarker, Satyajit D. (August 2007).
"Gedunin, a limonoid from Xylocarpus granatum, inhibits the growth of CaCo-2 colon cancer cell line In Vitro". Phytotherapy Research. 21 (8): 757–761.
doi:
10.1002/ptr.2159.
PMID
17450509.
S2CID
22441840.
-
^ Li, Min-Yi; Yang, Xiao-Bo; Pan, Jian-Yu; Feng, Gang; Xiao, Qiang; Sinkkonen, Jari; Satyanandamurty, Tirumani; Wu, Jun (2009-12-28).
"Granatumins A−G, Limonoids from the Seeds of a Krishna Mangrove, Xylocarpus granatum". Journal of Natural Products. 72 (12): 2110–2114.
doi:
10.1021/np900625w.
ISSN
0163-3864.
PMID
19888743.