CN102399259A - Method for separating and purifying liriope spicata saponin B - Google Patents
Method for separating and purifying liriope spicata saponin B Download PDFInfo
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- CN102399259A CN102399259A CN2011104201190A CN201110420119A CN102399259A CN 102399259 A CN102399259 A CN 102399259A CN 2011104201190 A CN2011104201190 A CN 2011104201190A CN 201110420119 A CN201110420119 A CN 201110420119A CN 102399259 A CN102399259 A CN 102399259A
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- Prior art keywords
- saponin
- ethanol
- radix liriopes
- methanol
- water
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Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 241001448331 Liriope spicata Species 0.000 title abstract description 5
- BMWPBKOFJSHJAW-UHFFFAOYSA-N Saponin B Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(OC6OC(CO)C(O)C(OC7OC(CO)C(O)C(O)C7O)C6=O)C(C)(C)C5CCC34C)C2C1)C(=O)O BMWPBKOFJSHJAW-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000605 extraction Methods 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004809 thin layer chromatography Methods 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000012535 impurity Substances 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 238000000746 purification Methods 0.000 claims abstract description 8
- 238000001514 detection method Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 7
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical group O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 241001521474 Liriope <hydrozoan> Species 0.000 claims description 43
- 229930182490 saponin Natural products 0.000 claims description 29
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 28
- 150000007949 saponins Chemical class 0.000 claims description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 230000006837 decompression Effects 0.000 claims 1
- 239000003480 eluent Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 229920005654 Sephadex Polymers 0.000 abstract 1
- 229940126678 chinese medicines Drugs 0.000 abstract 1
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 235000017709 saponins Nutrition 0.000 description 23
- 239000000470 constituent Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000039 congener Substances 0.000 description 3
- -1 saponins compound Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 244000248557 Ophiopogon japonicus Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000235935 Hilaria belangeri Species 0.000 description 1
- GMBQZIIUCVWOCD-UQHLGXRBSA-N Isosarsasapogenin Natural products O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-UQHLGXRBSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 241001532026 Liriope muscari Species 0.000 description 1
- 241001348277 Liriope spicata var. prolifera Species 0.000 description 1
- 241000756100 Muscari Species 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000005856 steroid saponins Chemical class 0.000 description 1
- 229930002600 steroidal saponin Natural products 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
The invention relates to a method for extracting liriope spicata saponin B from the underground part of Hubei liriope spicata and belongs to the technical field of separation and purification of Chinese medicines. The method particularly comprises the following process steps of: A, extracting by using ethanol, namely merging extracting liquid after ethanol refluxing extraction; B, enriching by using macroporous resin and removing impurities, namely concentrating the extracting liquid, performing macroporous resin column chromatography, performing thin layer chromatography and detecting effluent liquid on line; C, performing silica gel column chromatography chromatographic separation, wherein the eluent is chloroform-methanol-water and 10-15BV eluent is collected; and D, recrystallizing, namely dissolving the eluent by using methanol and recrystallizing. By the method, the process of repeatedly purifying by using dextrangel and C18 inverse phase column chromatography is eliminated. The whole technological process is easy and convenient to operate; the process is stable; water and ethanol are mainly used in the separation process; cost is low; the product purity is over 98 percent through liquid phase detection; and mass preparation or industrialized production of the liriope spicata saponin B can be realized.
Description
Technical field
The present invention relates to a kind of separation purification method of active ingredient of Chinese herbs, be specifically related to from Hubei that extraction separation a kind of steroidal saponin in the underground position of Radix Liriopes is the method for Radix Liriopes saponin(e B, belong to Chinese medicine separating and purifying technology field.
