CN104557836B - A kind of method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark - Google Patents
A kind of method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark Download PDFInfo
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- CN104557836B CN104557836B CN201410820123.XA CN201410820123A CN104557836B CN 104557836 B CN104557836 B CN 104557836B CN 201410820123 A CN201410820123 A CN 201410820123A CN 104557836 B CN104557836 B CN 104557836B
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- alcohol
- chloroform
- soluble material
- normal hexane
- filtrate
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- 238000000034 method Methods 0.000 title claims abstract description 52
- 239000002195 soluble material Substances 0.000 title claims abstract description 45
- 241000114025 Pinus sylvestris var. mongolica Species 0.000 title claims abstract description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000706 filtrate Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 230000008569 process Effects 0.000 claims abstract description 24
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 22
- 238000001914 filtration Methods 0.000 claims abstract description 16
- 239000008187 granular material Substances 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 16
- 150000002632 lipids Chemical class 0.000 claims abstract description 15
- 239000000843 powder Substances 0.000 claims abstract description 8
- 238000000643 oven drying Methods 0.000 claims description 7
- 229930003944 flavone Natural products 0.000 abstract description 18
- 235000011949 flavones Nutrition 0.000 abstract description 18
- 238000000605 extraction Methods 0.000 abstract description 15
- 241000218652 Larix Species 0.000 abstract description 7
- 235000005590 Larix decidua Nutrition 0.000 abstract description 7
- 150000002213 flavones Chemical class 0.000 abstract description 7
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 abstract description 6
- 241000779819 Syncarpia glomulifera Species 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 239000001739 pinus spp. Substances 0.000 abstract description 5
- 229940036248 turpentine Drugs 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 239000004615 ingredient Substances 0.000 abstract description 4
- MHXCIKYXNYCMHY-AUSJPIAWSA-N (+)-lariciresinol Chemical compound C1=C(O)C(OC)=CC(C[C@@H]2[C@@H]([C@H](OC2)C=2C=C(OC)C(O)=CC=2)CO)=C1 MHXCIKYXNYCMHY-AUSJPIAWSA-N 0.000 abstract description 3
- YVRYZXAHRGGELT-UHFFFAOYSA-N Lariciresinol Natural products C1=C2OCOC2=CC(C2C(C)C3(OC)C=C(CC=C)C(=O)CC3(O2)OC)=C1 YVRYZXAHRGGELT-UHFFFAOYSA-N 0.000 abstract description 3
- 235000006826 lariciresinol Nutrition 0.000 abstract description 3
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 11
- -1 nitrous acid aluminum-aluminum nitrate-sodium hydroxide Chemical compound 0.000 description 11
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 11
- 150000002212 flavone derivatives Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 6
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 6
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 6
- 235000005493 rutin Nutrition 0.000 description 6
- 229960004555 rutoside Drugs 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- 230000006837 decompression Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002481 ethanol extraction Methods 0.000 description 2
- 239000000469 ethanolic extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- GQODBWLKUWYOFX-UHFFFAOYSA-N Isorhamnetin Natural products C1=C(O)C(C)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 GQODBWLKUWYOFX-UHFFFAOYSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- RNDNBGULZNCSNB-UHFFFAOYSA-N abiesinol E Natural products C12=C3OC(C=4C=CC(O)=CC=4)C(O)CC3=C(O)C=C2OC(=O)C1(C1=C(O)C=C(O)C=C1O1)C1C1=CC=C(O)C=C1 RNDNBGULZNCSNB-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001147 anti-toxic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- KQNGHARGJDXHKF-UHFFFAOYSA-N dihydrotamarixetin Natural products C1=C(O)C(OC)=CC=C1C1C(O)C(=O)C2=C(O)C=C(O)C=C2O1 KQNGHARGJDXHKF-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 1
- AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 description 1
- 229960001587 hesperetin Drugs 0.000 description 1
- 235000010209 hesperetin Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 description 1
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N isorhamnetin Chemical compound C1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 IZQSVPBOUDKVDZ-UHFFFAOYSA-N 0.000 description 1
- 235000008800 isorhamnetin Nutrition 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/13—Coniferophyta (gymnosperms)
- A61K36/15—Pinaceae (Pine family), e.g. pine or cedar
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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Abstract
A kind of method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark, comprises the steps: that Pinus sylvestnis var. mongolica Litv. bark powder is broken into the granule of 20～80 order sizes by (1), puts in normal hexane/chloroform, carry out supersound process, obtain mixture A；(2) described mixture A is filtered, obtains filtrate a and filtering residue；Filtrate a is distilled, steams n-hexane/chloroform, obtain lipid material；(3) described filtering residue is put in alcoholic solution, it is carried out supersound process；(4) described mixture B is filtered, obtains filtrate b, filtrate b is distilled, steams alcoholic solution, obtain the concentrated solution of alcohol-soluble material, described concentrated solution is dried to obtain alcohol-soluble material.Use flavones content in the alcohol-soluble material of the method extraction high, possibly together with sinapic acid, the different lariciresinol of open loop, 9 '-to effective ingredient such as hydroxyl (trans) cinnamic acid-7-hydroxyl-different larch turpentine alcohol esters of open loop, there is antioxidation, the effect such as antibacterial.
