Gedunine

Gedunine
Structuurformule en molecuulmodel
Algemeen
Molecuulformule	C28H34O7
Molmassa	482,56536 g/mol
SMILES	CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)(C)C
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
PubChem	12004512
Wikidata	Q15917840
Portaal	Scheikunde

Gedunine is een organische verbinding die wordt ingedeeld bij de meliacinen en als dusdanig bij de triterpenoïden. De stof wordt gevonden in bomen uit de Mahoniefamilie (Meliaceae), waaronder de neem (Azadirachta indica)^[1], de krappa (Carapa guianensis) en de tiama (Entandrophragma angolense)^[2]. Ook komt het voor in de mangrove Xylocarpus granatum.^[3]

De medicinale werking van gedunine is aangetoond tegen filariasis^[4], kanker^[1]^[3]^[5], maagzweren^[6] en malaria^[7]^[8]. Ook heeft het een werking tegen de denguemug, Culex quinquefasciatus^[9] en de Europese maisboorder^[10]

Bronnen, noten en/of referenties

↑ ^a ^b Brandt, G.E.L. e.a. (2008) "Gedunin, a novel Hsp90 inhibitor: semisynthesis of derivatives and preliminary structure− activity relationships" Journal of Medicinal Chemistry 51(20), p. 6495–6502. Gearchiveerd op 13 juli 2023.
↑ Akisanya, A., e.a. (1961) "720. West african timbers. Part IV. Some reactions of gedunin" Journal of the Chemical Society (Resumed), p. 3705–3708
↑ ^a ^b Uddin, S.J. e.a. (2007) "Gedunin, a limonoid from Xylocarpus granatum, inhibits the growth of CaCo‐2 colon cancer cell line In Vitro" Phytotherapy Research 21(8), p. 757–761
↑ Misra, S. e.a. (2011) "Gedunin and photogedunin of Xylocarpus granatum possess antifilarial activity against human lymphatic filarial parasite Brugia malayi in experimental rodent host" Parasitology Research 109(5), p. 1351–1360
↑ Kamath, S.G. e.a. (2009) "Gedunin, a novel natural substance, inhibits ovarian cancer cell proliferation" International Journal of Gynecological Cancer 19(9), p. 1564–1569
↑ Lakshmi, V. e.a. (2010) "Gedunin and Photogedunin of Xylocarpus granatum show significant anti-secretory effects and protect the gastric mucosa of peptic ulcer in rats" Phytomedicine 17(8), p. 569–574
↑ MacKinnon, S. e.a. (1997) "Antimalarial activity of tropical Meliaceae extracts and gedunin derivatives" Journal of Natural Products 60(4), p. 336–341
↑ Omar, S. e.a. (2003) "Antimalarial activities of gedunin and 7‐methoxygedunin and synergistic activity with dillapiol"^{[dode link]} Annals of Applied Biology 143(2), p. 135–141
↑ Gurulingappa, H. e.a. (2009) "Susceptibility of Aedes aegypti and Culex quinquefasciatus larvae to gedunin‐related limonoids" Chemistry & Biodiversity 6(6), p. 897–902
↑ Ewete, F.K. e.a. (2000) "Toxicity of gedunin, piperine and crude extracts of their natural products on growth and development of Ostrinia nubilalis Hübner (Lepidoptera: Pyralidae)" Discovery and Innovation 12(1–2), p. 67–72

[brandt-1] Brandt, G.E.L. e.a. (2008) "Gedunin, a novel Hsp90 inhibitor: semisynthesis of derivatives and preliminary structure− activity relationships" Journal of Medicinal Chemistry 51(20), p. 6495–6502. Gearchiveerd op 13 juli 2023.

[2] Akisanya, A., e.a. (1961) "720. West african timbers. Part IV. Some reactions of gedunin" Journal of the Chemical Society (Resumed), p. 3705–3708

[uddin-3] Uddin, S.J. e.a. (2007) "Gedunin, a limonoid from Xylocarpus granatum, inhibits the growth of CaCo‐2 colon cancer cell line In Vitro" Phytotherapy Research 21(8), p. 757–761

[4] Misra, S. e.a. (2011) "Gedunin and photogedunin of Xylocarpus granatum possess antifilarial activity against human lymphatic filarial parasite Brugia malayi in experimental rodent host" Parasitology Research 109(5), p. 1351–1360

[5] Kamath, S.G. e.a. (2009) "Gedunin, a novel natural substance, inhibits ovarian cancer cell proliferation" International Journal of Gynecological Cancer 19(9), p. 1564–1569

[6] Lakshmi, V. e.a. (2010) "Gedunin and Photogedunin of Xylocarpus granatum show significant anti-secretory effects and protect the gastric mucosa of peptic ulcer in rats" Phytomedicine 17(8), p. 569–574

[7] MacKinnon, S. e.a. (1997) "Antimalarial activity of tropical Meliaceae extracts and gedunin derivatives" Journal of Natural Products 60(4), p. 336–341

[8] Omar, S. e.a. (2003) "Antimalarial activities of gedunin and 7‐methoxygedunin and synergistic activity with dillapiol"^{[dode link]} Annals of Applied Biology 143(2), p. 135–141

[9] Gurulingappa, H. e.a. (2009) "Susceptibility of Aedes aegypti and Culex quinquefasciatus larvae to gedunin‐related limonoids" Chemistry & Biodiversity 6(6), p. 897–902

[10] Ewete, F.K. e.a. (2000) "Toxicity of gedunin, piperine and crude extracts of their natural products on growth and development of Ostrinia nubilalis Hübner (Lepidoptera: Pyralidae)" Discovery and Innovation 12(1–2), p. 67–72

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