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CN1569886A - Radix asparagi steroid saponin extract and its preparing process and application - Google Patents

Radix asparagi steroid saponin extract and its preparing process and application Download PDF

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Publication number
CN1569886A
CN1569886A CN 200410018180 CN200410018180A CN1569886A CN 1569886 A CN1569886 A CN 1569886A CN 200410018180 CN200410018180 CN 200410018180 CN 200410018180 A CN200410018180 A CN 200410018180A CN 1569886 A CN1569886 A CN 1569886A
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extract
asparagus fern
compound
steroid saponin
saponin
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CN1315866C (en
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陈海生
刘建国
徐从立
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SHANGHAI ZHENGXIANG NAUTRAL DRUG TECHNOLOGY Co Ltd
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SHANGHAI ZHENGXIANG NAUTRAL DRUG TECHNOLOGY Co Ltd
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Abstract

The invention provides a Radix asparagi steroid saponin extract and its preparing process and use thereof, wherein six compounds are isolated from the asparagi steroid saponin extract, among which four of them are novel compounds, the preparing process includes n-butyl alcohol extraction method and macroporous resin absorption method.

Description

Asparagus fern total steroid saponin extract and preparation method thereof and application
Technical field
Effective component extracts that the present invention relates to obtain from natural drug and preparation method thereof and application are the total steroid saponin extract that obtains about by the Chinese medicine asparagus fern specifically, and its preparation method reaches in preparation cardiovascular medicament or Application in Food.
Background technology
The Chinese medicine asparagus fern is the piece root of liliaceous plant Radix Asparagi [Asparagus cochinchinensis (Lour.) Merr.], have nourshing Yin and drynsessmoistening prescription, effect of fire falls in clearing lung-heat, cure mainly cough caused by dryness-heat, consumption of YIN caused by febrile disease, interior heat is quenched one's thirst, the dry constipation of intestines, swelling and pain in the throat etc. [editorial committee of State Administration of Traditional Chinese Medicine's " China's book on Chinese herbal medicine " compiles. and " China's book on Chinese herbal medicine "; Shanghai science tech publishing house, 1999.8 (22): 63～69].Asparagus fern is a conventional Chinese medicine, and aboundresources.TenjiK etc. [Tenji K, et al.Chem Pharm Bull, 1979,27 (12): 3086] from asparagus fern isolation identification 4 asparagus fern furan sterol oligosaccharides glycosides (ASPIV; ASPV; ASPVI; ASPVII); [Liang Z Z such as Liang Z Z, et al.Planta Med, 1988,54 (4): 344] from asparagus fern isolation identification Smilax saponin B (Methylprotodiosin), pseudo-protodioscin (Pseudoprotodiosin) and 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl]-26-O-(β-D-glucopyranosyl)-(25R)-5,20-furan steroid diene-3 β-, the 26-glycol 3-O-[α-L-rhamanopyranosyl (1 → 4)-β-D-glucopyranosyl]-26-O-(β-D-glucopyranosyl)-(25R)-furosta-5,20-dien-3,20-diol}; [Masashi T, etal.Chem Pharm Bull, 1974,22 (10): 2306] such as Masashi T. have isolated 7 oligosaccharides and sucrose from asparagus fern; Holt just wait [holt just, etc. study of pharmacy (day), 1958,30:477] from asparagus fern, got glucose, fructose, 5-methoxymethyl furfural, β-Gu Zaichun; Masashi T. etc. [Masashi T, et al.CA, 1976,85:30677y] and Ni Jingman etc. [Ni Jingman, etc. herbal medicine, 1992,23 (4): 182] reported 19 seed amino acid compositions; Du Xuhua etc. [Du Xuhua etc. Shenyang Pharmacy College's journal, 1990,7 (3): 197] from asparagus fern, told 4 kinds of asparagus fern polysaccharide; Open the prosperous grade of portion [portion of opening is prosperous etc. the research University of Anhui journal (natural science edition) of the separation and purification of Radix Asparagi glycoprotein and cardohydrata-peptide linkage, 1996,20 (4): 51～54] reported the separation and purification and the structural research of asparagus fern glycoprotein.So far do not see that the compound that above-mentioned separation obtains has the active report of cardiovascular and cerebrovascular.
Summary of the invention
The invention provides a kind of asparagus fern total steroid saponin extract and preparation method thereof and application, separate obtaining 6 kinds of compounds from the total steroid saponin extract, their chemical structure is identified as follows:
Figure A20041001818000041
Compound (1): (25S)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 26-glycol-3-O-α-L-sandlwood pyrans glycosyl (1 → 4)]-β-D-glucopyranoside (25S)-and 26-O-β-D-glucopyranosyl-5 β-furosta-20 (22)-en-3 β, 26-diol-3-O-[α-L-rhamnopyranosyl (1 → 4)]-β-D-glucopyranoside}.Physico-chemical property and spectroscopic data are as follows: white amorphous powder (MeOH).mp：189-191℃。[α] D 20-33.06°(C＝4.84，MeOH)。The Liebermann-Burchard reaction is positive, and the Ehrlich reagent react takes on a red color, and illustrates that this compound is the steroidal saponin of F ring open loop.ESI-MS shows: 909[M+Na] +, point out this compound molecular weight to should be 886; Molecular formula is C 45H 74O 17 1H-NMR and 13C-NMR sees Table 1 and table 2.
