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| Names | |
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| IUPAC name
(22R,25R)-Spirosol-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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
- ^ 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.
- ^ 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.
- ^ 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
Media related to Solamargine at Wikimedia Commons
This page was last edited on 8 March 2024, at 23:29