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Semisynthetic trierpenoidsaponin with antitumor activity and medicinal composition thereof

A compound, pharmaceutical technology, applied in the field of natural medicinal chemistry and pharmacotherapeutics

Active Publication Date: 2013-09-18
亳州市君臣佐使药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ardisiacrispin B is a good anti-cancer lead compound, so far there is no related research on its derivatives

Method used

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  • Semisynthetic trierpenoidsaponin with antitumor activity and medicinal composition thereof
  • Semisynthetic trierpenoidsaponin with antitumor activity and medicinal composition thereof
  • Semisynthetic trierpenoidsaponin with antitumor activity and medicinal composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] 3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-glucopyranose-(1 →2) Preparation of ]-α-L-arabinopyranose}-16α-hydroxy-13β, 28-epoxyoleanane-30-methanol

[0076] 107mg Ardisiacrispin B (3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-pyranose Glucopyranose-(1→2)]-α-L-arabinopyranose}-16α-hydroxyl-13β, 28-epoxyoleanane-30-aldehyde) was dissolved in 3ml of methanol, stirred to dissolve, then added 2mg Sodium borohydride, continued to stir at room temperature for 30 minutes, concentrated to a small volume and separated by column chromatography to obtain 96 mg of off-white solid with a yield of 89.7%.

[0077] 1 H-NMR (400MHz, DMSO-d 6 ): mother core: 3.54(s, 2H), 3.27(d, 1H), 3.10(d, 1H), 3.00(dd, 1H), 2.85(d, 1H), 2.38(m, 1H), 2.08(dd , 1H), 1.93-1.96(m, 3H), 1.85(m, 1H), 1.74-1.78(m, 3H), 1.54(m, 1H), 1.44-1.45(m, 3H), 1.37-1.39(m , 2H), 1.33(m, 1H), 1.25(dd, 1H), 1.15-1.17(m, 4H), 1.06-1.09(m, 5H), 0.93-0.94(m, 4H), 0.89(s, 3H) ), 0...

Embodiment 2

[0081] 3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-glucopyranose-(1 →2)]-α-L-arabinopyranose}-16α-hydroxyl-13β, 28-epoxyoleanane-30-methylpentylamine preparation

[0082] 107mg Ardisiacrispin B (3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-pyranose Glucopyranose-(1→2)]-α-L-arabinopyranose}-16α-hydroxyl-13β, 28-epoxyoleanane-30-aldehyde) was dissolved in 3ml of ethanol, stirred to dissolve, then added 10mg of n-pentane, refluxed for 2 hours, cooled to room temperature, added 4mg of sodium cyanoborohydride, stirred at 50°C for 30 minutes, concentrated to a small volume and separated by column chromatography to obtain 55mg of off-white solid, yield 48.2% .

[0083] 1 H-NMR (400MHz, DMSO-d 6 ): mother core: 3.52(s, 2H), 3.25(d, 1H), 3.16(d, 1H), 3.05(dd, 1H), 2.79(d, 1H), 2.53(s, 2H), 2.47(t , 2H), 2.38(m, 1H), 2.06(m, 2H), 1.93-1.96(m, 3H), 1.86(m, 1H), 1.74-1.78(m, 3H), 1.54(m, 1H), 1.43-1.45(m, 5H), 1.37-1.40(m, 2H), 1.32(m, 3H), 1.2...

Embodiment 3

[0086] 3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-glucopyranose-(1 →2) Preparation of ]-α-L-arabinopyranose}-16α-hydroxyl-13β,28-epoxyoleanane-30-methyl-[N-(2-chlorophenyl)]imine

[0087] 107mg Ardisiacrispin B (3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O-β-D-pyranose Glucopyranose-(1→2)]-α-L-arabinopyranose}-16α-hydroxyl-13β, 28-epoxyoleanane-30-aldehyde) was dissolved in 3ml of ethanol, stirred to dissolve, then added 15 mg of 2-chloroaniline was refluxed for 2 hours, cooled to room temperature, concentrated to a small volume and separated by column chromatography to obtain 91 mg of off-white solid with a yield of 77%.

[0088] 1 H-NMR (400MHz, DMSO-d 6): mother nucleus: 7.56 (s, 1H), 7.12-7.36 (m, 4H), 3.51 (s, 2H), 3.22 (d, 1H), 3.14 (d, 1H), 3.07 (dd, 1H), 2.84 (d, 1H), 2.41(m, 1H), 2.12(dd, 1H), 1.93-1.95(m, 3H), 1.83(m, 1H), 1.74-1.78(m, 3H), 1.56(m, 1H ), 1.44-1.46(m, 3H), 1.35-1.39(m, 2H), 1.37(m, 1H), 1.24(dd, 1H), 1.15-1.18(...

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Abstract

The invention relates to saponins compounds with a structure of a formula (1), wherein R1 and R2 have the definition in the specification and pharmaceutically acceptable salts thereof, a preparation method thereof and application in treating tumor diseases.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry and pharmacotherapeutics, and relates to a class of saponin compounds with antitumor activity. More specifically, the invention relates to semi-synthetic triterpene saponin compounds, their preparation method and application. Background technique [0002] Ardisiacrispin B was first isolated from Ardisia crispa in the 1980s, through 1 H-and 13 The C-NMR spectrum determined to have the following nomenclature: 3β-O-{α-L-rhamnopyranose-(1→2)-O-β-D-glucopyranose-(1→4)-[O- β-D-glucopyranose-(1→2)]-α-L-arabinopyranose}-16α-hydroxy-13β,28-epoxyoleanane-30-aldehyde, and found to have certain anti Uterotonic analgesic effect (Jansakul, C; Bauman, H; Kenne, Let al, 53(5), 405-9, 1987.). Since then, it has been reported in New Zealand's Myrsine genus (Bloor, S.; Qi, L, J. Nat. Prod., 57(10), 1354-60, 1994.) and Ardisia mamillata (Huang, J.; Ogihara, Y. ; Zhang, H.et al, Phytochemistry, 54(8), 81...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/7048A61P35/00
Inventor 王振赵蕾
Owner 亳州市君臣佐使药业有限公司