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Prenylflavonoids from jackfruit and their new use in anti-osteoporosis

A technology for prenyl flavonoids and osteoporosis, which is applied in the field of medicine and can solve problems such as the application of osteoporosis that has not been reported in the literature

Active Publication Date: 2017-04-26
JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Jackfruit has multiple medicinal uses in the folk, such as treating anemia, asthma and skin diseases, relieving convulsions and ulcers, sedation, anti-syphilis, deworming, etc., but the application in the treatment of osteoporosis has not been reported in the literature

Method used

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  • Prenylflavonoids from jackfruit and their new use in anti-osteoporosis
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  • Prenylflavonoids from jackfruit and their new use in anti-osteoporosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Preparation of isopentenyl flavonoids in jackfruit

[0020] Take jackfruit root medicinal material (17Kg), extract with 95% ethanol leakage, and concentrate the extract under reduced pressure to obtain 1.5Kg of extract. The extract was suspended in 2 L of water, extracted with petroleum ether, chloroform, ethyl acetate and n-butanol in sequence (volume ratio 1:1), and concentrated to dryness respectively. Take 532g of the extract from the chloroform extraction part, mix the sample of HP-20 macroporous adsorption resin (weight ratio 1:1), and put it on a HP-20 macroporous adsorption resin column (column size: 15*55cm, 5.3Kg), and mix with ethanol-water Gradient elution (0-95%) followed by a final rinse with acetone. Take 60% ethanol elution fractions, and perform ODS reverse-phase silica gel column chromatography with ethanol-water (2:5, 9:10) to obtain 6 fractions: A-F. Fraction C was subjected to MCI column chromatography with ethanol-water (3:5, 9:10) to o...

Embodiment 2

[0023] Example 2 Structure identification of isopentenyl flavonoids in jackfruit

[0024] The isolated monomers were identified as seven prenylated flavonoids by high resolution mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance spectroscopy (1D NMR and 2D NMR). Among them, compounds 1-5 are known compounds, while compounds 6 and 7 are two new compounds that have not been reported in the literature.

[0025] Among them, compound 1 was identified as 5′-hydroxycudraflavone A. C 25 H 22 O 7 , yellow amorphous powder. 1 HNMR(CD 3 OD, 600MHz) δppm 7.15 (1H, s, H-6'), 6.65 (1H, d, J=10.0Hz, H-16), 6.39 (1H, s, H-H-3'), 6.35 (1H, s , H-8), 6.10 (1H, d, J=9.0Hz, H-11), 5.69 (1H, d, J=10.0Hz, H-17), 5.44 (1H, d, J=9.0Hz, H -12), 1.97 (3H, s, H-15), 1.70 (3H, s, H-14), 1.47 (6H, s, H-19, 20); 13 CNMR(CD 3 OD, 150MHz) δppm: 157.7(C-2), 110.5(C-3), 179.6(C-4), 157.8(C-5), 106.5(C-6), 160.3(C-7), 96.0( C-8), 157.3(C-9), 106.3(C-10), 70.2(C-11), 122.3(C-12), 139.7(C-13),...

Embodiment 3

[0034] Example 3 Experiment on the inhibitory activity of isopentenyl flavonoids in jackfruit on CatK

[0035] 40 [mu]L of CatK (diluted with 0.1% Brii35) was added to the 96-well plate. Then 35 μL of buffer solution containing the test compound (containing 400 mM NaH) was added 2 PO 4-Na 2 HPO 4 buffer, 88 mM DTT and 4 mM EDTA, pH 6.8), incubated at 25° for 10 minutes to allow sufficient binding of the compound to the enzyme. 25 μL of the substrate Z-GPR-AMC (diluted in 1% DMSO) was then added to the mixture to start the reaction. The final concentrations of substrate and CatK were 5 μM and 5.6 μM, respectively, with a total volume of 100 μL per well. After the reaction system was incubated at 37 °C for 2 h, 50 μL of reaction stop solution (containing 100 mM CH) was added. 3 COOH-CH 3 COONa, 100mMCl 3 CCOONa, pH 4.3) into each well. The fluorescence signal intensity of AMC in the reaction system was detected with an Omega microwell spectrophotometer (BMG LABTECH, Ger...

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Abstract

The invention relates to a kind of prenylflavonoids and their application in the preparation of anti-osteoporosis drugs. The invention isolated 7 prenylflavonoids from Jackfruit moraceae plants of the genus artocarpus (I) (Artocarpus / I) (I) (heterophyllus / I), were 5'HydroxycudraflavoneA, artochaminB, artelastoxanthone, artoindonesianinQ, kuwanonT, artoheteroidA and artoheteroidB. Activity tests showed that the prenylflavonoids of the invention has strong inhibitory activity on important therapeutic target for osteoporosis -- protease K, the prenylflavones' IC50 is 0.88 - 93.9mM, can be used for preparing drugs for treating osteoporosis.

Description

technical field [0001] The invention belongs to the field of medicine and relates to new application of medicine, in particular to the new application of isopentenyl flavonoids in jackfruit in preparing medicine for treating osteoporosis. Background technique [0002] Osteoporosis (OP) is a systemic skeletal disease characterized by degeneration of bone microstructure, increased fragility and susceptibility to fractures. With the prolongation of human lifespan and the arrival of an aging society, the incidence of OP is increasing year by year. According to epidemiological statistics, the incidence of OP has accounted for 10% of the global middle-aged and elderly population, and has become a common and frequently-occurring disease that seriously threatens the health of the middle-aged and elderly. The number of elderly people in my country ranks first in the world. There are 90 million OP patients, accounting for 7.01% of the total population. It is expected to increase to 2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C07D311/78A61K31/352A61P19/10C07D493/14C07D493/04C07D311/30C07D311/40
CPCA61K31/352C07D311/30C07D311/40C07D311/78C07D493/04C07D493/08C07D493/14
Inventor 任刚翟晓晓袁金斌元文君曾金祥蒋伟肖川云
Owner JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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