Solamargine

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title: "Solamargine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["steroidal-alkaloids", "alkaloid-glycosides", "plant-toxins", "steroidal-alkaloids-found-in-solanaceae"] topic_path: "general/steroidal-alkaloids" source: "https://en.wikipedia.org/wiki/Solamargine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | verifiedrevid = 464404773 | ImageFile = Solamargine.svg | ImageSize = 200px | IUPACName = (22R,25R)-Spirosol-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside | SystematicName = (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) | OtherNames = Solamargin; δ-Solanigrine | Section1 = {{Chembox Identifiers | CASNo = 20311-51-7 | CASNo_Ref = | UNII_Ref = | UNII = 8KG991E7BN | PubChem = 73611 | ChEMBL_Ref = | ChEMBL = 443114 | ChemSpiderID_Ref = | ChemSpiderID = 66278 | SMILES = O([C@H]8C@HOC@HC@@H[C@@H]8O)[C@@H]9OC@HC | 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 | InChIKey = MBWUSSKCCUMJHO-ZGXDEBHDBL | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = MBWUSSKCCUMJHO-ZGXDEBHDSA-N | Section2 = {{Chembox Properties | C=45|H=73|N=1|O=15 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

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.

References

References

  1. (2003). "Toxicological effects of α-solamargine in experimental animals". Phytotherapy Research.
  2. (1998). "Developmental toxicology of solamargine and solasonine glycoalkaloids in frog embryos". Food and Chemical Toxicology.
  3. (2016-04-01). "Solamargine production by a fungal endophyte of Solanum nigrum". Journal of Applied Microbiology.

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steroidal-alkaloidsalkaloid-glycosidesplant-toxinssteroidal-alkaloids-found-in-solanaceae