2, 3-dihydroxy cinnamomum lactone derivative and application thereof

A technology of dihydroxy and derivatives, applied in 2 fields, can solve the problems that the pharmacological effects have not been reported yet, and achieve good anti-inflammatory activity, good stability, and clear activity effect

Inactive Publication Date: 2011-05-25
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Cinnamolide fragrans Baillon, and Waburgia ugandensis, W.stublmanni have been isolated from Cinnamolide fragrans Baillon, and 3-hydroxycinnamolide and 6-hydroxycinnabar lactone, the compound has been from Peniopbora polygonia Bourd & Galzin plants It is isolated, and the pharmacological effects of this type of composition have not been reported (Tetrahedron Lett., 23, 2137 (1967); Isr.J.Chem..16, 28 (1977); J.Nat.Prod 55:1454-1461 (1988)

Method used

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  • 2, 3-dihydroxy cinnamomum lactone derivative and application thereof
  • 2, 3-dihydroxy cinnamomum lactone derivative and application thereof
  • 2, 3-dihydroxy cinnamomum lactone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] A method for preparing 2,3-dihydroxycinnamon lactone derivatives, the specific steps are as follows: the dried whole plant of Polygonum jucundum Meisn. is pulverized, extracted by heating and refluxing with 90% ethanol, recovering the organic solvent under reduced pressure, and sequentially using petroleum Ether, ethyl acetate extraction, ethyl acetate part extract through silica gel column chromatography, petroleum ether-ethyl acetate gradient elution (petroleum ether: ethyl acetate 15:1 ~ 9:1 ~ 5:1 ~ 3:1 ~2:1~1:1~methanol unloading column), wherein petroleum ether-ethyl acetate (2:1) was eluted to obtain compound 2; wherein the methanol eluted part was subjected to silica gel column chromatography, chloroform-methanol gradient elution, Chloroform:methanol (20:1) was eluted to obtain compound 1, and the above two substances were recrystallized from ethanol-water to obtain pure compound.

[0017] Compound 1 white needle crystal (methanol). mp134-136°C. GF under 254nm ...

Embodiment 2

[0024] Take 0.5g of compound 1, add 10ml of 20ml of absolute ethanol, stir, add 5ml of concentrated sulfuric acid, stir for 72 hours, add 20ml of 95% ethanol, adjust the pH to 7 with 50% NaoH, adjust the volume fraction of ethanol to 85%, and let it stand for reaction 36h, filtered, separated by D101 resin (50%-70% ethanol gradient elution) and ODS column chromatography to obtain compounds 3 and 4.

[0025] Take 1g of compound 2, add 25ml of 50ml of absolute ethanol, stir, add 10ml of concentrated sulfuric acid, stir for 72 hours, add 40ml of 95% ethanol, adjust the pH to 7 with 50% NaoH, adjust the volume fraction of ethanol to 85%, and let it stand for overnight reaction , filtered, and separated by D101 resin (70% ethanol gradient elution) and ODS column chromatography to obtain compound 5.

[0026] Compound 3 white powder. mp165-167°C. UV(methanol)λ max : 230.4nm. [α] 25 D -13.6 (c=0.1, MeOH). IR (KBr): 3426, 1750, 1646, 1465, 1035cm -1 , 1 H-NMR (CD 3OD, 300MHz)...

Embodiment 3

[0033] Take 0.2 g of compound 1, add 3 ml of dichloromethane, cool in an ice bath, add 0.3 ml of trifluoroacetic anhydride, stir for 2 h, and separate by silica gel column chromatography (petroleum ether-ethyl acetate 1:1 elution) to obtain compound 6 ( Formula I, R 1 = R 2 = CF 3 CO).

[0034] Take 0.2g of compound formula 2, add 5ml of dichloromethane, cool in an ice bath, add 0.5ml of trifluoroacetic anhydride, stir for 4 hours, and separate by silica gel column chromatography (petroleum ether-ethyl acetate 1:1 elution) to obtain compound 7 (formula I, R1=angeloyl, R2=CF 3 CO).

[0035] Compound 6 is white powder. mp130-132°C. UV(methanol)λ max : 222.4nm. IR (KBr):, 2913, 1757, 1692, 1178cm -1 . 1 H-NMR (CD 3 Cl, 300MHz) δ1.89 (1H, dd, J=12.6, 4.3Hz, H-1β), 1.28 (1H, t, J=12.6, 12.1Hz, H-1α), 4.05 (1H, ddd, J= 12.1, 4.3, 9.5Hz (H-2), 2.95 (1H, d, J=9.5Hz, H-3), 1.53 (1H, dd, J=11.5, 5.5Hz, H-5), 2.32 (1H, m , H-6β), 2.49 (1H, m, H-6α), 6.88 (1H, m, H-7), 2.96 (...

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Abstract

The invention relates to a 2, 3-dihydroxy cinnamomum lactone derivative and an anti-inflammatory effect thereof. The 2, 3-dihydroxy cinnamomum lactone derivative is structurally characterized in that in the 2, 3-dihydroxy cinnamomum lactone derivative, R1 is angelica acyl, acetyl, cinnamoyl, succinic monoacyl, trifluoroacetic acyl, sulfur acyl or H, and R2 is acetyl, cinnamoyl, succinic monoacyl,trifluoroacetic acyl, sulfur acyl or H. The invention also provides application of the prepared 2, 3-dihydroxy cinnamomum lactone derivative to inflammation treatment medicine. A first compound (R1=R2=H) and a second compound (R1 is angelica acyl, and R2 is H) prepared form natural plants have good stability and good anti-inflammatory activity and can be used for preparing medicine for treating corresponding diseases. The activity is explicit, experimental materials can be easily obtained, and the cost is low.

Description

technical field [0001] The present invention relates to 2,3-dihydroxycinnamon lactone derivatives and their anti-inflammatory effects. Background technique [0002] Cinnamolide fragrans Baillon, and Waburgia ugandensis, W.stublmanni have been isolated from Cinnamolide fragrans Baillon, 3-hydroxycinnamolide and 6-hydroxycinnabar lactone, which have been isolated from Peniopbora polygonia Bourd & Galzin plants The pharmacological action of this type of composition has not been reported yet (Tetrahedron Lett., 23, 2137 (1967); Isr.J.Chem..16, 28 (1977); J.Nat.Prod 55:1454-1461 (1988). Contents of the invention [0003] The object of the present invention is: novel 2,3-dihydroxycinnamon lactone derivatives with anti-inflammatory activity. [0004] A method for preparing 2,3-dihydroxycinnamon lactone derivatives, characterized in that the steps are as follows: the dried whole plant of Polygonum jucundum Meisn. is pulverized, extracted with 90% ethanol under reflux, and the or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88A61K31/365A61P19/02A61P25/02
Inventor 张朝凤张勉林云黄芳王磊
Owner CHINA PHARM UNIV
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