CN109160928A - New phenol glycosides compound and its application in moringa seeds - Google Patents

New phenol glycosides compound and its application in moringa seeds Download PDF

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CN109160928A
CN109160928A CN201810206498.5A CN201810206498A CN109160928A CN 109160928 A CN109160928 A CN 109160928A CN 201810206498 A CN201810206498 A CN 201810206498A CN 109160928 A CN109160928 A CN 109160928A
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compound
sulphur
ester
sugar
base
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CN109160928B (en
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叶文才
范春林
王英
刘辉
李满妹
刘俊珊
黄晓君
张晓琦
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Jinan University
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Abstract

The present invention relates to the new phenol glycosides compounds of 15 that separation is extracted from moringa seeds, the general structure of such compound is such as shown in (I), and the invention further relates to application of such compound in preparation treatment diabetes, antidepression and anti senile dementia drug and health care product.Experiment shows that the compound of the present invention has significant hypoglycemic, antidepression and anti-senile dementia effect.The active clear mechanism of the compound of the present invention, small toxicity, it is safe the features such as, have wide application prospect,

Description

New phenol glycosides compound and its application in moringa seeds
Technical field
Diabetes, anti-suppression are treated the present invention relates to new phenol glycosides compound isolated from moringa seeds and its in preparation Application in strongly fragrant and anti senile dementia drug and health care product.
Background technique
Moringa (Moringaoleifera Lam.) is Moringaceae platymiscium, for perennial tropical deciduous tree, is originated in Tropical, south subtropics arid and semi-arid lands, are now distributed widely in the heat such as Africa, Arab, Southeast Asia, Pacific Islands Band marine climate area (Anwar F, et al.PhytotherRes, 2007,21 (1): 17-25).After the sixties in last century, in The ground such as Yunnan, Hainan, Guangdong, the Guangxi of state have large area to plant (Guangdong the such as Dong little Ying feed, 2008,17 (9): 39- 41).Moringa is multipurpose fast-growing arbor, and plantation can yield positive results after 6 months, and root, stem, leaf, flower and seed can medicines With (Chinese Plants will, 1984:34 (1): 6).Main chemical compositions in Moringa are phenols and its glycosides, flavones and its glycosides, sterol And its glycosides and polysaccharide, amino acid and vitamin etc..Modern pharmacological studies have shown that Moringa has hypoglycemic, reducing blood lipid, protection liver Damage, nervous system protection, it is antitumor, anti-inflammatory antibacterial and analgesia spasmolysis isoreactivity (Tianjin the such as Kong Lingyu pharmacy, 2015, 27(2):57-59；The Food Science such as Xu Min, 2016,37 (23): 291-301).However, above-mentioned pharmacological activity is for peppery The research of the wooden water extract or alcohol extract there are no the related activity report of monomer component.
The present invention has found a series of phenolic compounds from moringa seeds, first by research including 15 noval chemical compounds Secondary these phenolic compounds of discovery have the function for the treatment of diabetes, antidepression and anti-senile dementia.
Summary of the invention
The present invention relates to new phenolic glycoside class chemical combination isolated from moringa seeds and it preparation treat diabetes, anti-suppression Application in strongly fragrant and anti senile dementia drug and health care product.
The chemical general formula of new phenol glycosides compound and its derivative of the present invention is as follows:
Wherein R1For hydrogen or glycosyl；R2For ester group or thioesters, urea or thiocarbamide, oxygen ether etc., the preferred methyl formate base of ester group, first Acetoacetic ester base, butyl formate base, acetate groups, butyric acid ester group；The amido of methyl formate base, sulphur substitution that the preferred sulphur of thioesters replaces Propyl formate base, the sulphur that urethane base, the sulphur of group-4 ethyl formate, sulphur substitution that methyl formate base, sulphur replace replace take The formic acid virtue that amidocarbonic acid butyl ester base, the sulphur that butyl formate base, the sulphur that amidocarbonic acid first propyl ester base, the sulphur in generation replace replace replace The amidocarbonic acid aryl ester that base ester, sulphur replace；The preferred urea of urea, thiocarbamide, semicarbazides, thiosemicarbazides, aryl ureas, aryl thiourea etc.； The alkane and aryl ether etc. such as the preferred methyl ether of oxygen ether, ethylether, propyl ether, butyl ether；Glycosyl preferably six carbon (glucose, sweet dew Sugar, rhamnose) pyranose, six carbofurans sugar, it is acylated sugared preferably six carbon (glucose, mannose, rhamnose) pyranose, six carbon Furanose or acyl group are sugared (acetyl group, propiono, benzoyl).See according to currently preferred compound substituent and title Table 1.
The new phenolic glycoside class compound substituent of table 1 and title
When the compounds of this invention is used as drug, it can directly use or be used in the form of pharmaceutical composition.Comprising at least A kind of structural formula (I) compound is as active constituent, in conjunction with one or more of pharmaceutically acceptable nontoxic to the human body and lazy Pharmaceutical acceptable carrier and excipient of property.
Carrier and excipient used is one or more solids, semisolid and liquid diluent, filler and drug system Product adjuvant.Various dosage forms are prepared into using the method that pharmaceutical field is generally acknowledged in pharmaceutical composition of the invention, such as liquid preparation (mixes Suspension, syrup, oral solutions or injection etc.), solid pharmaceutical preparation (tablet, capsule or granule etc.), spray etc..Above-mentioned medicine Object can by oral administration, the approach administration such as sublingual or injection (intravenous injection, intramuscular injection or subcutaneous injection etc.) administration.
