6822-47-5

Usage

Uses

Used in Pharmaceutical Industry:
Sophoradiol is used as an anti-mycobacterial agent for its strong activity against drug-resistant isolates of Mycobacterium tuberculosis. This makes it a potential candidate for the development of new treatments for tuberculosis, a disease that poses a significant global health challenge.
Used in Chemical Industry:
Sophoradiol's unique chemical structure and properties also make it a valuable compound for various applications in the chemical industry. Its potential uses in this field may include the development of new chemical processes, synthesis of other bioactive compounds, or as a starting material for the production of pharmaceuticals and other valuable chemicals.

InChI:InChI=1/C30H50O2/c1-25(2)17-20-19-9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-30(22,8)29(19,7)16-15-27(20,5)24(32)18-25/h9,20-24,31-32H,10-18H2,1-8H3/t20-,21-,22+,23-,24+,27+,28-,29+,30+/m0/s1

Upstream product

• 115330-94-4 C₄₈H₇₈O₁₆ 
• 83689-16-1 C₄₄H₅₈N₂O₅ 
• 115330-90-0 kaikasaponin III 
• 83689-13-8 (3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-4,6a,6b,8a,11,11,14b-Heptamethyl-4-trityloxymethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-3,9-diol 
• 115330-90-0 kaikasaponin III 
• 83689-15-0 C₄₄H₆₀N₂O₅ 
• 83689-14-9 C₆₃H₇₄N₂O₅ 
• 187394-38-3 3,24-O-benzylidene soyasapogenol B 
• 187393-81-3 3β,22β-dibenzyloxy-24-trityloxyolean-12-ene 
• 186415-74-7 (3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picene-4-carbaldehyde 
• 186415-77-0 C₄₄H₆₀O₃ 
• 186415-73-6 ((3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-3,9-Bis-benzyloxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-4-yl)-methanol 
• 124862-79-9 soyasapogenol B 
• 862248-29-1 3β,22β-dibenzyloxyolean-12-ene 

Downstream Products

• 24427-91-6 3,22-di-O-acetylsophoradiol 
• 86425-27-6 sophoradiol 22-O-acetate 
• 86425-26-5 3-O-acetylsophoradiol 
• 86425-22-1 anhydrosophoradiol 
• 124514-86-9 3β,22β-bis-benzoyloxy-olean-12-ene 

Relevant academic research and scientific papers

Triterpene glycosides from the bark of Robinia pseudo-acacia L. I

From the bark of Robinia pseudo-acacia L., five new triterpene glycosides, robiniosides A-D (3, 5-7) and compound III (4), were isolated and their structures were elucidated as 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β-dihydroxyolean-12-en-29-oic acid (3), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β,24-trihydroxyolean-12-en-29-oic acid (4), whose sapogenol was unambiguously characterized and designated as oxytrogenin, 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin (5), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin 22-O-α-L-rhamnopyranoside (6), 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranosyl oxytrogenin 22-O-α-L-rhamnopyranoside (7), respectively, together with two known triterpene glycosides, kaikasaponin III (1) and 3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 2)-β-D-glucuronopyranosyl 3β,22β-dihydroxyolean-12-en-29-oic acid (2).

Hepatoprotective and hepatotoxic activities of sophoradiol analogs on rat primary liver cell cultures

As a part of our studies of hepatoprotective drugs, we prepared kaikasaponin I (2), sophoradiol monoglucuronide (SoMG, 3) and sophoradiol (4) from kaikasaponin III (1). We examined the hepatoprotective effects of these analogs, using immunologically-induced liver injury in primary cultured rat hepatocytes and found that compound I was more effective than soyasaponin I (1a) while 2 was more effective than 1. On the other hand, 3 was less effective than 2 at 30 - 200 μM. Further, compound 3 was strongly cytotoxic at 500 μM while 4 exhibited hepatoprotective activity at the same dose, although less potent. When the cytotoxicity toward hepatocytes of these analogs was tested, only 3 was cytotoxic at doses of 200 and 500 μM. This is the first example of an oleanene glucuronide (OG) which is cytotoxic toward hepatocytes. Compound 3 exhibited hepatoprotective activity at 200 μM, while it was also cytotoxic at the same dose without antiserum. Therefore, the hepatoprotective activity of OG represents a balance between a hepatoprotective action and its cytotoxicity toward hepatocytes.

Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model

To shed light on the structure-activity relationship, various soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice. Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis. Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage. Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group, resulted in a greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage.

Synthesis and hepatoprotective effects of soyasapogenol B derivatives

Derivatives of soyasapogenol B (1), which is the aglycon moiety of soyasaponins from soybean, were synthesized and evaluated for their hepatoprotective effects in vitro.

Studies on the Constituents of the Bark of Dalbergia hupeana

Two new triterpenoid glycosides, 3-O-α-L-rhamnopyranosyl-(1-2)-β-D-galactopyranosyl-(1-2)-β-D-glucuronopyranosiduronic acids (2 and 3) of 3β,22β-dihydroxyolean-12-en-29-oic acid and 3β,21β,22β-trihydroxyolean-12-en-29-oic acid, along with a known glycoside, kaikasaponin III (1), were isolated from the bark of Dalbergia hupeana HANCE.Their structures were determined by chemical and spectral methods.

Saponin and Sapogenol. XLI. Reinvestigation of the Structures of Soyasapogenols A, B, and E, Oleanene-Sapogenols from Soybean. Structures of Soyasaponins I, II, and III

A full account of the structure revision of soyasapogenols is presented.The structures of soyasapogenols A, B, and E have been confirmed to be expressed as 3β,21β,22β,24-tetrahydroxyolean-12-ene (1), 3β,22β,24-trihydroxyolean-12-ene (2), and 3β,24-dihydroxyolean-12-en-22-one (5), respectively, rather than the previously reported 3β,21α,22α,24-tetrahydroxyolean-12-ene (1'), 3β,21α,24-trihydroxyolean-12-ene (2'), and 3β,24-dihydroxyolean-12-en-21-one (5').In consequence, the structures of soyasaponins I, II, and III are formulated as 3-O-2)-β-D-galactopyranosyl(1->2)-β-D-glucuronopyranosyl>soyasapogenol B (8), 3-O-2)-α-L-arabinopyranosyl(1->2)-β-D-glucuronopyranosyl>soyasapogenol B (9), and 3-O-2)-β-D-glucuronopyranosyl>soyasapogenol B (10), respectively.Keywords - soybean; Glycine max; oleanene-sapogenol; soyasapogenol A; soyasapogenol B; soyasapogenol E; soyasaponin I; soyasaponin II; soyasaponin III; bioactive triterpene oligoglycoside

REVISED STRUCTURES OF SOYASAPOGENOLS A, B, AND E, OLEANENE-SAPOGENOLS FROM SOYBEAN. STRUCTURES OF SOYASAPONINS I, II, AND III

The structures of soyasapogenols A, B, and E, three of five hitherto isolated sapogenols of soybean (Glycine max Merrill), were re-investigated.Based on the chemical and X-ray analyses, it has been shown that the structures of soyasapogenols A, B, and E should be partly revised respectively from 1', 2', and 3' to 1, 2, and 3 and consequently the structures of soyasaponins I, II, and III are expressed as 6, 7, and 8.KEYWORDS - soybean; Glycine max; oleanene-sapogenol; triterpene-oligoglycoside; soyasapogenols; soyasaponins; photolysis; X-ray analysis