CN1304542C - Magnolia flower oil - Google Patents
Magnolia flower oil Download PDFInfo
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- CN1304542C CN1304542C CNB200410060580XA CN200410060580A CN1304542C CN 1304542 C CN1304542 C CN 1304542C CN B200410060580X A CNB200410060580X A CN B200410060580XA CN 200410060580 A CN200410060580 A CN 200410060580A CN 1304542 C CN1304542 C CN 1304542C
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- Prior art keywords
- oil
- flos magnoliae
- magnolia
- steamer
- lily magnolia
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- 241000218378 Magnolia Species 0.000 title abstract description 5
- 239000003921 oil Substances 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000000605 extraction Methods 0.000 claims abstract description 10
- -1 redistillation Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 241000628997 Flos Species 0.000 claims description 52
- 239000000341 volatile oil Substances 0.000 claims description 22
- PEUUVVGQIVMSAW-RZTYQLBFSA-N (+)-Eudesmin Chemical compound C1=C(OC)C(OC)=CC=C1[C@@H]1[C@@H](CO[C@@H]2C=3C=C(OC)C(OC)=CC=3)[C@@H]2CO1 PEUUVVGQIVMSAW-RZTYQLBFSA-N 0.000 claims description 9
- AWOGQCSIVCQXBT-LATRNWQMSA-N (+)-Fargesin Natural products C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H](CO[C@@H]2C=3C=C4OCOC4=CC=3)[C@@H]2CO1 AWOGQCSIVCQXBT-LATRNWQMSA-N 0.000 claims description 9
- PEUUVVGQIVMSAW-UHFFFAOYSA-N Diaeudesmin Natural products C1=C(OC)C(OC)=CC=C1C1C(COC2C=3C=C(OC)C(OC)=CC=3)C2CO1 PEUUVVGQIVMSAW-UHFFFAOYSA-N 0.000 claims description 9
- AWOGQCSIVCQXBT-LYDRAKHJSA-N Fargesin Chemical compound C1=C(OC)C(OC)=CC=C1[C@@H]1[C@H](CO[C@H]2C=3C=C4OCOC4=CC=3)[C@H]2CO1 AWOGQCSIVCQXBT-LYDRAKHJSA-N 0.000 claims description 9
- FDABVSXGAMFQQH-XZWHSSHBSA-N berbamunine Chemical compound CN1CCC2=CC(OC)=C(O)C=C2[C@H]1CC1=CC=C(O)C(OC2=CC=C(C=C2)C[C@@H]2N(C)CCC=3C=C(C(=CC=32)O)OC)=C1 FDABVSXGAMFQQH-XZWHSSHBSA-N 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 9
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims description 9
- 235000011957 flavonols Nutrition 0.000 claims description 9
- 229930182470 glycoside Natural products 0.000 claims description 9
- AWOGQCSIVCQXBT-UHFFFAOYSA-N methyl piperitol Natural products C1=C(OC)C(OC)=CC=C1C1C(COC2C=3C=C4OCOC4=CC=3)C2CO1 AWOGQCSIVCQXBT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 241000218377 Magnoliaceae Species 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 230000003292 diminished effect Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000498 cooling water Substances 0.000 claims description 2
- 235000019628 coolness Nutrition 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 6
- PIRWNASAJNPKHT-SHZATDIYSA-N pamp Chemical compound C([C@@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)N)C(C)C)C1=CC=CC=C1 PIRWNASAJNPKHT-SHZATDIYSA-N 0.000 abstract description 6
- 241000007358 Magnolia biondii Species 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 235000019198 oils Nutrition 0.000 abstract 3
- 239000003205 fragrance Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000005445 natural material Substances 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- 241000218394 Magnolia liliiflora Species 0.000 description 54
- 239000013558 reference substance Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 9
- 206010061218 Inflammation Diseases 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 240000005819 Magnolia denudata Species 0.000 description 5
- 235000016094 Magnolia denudata Nutrition 0.000 description 5
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 230000007721 medicinal effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 241000007370 Magnolia sprengeri Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
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- 235000019504 cigarettes Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
The present invention provides a natural substance of biond magnolia flower (magnolia biondii pamp) oil and an extraction method thereof, which belongs to the technical field of vegetable oil. The present invention is mainly characterized in that magnoliaceae magnolia biondii pamp bud is used as raw materials to prepare light yellow transparent oily liquid with special fragrance by heating, pressurization, distillation on water, extraction by a solvent, redistillation, impurity removal and mixing; the oily liquid contains five monomeric compounds with the relative content of more than 4 %, wherein the content of lignanoid is from 40 to 50%. The biond magnolia flower (magnolia biondii pamp) oil keeps the quality of the original medicaments, enhances the utilization rate of effective components and enlarges the range of application. The biond magnolia flower (magnolia biondii pamp) oil also has new medicinal value and new application fields. The extraction method has the advantages of high extraction rate and high purity of extractives.