Detailed description of the invention:
Fig. 1 is that the ESI-MS of compound 1 schemes
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of compound 1
Fig. 3 is the carbon-13 nmr spectra figure of compound 1
Fig. 4 is that the ESI-MS of compound 2 schemes
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram of compound 2
Fig. 6 is the carbon-13 nmr spectra figure of compound 2
Fig. 7 is that the ESI-MS of compound 3 schemes
Fig. 8 is the hydrogen nuclear magnetic resonance spectrogram of compound 3
Fig. 9 is the carbon-13 nmr spectra figure of compound 3
Figure 10 is that the ESI-MS of compound 4 schemes
Figure 11 is the hydrogen nuclear magnetic resonance spectrogram of compound 4
Figure 12 is the carbon-13 nmr spectra figure of compound 4
Figure 13 is that the ESI-MS of compound 5 schemes
Figure 14 is the hydrogen nuclear magnetic resonance spectrogram of compound 5
Figure 15 is the carbon-13 nmr spectra figure of compound 5
Figure 16 is that the ESI-MS of compound 6 schemes
Figure 17 is the hydrogen nuclear magnetic resonance spectrogram of compound 6
Figure 18 is the carbon-13 nmr spectra figure of compound 6
Figure 19 is that the ESI-MS of compound 7 schemes
Figure 20 is the hydrogen nuclear magnetic resonance spectrogram of compound 7
Figure 21 is the carbon-13 nmr spectra figure of compound 7
Figure 22 is that the ESI-MS of compound 8 schemes
Figure 23 is the hydrogen nuclear magnetic resonance spectrogram of compound 8
Figure 24 is the carbon-13 nmr spectra figure of compound 8
Figure 25 is that the ESI-MS of compound 9 schemes
Figure 26 is the hydrogen nuclear magnetic resonance spectrogram of compound 9
Figure 27 is the carbon-13 nmr spectra figure of compound 9
Figure 28 is that the ESI-MS of compound 10 schemes
Figure 29 is the hydrogen nuclear magnetic resonance spectrogram of compound 10
Figure 30 is the carbon-13 nmr spectra figure of compound 10
Figure 31 is that the ESI-MS of compound 11 schemes
Figure 32 is the hydrogen nuclear magnetic resonance spectrogram of compound 11
Figure 33 is the carbon-13 nmr spectra figure of compound 11
Figure 34 is that the ESI-MS of compound 12 schemes
Figure 35 is the hydrogen nuclear magnetic resonance spectrogram of compound 12
Figure 36 is the carbon-13 nmr spectra figure of compound 12
Figure 37 is that the ESI-MS of compound 13 schemes
Figure 38 is the hydrogen nuclear magnetic resonance spectrogram of compound 13
Figure 39 is the carbon-13 nmr spectra figure of compound 13
Figure 40 is that the ESI-MS of compound 14 schemes
Figure 41 is the hydrogen nuclear magnetic resonance spectrogram of compound 14
Figure 42 is the carbon-13 nmr spectra figure of compound 14
Figure 43 is that the ESI-MS of compound 15 schemes
Figure 44 is the hydrogen nuclear magnetic resonance spectrogram of compound 15
Figure 45 is the carbon-13 nmr spectra figure of compound 15
Four, specific embodiment
It will become apparent to the present invention with reference to the following example, providing embodiment rather than is limited to illustrate the present invention The scope of the present invention processed.
The extraction separation of 1 noval chemical compound of embodiment and Structural Identification
It takes moringa seeds 10kg to crush, adds 10 times of 30% ethanol percolations of weight to extract twice, every time for 24 hours, combined extract is dense Contracting, filtering, the upper D101 macroporous resin column absorption of filtrate, successively with water and 10% ethanol elution removing impurity, then with 85% ethyl alcohol 80L elution, recycles 85% ethanol eluate, and concentration is dried under reduced pressure, obtains total medicinal extract.Silica gel column chromatography on total medicinal extract 350g, with Chloroform-methanol system (chloroform and methanol volume ratio are from 100:0 to 0:1) gradient elution, the recycling of each gradient are molten Merge after agent and obtains fraction Fr.1-Fr.8.Fr.3 (18g) is chromatographed through ODS (reversed octadecyl silane) column, methanol-water System gradient elution (methanol-water volume ratio is from 2:8 to 1:0) obtains 10 fractions, Fr.3a-Fr.3j, wherein Fr.3c (0.7g) Through preparative HPLC, using 30% methanol-water as mobile phase, compound 1 (350mg) is made.Fr.3e (1.1g) is through preparative Compound 3 (215mg) is made using 43% methanol-water as mobile phase in HPLC.Fr.3f (1.3g) through preparative HPLC, with Compound 4 (260mg) is made as mobile phase in 45% methanol-water.Fr.3g (0.65g) is through preparative HPLC, with 28% methanol- Compound 13 (420mg) is made as mobile phase in water.Fr.3i (0.86g) is through preparative HPC, using 50% methanol-water as stream Dynamic phase, is made compound 8 (308mg).Fr.5 (20g) through silica gel column chromatography, with cyclohexane-ethyl acetate system (hexamethylene with Ethyl acetate volume ratio is from 100:0 to 1:1) gradient elution, merge eluent and obtains 6 fractions, Fr.5a-Fr.5f, wherein Fr.5a (1.2g) is through preparative HPLC, and using 60% methanol-water as mobile phase, compound 6 (365mg) is made. Fr.5c Through preparative HPLC, using 48% methanol-water as mobile phase, compound 11 (342mg) is made in (0.8g).Fr.5d (1.1g) warp Compound 9 (517mg) is made using 55% methanol-water as mobile phase in preparative HPLC.Fr.5e (2.1g) is through preparative Compound 12 (338mg) and 14 (305mg) are made using 38% methanol-water as mobile phase in HPLC.Fr.6 (25g) is through ODS column Chromatography, methanol-water system gradient elution (methanol-water volume ratio is from 15:85 to 1:0) obtain 7 fractions, Fr.6a-Fr.6g, Wherein Fr.6a (0.9g) is through preparative HPLC, and using 30% methanol-water as mobile phase, compound 15 (345mg) is made.Fr.6c Through preparative HPLC, using 43% methanol-water as mobile phase, compound 2 (503mg) and 7 (384mg) are made in (1.2g).Fr.6e Through preparative HPLC, using 63% methanol-water as mobile phase, compound 5 (407mg) is made in (0.6g).Fr.6c (1.1g) warp Compound 10 (461mg) is made using 38% methanol-water as mobile phase in preparative HPLC.
Compound 1 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:297.0972 [M-H]-.ESI-MS is as shown in Figure 1.1H-NMR(CD3OD) δ: 7.20 (2H, d, J=8.5Hz, H-2 and H-6), 7.01 (1H, d, J=8.5Hz, H-3 and H-5), 5.41 (1H, d, J= 1.5Hz, H-1 '), 4.00 (1H, m, H-2 '), 3.86 (1H, dd, J=9.5,3.5Hz, H-3 '), 3.64 (1H, m, H-5 '), 3.54 (2H, s, H-7), 3.46 (1H, t, J=9.5Hz, H-4 '), 1.23 (3H, d, J=6.5Hz, H-6 ').Nuclear magnetic resonance spectroscopy As shown in Figure 2.13C-NMR(CD3OD) δ: 175.8 (C-9), 156.8 (C-4), 131.4 (C-1), 129.7 (C-2 and C-6), 117.5 (C-3 and C-5), 99.8 (C-1 '), 73.8 (C-4 '), 72.2 (C-3 '), 72.0 (C-2 '), 70.6 (C-5 '), 41.0 (C-7), 18.0 (C-6 ').Carbon-13 nmr spectra is as shown in Figure 3.
1 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 1 are O- Benzylcarbamate -4-O- alpha-L-rhamnoside, are a noval chemical compound.
