Solamargine

Solamargine
Names
IUPAC name
(22R,25R)-Spirosol-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside
Systematic IUPAC name
(2S,2′S,3R,3′R,4R,4′R,5R,5′R,6S,6′S)-2,2′-{[(2R,3S,4S,5R,6R)-4-Hydroxy-2-(hydroxymethyl)-6-{[(2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5′,6a,7-tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naptho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidin]-2-yl]oxy}oxane-3,5-diyl]bis(oxy)}bis(6-methyloxane-3,4,5-triol)
Other names
Solamargin; δ-Solanigrine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1 checkY
    Key: MBWUSSKCCUMJHO-ZGXDEBHDSA-N checkY
  • InChI=1/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
    Key: MBWUSSKCCUMJHO-ZGXDEBHDBL
  • O([C@H]8[C@H](O[C@@H]5C/C4=C/C[C@H]3[C@@H]6C[C@@H]2O[C@@]1(NC[C@H](C)CC1)[C@@H](C)[C@@H]2[C@@]6(C)CC[C@@H]3[C@@]4(C)CC5)O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@@H]8O)[C@@H]9O[C@H]([C@H](O)[C@@H](O)[C@H]9O)C
Properties
C45H73NO15
Molar mass 868.071 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants.[1][2] It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus.[3] It is a glycoalkaloid derived from the steroidal alkaloid solasodine.

Solamargine was one component of the unsuccessful experimental cancer drug candidate Coramsine.

See also

References

  1. ^ Al Chami, L.; Mendez, R.; Chataing, B.; et al. (2003). "Toxicological effects of α-solamargine in experimental animals". Phytotherapy Research. 17 (3): 254–8. doi:10.1002/ptr.1122. PMID 12672156. S2CID 86042610. Archived from the original on 2012-06-16. Retrieved 2009-09-01.
  2. ^ Blankemeyer, J. T.; McWilliams, M. L.; Rayburn, J. R.; et al. (1998). "Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos". Food and Chemical Toxicology. 36 (5): 383–9. doi:10.1016/s0278-6915(97)00164-6. PMID 9662413.
  3. ^ El-Hawary, S.s.; Mohammed, R.; AbouZid, S.f.; et al. (2016-04-01). "Solamargine production by a fungal endophyte of Solanum nigrum". Journal of Applied Microbiology. 120 (4): 900–911. doi:10.1111/jam.13077. ISSN 1365-2672. PMID 26811095.

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