Description
Technical field:
The invention belongs to the vegetables oil technical field, relate to a kind of crude substance flower bud of lily magnolia (Flos Magnoliae) oil.
Background technology:
The flower bud of lily magnolia (Flos Magnoliae) is a kind of rare traditional Chinese medicine, derives from the dry flower of Magnoliaceae magnolia, is one of complicated Chinese medicinal materials of former plant variety.
Chinese Pharmacopoeia nineteen fifty-three version is not recorded, version had only been stipulated 1 former plant variety lily magnolia for flower bud of lily magnolia medicinal material in 1963, version in 1977 has increased Flos Magnoliae and yulan again with the former plant variety of flower bud of lily magnolia medicinal material except that lily magnolia, each edition replaced lily magnolia with the Wudang yulan after 1985, stipulates that all dry flower with Flos Magnoliae, yulan, Flos Magnoliae 3 kind of plant is as flower bud of lily magnolia medicinal material.
Flower bud of lily magnolia flavor warm in nature is hot, returns lung stomach warp, have in loosing cold, the merit of relieving stuffy nose.Usually the flower bud of lily magnolia (Flos Magnoliae) directly is used as medicine into decoction, pill, powder use, the effective ingredient that wherein contains (volatile oil) can not be fully utilized, and not only cause very big waste, and result of use is poor, some illness also is inconvenient to execute control, has limited the scope of using of the flower bud of lily magnolia (Flos Magnoliae).
Summary of the invention:
Henan Province's Nanzhao County is located in the Funiu Shan Mountain district, the flower bud of lily magnolia (Flos Magnoliae) resource is with a long history, so far still have the flower bud of lily magnolia (Flos Magnoliae) the natural phant group more than more than 500 year, have the title in " flower bud of lily magnolia first county all over the world ", enjoy the reputation of " Nan Zhao's flower bud of lily magnolia is not examined goods ", " science of identification of Chinese materia medica " claims Nan Zhao's Flos Magnoliae volatile oil content to reach 4～5%, is higher than 1～2 times of other kind.Nan Zhao's flower bud of lily magnolia is accredited as the Magnoliacea plant Flos Magnoliae, by the high genuine top grade medicinal material of high-quality that is of all times.Version Chinese Pharmacopoeia in 1997 is classified Nan Zhao's flower bud of lily magnolia (Flos Magnoliae) as certified products and is recorded, and is the protection of place of origin by national authentication.Nanzhao County now, the extensive artificial culture of the flower bud of lily magnolia, output accounts for the whole nation more than 70%, and quality has raising again, becomes flower bud of lily magnolia main product ground.
The objective of the invention is the volatile oil in the Magnoliaceae Flos Magnoliae extracted becomes essential oil, for utilization, and explores the oily process for extracting of the flower bud of lily magnolia that a kind of extraction yield is higher, purity is higher (Flos Magnoliae).
The technical solution used in the present invention is: a kind of extracting method of Flos Magnoliae oil, 1. make raw material with Magnoliaceae Flos Magnoliae bud: and shady doing, do not go mouldy, inclusion-free is pulverized 0.1～0.5 centimetre wound sheet; 2. heat, pressurization, distilling above water combine and extract direct essential oil: in still pot, feed, inject 1/3 clear water, vexed profit 30-50 minute, slowly heating in preceding 1 hour strengthens thermal source gradually and makes the distillation kettle temperature reach 80-150 ℃, pot inner pressure is maintained to 0.8～2.0Mpa, per hour the speed of distillating is volumetrical 5～15%, front and back 24～28 hours, and the distillate temperature maintenance is at 45～60 ℃, temperature of cooling water maintains 15～20 ℃ of coolings, and distillate was placed in separator 10～30 minutes; 3. hydromining will be distillated and thick oil must be extracted with solvent extraction and separation; 4. extracting thick oil heats up in a steamer extraction separation again and go out to heat up in a steamer again essential oil: will extract thick oily redistillation, and increase quantity of distillate, and be pressurized to 2～4Mpa, temperature will be heated up in a steamer distillate again and carry out oily water separation at 120-160 ℃, must heat up in a steamer essential oil again; The direct essential oil that 5. will extract, it is mixed to heat up in a steamer essential oil again: to take to staticly settle, dewater, filtration under diminished pressure, pressure be-0.3～-0.6Mpa, mixed stirring promptly gets Flos Magnoliae oil.