Compound 2 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:371.1357 [M+HCOO]-.ESI-MS is as shown in Figure 4.1H-NMR (CD3OD) δ: 7.14 (2H, d, J=8.5Hz, H-2 and H-6), 6.95 (1H, d, J=8.5Hz, H-3 and H-5), 5.34 (1H, D, J=1.5Hz, H-1 '), 4.08 (1H, q, J=7.1Hz, H-9), 3.93 (1H, m, H-2 '), 3.77 (1H, dd, J=9.5, 3.5Hz, H-3 '), 3.58 (1H, m, H-5 '), 3.51 (2H, s, H-7), 3.39 (1H, t, J=9.5Hz, H-4 '), 1.18 (3H, D, J=6.5Hz, H-6 '), 1.16 (1H, t, J=7.1Hz, H-10).Nuclear magnetic resonance spectroscopy is as shown in Figure 5.13C-NMR(CD3OD) δ: 173.8 (C-8), 156.9 (C-4), 131.4 (C-1), 129.4 (C-2 and C-6), 117.6 (C-3 and C-5), 99.9 (C- 1 '), 73.9 (C-4 '), 72.2 (C-2 '), 72.0 (C-3 '), 70.6 (C-5 '), 61.6 (C-9), 41.2 (C-7), 18.0 (C- 6 '), 14.5 (C-10).Carbon-13 nmr spectra is as shown in Figure 6.
2 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 2 are O- ethyl-ethyl phenylacetate -4-O- alpha-L-rhamnoside, are newization Close object.
Compound 3 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:399.1635 [M+HCOO]-.ESI-MS is as shown in Figure 7.1H-NMR (CD3OD) δ: 7.20 (2H, d, J=8.7Hz, H-2 and H-6), 6.95 (1H, d, J=8.5Hz, H-3 and H-5), 5.40 (1H, D, J=1.8Hz, H-1 '), 4.08 (1H, t, J=6.6Hz, H-9), 3.99 (1H, m, H-2 '), 3.83 (1H, dd, J=9.5, 3.5Hz, H-3 '), 3.63 (1H, m, H-5 '), 3.58 (2H, s, H-7), 3.45 (1H, t, J=9.5Hz, H-4 '), 1.59 (2H, M, H-10), 1.33 (2H, m, H-11), 1.18 (3H, d, J=6.2Hz, H-6 '), 0.92 (1H, t, J=7.4Hz, H-12).Core Magnetic resonance hydrogen spectrum is as shown in Figure 8.13C-NMR(CD3OD) δ: 173.8 (C-8), 156.9 (C-4), 131.4 (C-1), 129.4 (C- 2 and C-6), 117.5 (C-3 and C-5), 99.8 (C-1 '), 73.8 (C-4 '), 72.2 (C-2 '), 72.1 (C-3 '), 70.6 (C- 5 '), 65.9 (C-9), 41.2 (C-7), 31.8 (C-10), 20.1 (C-11), 18.0 (C-6 '), 14.5 (C-12).Nuclear magnetic resonance Carbon spectrum is as shown in Figure 9.
3 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 3 are O- butyl-benzene butyl acetate -4-O- alpha-L-rhamnoside, are newization Close object.
Compound 4 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:403.1043 [M+HCOO]-.ESI-MS is as shown in Figure 10.1H-NMR (CD3OD) δ: 7.27 (2H, d, J=8.7Hz, H-2 and H-6), 7.20 (1H, d, J=8.5Hz, H-3 and H-5), 5.40 (1H, D, J=1.6Hz, H-1 ', 4.26 (1H, q, J=7.1Hz, H-9), 4.06 (2H, s, H-7), 3.98 (1H, m, H-2 '), 3.84 (1H, dd, J=9.5,3.4Hz, H-3 '), 3.62 (1H, m, H-5 '), 3.45 (1H, t, J=9.5Hz, H-4 '), 1.27 (1H, T, J=7.1Hz, H-10), 1.22 (3H, d, J=6.2Hz, H-6 ').Nuclear magnetic resonance spectroscopy is as shown in figure 11.13C-NMR (CD3OD) δ: 172.0 (C-8), 157.1 (C-4), 132.7 (C-1), 131.1 (C-2 and C-6), 117.5 (C-3 and C-5), 99.7 (C-1 '), 73.8 (C-4 '), 72.2 (C-2 '), 72.0 (C-3 '), 70.6 (C-5 '), 64.6 (C-9), 35.4 (C-7), 18.0 (C-6 '), 14.6 (C-10).Carbon-13 nmr spectra is as shown in figure 12.
4 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 4 are O- ethyl-benzyl sulfenyl Ethyl formate -4-O- alpha-L-rhamnoside, are One noval chemical compound.
Compound 5 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:431.1355 [M+HCOO]-.ESI-MS is as shown in figure 13.1H-NMR (CD3OD) δ: 7.27 (2H, d, J=8.6Hz, H-2 and H-6), 6.99 (1H, d, J=8.6Hz, H-3 and H-5), 5.40 (1H, D, J=1.5Hz, H-1 '), 4.23 (2H, d, J=6.6Hz, H-9), 4.06 (1H, m, H-7), 3.98 (1H, m, H-2 '), 3.84 (1H, dd, J=9.5,3.4Hz, H-3 '), 3.63 (1H, m, H-5 '), 3.45 (1H, t, J=9.5Hz, H-4 '), 1.63 (2H, M, H-10), 1.38 (2H, m, H-11), 1.22 (3H, d, J=6.2Hz, H-6 '), 0.95 (3H, t, J=7.4Hz, H-12).Core Magnetic resonance hydrogen spectrum is as shown in figure 14.13C-NMR(CD3OD) δ: 172.2 (C-9), 157.1 (C-4), 132.7 (C-1), 131.1 (C-2 and C-6), 117.6 (C-3 and C-5), 98.9 (C-1 '), 73.8 (C-4 '), 72.2 (C-2 '), 72.0 (C-3 '), 70.6 (C-5 '), 68.4 (C-9), 35.4 (C-7), 31.9 (C-10), 20.0 (C-11), 18.0 (C-6 '), 14.0 (C-12).Nuclear-magnetism is total Carbon spectrum of shaking is as shown in figure 15.
5 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 5 are O- butyl-benzyl sulfenyl butyl formate -4-O- alpha-L-rhamnoside, are One noval chemical compound.
Compound 6 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:402.1224 [M+HCOO]-.ESI-MS is as shown in figure 16.1H-NMR (CD3OD) δ: 7.14 (2H, d, J=8.6Hz, H-2 and H-6), 6.94 (1H, d, J=8.6Hz, H-3 and H-5), 5.33 (1H, D, J=1.5Hz, H-1 '), 4.25 (2H, s, H-7), 3.91 (1H, m, H-2 '), 3.75 (1H, dd, J=9.5,3.4Hz, H- 3 '), 3.54 (1H, m, H-5 '), 3.37 (1H, t, J=9.5Hz, H-4 '), 2.80 (2H, q, J=7.3Hz, H-9), 1.18 (3H, t, J=7.3Hz, H-10), 1.14 (3H, d, J=6.2Hz, H-6 ').Nuclear magnetic resonance spectroscopy is as shown in figure 16.13C-NMR (CD3OD) δ 157.0 (C-4), 133.7 (C-1), 129.8 (C-2 and C-6), 117.5 (C-3 and C-5), 99.8 (C-1 '), 73.8 (C-4 '), 72.2 (C-2 '), 72.0 (C-3 '), 70.6 (C-5 '), 45.0 (C-7), 24.7 (C-9), 18.0 (C-6 '), 16.3(C-10).Carbon-13 nmr spectra is as shown in figure 18.