Table 1 compound (1) 1H-NMR (C 5D 5N, 400MHz)
NO. δ H/ppm NO. δ H/ppm
17-H 2.49(1H，d，J＝10.1) 26-Glu?1 4.81(1H，d，J＝7.7)
CH 3-18 0.69(3H，s) 6 4.39(1H，br?d，J＝12.4)
4.57(1H，br?d，J＝12.4)
CH 3-19 0.85(3H，s) 3-Glu?1 4.83(1H，d，J＝7.8)
CH 3-21 1.63(3H，s，) 6 4.12(1H，br?d，J＝10.3)
4.26(1H，br?d，J＝10.3)
CH 3-27 1.05(3H，d，J＝6.0) 4’-Rha?1 5.9(1H，brs)
6 1.7(3H，d，J＝6.2)
Table 2 compound (1) 13C-NMR (C 5D 5N, 400MHz)
NO. δ C/ppm NO. δ C/ppm
1 30.6 26-Glu
2 26.5 1 104.8
3 74.2 2 75.2
4 30.2 3 78.2
5 36.6 4 72.5
6 26.6 5 78.1
7 26.6 6 62.5
8 34.9 3-Glu
9 39.8 1 102.7
10 34.9 2 74.9
11 21.0 3 76.4
12 39.8 4 78.01
13 43.5 5 76.8
14 54.4 6 61.8
15 31.1 4’-Rha
16 84.2 1 102.3
17 64.3 2 72.3
18 14.1 3 72.5
19 23.5 4 73.7
20 103.2 5 69.8
21 11.5 6 18.2
22 152.1
23 34.1
24 23.3
25 33.4
26 74.9
27 16.8
Figure A20041001818000051
Compound (2): Sarsasapogenin-3-O-[α-L-sandlwood pyrans glycosyl (1 → 4)]-β-D-glucopyranoside 3-O-[α-L-rhamnopyranosyl (1 → 4)]-β-D-glucopyranoside-(25S)-5 β-spirostan-3 beta-ol }.Physico-chemical property and spectroscopic data are as follows: colourless needle crystal (CHCl 3).The Liebermann-Burchard reaction is positive.mp：252-254℃。[α] D 20-61.5°[C＝0.80，CHCl 3/MeOH(1∶1)]。ESI-MS provides [M+Na] +Peak 747 infers that compound molecular weight is 724; Molecular formula is C 39H 64O 12NMR sees Table 3.With document [the black positive allusion quotation of willow etc., foreign medical science, traditional Chinese medicine fascicle, 1988; 10 (1): 56] unanimity.
Table 3 compound (2) 1H-NMR (DMSO-D6,400MHz)
NO. δ H(J Hz)δ C NO. δ H(J Hz) δ C
1 29.3 22 108.8
2 26.1 23 25.5
3 73.7 24 25.4
4 30.0 25 26.4
5 35.8 26 3.35(1H，d，J＝9.3)， 64.9
4.09(1H，dd，J＝5.3，
10.6)
6 26.3 27 0.92(3H，d，J＝6.9) 15.9
7 25.9 3-Glu
8 34.8 1 4.19(1H，d，J＝7.8) 100.5
9 39.6 2 72.6
10 34.6 3 75.3
11 20.4 4 76.8
12 39.6 5 75.3
13 40.1 6 60.0
14 55.6 Rha
15 31.4 1 4.71(1H，brs) 100.8
16 80.3 2 70.6
17 61.8 3 70.7
18 0.9(3H，s)?16.1 4 71.9
19 0.7(3H，s)?23.5 5 68.6
20 41.5 6 1.11(3H，d，J＝6.16) 17.7
21 1.02(3H， 14.4
d，J＝7.06)
Figure A20041001818000061
Compound (3): (25R)-26-O-β-D-glucopyanosyl base-furan steroid-5,20-diene-3 β, 26-glycol-3-O-[α-L-sandlwood pyrans glycosyl (1 → 2)]-[(β-D-glucopyanosyl-(1 → 4))-α-L-sandlwood pyrans glycosyl-(1 → 4)]-β-D-glucopyranoside (25R)-26-O-β-D-glucopyranosyl-furosta-5,20-diene-3 β, 26-diol-3-O-[α-L-rhamnopyranosyl (1 → 2)]-[(β-D-glucopyranoside-(1 → 4)-α-L-rhamnopyranosyl-(1 → 4))-β-D-glucopyranoside].Physico-chemical property and spectroscopic data are as follows: white amorphous powder (MeOH).mp：190-192℃。The Liebermann-Burchard reaction is positive, and the Ehrlich reagent react takes on a red color, and illustrates that this compound is the steroidal saponin of F ring open loop.ESI-MS shows: 1215[M+Na] +, point out this compound molecular weight to should be 1192.Molecular formula is C 57H 92O 26 1H-NMR and 13C-NMR sees Table 4 and table 5.