Description
Technical field
The invention belongs to effective ingredients in plant extraction process, specifically, relate to a kind of method of natural product in ultrasonic assistant solvent stage extraction Pinus sylvestnis var. mongolica Litv. bark.
Background technology
Pinus sylvestnis var. mongolica Litv. is one of China's three northern areas of China Major Fine reproducting tree species, widely distributed, and aboundresources, Pinus sylvestnis var. mongolica Litv. bark is as important forestry by-product, and its resource utilization is relatively low.
Research shows, containing effective ingredient such as polysaccharide, phenolic substance, organic acid, tannin, flavone in the alcohol-soluble material of Pinus sylvestnis var. mongolica Litv. bark ethanol extraction.Wherein with flavone for the generally acknowledged natural extract with various health care functions.Fat content in Pinus sylvestnis var. mongolica Litv. is relatively low, is about the 1%-3% of bark dry weight.
Owing in Pinus sylvestnis var. mongolica Litv. bark, fat content is relatively low, so there is no cause the attention of people, in current extraction Pinus sylvestnis var. mongolica Litv. bark, the method for alcohol-soluble material is mainly direct ethanol extraction, uses the method, and in the alcohol-soluble natural product of gained, the content of flavone is relatively low.
Summary of the invention
For in current method, directly by the defect that the extraction ratio of the method existence of the active component in alcohols material extraction sample Pinus sylvestnis var. mongolica Litv. bark is low.The present invention provides a kind of method of natural product in stage extraction Pinus sylvestnis var. mongolica Litv. bark.
The method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark of the present invention, comprises the steps:
(1) Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 20～80 order sizes, puts in normal hexane/chloroform, carry out supersound process, the condition of described supersound process is: temperature 30～60 DEG C, time 15～60min, frequency 15～40KHz；, obtain mixture A；
(2) described mixture A is filtered, obtains filtrate a and filtering residue；Described filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material；
(3) putting in alcoholic solution by described filtering residue, it is carried out supersound process, the condition of described supersound process is: temperature 30～55 DEG C, ultrasonic time 15～60min, frequency 10～35KHz obtains mixture B；
(4) described mixture B is filtered, obtains filtrate b, filtrate b is distilled, steams alcoholic solution, obtain the concentrated solution of alcohol-soluble material, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol-soluble material；
Temperature in described step (1) is higher than the temperature in step (3) 5～15 DEG C, the supersonic frequency height 5-10KHz in frequency ratio step (3) in described step (1).
It is 1: 5～5: 1 that the present invention urgees the volume ratio of normal hexane and chloroform in described normal hexane/chloroform, owing in Pinus sylvestnis var. mongolica Litv. bark, fat content is low, with traditional organic solvent, such as the extraction effect such as petroleum ether, ether is bad, adopts compound extractant normal hexane/chloroform extraction effect to be obviously improved.
The mass volume ratio of heretofore described granule and normal hexane/chloroform is 1: 10～1: 30.
The concentration of heretofore described alcoholic solution is 40%～80%.