6 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 6 are S- ethyl-benzyl urethane -4-O- alpha-L-rhamnoside, are One noval chemical compound.
7 Yellow amorphous powder of compound, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:563.2242 [M+HCOO]-.ESI-MS is as shown in Figure 1.1H-NMR (DMSO- d6) δ: 7.18 (2H, d, J=8.5Hz, H-2 and H-6), 6.98 (1H, d, J=8.5Hz, H-3 and H-5), 5.33 (1H, d, J= 1.5Hz, H-1 '), 4.16 (2H, d, J=5.9Hz, H-7), 3.82 (1H, m, H-2 '), 3.64 (1H, dd, J=9.3,3.5Hz, H-3 '), 3.45 (1H, m, H-5 '), 3.28 (1H, t, J=9.3Hz, H-4 '), 1.10 (3H, d, J=6.2 Hz, H-6 ').Nuclear-magnetism The hydrogen spectrum that resonates is as shown in Figure 2.13C-NMR(DMSO-d6) δ: 158.1 (C-8), 154.9 (C-4), 134.3 (C-1), 128.3 (C-2 And C-6), 116.4 (C-3 and C-5), 98.5 (C-1 '), 71.9 (C-4 '), 70.5 (C-2 '), 70.3 (C-3 '), 69.5 (C- 5 '), 42.6 (C-7), 18.0 (C-6 ').Carbon-13 nmr spectra is as shown in Figure 3.According to above data show compound 7 be containing The phenol glycosides compound of the high degree of symmetry of urea groups.
7 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 7 are N, and N '-two [(4-O- α-L- rhamnopyranosyl) benzyl]-urea is newization Close object.
8 Yellow amorphous powder of compound, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:433.1435 [M-H]-.ESI-MS is as shown in Figure 4.1H-NMR(CD3OD) δ: 7.21 (2H, d, J=8.5Hz, H-2 ' and H-6 '), 7.11 (2H, d, J=8.5Hz, H-2 and H-6), 7.01 (1H, d, J= 8.5Hz, H-3 ' and H-5 '), 6.72 (1H, d, J=8.5Hz, H-3 and H-5), 5.40 (1H, d, J=1.5Hz, H-1 "), 3.98 (1H, m, H-2 "), 3.84 (1H, dd, J=9.5,3.5Hz, H-3 "), 3.62 (1H, m, H-5 "), 3.45 (1H, t, J= 9.5Hz, H-4 "), 1.20 (3H, d, J=6.5Hz, H-6 ").Nuclear magnetic resonance spectroscopy is as shown in Figure 5.13C-NMR (CD3OD) δ: 157.8 (C-4 '), 157.0 (C-4), 130.0 (C-2 ' and C-6 '), 129.8 (C-2 and C-6), 117.5 (C-3 ' and C-5 '), 116.2 (C-3 and C-5), 99.8 (C-1 "), 73.8 (C-4 "), 72.2 (C-2 "), 72.0 (C-3 "), 70.6 (C-5 "), 18.0 (C-6″).Carbon-13 nmr spectra is as shown in Figure 6.Show that compound 8 is the phenol glycosides compound containing urea groups according to above data.
8 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 8 are N- [(4-O- α-L- rhamnopyranosyl) benzyl]-N '-(4 '-hydroxyl benzyls Base)-thiocarbamide is a noval chemical compound.
9 Yellow amorphous powder of compound, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:342.1123 [M-H]-.ESI-MS is as shown in Figure 7.1H-NMR(CD3OD) δ: 7.22 (2H, d, J=8.7Hz, H-2 and H-6), 6.01 (1H, d, J=8.5Hz, H-3 and H-5), 5.38 (1H, d, J= 1.8Hz, H-1 '), 4.62 (2H, s, H-7), 3.94 (1H, m, H-2 '), 3.78 (1H, dd, J=9.5,3.5Hz, H-3 '), 3.55 (1H, m, H-5 '), 3.40 (1H, t, J=9.5Hz, H-4 '), 1.16 (3H, d, J=6.2Hz, H-6 ').Hydrogen nuclear magnetic resonance Spectrum is as shown in Figure 8.13C-NMR(CD3OD) δ: 157.7 (C-4), 129.6 (C-2 and C-6), 117.8 (C-3 and C-5), 99.7 (C-1 '), 73.7 (C-4 '), 72.1 (C-2 '), 71.9 (C-3 '), 70.7 (C-5 '), 18.0 (C-6 ').Carbon-13 nmr spectra is such as Shown in Fig. 9.Show that compound 9 is the phenol glycosides compound containing ghiourea group according to above data.
9 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, by HPLC liquid phase analysis with The derivative of standard sugar compares, identify that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value should The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 9 are N- [(4-O- α-L- rhamnopyranosyl) benzyl]-N '-amino-thiourea, are One noval chemical compound.
10 Yellow amorphous powder of compound, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:357.1318 [M+HCOO]-.ESI-MS is as shown in Figure 10.1H-NMR (CD3OD) δ: 7.22 (2H, d, J=8.5Hz, H-2 and H-6), 7.01 (1H, d, J=8.5Hz, H-3 and H-5), 5.40 (1H, D, J=1.5Hz, H-1 '), 4.24 (2H, s, H-7), 3.99 (1H, m, H-2 '), 3.84 (1H, dd, J=9.5,3.5Hz, H- 3 '), 3.63 (1H, m, H-5 '), 3.45 (1H, t, J=9.5Hz, H-4 '), 1.21 (3H, d, J=6.5Hz, H-6 ').Nuclear-magnetism is total Hydrogen spectrum of shaking is as shown in figure 11.13C-NMR(CD3OD) δ: 162.1 (C-8), 157.0 (C-4), 134.8 (C-1), 129.6 (C-2 and C-6), 117.6 (C-3 and C-5), 99.9 (C-1 '), 73.9 (C-4 '), 72.2 (C-3 '), 72.1 (C-2 '), 70.6 (C-5 '), 44.2 (C-7), 18.0 (C-6 ').Carbon-13 nmr spectra is as shown in figure 12.Show that compound 10 is to contain urea according to above data The phenol glycosides compound of base.
10 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 10 are N- [(4-O- α-L- rhamnopyranosyl) benzyl]-urea, are a new chemical combination Object.
Compound 11 is Yellow amorphous powder, and chemical structural formula is
Spectroscopic data is as follows: ESI-MSm/z:414.1771 [M+HCOO]-.ESI-MS is as shown in Figure 7.1H-NMR (CD3OD) δ: 7.15 (2H, d, J=8.6Hz, H-2 and H-6), 6.96 (1H, d, J=8.6Hz, H-3 and H-5), 5.32 (1H, D, J=1.5Hz, H-1 '), 4.09 (2H, d, J=6.1Hz, H-7), 3.80 (1H, m, H-2 '), 3.94 (2H, t, J=6.6 Hz, H-9), 3.61 (1H, dd, J=9.3,3.5Hz, H-3 '), 3.43 (1H, m, H-5 '), 3.26 (1H, t, J=9.3Hz, H-4 '), 1.51 (2H, m, H-10), 1.31 (2H, m, H-11), 1.06 (3H, d, J=6.1Hz, H-6 '), 0.87 (3H, t, J=7.4Hz, H-12).Nuclear magnetic resonance spectroscopy is as shown in Figure 8.13C-NMR(CD3OD) δ: 156.6 (C-8), 155.0 (C-4), 133.3 (C-1), 128.4 (C-2 and C-6), 116.3 (C-3 and C-5), 98.4 (C-1 '), 71.8 (C-4 '), 70.5 (C-2 '), 70.3 (C-3 '), 69.6 (C-5 '), 63.6 (C-9), 43.2 (C-7), 30.8 (C-10), 18.7 (C-11), 18.0 (C-6 '), 13.7 (C-12).Core Magnetic resonance carbon spectrum is as shown in Figure 9.