The Flos Magnoliae oil of the present invention that adopts the said extracted method to obtain, transparent for faint yellow, have the multiple important oily liquids that fragrant composition organically combines the formation special aroma that causes.Separate and solvent recrystallization through chromatography, include relative content at 5 monomeric compounds 4% or more, after measured with the UV spectrum of each compound of parsing, infrared spectra,
1The H nuclear magnetic resonance spectrum,
13C nuclear magnetic resonance spectrum and mass-spectrometric data are accredited as it respectively: Fargesin, and Pinoresinol Dimethyl Ether, Magnoline, the plain B dme of the upright fat in lining, Flos Magnoliae flavonol glycosides I, wherein the lignanoids composition accounts for 40-50%.
With above-mentioned 5 kinds of compounds is reference substance, the volatile oil (experiment is extracted) that adopts tlc that the different former plant varieties of the flower bud of lily magnolia are extracted carries out quality evalution, the result shows, the content of above-claimed cpd in the flower bud of lily magnolia medicinal material of different varieties has than big-difference, the contained Chemical Composition of institute's control material (the present invention) is the lignanoids composition especially, not only kind is more, and content is also apparently higher than other kind, the lignanoids composition is the effective ingredient of anti-inflammatory and anti-allergic effects, come its inner quality of scientific evaluation from this angle, the present invention really belongs to the fine quality of volatile oil in the former plant variety medicinal material of the flower bud of lily magnolia.
The flower bud of lily magnolia of the present invention (Flos Magnoliae) oil does not change effective ingredient and original medicinal properties of Flos Magnoliae, finds that again it has significant anti-inflammatory and anti-allergic effects.
At present, though the pharmacological research of relevant flower bud of lily magnolia single medicinal material has report, it is less to relate to antiphlogistic data.Through anti-inflammatory action to the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil, the test of employing several animal models, observe of the influence of the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil to inflammatory reaction, the result can reduce the permeability that inflammation is organized capillary vessel, inflammation-inhibiting swelling, the generation of inflammation-inhibiting medium (histamine and carrageenin) has tangible anti-acute inflammation effect, synthetic and secretion to body sugar, adrenocortical hormone does not have obviously influence, and its anti-inflammatory swelling effect does not rely on adrenal existence yet.Pollution-free, have no side effect.
From the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil can inflammation-inhibiting medium (histamine and carrageenin) generation, visible the present invention provides experimental basis for the treatment diseases associated with inflammation.
From the former medicinal properties of the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil, new effect with have and do not have assorted gas peat-reek, again for the present invention at perfuming cigarette, the application that reduces during Smoking is harmful to your health provides experimental basis.
From the form that the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil is had, original performance and new performance, the ear nose ophthalmic diseases of executing cure the disease disease such as need dropping liquid in some inconvenience for the present invention is used again, provides convenience to execute the experimental basis of controlling.
The application that the present invention also can be at cosmetics, daily chemical products provides experimental basis.
The flower bud of lily magnolia of the present invention (Flos Magnoliae) oil owing to be that raw material extracts with the Flos Magnoliae, changed the tradition that the flower bud of lily magnolia (Flos Magnoliae) directly is used as medicine and has utilized mode, the quality that has kept former medicine, improved the wherein utilization ratio of effective ingredient, not only curative effect improves, and has enlarged the scope of controlling of executing; Because some Chemical Composition content height of volatile oil of other Magnoliaceae extraction that former plant variety is tested of the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil ratio so have new pharmaceutical use, provides experimental basis for inquiring into medicinal use; The present invention also provides experimental basis for the application in field beyond medicine simultaneously; Extracting method among the present invention has extraction yield height, advantage that dna purity is high.