The w/v of heretofore described granule and alcoholic solution is 1: 10～1: 50
Extracting method of the present invention includes following preferred version:
1) Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 20～80 order sizes, puts in normal hexane/chloroform, described normal hexane/chloroform, the volume ratio of normal hexane chloroform is 1: 1～1: 2, and the mass volume ratio of described granule and normal hexane/chloroform is 1: 15-1: 20；Carrying out supersound process, the condition of described supersound process is: temperature 35～50 DEG C, time 15～60min, frequency 25～35KHz；, obtain mixture A；
(2) described mixture A is filtered, obtains filtrate a and filtering residue；Filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material；
(3) described filtering residue is put in alcoholic solution, the concentration of described alcoholic solution is 50%-80%, the mass volume ratio of described granule and alcoholic solution is 1: 20-1: 25, it is carried out supersound process, the condition of described supersound process is: temperature 30～35 DEG C, ultrasonic time 15～60min, frequency 15～25KHz, obtain mixture B；
(4) described mixture B is filtered, obtains filtrate b, filtrate b is distilled, steams alcoholic solution, obtain the concentrated solution of alcohol-soluble material, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol-soluble material；
Temperature in described step (1) is higher than the temperature in step (3) 5～15 DEG C, the supersonic frequency height 5-10KHz in frequency ratio step (3) in described step (1).
In a kind of ultrasonic assistant solvent stage extraction Pinus sylvestnis var. mongolica Litv. bark provided by the invention, the method for natural product, has the advantage that
(1) method of the stage extraction that the present invention adopts, first extracts lipid and extracts alcohol-soluble material again, effectively reduce the interference of oils and fats in ethanol extract, improve the extraction ratio of flavone isoreactivity material in ethanol extract, reduce the difficulty of subsequent purification technique.
(2) adopt the inventive method successfully to extract and isolate lipid and alcohol-soluble material two series products, extraction efficiency is high, good separating effect, it is successfully realized the utilization that becomes more meticulous that modern extraction and separation technology is applied to Pinus sylvestnis var. mongolica Litv. bark, the diversification of Pinus sylvestnis var. mongolica Litv. bark, high-valued, the utilization that becomes more meticulous are had great importance.
Accompanying drawing explanation
Fig. 1: the LC/MS/MS spectrogram of sectioned extracting method gained alcohol-soluble material；
Detailed description of the invention
Following example are used for illustrating the present invention, but are not limited to the scope of the present invention.If not specializing, the conventional means that technological means used in embodiment is well known to those skilled in the art, raw materials used it is commercial goods.
The Pinus sylvestnis var. mongolica Litv. bark used in following example gathers from Daxing ' anling, heilongjiang.
Embodiment 1 one kinds extracts the method for alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark
Comprise the steps:
(1) 20g Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 20～80 order sizes, and puts in the normal hexane/chloroform of 300mL, the volume ratio of normal hexane and chloroform is 1: 5, and ul-trasonic irradiation 30min under 35 DEG C of conditions, supersonic frequency is 25KHz.
(2) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate a and filtering residue.Filtrate a is placed in Rotary Evaporators and carries out decompression distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filtering residue put in 400mL, 50% alcoholic solution, ul-trasonic irradiation 30min under 30 DEG C of conditions, supersonic frequency is 19KHz.
(4) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate b.Filtrate a is placed in Rotary Evaporators and carries out decompression distillation, steam alcoholic solution, obtain the concentrated solution of alcohol-soluble material, then residue is placed in 35 DEG C of oven drying 12h.
Lipid material in the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted is 18.60mg/g, and the total amount of alcohol-soluble material is 88.63mg/g.
Detecting with the flavone in the nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) alcohol-soluble material to gained, wherein flavones content is 23.09mg/g.
Embodiment 2 one kinds extracts the method for alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark
(1) 20g Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 30～60 order sizes, and puts in the normal hexane/chloroform of 400mL, the volume ratio of normal hexane and chloroform is 1: 1, and ul-trasonic irradiation 60min under 50 DEG C of conditions, supersonic frequency is 30KHz.
(2) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate a and filtering residue.Filtrate a is placed in Rotary Evaporators and carries out decompression distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filtering residue put in 500mL, 80% alcoholic solution, ul-trasonic irradiation 60min under 35 DEG C of conditions, supersonic frequency is 25KHz.