11 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 11 are O- butyl-benzyl butyl carbamate -4-O- alpha-L-rhamnoside, For a noval chemical compound.
Compound 12 is Yellow amorphous powder, and chemical structural formula is
(CD3OD) δ: 7.15 (2H, d, J=8.6Hz, H-2 and H-6), 6.96 (1H, d, J=8.6Hz, H-3 and H-5), 5.32 (1H, d, J=1.5Hz, H-1 '), 4.09 (2H, d, J=6.1Hz, H-7), 3.80 (1H, m, H-2 '), 3.94 (2H, t, J =6.6Hz, H-9), 3.61 (1H, dd, J=9.3,3.5Hz, H-3 '), 3.43 (1H, m, H-5 '), 3.26 (1H, t, J= 9.3Hz, H-4 '), 1.51 (2H, m, H-10), 1.31 (2H, m, H-11), 1.06 (3H, d, J=6.1Hz, H-6 '), 0.87 (3H, t, J=7.4Hz, H-12).Nuclear magnetic resonance spectroscopy is as shown in Figure 8.13C-NMR(CD3OD) δ: 156.6 (C-8), 155.0 (C-4), 133.3 (C-1), 128.4 (C-2 and C-6), 116.3 (C-3 and C-5), 98.4 (C-1 '), 71.8 (C-4 '), 70.5 (C-2 '), 70.3 (C-3 '), 69.6 (C-5 '), 63.6 (C-9), 43.2 (C-7), 30.8 (C-10), 18.7 (C-11), 18.0 (C-6 '), 13.7 (C-12).Carbon-13 nmr spectra is as shown in Figure 9.
12 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 12 are O- butyl-benzyl butyl carbamate -4-O- alpha-L-rhamnoside, For a noval chemical compound.
Compound 13 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:283.0309 [M-H]-.ESI-MS is as shown in Figure 1.1H-NMR(CD3OD) δ: 7.89 (2H, d, J=8.8Hz, H-2 and H-6), 7.05 (1H, d, J=8.8Hz, H-3 and H-5), 5.46 (1H, d, J= 1.5Hz, H-1 '), 3.93 (1H, m, H-2 '), 3.76 (1H, dd, J=9.5,3.5Hz, H-3 '), 3.50 (1H, m, H-5 '), 3.39 (1H, t, J=9.5Hz, H-4 '), 1.15 (3H, d, J=6.2Hz, H-6 ').Nuclear magnetic resonance spectroscopy is as shown in Figure 2.13C- NMR(CD3OD) δ: 169.6 (C-7), 161.5 (C-4), 125.4 (C-1), 132.8 (C-2 and C-6), 116.9 (C-3 and C- 5), 99.5 (C-1 '), 73.6 (C-4 '), 72.1 (C-3 '), 71.8 (C-2 '), 70.9 (C-5 '), 18.0 (C-6 ').Nuclear magnetic resonance Carbon spectrum is as shown in Figure 3.
13 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 13 are 4-O- α-L- rhamnopyranosyl benzoic acid, are a noval chemical compound.
Compound 14 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:445.1357 [M-H]-.ESI-MS is as shown in Figure 4.1H-NMR(CD3OD) δ: 7.95 (2H, d, J=8.8Hz, H-2 and H-6), 6.12 (1H, d, J=8.8Hz, H-3 and H-5), 5.33 (1H, d, J= 1.5Hz, H-1 '), 4.58 (1H, d, J=7.7Hz, H-1 "), 4.29 (1H, m, H-2 '), 3.92 (1H, m, H-3 '), 3.82 (1H, m, H-6 "), 3.71 (1H, dd, J=11.9,4.6Hz, H-6 "), 3.61 (1H, m, H-4 '), 3.60 (1H, m, H-5 '), 3.37 (1H, m, H-5 "), 3.35 (1H, m, H-4 "), 3.31 (1H, m, H-2 "), 3.30 (1H, m, H-3 "), 1.20 (3H, d, J =5.8Hz, H-6 ').Nuclear magnetic resonance spectroscopy is as shown in Figure 5.13C-NMR(CD3OD) δ: 169.5 (C-7), 161.4 (C-4), 125.5 (C-1), 132.7 (C-2 and C-6), 116.9 (C-3 and C-5), 105.9 (C-1 "), 99.2 (C-1 '), 82.6 (C- 3 '), 77.7 (C-5 "), 77.6 (C-2 "), 75.4 (C-3 "), 72.4 (C-4 '), 71.2 (C-2 '), 70.9 (C-4 "), 70.5 (C-5 '), 62.1 (C-6 "), 18.1 (C-6 ').Carbon-13 nmr spectra is as shown in Figure 6.
14 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is D- grape and L- rhamnose, according to glucose anomeric proton coupling constant (J= It 7.7Hz) can determine whether as β-D-Glucose, according to C-3-C-5's of rhamnose13C chemical displacement value identifies that the glycosyl is α-L- Rhamnopyranosyl.
In summary information, authenticating compound 14 are 4-O- β-D-Glucose-(1 → 3)-α-L- rhamnopyranosyl benzoic acid, For a noval chemical compound.
Compound 15 is Yellow amorphous powder, chemical structural formula are as follows:
Spectroscopic data is as follows: ESI-MSm/z:298.1293 [M]+.ESI-MS is as shown in Figure 10.1H-NMR(D2O) δ: 7.45 (2H, d, J=8.7Hz, H-2 and H-6), 7.20 (1H, d, J=8.7Hz, H-3 and H-5), 5.61 (1H, d, J= 1.5Hz, H-1 '), 4.19 (1H, m, H-2 '), 4.16 (2H, s, H-7), 4.02 (1H, dd, J=9.5,3.5Hz, H-3 '), 3.81 (1H, m, H-5 '), 3.54 (1H, t, J=9.5Hz, H-4 '), 1.92 (3H, s, H-8), 1.24 (3H, d, J=6.2Hz, H-6′).Nuclear magnetic resonance spectroscopy is as shown in figure 11.13C-NMR(D2O) δ: 155.8 (C-4), 130.6 (C-2 and C-6), 127.2 (C-1), 117.5 (C-3 and C-5), 98.0 (C-1 '), 71.9 (C-4 '), 70.1 (C-3 '), 69.9 (C-2 '), 69.5 (C-5 '), 42.5 (C-7), 23.4 (C-8), 18.0 (C-6 ').Carbon-13 nmr spectra is as shown in figure 12.
