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

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

Used in Pharmaceutical Industry:
Solamargine is used as an anticancer agent for the suppression of human lung cancer cells. It works by inactivating the PI3-L/Akt pathway and reducing the expression of SP1 and p65, which are key factors in the development and progression of lung cancer. This makes Solamargine a promising candidate for the development of novel cancer treatments.
Additionally, Solamargine's potential applications in other areas of the pharmaceutical industry may be explored, such as in the development of targeted drug delivery systems or as a component in combination therapies for various types of cancer. Further research is needed to fully understand its potential and optimize its use in these applications.

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)

An alternative total synthesis of solamargine

Solamargine, (25R)-3β-{O-α-L-rhamnopyranosyl-(1→2)-[O- α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyloxy} -22α-Nspirosol-5-ene, isolated from the berries of solanum aculeastrum, has been synthesized in 26.8% overall yield. First glycosylation before N-cyclization significantly facilitated synthesis of the desired molecule. We anticipate that this work will provide a new approach to access solamargine and its diversified analogues. Science China Press and Springer-Verlag Berlin Heidelberg 2012.

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.