Background technology
The Hubei Radix Liriopes
Liriope spicata(Thunb.) Lour. var. prolifera Y. T. Ma is a Liliaceae Radix Liriopes platymiscium, increases one of basic former plant of kind Radix Liriopes newly for the Pharmacopoeia of the People's Republic of China (nineteen ninety-five version), extensively cultivate in Hubei Province, and as the main flow commodity.Pharmacological research shows, the Hubei Radix Liriopes have the tangible prolongation mouse survival time, extremely significantly increase the spleen weight of mouse, significantly strengthen the carbon clearance effect of mouse.Mainly contain compounds such as steroid saponin, terpene, acid amides, alkaloids, fatty acid in the Radix Liriopes of Hubei, wherein saponins compound is this plant main active ingredient.[Yu Baiyang, Xu Guojun, horizontal well Kang Zhao etc. the chemical constitution study (II) of the Hubei tuber of dwarf lilyturf and short grass Radix Liriopes. China Medicine University's journal, 1988,19 (4): 209-12; Watanabe, Yoshiaki; Sanada, Shuichi; Comparative studies on the constituents of
Ophiopogonis tuberAnd its congeners.I.Studies of the constituents of the subterranean part of
Liriope platyphyllaWang et Tang. (1). Chemical Pharmaceutical Bulletin, 1983,31 (6): 1980-90.; Yu, Boyang; Hirai, Yasuaki; Shoji, Junzo; Xu, Guojun. Comparative studies on the constituents of
Ophiopogonis tuberAnd its congeners.VI.Studies on the constituents of the subterranean part of
Liriope spicatavar. prolifera and L. muscari. (1). Chemical Pharmaceutical Bulletin, 1990,38 (7): 1931-5; Branke, Jueren Thomas; Haslinger, Ernst. Spirostanol glycoside from the tuber of
Ophiopogon japonicus. Liebigs Annalen, 1995, (3): 587-9.].The structural formula of Radix Liriopes saponin(e B is following:
Radix Liriopes saponin(e B is a kind of steroid saponin compound, and the preparation method of following bibliographical information is: the Radix Liriopes raw material is used 95% alcohol reflux, and behind the extracting solution concentrating under reduced pressure, liquid concentrator is used sherwood oil, chloroform and n-butanol extraction respectively.After butanol extraction liquid reclaimed solvent, residue carried out chromatography processes such as silica gel column chromatography and C18 anti-phase preparative column chromatography again and just obtains pure compound.Boyang;?Hirai,?Yasuaki;?Shoji,?Junzo;?Xu,?Guojun.?Comparative?studies?on?the?constituents?of?
ophiopogonis?tuber?and?its?congeners.VI.Studies?on?the?constituents?of?the?subterranean?part?of?
Liriope?spicatavar.?prolifera?and?L.?muscari.?(1).?Chemical?&?Pharmaceutical?Bulletin(1990),38(7),?1931-5。This method complex process, preparation cost is high, and the cycle is long, can't suitability for industrialized production.
Summary of the invention
The present invention is intended to overcome the defective of prior art, provide a kind of fast and convenient, with low cost, applicable to the preparation method of the Radix Liriopes saponin(e B of a large amount of preparations or suitability for industrialized production.Its concrete process step is following:
A. extraction using alcohol: get the underground position 1kg of Hubei Radix Liriopes, once add the ethanolic soln 8-12L of 50%-70%, refluxing extraction 3-5 time, each 1.5-3 hour, keeps little boiling, behind the filtration dregs of a decoction, united extraction liquid;
B. macroporous resin enrichment removal of impurities: go up macroporous resin column chromatography after the extracting solution of steps A is evaporated to density 1.20-1.40; Water 5-8 BV, 20%-30% ethanol 8-10 BV drip washing removal of impurities successively; Drip washing to effluent is used 60%-70% ethanol 4-8 BV wash-out instead, then the online detection effluent of thin-layer chromatography after becoming clearly; And the ethanol elution flow part of collecting this 60%-70%, collect 6 column volumes altogether;
Said thin-layer chromatography developping agent is a chloroform: methyl alcohol: water=100:35:5.
Said macroporous resin is D101 type or AB-8 type.
C. silica gel column chromatography separates: behind the ethanol eluate concentrating under reduced pressure that step B is collected; Carrying out silica gel column chromatography separates; Elder generation is with chloroform-methanol-water during wash-out; Its volume ratio is the mixed solvent 8-10BV removal of impurities of 10:1:0.05, uses the mixed solvent wash-out of chloroform-methanol-water again, collects the elutriant of 10-15BV; Concentrating under reduced pressure obtains Radix Liriopes saponin(e first product.
Said mixed solvent is: by volume, chloroform-methanol-water is 10:1:0.05.
D. recrystallization: the elutriant that step C is collected carries out recrystallization after with the dissolve with methanol of 50%-80%, and cultivating the crystal time is 5-10 hour; Suction filtration then, filter cake with the 70%-90% methanol wash after, vacuum-drying obtains Radix Liriopes saponin(e B content and reaches the white solid product more than 98%.
Per-cent related in the technical scheme of the present invention is volume percent.
Compared with prior art, the technique effect that the present invention had mainly shows:
The present invention has got rid of in the prior art through polydextran gel and the C18 reversed phase column chromatography process of purifying repeatedly; Whole simple operation of process; Process stabilizing is mainly used water and ethanol in the sepn process, with low cost; And the Liquid Detection product purity can realize a large amount of preparations or the suitability for industrialized production of Radix Liriopes saponin(e B up to more than 98%.
