Gedunin

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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.215.769 Edit this at Wikidata
EC Number
  • 689-008-9
UNII
  • InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
    Key: YJXDGWUNRYLINJ-BHAPSIHVSA-N
  • CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1([C@]45[C@H](O4)C(=O)O[C@H]([C@@]5(CC3)C)C6=COC=C6)C)C
Properties
C28H34O7
Molar mass 482.573 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ^ 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. Bibcode:2002JNAtP..65.1177H. doi:10.1021/np0105174. ISSN 0163-3864. PMID 12193026.
  2. ^ 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. Bibcode:2011JNAtP..74..866K. doi:10.1021/np100783k. ISSN 1520-6025. PMID 21381696.
  3. ^ 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. Bibcode:2018NeuTx..65..166R. doi:10.1016/j.neuro.2018.02.012. ISSN 1872-9711. PMC 5857252. PMID 29471019.
  4. ^ 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.
  5. ^ 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. Bibcode:2010JNAtP..73.1448C. doi:10.1021/np100325q. ISSN 0163-3864. PMID 20669933.
  6. ^ 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. Bibcode:2008PlMed..74.1795L. doi:10.1055/s-0028-1088323. ISSN 0032-0943. PMID 18991203. S2CID 260248307.
  7. ^ 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. Bibcode:1991PChem..30.1225C. doi:10.1016/S0031-9422(00)95206-3.
  8. ^ 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. Bibcode:2012JMoSt1008...83C. doi:10.1016/j.molstruc.2011.11.028.
  9. ^ 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. Bibcode:2000JAFC...48.1903C. doi:10.1021/jf990443q. ISSN 0021-8561. PMID 10820113.
  10. ^ Okorie, Domingo A.; Taylor, David A.H. (January 1977). "Triterpenes from the seed of Entandrophragma species". Phytochemistry. 16 (12): 2029–2030. Bibcode:1977PChem..16.2029O. doi:10.1016/0031-9422(77)80123-4.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ 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. Bibcode:2006JNAtP..69.1310M. doi:10.1021/np068021f. ISSN 0163-3864. PMID 16989525.
  15. ^ 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.
  16. ^ 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. Bibcode:2009JNAtP..72.2110L. doi:10.1021/np900625w. ISSN 0163-3864. PMID 19888743.


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