Description of drawings:
Fig. 1 represents the structural formula with the contained Compound I Fargesin of the present invention;
Fig. 2 represents the structural formula with the contained Compound I I Pinoresinol Dimethyl Ether of the present invention;
Fig. 3 represents the structural formula with the contained compound III Magnoline of the present invention;
Fig. 4 represents the structural formula with the plain B dme of upright fat in the contained compound IV of the present invention;
Fig. 5 represents the structural formula with the contained compound V of the present invention Flos Magnoliae flavonol glycosides I;
The thin-layer chromatography of the different varieties flower bud of lily magnolia that it is reference substance that Fig. 6 represents with the contained Compound I Fargesin of the present invention;
The thin-layer chromatography of the different varieties flower bud of lily magnolia that it is reference substance that Fig. 7 represents with the contained Compound I I Pinoresinol Dimethyl Ether of the present invention;
The thin-layer chromatography of the different varieties flower bud of lily magnolia that it is reference substance that Fig. 8 represents with the contained compound III Magnoline of the present invention;
Fig. 9 represents that with the plain B dme of upright fat in the contained compound IV of the present invention be the thin-layer chromatography of the different varieties flower bud of lily magnolia of reference substance;
Figure 10 represents that with the contained compound V of the present invention Flos Magnoliae flavonol glycosides I be the thin-layer chromatography of the different varieties flower bud of lily magnolia of reference substance.
Embodiment:
In conjunction with the accompanying drawings and embodiments, further specify the extracting method of the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil, structure evaluation, quality evalution etc., its feature and advantage will be clearer.
The extraction experimental raw of the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil adopts Nan Zhao's flower bud of lily magnolia Flos Magnoliae bud of plucking March in early spring, and shady doing do not gone mouldy inclusion-free; Pulverizing 0.1～0.5 centimetre wound sheet is advisable; In still pot, feed, and inject 1/3 full clear water, vexed profit 30～50 minutes; Slowly heating in preceding 1 hour strengthens thermal source gradually and makes the distillation kettle temperature reach 80～150 ℃; Close the still pot outlet valve, make pot inner pressure be maintained to 0.8～2.0Mpa; Per hour the speed of distillating is that volumetrical 5～15% is advisable, front and back 24～28 hours; Distillate (profit gas mixture) temperature maintenance is at 45～60 ℃, and the temperature maintenance of water coolant is cooled off 15～20 ℃ of condensations, and distillate was placed in separator 10～30 minutes, isolated direct essential oil; Tail washings is adopted the petroleum ether solvent extraction, wherein contained oil content is separated, must extract thick oil; To extract thick oil and carry out redistillation, increase quantity of distillate, be pressurized to 2～4Mpa, temperature will be heated up in a steamer distillate again and carry out oily water separation at 120～160 ℃, must heat up in a steamer essential oil again: with the above-mentioned direct essential oil of gained, heat up in a steamer that essential oil is taked to leave standstill, dewatered, filtration under diminished pressure again, pressure is-0.3～-0.6Mpa, stir the gained essential oil is mixed at last, promptly get the flower bud of lily magnolia of the present invention (Flos Magnoliae) oil, the rate of collecting is more than 90%, and purity is more than 99%.
The flower bud of lily magnolia of the present invention (Flos Magnoliae) oil adopts Shimadzu UV-265FW ultraviolet ray-visible spectrophotometer through chromatographic separation and solvent recrystallization; Perkin-Elmer1720X Fourier transform infrared spectrometer: WP100SY nuclear magnetic resonance analyser; The FinniganMAT-212 mass spectrograph obtains 5 monomeric compounds, numbers I respectively, II, III, IV, V.
(1) Compound I, clear crystal, 130 ℃ of fusing points.UVλ
max MeOH?nm：232.0，283.4。IR(KBr)cm
-1：1609，1591，1516，1488，1465，1440，1416，1398，1363，1329，1272，1245，1234，1190，1158，1141，1101，1053，1028。
1HNMR(CDCl
3)：3.27(1H，m)，2.88(IH，m)，4.42(IH，d)；4.10(IH，d)，3.38(2H，m)，3.35(IH，)；3.90(3H，s)，3.87(3H，s)；5.92(2H，s)；6.78～6.93(6H，m)。
13CNMR(CDCl
3)δ：50.01，54.47，69.58，70.85，81.85，87.51，130.86，108.89，148.73，147.85×2，110.95，11758，135.07，106.38，147.04，107.97，119.37，55076×2，100.89。MSm/z：370(M
+)，339，219，203，177，165，151，149，138，137，135，122，121.
According to above spectral data Compound I is accredited as Fargesin, its structural formula is seen Fig. 1.
(2) Compound I I, clear crystal, 95 ℃ of fusing points.UVλ
max MeOHnm：231.2，278.4。IR(KBr)cm
-1：1605，1591，1515，145，1450，1427，1344，1326，1266，1233，1183，1144，1110.