Description of drawings
Fig. 1 is the HPLC collection of illustrative plates of the embodiment of the invention 1 Radix Liriopes saponin(e B monomer product.
Embodiment
Below in conjunction with embodiment the present invention is made further detailed description.But should this be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following embodiment.
Among following each embodiment, the monomeric purity of finished product Radix Liriopes saponin(e B is rechecked and is all adopted RPLC-light scattering detector (RP-HPLC-ELSD) method, and chromatographic condition is following:
With the octadecylsilane chemically bonded silica is weighting agent; With acetonitrile: water (45:55) is moving phase; 30 ℃ of column temperatures; Flow velocity 1.0ml/min; 105 ℃ of gasification temperatures; Gas flow rate (N
2) 3.0L/min.
Embodiment 1
Get the underground position 1kg of Hubei Radix Liriopes, once add 50% ethanolic soln 8L, refluxing extraction 3 times, each 2 hours of first, second time, 1.5 hours for the third time, keep little boiling, filter the dregs of a decoction, united extraction liquid; Last D101 type macroporous resin separated after extracting solution was concentrated into 2L; Water 5 BV, 30% ethanol 8BV removal of impurities successively; Drip washing to effluent is used 70% ethanol elution instead after becoming clearly, and thin-layer chromatography detects effluent; The thin-layer chromatography developping agent is a chloroform: methyl alcohol: water (100:35:5), collect the part that contains Radix Liriopes saponin(e B; Separate with silicagel column behind the concentrating under reduced pressure, eluent system is a chloroform: methyl alcohol: water (10:1:0.05), and thin-layer chromatography carries out online detection, begins to collect after having sample to flow out, and receives 15 column volumes altogether; This part of concentrating under reduced pressure obtains the bullion of Radix Liriopes saponin(e B.Bullion is carried out recrystallization after with 50% dissolve with methanol, and cultivating the crystal time is 5 hours, suction filtration, filter cake with 90% methanol wash after, vacuum-drying, white solid that must Radix Liriopes saponin(e B.The yield of this Radix Liriopes saponin(e B is 58.9%, and purity is 98.6%.
Embodiment 2
Get the underground position 1Kg of Hubei Radix Liriopes, once add 70% ethanolic soln 10L, refluxing extraction 4 times, each 2 hours of first and second time, each 1.5 hours of third and fourth time keeps little boiling, and filters the dregs of a decoction, united extraction liquid; Last D101 type macroporous resin separated after extracting solution was concentrated into 2L; Water 6 BV, the 8 BV removal of impurities of 25% ethanol successively; Drip washing to effluent is used 60% ethanol elution instead after becoming clearly, and thin-layer chromatography detects effluent; The thin-layer chromatography developping agent is a chloroform: methyl alcohol: water (100:35:5), collect the part that contains Radix Liriopes saponin(e B; Separate with silicagel column behind the concentrating under reduced pressure, eluent system is a chloroform: methyl alcohol: water (20:1:0.05), and thin-layer chromatography carries out online detection, begins to collect after having sample to flow out, and receives 12 column volumes altogether; This part of concentrating under reduced pressure obtains the bullion of Radix Liriopes saponin(e B.Bullion is carried out recrystallization after with 70% dissolve with methanol, and cultivating the crystal time is 7 hours, suction filtration, filter cake with 70% methanol wash after, vacuum-drying, white solid that must Radix Liriopes saponin(e B.The yield of this Radix Liriopes saponin(e B is 55.3%, and purity is 98.8%.
Embodiment 3
Get the underground position 1Kg of Hubei Radix Liriopes, once add 70% ethanolic soln 12L, refluxing extraction 5 times; Each 3 hours of first and second time, each 2 hours of third and fourth time, the 5th time 1.5 hours little the boiling of maintenance; Filter the dregs of a decoction, last AB-8 type macroporous resin separated after united extraction liquid, extracting solution were concentrated into 2L; Water 8BV, 20% ethanol 8BV removal of impurities successively, drip washing to effluent are used 65% ethanol elution instead after becoming clearly; Thin-layer chromatography detects effluent, and the thin-layer chromatography developping agent is a chloroform: methyl alcohol: water (150:35:5), collect the part that contains Radix Liriopes saponin(e B; Separate with silicagel column behind the concentrating under reduced pressure, eluent system is a chloroform: methyl alcohol: water (10:1:0.05), and thin-layer chromatography carries out online detection, begins to collect after having sample to flow out, and receives 10 column volumes altogether; This part of concentrating under reduced pressure obtains the bullion of Radix Liriopes saponin(e B.Bullion is carried out recrystallization after with 80% dissolve with methanol, and cultivating the crystal time is 10 hours, suction filtration, filter cake with 90% methanol wash after, vacuum-drying, white solid that must Radix Liriopes saponin(e B.The yield of this Radix Liriopes saponin(e B is 53.7%, and purity is 99.0%.