Table 4 compound (3) 1H-NMR (C 5D 5N, 400MHz)
NO. δ H/ppm NO. δ H/ppm
17-H 2.45(1H，d，J＝10.1) 3-Glu?1 4.92(1H，d，J＝7.0)
CH 3-18 0.72(3H，s) 6 4.05(1H，br?d，J＝10.5)
4.20(1H，br?d，J＝10.5)
CH 3-19 1.04(3H，s) 2’-Rha?1 5.83(1H，brs)
CH 3-21 1.61(3H，s，) 6 1.75(3H，d，J＝6.2)
CH 3-27 1.02(3H，d，J＝6.7) 4’-Rha?1 6.35(1H，brs)
26-Glu?1 4.82(1H，d，J＝7.7) 6 1.65(3H，d，J＝6.2)
6 4.34(1H，br?d，J＝12.4) 4”-Glu?1 5.21(1H，d，J＝7.7)
4.41(1H，br?d，J＝12.4)
6 4.32(1H，br?d，J＝12.4)
4.41(1H，br?d，J＝12.4)
Table 5 compound (3) 13C-NMR (C 5D 5N, 400MHz)
NO. δ C/ppm NO. δ C/ppm
1 37.2 26-Glu?1 104.8
2 29.8 2 78.24
3 77.73 3 74.86
4 38.6 4 72.13
5 142.1 5 78.2
6 121.5 6 62.15
7 32.1 3-Glu?1 100.1
8 31.1 2 77.45
9 50.0 3 73.78
10 36.8 4 77.59
11 20.9 5 76.64
12 39.3 6 60.93
13 43.1 2’-Rha?1 101.64
14 54.6 2 71.40
15 31.1 3 72.48
16 84.1 4 73.78
17 64.1 5 69.15
18 13.8 6 18.26
19 19.1 4’-Rha?1 101.69
20 103.2 2 71.59
21 11.4 3 72.17
22 152.1 4 84.97
23 34.1 5 68.25
24 23.3 6 17.98
25 33.4 4”-Glu?1 106.45
26 74.2 2 76.2
27 16.8 3 78.12
4 71.01
5 76.6
6 62.53
Figure A20041001818000081
Compound (4): (25S)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 15,26-triol-3-O-α-L-sandlwood pyrans glycosyl (1 → 4)]-β-D-glucopyranoside (25S)-26-O-β-D-glucopyranosyl-5 β-furosta-20 (22)-en-3 β, 15,26-triol-3-O-[α-L-rhamnopyranosyl (1 → 4)]-β-D-glucopyranoside}.Physico-chemical property and spectroscopic data are as follows: white amorphous powder (MeOH).mp：210-212℃。The Liebermann-Burchard reaction is positive, and the Ehrlich reagent react takes on a red color, and illustrates that this compound is the steroidal saponin of F ring open loop.ESI-MS shows: 925[M+Na] +, point out this compound molecular weight should be: 902.Molecular formula is C 45H 74O 18 1H-NMR and 13C-NMR sees Table 6 and table 7.
Table 6 compound (4) 1H-NMR (C 5D 5N, 400MHz)
NO. δ H/ppm NO. δ H/ppm
17-H 2.5(1H，d，J＝10.3) 26-Glu?1 4.82(1H，d，J＝7.8Hz)
CH 3-18 0.7(3H，s) 6 4.38(1H，br?d，J＝12.3)
4.56(1H，br?d，J＝12.3)
CH 3-19 0.85(3H，s) 3-Glu?1 4.82(1H，d，J＝7.8)
CH 3-21 1.72(3H，s，) 6 4.14(1H，br?d，J＝10.5)
4.27(1H，br?d，J＝10.5)
CH 3-27 1.18(3H，d，J＝6.7) 4’-Rha?1 5.9(1H，brs)
6 1.7(3H，d，J＝6.2)
Table 7 compound (4) 13C-NMR (C 5D 5N, 400MHz)
NO. δ C/ppm NO. δ C/ppm
1 30.601 26-Glu
2 26.642 1 104.86
3 74.894 2 74.948
4 29.292 3 78.130
5 36.647 4 71.384
6 25.516 5 76.473
7 26.642 6 62.515
8 34.808 3-Glu
9 39.845 1 102.69
10 34.884 2 75.210
11 20.984 3 78.227
12 39.736 4 78.084
13 43.567 5 76.825
14 54.42 6 61.272
15 84.37 4’-Rha
16 90.094 1 102.36
17 64.64 2 72.297
18 14.182 3 72.489
19 23.538 4 73.696
20 104.96 5 70.003
21 11.36 6 18.188
22 153.79
23 34.109
24 39.421
25 30.713
26 75.368
27 17.697
Compound (5): (25R)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 26-glycol-3-O-[β-D-glucopyanosyl base-(1 → 2)]-β-D-glucopyranoside (25R)-and 26-O-β-D-glucopyranosyl-5 β-furost-20 (22)-en-3 β, 26-diol-3-O-[β-D-glucopyranosyl-(1 → 2)]-β-D-glucopyranoside}.Physico-chemical property and spectroscopic data are as follows: white amorphous powder (MeOH).mp：188-190℃。The Liebermann-Burchard reaction is positive, and the Ehrlich reagent react takes on a red color, and illustrates that this compound is the steroidal saponin of F ring open loop.ESI-MS shows: 925[M+Na] +, point out this compound molecular weight should be: 902.Molecular formula is C 45H 74O 18 1H-NMR and 13C-NMR sees Table 8 and table 9.