15 sour water solution of compound is obtained into aglycon and saccharide part, reaction is performed the derivatization to sugar, passes through HPLC liquid phase analysis It is compareed with the derivative of standard sugar, identifies that sugar is L- rhamnose, in conjunction with C-3-C-5 of rhamnose13The identification of C chemical displacement value The glycosyl is α-L- rhamnopyranosyl.
In summary information, authenticating compound 15 are N- oxidation-methyl-phenyl ethylamine -4-O- alpha-L-rhamnoside, are one new Compound.
2 injection of embodiment
10 parts of weight of compound that Example 1 obtains or derivatives thereof, 8.5 parts of weight of sodium chloride, water for injection 1000 2 parts of weight of active carbon are added in part weight, mixed dissolution, stirring, stir 30min, and solution passes through miillpore filter (0.22 μm) mistake Filter, is sub-packed in peace and cuts open in bottle, every 5ml, and every liquid drugs injection containing 50mg is made in sterilizing, passed examination.Other check items should accord with It closes and is required under the Pharmacopoeia of the People's Republic of China (2015 editions) injection item.
3 freeze-dried powder of embodiment
10 parts of weight of compound that Example 1 obtains or derivatives thereof, are dissolved in the mannitol water for injection containing 1% 5 parts of weight activity charcoals are added in 1000 parts of weight, stir 20min, and solution is clarified by (0.22 μm) of miillpore filter filtering Solution is sub-packed in the cillin bottle of 10ml, every 2ml, and every freeze drying powder injection containing 20mg is made in freeze-drying.Other inspections It looks into item and should meet and required under the Pharmacopoeia of the People's Republic of China (2015 editions) injection item.
4 tablet of embodiment
20 parts of weight of compound that Example 1 obtains or derivatives thereof, filler select 30 parts of weight of starch, adhesive 5 parts of weight of hydroxypropyl methyl cellulose are selected, disintegrating agent selects 10 parts of weight of microcrystalline cellulose；Lubricant selects magnesium stearate The granulation of 50% appropriate amount of ethanol is added in 0.5 part of weight, mixing, and dry, tabletting to obtain the final product.Other check items should meet that " the Chinese people are total With state's pharmacopeia " it requires under (2015 editions) tablet item.
The hypoglycemic activity of phenol glycosides compound in 5 moringa seeds of embodiment
(1) experimental principle
Using the diabetes mice mould of high fat diet (HFD) plus streptozotocin (Streptozotocin, STZ) induction Type observes phenolic glycoside class noval chemical compound to the blood glucose of diabetic mice, the influence of weight, evaluation respectively with different compound stomach-fillings The effect of moringa seeds phenolic glycoside class noval chemical compound treatment diabetes.
(2) experimental material
Kunming mice；Moringa seeds phenol glycosides compound 1-15；Streptozotocin；Lard；Blood sugar test paper and blood glucose meter；Lemon Sour sodium buffer (PH 4.4)；Gloves；Mouse box；Distilled water.
(3) experimental group
Phenolic glycoside class noval chemical compound experimental group；Normal group (distilled water)；Model group (HFD+STZ).
(4) preparation and processing of model
3/cage of male mouse of kunming, room temperature (22 ± 3) DEG C, relative humidity 60% ± 10%, daily illumination 12h, ingest, Drinking-water is freely.Random to be grouped after adaptable fed 1 week, every group 10: normal group gives normal diet nursing, high fat diet sugar It urinates sick (HFD+STZ) group and gives high lipid food nursing, after 3 weeks, mouse is deprived of food but not water 12h, (HFD+STZ) mouse and gives STZ solution is injected intraperitoneally by 100mg/kg, and normal group of group mouse is buffered with same dosage intraperitoneal injection citric acid-lemon acid sodium Liquid.Continue after STZ injection with same forage feed, continue to be recorded with same forage feed the diet of mouse and takes the photograph regimen condition. Administration one, tail vein takes blood to be detected with blood glucose meter after two weeks.The mouse 10 of normal diet is only used as normal group, and modeling is successfully sugared Sick mouse 50 is urinated, is randomly divided into 5 groups.It is administered according to following grouping: moringa seeds phenolic glycoside class noval chemical compound group 30mg/kg, model Group is organized distilled water 0.3~0.4ml/ days with normal, is administered in a manner of stomach-filling, one time a day.
(5) specific experiment process
The situations such as feeding, drinking-water, weight, the state of mind, hair color are observed after administration 1,2 week；It measures respectively: blood glucose value, Weight.
(6) experimental result
1. ordinary circumstance is observed
There are more drinks, mostly food, diuresis, weight loss in mouse after modeling, and has slow in reacting, the mixed and disorderly unglazed equal diseases of coat Shape, the above symptom of each group mouse has different degrees of improvement after phenolic glycoside class noval chemical compound in administration moringa seeds, reacts cleverer Living, hair is calm and glossy.
2. influence of the moringa seeds phenolic glycoside class noval chemical compound to HFD+STZ blood glucose in diabetic mice content
From result (table 2): the diabetic mice average blood sugar of HFD+STZ induction is significantly raised, compared with normal group There were significant differences (P < 0.001).Moringa seeds phenolic glycoside class noval chemical compound group compared with model group mouse blood glucose significantly reduce (P < 0.05, P < 0.01).The result shows that moringa seeds phenolic glycoside class noval chemical compound can reduce the blood glucose of diabetic mice.
Influence of the 2 moringa seeds phenol glycosides compound of table to HFD+STZ blood glucose in diabetic mice content
###P < 0.001, model group ν s blank group；* P < 0.01 P < 0.05, * *, administration group ν s model group
3. influence of the moringa seeds phenolic glycoside class noval chemical compound to HFD+STZ diabetic mice weight is from result (table 3): sugar Urine disease model group mouse weight dramatically increases (P < 0.01, P < 0.001) compared with the weight of medication therapy groups mouse, moringa seeds phenolic glycoside class Noval chemical compound weight compared with model group is remarkably decreased (P < 0.05).
Influence of the 3 moringa seeds phenol glycosides compound of table to diabetic mice weight
##P < 0.01,###P < 0.001, normal group of administration group ν s；* P < 0.05, administration group ν s model group
Phenol glycosides compound antidepressant activity in 6 moringa seeds of embodiment
(1) experimental principle
Forced swim test (Forced Swimming Test, FST) system is mainly used for antidepression, calmness and analgesic The research of class drug.By being placed in experimental animal in the environment of one limitation (such as in water), animal risks one's life earn in this context Bundle makes an attempt at escaping and can not escape, to provide one without avoidable compressing environment, after the experiment of a period of time, animal is Typical " motionless state " is shown, one kind is reflected and is referred to as " behavioral despair state ", record is in the animal of the environment Generate the series of parameters in desperate motionless state procedure.The dead time of mouse is the pharmaceutically-active index of judgement depression, Dead time is shorter, and antidepressant effect is stronger.Rat force swimming test (Tail suspension test, TST): being a kind of classics And the method for energy Fast Evaluation antidepressant, analeptic drug, downern drug effect.Its principle is looked forward to after utilizing mouse tail suspension Figure is escaped but can not be escaped, to abandon struggling, it is motionless that animal is recorded into the distinctive motionless state of depression, in experimentation Time reflects depressive state, and antidepressant, analeptic drug, which can significantly shorten, changes its state.