1HNMR(CDCl
3)δ：3.11(2H，m)；4.76(2H，)；4.26(2H，m)，3.94(2H，m)；3.89(6H，s)；6.86～6.90(6H，m)。
13CNMR(CDCl
3)δ：54.09×2，71.62×2，85.69×2。133.49×2，109.18×2，149.13×2，148.55×2，111.00×2，118.162，55.85×4。MSm/z：386(M
+)，356，355，219，177，166，151，138，137。
According to above spectral data Compound I I is accredited as Pinoresinol Dimethyl Ether, its structural formula is seen Fig. 2.
(3) compound III, clear crystal, 90 ℃ of fusing points.UVλ
max MeOHnm：229.6，277.4。IR(KBr)cm
-1：1589，1520，1465，1331，1267，1237，1165，1132，1080，1063，1026，1003。
1HNMR(CDCl
3)δ：54.13，54.34。71.59，71.74，85.49，85.75，136.80，104.05×2，153.41×2，153.41×2，138.58，134.22，110.62，149.67，149.08，112.48，118.20，56.65×2，60.28。MSm/z；416(M
+)，385，249，219，207，195，181，177，168，167，165，151，138，137。
According to above spectral data compound III is accredited as Magnoline, its structural formula is seen Fig. 3.
(4) compound IV, clear crystal, 132 ℃ of fusing points.UVλ
max MeOH?nm：224.4，270.4。IR(KBr)cm
-1：1588，1511，1464，1423，1375，1238，1189，1178，1131，1110，1088，1059，1013。
1HNMR(CDCl
3)δ：3.12(2H，m)；4.75(2H，m)；4.27(2H，m)，3.96(2H，m)；3.88(12H，s)，3.84(6H，s)；6.57(4H，s).
13CNMR(CDCl
3)：54.21×2，85.73×2，71.78×2，137.47×2，102.84×4，15324×4，136.58×2，56.03×4，60.56×2，MSm/Z：446(M
+)，415，249，207，195，181，168，167。
The plain B dme of upright fat in according to above spectral data compound IV being accredited as, its structural formula is seen Fig. 4.
(5) compound V, yellow powder, 220 ℃ of fusing points.UVλ
max MeOH?nm：268.2，314.4。IR(KBr)cm
-1：3460，2882，1682，1655，1604，1588，1498，1365，1297，1182，1064，826。
1HNMR (DMSO) δ: 6.17 (IH, d), 6.40 (1H, d), 8.01 (2h, d), 6.88 (2H, d); 5.46～3.28 (protons on the sugar); 7.38 (2H, d); 7.37 (1H, d), 6.12 (1H, d); 12.58,10.14 (reactive hydrogens).
13CNMR(DMSO)δ：156.37，133.15177.40，161.18，98.82，164.15，93.71，156.52，103.96；120.85，130.06×2，115.81×2，159.73，74.26×2，76.39，70.08，63.17；124.99，130.79×2，115.09×2，159.95，144.55，113.75，166.14。MSm/z：594.1(M
+)，593.1(M-H)
+，432，404，389，308，286(aglycone)，258，229，164，147，121，119。
According to above spectral data compound V is accredited as Flos Magnoliae flavonol glycosides I, its structural formula is seen Fig. 5.
Flos Magnoliae Magnolia biondii Pamp. dry flower (Nan Zhao's flower bud of lily magnolia), medicinal material company in Henan Province's provides; Yulan Manolia denudeata Desr. dry flower is available from Jiangsu Province's medicinal material company; Flos Magnoliae Magnolia sprengeri Pamp. dry flower is available from Shaanxi Province Ankang City medicinal material company; Lily magnolia Magnolia liliflora Desr. dry flower, lily magnolia garden, Botanical gardens, Jinan provides.Above former plant variety has all been carried out biological assay.
Fargesin reference substance, Pinoresinol Dimethyl Ether reference substance, Magnoline reference substance, the plain B dme of the upright fat in lining reference substance, Flos Magnoliae flavonol glycosides I reference substance are self-control.
The thin layer plate self-control.Reagent such as sherwood oil (60～90 ℃), vinyl acetic monomer, chloroform, methyl alcohol, sulfuric acid, iron trichloride are analytical pure.
Get Fargesin reference substance, Pinoresinol Dimethyl Ether reference substance, Magnoline reference substance, the plain B dme of the upright fat in lining reference substance, Flos Magnoliae flavonol glycosides I reference substance, add methyl alcohol respectively and make the solution that every 1ml contains 0.1mg, as each reference substance solution.Among Fig. 6～Figure 10, label 1,6 is all represented above-mentioned reference substance.