Table 8 compound (5) 1H-NMR (C 5D 5N, 400MHz)
NO. δ H/ppm NO. δ H/ppm
17-H 2.45(1H，d，J＝10.0) 26-Glu?1 4.80(1H，d，J＝7.0)
CH 3-18 0.72(3H，s) 6 4.34(1H，br?d，J＝12.5)
4.42(1H，br?d，J＝12.5)
CH 3-19 1.02(3H，s) 3-Glu?1 4.95(1H，d，J＝7.0)
CH 3-21 1.65(3H，s，) 6 4.36(1H，br?d，J＝10.6)
4.49(1H，br?d，J＝10.6)
CH 3-27 1.05(3H，d，J＝5) 2’-Glu?1 5.4(1H，d，J＝7.0)
6 4.37(1H，br?d，J＝12.3)
4.5(1H，br?d，J＝12.3)
Table 9 compound (5) 13C-NMR (C 5D 5N, 400MHz)
NO. δ C/ppm NO. δ C/ppm
1 30.656 26-Glu
2 26.557 1 104.75
3 74.90 2 76.60
4 30.488 3 78.07
5 36.575 4 71.46
6 26.595 5 78.24
7 26.690 6 62.42
8 34.944 3-Glu
9 39.940 1 101.56
10 34.944 2 82.76
11 21.04 3 75.01
12 39.835 4 71.34
13 43.58 5 77.89
14 54.50 6 62.58
15 31.116 2’-Glu
16 84.29 1 105.52
17 64.43 2 74.86
18 14.10 3 77.62
19 23.17 4 71.59
20 103.25 5 78.12
21 11.48 6 62.67
22 152.12
23 34.124
24 23.337
25 33.396
26 74.90
27 16.87
Figure A20041001818000111
Compound (6): (25R)-26-O-β-D-glucopyanosyl base-furan steroid-5,20-diene-3 β, 26-glycol-3-O-[α-L-sandlwood pyrans glycosyl (1 → 2)]-[α-L-sandlwood pyrans glycosyl-(1 → 4)]-β-D-glucopyranoside (25R)-26-O-β-D-glucopyranosyl-furost-5,20-diene-3 β, 26-diol-3-O-[α-L-rhamnopyranosyl (1 → 2)]-[α-L-rhamnopyranosyl-(1 → 4)]-β-D-glucopyranoside}.Physico-chemical property and spectroscopic data are as follows: white amorphous powder (MeOH).mp：175-177℃。The Liebermann-Burchard reaction is positive, and the Ehrlich reagent react takes on a red color, and illustrates that this compound is the steroidal saponin of F ring open loop.ESI-MS shows: 1053[M+Na] +, point out this compound molecular weight should be: 1030.Molecular formula is C 51H 82O 21 1H-NMR and 13C-NMR sees Table 10 and table 11.With document [Liang Z Z etal, Planta Med.1988; 54 (4): 344] unanimity.
Table 10 compound (6) 1H-NMR (C 5D 5N, 400MHz)
NO. δ H/ppm NO. δ H/ppm
17-H 2.45(1H，d，J＝10.0) 26-Glu?1 4.80(1H，d，J＝7.0)
CH 3-18 0.72(3H，s) 6 4.34(1H，br?d，J＝12.5)
4.42(1H，br?d，J＝12.5)
CH 3-19 1.04(3H，s) 3-Glu?1 4.95(1H，d，J＝7.0)
CH 3-21 1.61(3H，s，) 6 4.05(1H，br?d，J＝10.4)
4.10(1H，br?d，J＝10.4)
CH 3-27 1.02(3H，d，J＝6.0) 2’-Rha?1 5.85(1H，brs)
6 1.64(3H，d，J＝6.0)
4’-Rha?1 6.4(1H，brs)
6 1.75(3H，d，J＝6.0)
Table 11 compound (6) 13C-NMR (C 5D 5N, 400MHz)
NO. δ C/ppm NO. δ C/ppm
1 37.2 26-Glu
2 29.8 1 104.82
3 77.67 2 77.37
4 38.6 3 74.85
5 140.4 4 72.18
6 121.4 5 78.15
7 32.04 6 62.49
8 31.02 3-Glu
9 49.95 1 99.89
10 39.92 2 78.27
11 20.89 3 76.56
12 39.27 4 77.59
13 43.04 5 78.24
14 54.58 6 60.92
15 31.02 2’-Rha
16 84.11 1 102.54
17 64.17 2 71.36
18 13.74 3 70.04
19 19.04 4 72.36
20 103.2 5 73.55
21 11.4 6 18.11
22 153.2 4’-Rha?1 101.63
23 43.14 2 72.15
24 23.29 3 69.13
25 33.37 4 72.45
26 74.57 5 73.77
27 16.8 6 18.27
In the above-claimed cpd, compound (2) and (6) are known compound; Compound (1), (3), (4) and (5) are new compound.
Asparagus fern total steroid saponin preparation method of extract of the present invention has two kinds of following n-butanol extraction and macroreticular resin absorbing methods.Concrete preparation process is:
One, n-butanol extraction:
The asparagus fern meal, with 20 times of amount 70～80% ethanol percolate extraction, decompression recycling ethanol gets medicinal extract.Medicinal extract is diluted with suitable quantity of water,, remove fat-soluble component with chloroform extraction.The aqueous solution is with n-butanol extraction 3-5 time, and the reclaim under reduced pressure propyl carbinol is to doing, and residue dissolves with small amount of methanol, add acetone under stirring and no longer produce to precipitation, filtration under diminished pressure, vacuum-drying gets asparagus fern total steroid saponin extract, yield is about 4-5%, and wherein content of furostanol saponin is about 70-80%.
Two, macroreticular resin absorbing method:
Get the asparagus fern meal, doubly measure 70～80% alcohol reflux 3 times with 7-15, the extracting solution reduction vaporization reclaims ethanol to there not being the alcohol flavor, behind the thin up with macroporous resin column (D101 macroporous resin column for example, the ZTC-1 macroporous resin column, AB-8 macroporous resin column etc.) carry out chromatographic separation, successively with water, 20% ethanol, the 70%-80% ethanol elution, to get asparagus fern total steroid saponin extract behind the 70%-80% ethanol elution part decompression recycling ethanol evaporate to dryness, yield is about 4～5%, and wherein content of furostanol saponin is 80～85%.