(2) experimental material
C57BL/6 mouse；Phenolic glycoside class noval chemical compound in moringa seeds；Fluoxetine hydrochloride；Gloves；Mouse box；Deionized water；It is organic Glass water vat；Video camera；No. 12 intragastric administration on mice needles.
(3) experimental group
Phenolic glycoside class noval chemical compound experimental group in moringa seeds: every group 10,20mg/kg；Positive drug group (Fluoxetine hydrochloride): 10,20mg/kg；Blank group: 10, deionized water is given.
(4) specific experiment process
Forced swim test: taking mouse, is deprived of food but not water raising 12h, and 1h moves into laboratory to adapt to environment before experiment. After stomach-filling 1h, mouse is respectively placed in glass jar water went swimming, preceding 2min stops swimming in 4min after record as adaptation time Float the motionless cumulative time.The administration of administration group every morning 9-10 point, successive administration 6 days, the 7th day, 1h was empty in advance before administration Mouse after stomach-filling 1h, is respectively placed in glass jar water went swimming by abdomen, and preceding 2min stops after record in 4min as adaptation time Swimming floats the motionless cumulative time.
Qutstanding tail test: mouse tail is fixed on homemade outstanding tail bracket away from the part at the 2cm of root by 1h after the last administration On, making mouse head destage face about 5cm is in projecting state, and every animal two sides are separated with plate, block animal sight, be allowed to mutual It does not interfere.Observe the accumulative dead time of groups of animals rear 5min in 6min after outstanding tail.
(5) experimental result:
1. phenolic glycoside class noval chemical compound can be obviously shortened accumulative in mouse forced swimming test in moringa seeds compared with model group Dead time (P < 0.01), it the results are shown in Table 4.
Influence of the phenol glycosides compound to mouse forced swimming test in 4 moringa seeds of table
P < 0.01 *, administration group ν s blank group
2. phenolic glycoside class noval chemical compound can be obviously shortened the accumulative dead time of outstanding tail mouse in moringa seeds compared with model group (P < 0.05), the results are shown in Table 5.
Influence of the phenol glycosides compound to Tail suspension test in 5 moringa seeds of table
* P < 0.05, administration group ν s blank group.
(6) experiment conclusion:
The experimental results showed that in moringa seeds prepared by the present invention phenol glycosides compound can shorten forced swim test and The dead time of mouse in tail-suspention test.Show: phenolic glycoside in the moringa seeds that Moringa seed is prepared through certain extraction separation method Class compound has preferable antidepressant effect, can be used for preparing and developing antidepression preparation.
7 moringa seeds phenol glycosides compound anti-senile dementia activity of embodiment
(1) experimental principle
A β deposition is one of most typical pathological characters of senile dementia, during the occurrence and development of senile dementia With key effect.Senile dementia accuracy rate is diagnosed up to 80% according to A β deposition.Studies have shown that intracerebral A β40With A β42 Content and the degree of patients of senile dementia cognition dysfunction be positively correlated.Morris water maze laboratory is for evaluating sky Between ability of learning and memory classical way, be evaluate dementia animal model duplication result objective indicator.In recent years, dementia animals Model has become the important means of research senile dementia.A β is prepared using SD rat1-42Intracerebroventricular causes Model of Dementia, respectively Phenolic glycoside class noval chemical compound and physiological saline in moringa seeds are given, by Morris water maze laboratory, evaluates phenolic glycoside class in moringa seeds Improvement situation of the compound to senile dementia learning and memory in rats ability.
(2) experimental material
SPF grades of SD male rats；Phenolic glycoside class noval chemical compound in moringa seeds；Amyloid protein segment (A β1-42)；DW-5 is big Mouse stereotaxic apparatus；WMT-100Morris water maze video analytic system；Gloves；Mouse box；Deionized water；Organic glass water Cylinder；Video camera；Gastric perfusion needle.
(3) experimental group
Control group (physiological saline), model group (condensed state A β1-42), phenolic glycoside class noval chemical compound experimental group in moringa seeds.Often Group 10.
(4) dosage and number
Phenolic glycoside class noval chemical compound experimental group 20mg/kg, is administered in a manner of stomach-filling in moringa seeds, one time a day, continuous 7 days.
(5) specific experiment process
1. prepared by model: after SD rat is anaesthetized with 10% urethane, flat cranium head position is fixed, and is positioned through stereotaxic apparatus 2.0mm is opened by 3.4mm, brain median line or so after bregma, depth is slowly at the uniform velocity to inject 5 μ under skull surface at 2.7mm respectively L condensed state A β1-42.The isotonic saline solution of A β model control group injection isometric(al).The behavior of Morris water maze is carried out after modeling 1 week Learn test.
2. Morris water maze Behavior test: selection peace and quiet, half-light, isoperibol are tested, and laboratory wall can Different graphic suitably is pasted, to help animal to determine orientation.Bucket is filled with clear water to predetermined altitude (about 40 cm) before experiment, Appropriate antholeucin is added, water is made to become opaque milky white liquid, heater heats water temperature to 25 DEG C.Platform is placed in the 4th Quadrant center is located at the water surface or less about 1.5cm, and position of platform remains unchanged in whole experiment process.Orientation navigation test: positioning Sea trial continues four days.Platform is placed in the second quadrant center, rat successively enters water from four quadrants towards pool wall, and record is big Mouse finds time used in platform, i.e. escape latency (EL) in 120s.If rat does not find platform in 120s, escape Incubation period is 120s, rat should be guided to climb up platform at this time.All rats for climbing up platform should stop 15s on platform, make it Cognition underwater platform is escape point, and remembers the spatial position of platform.It is latent in the escape of four quadrants daily to calculate every group of rat Volt phase average value, i.e. average escape latency.The length of average escape latency (AEL) reflects the learning and memory energy of rat Power, AEL is shorter to illustrate rat to the faster of the spatial position learning cognition of underwater platform.Space search test: orientation navigation examination Space search test is carried out after testing for 24 hours.Specific method is to remove platform, finds rat memoriter in no platform Platform records cross-platform number of the rat in 120s, distance and total distance in each quadrant swim.In entire test process In, peripheral pool object of reference includes that the position of experimenter should be fixed.
(6) experimental result
As shown in table 6, in orientation navigation test, compared with model group, being averaged for moringa seeds phenolic glycoside class noval chemical compound is escaped Keep away incubation period significantly shortening P < 0.05, P < 0.01).In space search test, compared with model group, moringa seeds phenolic glycoside class is newly changed The cross-platform number and distance for closing object high dose group significantly improve P < 0.05, P < 0.01) (table 7).The above result shows that: moringa seeds Phenol glycosides compound has the function of improving senile dementia Rats With Memory obstacle.
