20311-51-7

Basic information

• Product Name: Solamargine
• Synonyms: SOLAMERGINE;[(22R,25R)-Spirosola-5-ene-3β-yl]2-O,4-O-bis(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside;(3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-4)]-beta-D-glucopyranoside;NSC 407810;Solamargin;δ-Solanigrine;2)-O-[6-deoxy-a-L-Mannopyranosyl-(1®b-D-Glucopyranoside, (3b,22a,25R)-spirosol-5-en-3-yl O-6-deoxy-a-L-Mannopyranosyl-(1®
• CAS NO: 20311-51-7
• Molecular Formula: C₄₅H₇₃NO₁₅
• Molecular Weight: 868.064
• Product Categories: Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 20311-51-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 301 °C
• Appearance: /
• Density: 1.38
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12?+-.0.70(Predicted)
• CAS DataBase Reference: Solamargine(CAS DataBase Reference)
• NIST Chemistry Reference: Solamargine(20311-51-7)
• EPA Substance Registry System: Solamargine(20311-51-7)

Safety Data

• Hazardous Substances Data: 20311-51-7(Hazardous Substances Data)

Usage

Uses

α-Solamargine is a steroidal glycosyl-alkaloid which displays inactivation of PI3-L/Akt and reduction for SP1 and p65 in the suppression of human lung cancer cells.

Downstream Products

• 126-17-0 solasodine 

Relevant articles and documents

spiral steroid alkali alkane xylosides alkloids method for the synthesis of (by machine translation)

The invention discloses a convergent spiral steroid alkali alkane xylosides alkaloid chemical synthesis method, the method comprises the following steps: (a) the 3?Hydroxy acyl silicon-based or for the protection of sapogenin spiral steroid (II) into the corresponding 16?Acetoxy?22?Carbonyl?26?(III) hydroxyl gallbladder gonanes; (b) 3?Hydroxy silicon-based or acyl group protection for 16?Acetoxy?22?Carbonyl?26?Preparation of sulfonic acid ester gallbladder gonanes (IV); (c) 3?Hydroxy silicon-based or acyl group protection for 16?Acetoxy?22?Carbonyl?26?Preparation of azide interior gonanes (V); (d) (VI) spiral steroid alkali alkane sapogenin the preparation; (e) acyl protecting spiral steroid alkali alkane xylosides alkloids preparation (VII); (f) spiral steroid alkali alkane xylosides alkloids (I) of the preparation. The preparation method of this invention simple process, high yield, has strong utility value. (by machine translation)

Total synthesis of solamargine

Solamargine, (25R)-3β-{O-α-l-rhamnopyranosyl-(1→2)-[O- α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosyloxy} -22α-N-spirosol-5-ene, has been synthesized in 13 steps in a 10.5% overall yield starting from the naturally abundant diosgenin. Condensation of a partially protected glucopyranosyl donor with an oxaza-spiro moiety, which was formed in one-pot azido reduction, significantly improved the synthesis of desired molecule. The target compound exhibited good cytotoxic activities against tumor cells HeLa, A549, MCF-7, K562, HCT116, U87, and HepG2 with IC 50 ranging from 2.1 to 8.0 μM.