The asparagus fern total steroid saponin extract that the present invention makes with the piece root of asparagus fern through pharmacology activity research, finds that asparagus fern total steroid saponin extract has remarkable cardiovascular and cerebrovascular active function.The total steroid saponin extract is given anesthetized dog intravenous drip (5mg/Kg) test, finds that this total steroid saponin extract can significantly increase the anesthetized dog cerebral blood flow (CBF); Can significantly reduce the anesthetized dog cerebral vascular resistance; Anesthetized dog mean arterial pressure and heart rate there is not obvious influence; Quiet of dog (2.5mg/Kg) is given in the new compound of getting (1), (3), and specific activity total steroid saponin extract is better.Therefore, asparagus fern total steroid saponin extract can be used for preparation control cardiovascular and cerebrovascular medicine or food.
Embodiment
Below by embodiment, the invention will be further described.
Embodiment 1 n-butanol extraction:
Asparagus fern meal 1kg, with 20 times of amount 70～80% ethanol percolate extraction, the percolate decompression recycling ethanol gets medicinal extract.Medicinal extract is diluted with suitable quantity of water, with chloroform extraction 2 times (using chloroform 500ml) at every turn.The aqueous solution that chloroform extraction is crossed uses n-butanol extraction 4-5 time (to use propyl carbinol 400～500ml) more at every turn, merge butanol extraction liquid, the reclaim under reduced pressure propyl carbinol is to doing, residue dissolves with small amount of methanol, add acetone under stirring and no longer produce to precipitation, filtration under diminished pressure precipitates, and precipitation gets the total steroid saponin extract through vacuum-drying, yield is about 4%, and wherein content of furostanol saponin is about 75%.
Embodiment 2 macroreticular resin absorbing methods:
Asparagus fern meal 1kg, with 70～80% alcohol reflux 3 times (using ethanol 1000ml) at every turn, the alcohol extract reclaim under reduced pressure is not distinguished the flavor of to there being alcohol, behind the thin up, last D101 macroporous resin column is carried out chromatographic separation, successively with water, 20% ethanol, 70-80% ethanol elution, 70%-80% ethanol elution part decompression and solvent recovery is extremely done, residue promptly gets the total steroid saponin extract through vacuum-drying, and yield is about 5%, and wherein content of furostanol saponin is about 83%.
The cerebrovascular activity test of embodiment 3 asparagus fern total steroid saponin extracts
3.1 test objective: observation asparagus fern total steroid saponin extract, compound (1), compound (3) influence the anesthetized dog cerebrovascular.
3.2 be subjected to the reagent thing: see Table 12.
3.3 animal: 27 of healthy hybrid dogs are provided conformity certification number by the The 2nd Army Medical College Experimental Animal Center: SCXK (Shanghai) 2003-0002, body weight 13～15kg, the male and female dual-purpose, be divided at random 5 groups as follows, see Table 12:
Table 12
Grouping number of animals (only) dosed administration approach
Negative control group 6 physiological saline 5ml/kg intravenous drips
The 6 nimodipine 300ug/kg intravenous drips of nimodipine group
The 6 5mg/kg intravenous drips of asparagus fern total steroid saponin group
The 5 2.5mg/kg intravenous drips of compound (1) group
The 4 2.5mg/kg intravenous drips of compound (3) group
3.4 test method: animal is used Nembutal vein anesthetic (30mgkg -1); Separate right common carotid artery and external carotid artery, after ligation external carotid artery and other arteriole branches, laying diameter on arteria carotis communis is the magnetic flow meter probe of 3mm, with MFV-3200 type Electromagnetic Flow instrument (Japanese photoelectricity Co., Ltd.) record volume of blood flow, and expression ICAF amount.Separate femoral artery, parallel intubate is thrust four limbs and the front is subcutaneous with needle electrode, and the FAP force transducer is connected bioelectrical signals amplifier (productions of Shanghai Alcott company) and by the computer demonstration, writes down arteriotony with cardiac diagnosis lead-line; Separate femoral vein, parallel intubate (intravenously administrable is used).Separate tracheae, insert trachea cannula.After operation finishes, stablized 30 minutes, write down once every index as administration before control value; The administration volume is 5ml/kg, and the quiet notes time is 30min.Quiet notes back was write down every desired value in 5,15,30,60,90,120 minutes respectively.Put to death dog after 120 minutes, get brain and weigh.Multiply by 2 representative full cerebral blood flow (CBF)s (CBF) with the right common carotid artery volume of blood flow.Cerebral vascular resistance can be calculated with formula: R=MBP (kPa)/[CBF (ml/min) 100g brain].
3.5 route of administration: intravenous drip.
3.6 administration number of times: equal single-dose.
3.7 observation index and observing time: observed and recorded ICAF amount, blood pressure, be after the administration 5,15,30,60,90,120 minutes observing times.
3.8 data and statistical procedures:
Experimental result is represented with X ± s, adopts one-tenth team two sample analyses of t check paired value to do administration front and back statistical study, comparative analysis between variance t such as two samples check work group, and P＜0.05 is judged as the significant difference with significance.
3.9 observed content:
1, to the influence of cerebral blood flow (CBF): to the influence of cerebral blood flow (CBF), its velocity of variation and physiological saline control group relatively have there was no significant difference with time point before and after the medication.
2, to the influence of cerebral vascular resistance: the variation of cerebral vascular resistance before and after the medication, its velocity of variation and physiological saline control group relatively have there was no significant difference with time point.
3, to the influence of mean blood pressure: to the influence of mean blood pressure, velocity of variation and physiological saline control group before and after the administration have not statistically significant with the time point comparing difference before and after the medication.