6 moringa seeds phenol glycosides compound of table is to A β1-42The influence of the senile dementia rat escape latency of induction
#P < 0.05, model group ν s control group；* P < 0.01 P < 0.05, * *, administration group ν s model group
7 moringa seeds phenol glycosides compound of table is to A β1-42The influence of the senile dementia rat space search experiment of induction
##P < 0.01,###P < 0.01, model group ν s control group；* P < 0.01 P < 0.05, * *, administration group ν s model group
It is pointed out that the technical concepts and features of above-described embodiment only to illustrate the invention, it is ripe its object is to allow The personage for knowing technique cans understand the content of the present invention and implement it accordingly, and protection model of the invention can not be limited with this It encloses.Any equivalent change or modification in accordance with the spirit of the invention should be covered by the protection scope of the present invention.

Claims (3)

1. phenol glycosides compound in moringa seeds, which is characterized in that indicated by following structural formula (I):
Wherein R1For hydrogen or glycosyl；R2For ester, amino ester or thioesters, urea or thiocarbamide, oxygen ether etc..
2. in the structural formula (I) of phenol glycosides compound as described in claim 1, the preferred methyl formate base of ester group, Ethyl formate Base, butyl formate base, acetate groups, butyric acid ester group；The preferred methyl carbamate of amino ester, urethanes, carbamic acid Propyl ester, butyl carbamate etc.；Amidocarbonic acid carbomethoxy, the sulphur of methyl formate base, sulphur substitution that the preferred sulphur of thioesters replaces replace Group-4 ethyl formate, sulphur replace urethane base, sulphur replace propyl formate base, sulphur replace amidocarbonic acid first propyl ester The amido that formic acid aryl ester, the sulphur that amidocarbonic acid butyl ester base, the sulphur of butyl formate base, sulphur substitution that base, sulphur replace replace replace Formic acid aryl ester；The preferred urea of urea, thiocarbamide, semicarbazides, thiosemicarbazides, aryl ureas, aryl thiourea etc.；The preferred methyl ether of oxygen ether, second The alkane such as base ether, propyl ether, butyl ether and aryl ether etc.；Glycosyl preferably six carbon pyranoses, six carbofurans sugar, are acylated sugar preferably Six carbon pyranoses, six carbofurans sugar.
3. phenol glycosides compound described in claim 1 and its preparation treatment diabetes, antidepression and anti senile dementia drug and Application in health care product.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114805455A (en) * 2022-05-12 2022-07-29 遵义医科大学 Moringa seed extract with anti-influenza virus activity

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1511520A (en) * 2002-12-31 2004-07-14 �й�ҽѧ��ѧԺҩ���о��� Use of succinate derivative for biologically treating dementia
CN101810632A (en) * 2010-03-16 2010-08-25 云南大学 Purpose of 4-cyan-beta-D-glucoside for curing tristimania
CN101829127A (en) * 2010-05-18 2010-09-15 云南大学 Application of 3-carbethoxyphenyl-beta-D-acetylated glucoside in treating depression
CN103467543A (en) * 2013-09-17 2013-12-25 南京通泽农业科技有限公司 Purification method of moringa oleifera micine
CN103588830A (en) * 2013-06-07 2014-02-19 江西本草天工科技有限责任公司 New benzyl alcohol ester glycoside compound in gastrodia elata and application thereof
CN103626812A (en) * 2013-12-10 2014-03-12 江西本草天工科技有限责任公司 Novel parishin compound in gastrodia elata and application of compound
CN104706656A (en) * 2013-12-13 2015-06-17 中国科学院大连化学物理研究所 Dementia prevention and treatment rhizoma gastrodiae extract or composition
US20150209395A1 (en) * 2013-11-01 2015-07-30 Rutgers, The State University Of New Jersey Extracts From Plants of the Moringaceae Family and Methods of Making
CN105541934A (en) * 2015-12-16 2016-05-04 昆明贝克诺顿制药有限公司 Helicid analogues for treating depression
CN105748500A (en) * 2014-12-16 2016-07-13 中国科学院大连化学物理研究所 Rhizoma gastrodiae effective constituent composition for preventing and curing dementia and application of composition
CN107184622A (en) * 2017-06-07 2017-09-22 暨南大学 The total phenolic glycoside of moringa seeds and its application in medicine and health products is prepared

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1511520A (en) * 2002-12-31 2004-07-14 �й�ҽѧ��ѧԺҩ���о��� Use of succinate derivative for biologically treating dementia
CN101810632A (en) * 2010-03-16 2010-08-25 云南大学 Purpose of 4-cyan-beta-D-glucoside for curing tristimania
CN101829127A (en) * 2010-05-18 2010-09-15 云南大学 Application of 3-carbethoxyphenyl-beta-D-acetylated glucoside in treating depression
CN103588830A (en) * 2013-06-07 2014-02-19 江西本草天工科技有限责任公司 New benzyl alcohol ester glycoside compound in gastrodia elata and application thereof
CN103467543A (en) * 2013-09-17 2013-12-25 南京通泽农业科技有限公司 Purification method of moringa oleifera micine
US20150209395A1 (en) * 2013-11-01 2015-07-30 Rutgers, The State University Of New Jersey Extracts From Plants of the Moringaceae Family and Methods of Making
CN103626812A (en) * 2013-12-10 2014-03-12 江西本草天工科技有限责任公司 Novel parishin compound in gastrodia elata and application of compound
CN104706656A (en) * 2013-12-13 2015-06-17 中国科学院大连化学物理研究所 Dementia prevention and treatment rhizoma gastrodiae extract or composition
CN105748500A (en) * 2014-12-16 2016-07-13 中国科学院大连化学物理研究所 Rhizoma gastrodiae effective constituent composition for preventing and curing dementia and application of composition
CN105541934A (en) * 2015-12-16 2016-05-04 昆明贝克诺顿制药有限公司 Helicid analogues for treating depression
CN107184622A (en) * 2017-06-07 2017-09-22 暨南大学 The total phenolic glycoside of moringa seeds and its application in medicine and health products is prepared

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ANWAR H. GILANI，等: "Pharmacological studies on hypotensive and spasmolytic activities of pure compounds from Moringa oleifera", 《PHYTOTHERAPY RESEARCH》 *
HUSSAIN S，等: "An exposition of medicinal preponderance of Moringa oleifera (Lank.).", 《PAKISTAN JOURNAL OF PHARMACEUTICAL SCIENCES》 *
WANG, FANG，等: "Potential hypoglycaemic activity phenolic glycosides from Moringa oleifera seeds.", 《NATURAL PRODUCT RESEARCH》 *
刘长倩，等: "辣木的化学成分研究", 《安徽农业科学》 *
许敏,等: "辣木的研究进展", 《食品科学》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114805455A (en) * 2022-05-12 2022-07-29 遵义医科大学 Moringa seed extract with anti-influenza virus activity

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