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Solamargine

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Solamargine
Names
IUPAC name (22R,25R)-Spirosol-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)--β-D-glucopyranoside
Systematic IUPAC name (2S,2′S,3R,3′R,4R,4′R,5R,5′R,6S,6′S)-2,2′-{indenofuran-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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: MBWUSSKCCUMJHO-ZGXDEBHDSA-N
  • 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/s1Key: MBWUSSKCCUMJHO-ZGXDEBHDBL
SMILES
  • O(8(O5C/C4=C/C36C2O1(NC(C)CC1)(C)26(C)CC34(C)CC5)O(CO)(O7O(C)(O)(O)7O)8O)9O((O)(O)9O)C
Properties
Chemical formula C45H73NO15
Molar mass 868.071 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. 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.

External links

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