Claims (5)
1. the separation purification method of a Radix Liriopes saponin(e B is characterized in that concrete process step is following:
A. extraction using alcohol: get the underground position 1kg of Hubei Radix Liriopes, once add the ethanolic soln 8-12L of 50%-70%, refluxing extraction 3-5 time, each 1.5-3 hour, keeps little boiling, behind the filtration dregs of a decoction, united extraction liquid;
B. macroporous resin enrichment removal of impurities: go up macroporous resin column chromatography after the extracting solution of steps A is evaporated to density 1.20-1.40; Water 5-8 BV, 20%-30% ethanol 8-10 BV drip washing removal of impurities successively; Drip washing to effluent is used 60%-70% ethanol 4-8 BV wash-out instead, then the online detection effluent of thin-layer chromatography after becoming clearly; And the ethanol elution flow part of collecting this 60%-70%, collect 6 column volumes altogether;
C. silica gel column chromatography separates: after the ethanol eluate decompression that step B is collected; Carrying out silica gel column chromatography separates; Use earlier of the mixed solvent 8-10BV removal of impurities of chloroform-methanol-water volume ratio during wash-out, continue wash-out, collect the elutriant of 10-15BV with same solvent as 10:1:0.05;
D. recrystallization: the elutriant that step C is collected carries out recrystallization after with the dissolve with methanol of 50%-80%, and cultivating the crystal time is 5-10 hour; Suction filtration then, filter cake with the 70%-90% methanol wash after, vacuum-drying obtains Radix Liriopes saponin(e B content and reaches the white solid product more than 98%.
2. the separation purification method of Radix Liriopes saponin(e B according to claim 1, the developping agent that it is characterized in that the said thin-layer chromatography of step B is a chloroform: methyl alcohol: water=100:35:5.
3. the separation purification method of Radix Liriopes saponin(e B according to claim 1 is characterized in that the said macroporous resin of step B is D101 type or AB-8 type.
4. the separation purification method of Radix Liriopes saponin(e B according to claim 1 is characterized in that the said mixed solvent of step C is: be 10:1:0.05 for chloroform-methanol-water by volume.
5. the separation purification method of Radix Liriopes saponin(e B according to claim 1, the solvent that it is characterized in that the said recrystallization of step D can also use in ethanol, ETHYLE ACETATE or the propyl carbinol any one to substitute.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044516A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Novel technology method for extracting convallamarin from wild convallaria |
| CN105104922A (en) * | 2015-07-23 | 2015-12-02 | 江西省添美食品有限公司 | Additive used for quick-frozen pastries |
| CN109053852A (en) * | 2018-08-31 | 2018-12-21 | 河北神威药业有限公司 | A kind of isolation and purification method of Lilium brownie monomer |
| CN111658663A (en) * | 2020-07-23 | 2020-09-15 | 五邑大学 | Application of liriope spicata saponin B in preparation of medicine for treating skin inflammation |
-
2011
- 2011-12-15 CN CN 201110420119 patent/CN102399259B/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 郝羚竹: "麦冬甾体皂苷化学成分的研究", 《延边大学硕士学位论文》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044516A (en) * | 2012-12-13 | 2013-04-17 | 大兴安岭林格贝有机食品有限责任公司 | Novel technology method for extracting convallamarin from wild convallaria |
| CN103044516B (en) * | 2012-12-13 | 2015-11-25 | 大兴安岭林格贝寒带生物科技股份有限公司 | A kind of processing method extracting convallamarin from the wild lily of the valley |
| CN105104922A (en) * | 2015-07-23 | 2015-12-02 | 江西省添美食品有限公司 | Additive used for quick-frozen pastries |
| CN105104922B (en) * | 2015-07-23 | 2018-09-07 | 帅兵 | A kind of additive for quick-frozen pastry |
| CN109053852A (en) * | 2018-08-31 | 2018-12-21 | 河北神威药业有限公司 | A kind of isolation and purification method of Lilium brownie monomer |
| CN111658663A (en) * | 2020-07-23 | 2020-09-15 | 五邑大学 | Application of liriope spicata saponin B in preparation of medicine for treating skin inflammation |
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| CN102399259B (en) | 2013-08-14 |
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