4, to the influence of heart rate: to the influence of heart rate, its velocity of variation and physiological saline control group relatively have there was no significant difference with time point before and after the medication.
3.10 experimental result:
1, the intravenous drip of asparagus fern total steroid saponin extract is to the influence of anesthetized dog cerebral blood flow (CBF): before the medication of physiological saline control group with medication after each time point comparison cerebral blood flow (CBF) slightly reduce and cerebral blood flow (CBF) in 30 minutes, raise (P＜0.05) relatively before and after the asparagus fern total steroid saponin extract, compound (1), the medication of compound (3) group.And velocity of variation between physiological saline group comparative group, asparagus fern total steroid saponin extract, compound (1), compound (3) group raise in 30 minutes obviously, (P＜0.05-0.01).See Table 13.
2, to the influence of anesthetized dog cerebral vascular resistance
Before the medication of physiological saline group relatively cerebral vascular resistance do not have considerable change, after asparagus fern total steroid saponin extract, compound (1), the medication of compound (3) group with medication before relatively cerebral vascular resistance in 60min, reduce.Its velocity of variation and physiological saline group relatively obviously reduced (P＜0.05～0.01) and see Table 14 in 30 minutes.
3, to the influence of anesthetized dog mean blood pressure and heart rate
Physiological saline group and asparagus fern total steroid saponin extract, compound (1), compound (3) group all do not have obvious influence to anaesthetized dog blood pressure and heart rate.See Table 15 and 16.
The influence of table 13 pair anesthetized dog cerebral blood flow (CBF) (ml/min.100g, x ± SD, n=6)
After the preceding administration of administration
Group 5min 15min 30min 60min 90min 120min
Physiological saline group 428.45.52 ± 122.81 405.07 ± 140.47 409.08 ± 126.98 399.31 ± 119.82 387.87 ± 70.28 321.49 ± 54.86 290.010 ± 80.64
Velocity of variation %-5.97 ± 16.14-4.89 ± 9.95-20.10 ± 35.43-6.51 ± 17.06-22.30 ± 14.05-30.00 ± 19.18
Nimodipine group 299.46 ± 35.85 334.82 ± 61.90 339.06 ± 44.57 331.95 ± 20.42 355.02 ± 29.94 *332.65 ± 60.56 322.23 ± 69.21
Velocity of variation % 13.11 ± 24.56 14.37 ± 18.84 *12.04 ± 13.87 *19.96 ± 17.22 *10.98 ± 14.23 *6.91 ± 14.60 *
The total steroidal soap of asparagus fern
Glucoside extract group 265.15 ± 79.96 338.10 ± 98.70 △ △310.40 ± 103.29 △280.21 ± 101.48 227.66 ± 114.58 206.69 ± 122.78 195.48 ± 113.01
Velocity of variation % 28.32 ± 16.29 *16.70 ± 12.67 *4.58 ± 13.27 *-17.30 ± 23.00-26.41 ± 48-30.00 ± 24.83
Compound (1) group 371.75 ± 30.96 445.96 ± 70.72 419.41 ± 58.72 357.89 ± 35.38 329.25 ± 44.23 280.63 ± 41.13 217.55 ± 43.17
Velocity of variation % 21.44 ± 26.67 14.12 ± 23.59-2.74 ± 16.16-10.39 ± 17.85-24.08 ± 13.15-41.77 ± 8.00
Compound (3) group 381.54 ± 37.43 450.03 ± 40.45 427.36 ± 49.06 404.01 ± 38.84 327.17 ± 30.63 285.15 ± 33.37 224.26 ± 60.59
Velocity of variation % 18.14 ± 642 12.06 ± 8.03 6.15 ± 8.77-13.20 ± 15.09-24.10 ± 15.95-39.65 ± 21.72
Velocity of variation and physiological saline control group compare with time point, *P＜0.05, *P＜0.01; △P＜0.05, △ △Compare before and after group innerlich anwenden of p＜0.01
The influence of table 14 pair anesthetized dog cerebral vascular resistance (the kPamin/ml100g brain, x ± SD, n=6)
After the preceding administration of administration
Group 5min 15min 30min 60min 90min 120min
Physiological saline group 4.01 ± 1.67 4.22 ± 1.36 4.17 ± 1.35 4.17 ± 1.15 4.27 ± 0.73 5.72 ± 1.35 6.92 ± 1.94
Velocity of variation % 7.00 ± 18.07 7.59 ± 20.80 8.52 ± 19.94 18.96 ± 35.10 55.05 ± 47.32 85.79 ± 66.48
Nimodipine group 5.09 ± 1.92 2.60 ± 0.77 △2.65 ± 0.66 △3.11 ± 0.65 △3.36 ± 0.92 △4.32 ± 2.08 4.45 ± 2.25
Velocity of variation %-57.98 ± 10.92 *-38.62 ± 36.63 *-28.66 ± 39.56 *-22.65 ± 46.17 *-10.31 ± 33.84 *-9.18 ± 33.21 *
The total steroidal soap of asparagus fern
Glucoside extract group 5.26 ± 1.13 4.12 ± 0.76 4.37 ± 1.08 4.40 ± 1.74 5.25 ± 2.44 7.17 ± 3.86 8.62 ± 4.63