(4) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate b.Filtrate b Rotary Evaporators carries out concentrating under reduced pressure, steams alcohol solvent, obtains the concentrated solution of liposoluble substance, concentrated solution is placed in 35 DEG C of oven drying 16h, obtains alcohol-soluble material.
Lipid material in the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted is 24.72mg/g, and the total amount of alcohol-soluble material is 95.24mg/g.
The flavone measured in the alcohol-soluble material to gained with nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) detects, and wherein flavones content is 26.28mg/g.
Embodiment 3 one kinds extracts the method for alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark
(1) 20g Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 30-70 order size, and puts in the normal hexane/chloroform of 350mL, the volume ratio of normal hexane and chloroform is 1: 2, and ul-trasonic irradiation 50min under 40 DEG C of conditions, supersonic frequency is 35KHz.
(2) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate a and filtering residue.Filtrate a is placed in Rotary Evaporators and carries out decompression distillation, steam normal hexane/chloroform solvent, obtain lipid material.
(3) by step 2) in filtering residue put in 500mL, 70% alcoholic solution, ul-trasonic irradiation 55min under 30 DEG C of conditions, ultrasonic frequency is 25KHz.
(4) while hot the mixture after processing is carried out vacuum filtration, obtain filtrate b.Filtrate b Rotary Evaporators carries out concentrating under reduced pressure, steams alcohol solvent, obtains the concentrated solution of alcohol-soluble material, concentrated solution is placed in 35 DEG C of oven drying 14h, obtains alcohol-soluble material.
Lipid material in the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted is 24.35mg/g, and the total amount of alcohol-soluble material is 93.52mg/g.
The flavone measured in the alcohol-soluble material to gained with nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) detects, and wherein flavones content is 25.86mg/g.
Comparative example 1
Compare with embodiment 2, differ only in, the normal hexane/chloroform in step (1) is replaced with ether.Lipid material in the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted is 10.72mg/g, and the total amount of alcohol-soluble material is 100.24mg/g.
The flavone measured in the alcohol-soluble material to gained with nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) detects, and wherein flavones content is 19.28mg/g.
Comparative example 2
Comparing with embodiment 2, it differs only in, and described step (1) and the Ultrasonic Conditions in step (2) are: acting on 60min under 35 DEG C of conditions, supersonic frequency is 25KHz.
Lipid material in the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted is 15.72mg/g, and the total amount of alcohol-soluble material is 99.52mg/g.
The flavone measured in the alcohol-soluble material to gained with nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) detects, and wherein flavones content is 21.28mg/g.
Comparative example 3
Comparing with embodiment 2, omit step (1) and the operation of (2) extraction oils and fats, other operations are identical.
In the Pinus sylvestnis var. mongolica Litv. bark according to said method extracted, the total amount of alcohol-soluble material is 103.68mg/g.
The flavone measured in the alcohol-soluble material to gained with nitrous acid aluminum-aluminum nitrate-sodium hydroxide development process (in rutin) detects, and wherein flavones content is 20.15mg/g.
Experimental example 1
Experimental subject: the alcohol-soluble material that embodiment 2 is extracted.
Experimental technique: utilize the material composition in high performance liquid chromatography series connection second mass analysis detection alcohol-soluble material.INSTRUMENT MODEL: ThermoScientific-QExactive, data processing software: Xcalibur.UV-detector model: Ultimate3000, detects wavelength: 280nm.Column type number: HypersilGoldDim (mm) 1002.1.Mobile phase: A is water, and B is methanol, flow velocity: 200 μ L/min.Gradient: 0min, 5%B → 10min, 10%B → 30min, 15%B → 45min, 20%B → 60min, 30%B → 70min, 50%B → 100min, 50%B.Ion source: ESI-, m/z sweep limits: 0-1500, spray voltage (-): 2500.00.Sample size 5 μ L.
Experimental result:
LC/MS/MS spectrogram such as Fig. 1 of embodiment 2, is analyzed comparison and obtains the composition in the alcohol-soluble material of embodiment 2 and form such as table 1 Fig. 1
Table 1
As can be seen from Table 1, the alcohol-soluble separating substances that embodiment 2 is extracted obtains 13 chromatographic peaks, analyzed by HPLC-MS-MS, Preliminary Identification goes out wherein 8 kinds of main components, for taxifolin, hesperetin, isorhamnetin, larch lactone larixinol flavone component, and sinapic acid, the different lariciresinol of open loop, 9 '-to hydroxyl (trans) cinnamic acid-7-hydroxyl-open loop different larch turpentine alcohol ester 1,9 '-to hydroxyl (trans) cinnamic acid-7-hydroxyl-different larch turpentine alcohol ester 2 of open loop.