Velocity of variation %-20.67 ± 12.49 *-16.42 ± 17.51 *-17.38 ± 23.84 *4.80 ± 37.35 36.78 ± 75.32 62.45 ± 87.00
Compound (1) group 7.11 ± 0.91 5.87 ± 0.92 5.92 ± 0.65 7.40 ± 0.69 7.42 ± 0.56 8.23 ± 0.90 11.77 ± 2.94
Velocity of variation %-17.19 ± 9.89 *-16.04 ± 11.57 *4.74 ± 9.89 5.31 ± 12.15 17.58 ± 20.77 66.03 ± 40.80
Compound (3) group 6.77 ± 1.57 5.66 ± 1.49 5.77 ± 1.07 6.14 ± 2.15 7.76 ± 2.25 9.02 ± 2.50 11.29 ± 3.87
Velocity of variation %-16.78 ± 3.71 *-14.02 ± 4.79 *-10.99 ± 11.82 *14.33 ± 25.67 33.12 ± 26.52 66.74 ± 51.48
Velocity of variation and solvent control group compare with time point, *P＜0.05, *P＜0.01
The influence of table 15 pair anesthetized dog mean blood pressure (kPa, x ± SD, n=6)
Time after the administration before the administration
Group 5min 15min 30min 60min 90min 120min
Physiological saline group 15.43 ± 3.76 14.78 ± 2.07 15.15 ± 1.83 15.12 ± 1.31 15.93 ± 1.58 17.50 ± 2.95 18.18 ± 2.53
Velocity of variation %-0.68 ± 21.12 2.53 ± 24.23 2.65 ± 23.53 7.73 ± 24.22 17.79 ± 31.02 21.88 ± 26.46
Nimodipine group 14.85 ± 4.69 8.63 ± 2.59 △8.87 ± 2.05 △10.28 ± 1.98 12.12 ± 2.27 13.53 ± 3.75 13.22 ± 3.61
Velocity of variation %-34.15 ± 41.15-33.05 ± 34.37-22.09 ± 37.22-8.96 ± 39.59-2.69 ± 29.46-4.28 ± 31.73
The total soap body soap of asparagus fern
Glucoside extract group 13.55 ± 3.10 13.57 ± 3.24 12.95 ± 3.18 11.40 ± 3.26 10.18 ± 3.19 11.40 ± 2.99 12.73 ± 3.70
Velocity of variation % 0.49 ± 10.34-3.80 ± 13.55-16.20 ± 12.02-23.64 ± 19.14-14.38 ± 19.41-3.75 ± 28.92
Compound (1) group 17.44 ± 1.36 18.12 ± 1.52 16.96 ± 1.28 18.56 ± 1.36 17.08 ± 1.44 16.18 ± 2.25 17.34 ± 1.23
Velocity of variation % 0.04 ± 0.05-0.02 ± 0.10 0.07 ± 0.11-0.02 ± 0.07-0.07 ± 0.15 0.00 ± 0.12
Compound (3) group 17.40 ± 4.44 17.00 ± 4.14 16.50 ± 3.43 16.30 ± 4.37 16.85 ± 4.59 16.98 ± 4.14 15.90 ± 3.44
Velocity of variation %-1.78 ± 5.42-3.52 ± 11.16-5.92 ± 10.05-3.64 ± 3.58-2.06 ± 3.11-7.49 ± 7.35
Compare before and after △ P＜0.05, medication.
The influence of table 16 pair anesthetized dog heart rate (inferior/minute)
After the preceding administration of administration
Group 5min 15min 30min 60min 90min 120min
Physiological saline group 202 ± 37 178 ± 26 184 ± 19 188 ± 18 184 ± 30 179 ± 53 203 ± 35
Velocity of variation %-9 ± 23-6 ± 20-5 ± 17-7 ± 16-11 ± 25 2 ± 15
Nimodipine group 182 ± 32 157 ± 38 166 ± 34 155 ± 45 166 ± 40 172 ± 38 180 ± 34
Velocity of variation %-12.96 ± 19.31-7.94 ± 18.72 13.78 ± 25.46-7.21 ± 21.94-3.35 ± 24.78 1.25 ± 23.31
The total steroidal soap of asparagus fern
Glucoside extract group 173 ± 36 163 ± 31 158 ± 29 153 ± 23 148 ± 23 152 ± 28 146 ± 38
Velocity of variation %-5 ± 5-8 ± 10-10 ± 13-13 ± 10-11 ± 10-15 ± 12
Compound (1) group 205 ± 36 190 ± 18 186 ± 13 184 ± 13 170 ± 21 175 ± 30 174 ± 34
Velocity of variation %-0.06 ± 0.10-0.08 ± 0.12-0.09 ± 0.12-0.16 ± 0.12-0.14 ± 0.17-0.14 ± 0.21
Compound (3) group 199 ± 27 179 ± 36 185 ± 48 168 ± 37 170 ± 55 166 ± 43 153 ± 46
Velocity of variation %-11 ± 11-8 ± 16-16 ± 10-16 ± 17-18 ± 11-24 ± 15
Conclusion
The test-results of above embodiment 3 shows:
1. asparagus fern total steroid saponin extract, compound (1) and compound (3) intravenous drip can obviously increase the anesthetized dog cerebral blood flow (CBF).
2. asparagus fern total steroid saponin extract, compound (1) and compound (3) intravenous drip have obvious reduction anesthetized dog cerebral vascular resistance effect.
3. asparagus fern total steroid saponin extract, compound (1) and compound (3) intravenous injection do not have obvious influence to anesthetized dog mean arterial pressure and heart rate.
Test-results shows that asparagus fern total steroid saponin extract, compound (1) and compound (3) have as the primary condition of effectively preventing and treating the medicine of cardiovascular and cerebrovascular diseases.Therefore, total steroid saponin extract, compound (1) and the compound (3) of Chinese medicine asparagus fern preparation of the present invention can be used for preparation control cardiovascular and cerebrovascular medicine or food.