Experiment conclusion:
The above results shows, take sectioned extracting method that the alcohol-soluble material in Pinus sylvestnis var. mongolica Litv. bark is extracted, the active component of flavonoid can be obtained, also can obtain the different lariciresinol of open loop, 9 '-to hydroxyl (trans) cinnamic acid-7-hydroxyl-open loop different larch turpentine alcohol ester isoreactivity composition.Sinapic acid is one of effective ingredient of middle Semen Sinapis Albae, has antifungal, anti-toxic swelling effect.9 '-it is the compounds being similar to that estrogen to hydroxyl (trans) cinnamic acid-7-hydroxyl-open loop different larch turpentine alcohol ester and the different larch ester of open loop, there is antioxidation, resisting mitosis, antiviral, anticancer, more weak estrogen-like effects, reduce T-CHOL and low-density lipoprotein cholesterol.Therefore, this alcohol-soluble material has good functional, can apply further.
Although, above the present invention is described in detail with a general description of the specific embodiments, but on basis of the present invention, it is possible to it is made some modifications or improvements, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the scope of protection of present invention.
Claims (2)
1. the method extracting alcohol-soluble material from Pinus sylvestnis var. mongolica Litv. bark, comprises the steps:
(1) Pinus sylvestnis var. mongolica Litv. bark powder being broken into the granule of 20～80 order sizes, puts in normal hexane/chloroform, carry out supersound process, the condition of described supersound process is: temperature 30～60 DEG C, time 15～60min, frequency 15～40KHz, obtains mixture A；
(2) described mixture A is filtered, obtains filtrate a and filtering residue；Described filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material；
(3) putting in alcoholic solution by described filtering residue, it is carried out supersound process, the condition of described supersound process is: temperature 30～55 DEG C, time 15～60min, frequency 10～35KHz obtains mixture B；
(4) described mixture B is filtered, obtains filtrate b, filtrate b is distilled, steams alcoholic solution, obtain the concentrated solution of alcohol-soluble material, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol-soluble material；
In described normal hexane/chloroform, the volume ratio of normal hexane and chloroform is 1:5～5:1；
The mass volume ratio of described granule and normal hexane/chloroform is 1:10～1:30；
The concentration of described alcoholic solution is 40%～80%；
The mass volume ratio of described granule and alcoholic solution is 1:10～1:50；
Temperature in described step (1) is higher than the temperature in step (3) 5～15 DEG C, the frequency height 5-10KHz in frequency ratio step (3).
2. method according to claim 1, it is characterized in that, comprise the steps: 1) Pinus sylvestnis var. mongolica Litv. bark powder is broken into the granule of 20～80 order sizes, put in normal hexane/chloroform, described normal hexane/chloroform, the volume ratio of normal hexane chloroform is 1:1～1:2, and the mass volume ratio of described granule and normal hexane/chloroform is 1:15-1:20；Carrying out supersound process, the condition of described supersound process is: temperature 35～50 DEG C, time 15～60min, frequency 25～35KHz；, obtain mixture A；
(2) described mixture A is filtered, obtains filtrate a and filtering residue；Filtrate a is distilled, steams normal hexane/chloroform, obtain lipid material；
(3) described filtering residue is put in alcoholic solution, the concentration of described alcoholic solution is 50%-80%, the mass volume ratio of described granule and alcoholic solution is 1:20-1:25, it is carried out supersound process, the condition of described supersound process is: temperature 30～35 DEG C, ultrasonic time 15～60min, frequency 15～25KHz, obtain mixture B；
(4) described mixture B is filtered, obtains filtrate b, filtrate b is distilled, steams alcoholic solution, obtain the concentrated solution of alcohol-soluble material, more described concentrated solution is placed in 35 DEG C of oven drying 12-24h, obtain alcohol-soluble material.
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