Claims (4)

1, a kind of asparagus fern total steroid saponin extract is characterized in that content of furostanol saponin is 70-85% in the described extract, from described extract, separate 6 kinds of compounds, wherein 4 kinds of compounds are:
Compound (1): (25S)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 26-glycol-3-O-α-L-sandlwood pyrans glycosyl (1 → 4)]-β-D-glucopyranoside;
Compound (3): (25R)-26-O-β-D-glucopyanosyl base-furan steroid-5,20-diene-3 β, 26-glycol-3-O-[α-L-sandlwood pyrans glycosyl (1 → 2)]-[(β-D-glucopyanosyl-(1 → 4))-α-L-sandlwood pyrans glycosyl-(1 → 4)]-β-D-glucopyranoside;
Compound (4): (25S)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 15,26-triol-3-O-α-L-sandlwood pyrans glycosyl (1 → 4)]-β-D-glucopyranoside;
Compound (5): (25S)-26-O-β-D-glucopyanosyl base-5 β-furan steroid-20 (22)-alkene-3 β, 26-glycol-3-O-[β-D-glucopyanosyl base-(1 → 2)]-β-D-glucopyranoside.
2, the described asparagus fern total steroid saponin of claim 1 preparation method of extract is characterized in that preparation process is: the asparagus fern meal is doubly measured the 70-80% ethanol percolate extraction with 20-30, gets medicinal extract with the n-butanol extraction preparation; Medicinal extract dilutes with suitable quantity of water, and behind chloroform extraction, the aqueous solution is with n-butanol extraction, evaporate to dryness, and the residue dissolve with methanol adds acetone to precipitation and no longer produces, and filters, dry asparagus fern total steroid saponin extract.
3, the described asparagus fern total steroid saponin of claim 1 preparation method of extract, it is characterized in that preparing with macroreticular resin absorbing method, preparation process is: get the asparagus fern meal, 70-80% alcohol reflux so that 7-15 doubly measures boils off ethanol, carries out chromatographic separation with macroporous resin column, successively with water, 20% ethanol, the 70%-80% ethanol elution gets asparagus fern total steroid saponin extract with 70-80 ethanol elution part evaporate to dryness.
4, the application of the described asparagus fern total steroid saponin of claim 1 extract is characterized in that described asparagus fern steroidal saponin extract is in preparation control cardiovascular and cerebrovascular medicine or Application in Food.
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WO2008031264A1 (en) * 2006-09-07 2008-03-20 Lotus Pharmaceutical Co., Ltd. Furost-5-ene-3, 22, 26-triol glycoside compound for preventing and treating cancer
US20090068293A1 (en) * 2007-09-07 2009-03-12 Bionovo, Inc. ESTROGENIC EXTRACTS OF Asparagus conchinchinensis (Lour.) Merr of the Liliaceae Family AND USES THEREOF
CN101307090B (en) * 2007-05-16 2011-04-13 中国科学院上海药物研究所 Method for preparing timosaponin BIII and uses thereof
CN101548639B (en) * 2009-01-15 2011-04-13 北京林业大学 Flower cultivation medium and preparing method thereof
CN102430041A (en) * 2011-12-10 2012-05-02 重庆市秀山红星中药材开发有限公司 Method for extracting total saponins of asparagus by ultrasonic wave

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JPH0348694A (en) * 1989-07-18 1991-03-01 Dowa Mining Co Ltd Novel saponin substance
CN1102186A (en) * 1993-10-29 1995-05-03 沈阳医学院 Determination and usage of new component of traditional Chinese medicine Chinese onion
CN1131237C (en) * 1997-09-26 2003-12-17 中国人民解放军军事医学科学院放射医学研究所 Usage of steroi saponin for preventing and curing senile dementia and new steroid saponin
US6670459B2 (en) * 2002-03-20 2003-12-30 Zandu Pharmaceutical Works Ltd. Process for the isolation of novel oligospirostanoside
EP1523315A1 (en) * 2002-03-21 2005-04-20 Council Of Scientific And Industrial Research 3-o-[alfa-l-rhamnopyranosyl-(1-2)-alfa-l-rhamnopyranosyl-(1-4)-3beta-d-glucopyranosyl]-25(s)-spirostan-3beta-ol, process for its isolation, and its use as immunomodulator
KR100458003B1 (en) * 2002-05-27 2004-11-18 대한민국 New anticancer compound and its purification from Asparagus oligoclonos

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* Cited by examiner, † Cited by third party
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WO2008031264A1 (en) * 2006-09-07 2008-03-20 Lotus Pharmaceutical Co., Ltd. Furost-5-ene-3, 22, 26-triol glycoside compound for preventing and treating cancer
CN101307090B (en) * 2007-05-16 2011-04-13 中国科学院上海药物研究所 Method for preparing timosaponin BIII and uses thereof
US20090068293A1 (en) * 2007-09-07 2009-03-12 Bionovo, Inc. ESTROGENIC EXTRACTS OF Asparagus conchinchinensis (Lour.) Merr of the Liliaceae Family AND USES THEREOF
US9339523B2 (en) * 2007-09-07 2016-05-17 Bionovo, Inc. Estrogenic extracts of Asparagus conchinchinensis (Lour.) Merr of the Liliaceae family and uses thereof
CN101548639B (en) * 2009-01-15 2011-04-13 北京林业大学 Flower cultivation medium and preparing method thereof
CN102430041A (en) * 2011-12-10 2012-05-02 重庆市秀山红星中药材开发有限公司 Method for extracting total saponins of asparagus by ultrasonic wave

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