Get the dry flower of Flos Magnoliae (Nan Zhao's flower bud of lily magnolia), yulan, Flos Magnoliae and lily magnolia, add methyl alcohol respectively and make the solution that every 1ml contains 0.1mg, as each need testing solution.Among Fig. 6～Figure 10, label 2,3,4,5 represent above-mentioned trial-product respectively.
Is the quality that reference substance is estimated different varieties flower bud of lily magnolia medicinal material with the Fargesin, it is an amount of to get above-mentioned each need testing solution and Fargesin reference substance solution, puts respectively on same block of thin layer plate, launches, and takes out, and dries, and colour developing the results are shown in Figure 6.
Is the quality that reference substance is estimated different varieties flower bud of lily magnolia medicinal material with the Pinoresinol Dimethyl Ether, it is an amount of to get above-mentioned each need testing solution and Pinoresinol Dimethyl Ether reference substance solution, puts respectively on same block of thin layer plate, launches, and takes out, and dries, and colour developing the results are shown in Figure 7.
Is the quality that reference substance is estimated different varieties flower bud of lily magnolia medicinal material with the Magnoline, it is an amount of to get above-mentioned each need testing solution and Magnoline reference substance solution, puts respectively on same block of thin layer plate, launches, and takes out, and dries, and colour developing the results are shown in Figure 8.
With the plain B dme of the upright fat in lining is the quality that reference substance is estimated different varieties flower bud of lily magnolia medicinal material, and it is an amount of to get the plain B dme of above-mentioned each need testing solution and Li Li fat reference substance solution, puts respectively on same block of thin layer plate, launches, and takes out, and dries, and colour developing the results are shown in Figure 9.
With Flos Magnoliae flavonol glycosides I is the quality that reference substance is estimated different varieties flower bud of lily magnolia medicinal material, gets above-mentioned each need testing solution and Flos Magnoliae flavonol glycosides I reference substance solution is an amount of, puts respectively on same block of thin layer plate, launches, and takes out, and dries, and colour developing the results are shown in Figure 10.
Claims (2)
1, a kind of extracting method of Flos Magnoliae oil is characterized in that
1. make raw material with Magnoliaceae Flos Magnoliae bud: shady doing, do not go mouldy, inclusion-free is pulverized 0.1～0.5 centimetre wound sheet;
2. heat, pressurization, distilling above water combine and extract direct essential oil: in still pot, feed, inject 1/3 clear water, vexed profit 30-50 minute, slowly heating in preceding 1 hour strengthens thermal source gradually and makes the distillation kettle temperature reach 80-150 ℃, pot inner pressure is maintained to 0.8～2.0Mpa, per hour the speed of distillating is volumetrical 5～15%, front and back 24～28 hours, and the distillate temperature maintenance is at 45～60 ℃, temperature of cooling water maintains 15～20 ℃ of coolings, and distillate was placed in separator 10～30 minutes;
3. hydromining will be distillated and thick oil must be extracted with solvent extraction and separation;
4. extracting thick oil heats up in a steamer extraction separation again and go out to heat up in a steamer again essential oil: will extract thick oily redistillation, and increase quantity of distillate, and be pressurized to 2～4Mpa, temperature will be heated up in a steamer distillate again and carry out oily water separation at 120-160 ℃, must heat up in a steamer essential oil again;
The direct essential oil that 5. will extract, it is mixed to heat up in a steamer essential oil again: to take to staticly settle, dewater, filtration under diminished pressure, pressure be-0.3～-0.6Mpa, mixed stirring promptly gets Flos Magnoliae oil.
2, the Flos Magnoliae oil that extracts by the method for claim 1, what it is characterized in that being extracted is faint yellow, transparent, have the multiple oily liquids that fragrant composition organically combines the special aroma that forms that causes, include relative content at following 5 monomeric compounds more than 4%: Fargesin, Pinoresinol Dimethyl Ether, Magnoline, in the plain B dme of upright fat, Flos Magnoliae flavonol glycosides I, wherein the lignanoids composition accounts for 40～50%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1837392A1 (en) * | 2006-03-21 | 2007-09-26 | Chanel Parfums Beauté | Oil of magnolia champaca, method for its preparation and compositions containing same |
| WO2007107856A1 (en) * | 2006-03-21 | 2007-09-27 | Chanel Parfums Beaute | Magnolia champaca oil, its process of preparation and compositions comprising it |
| JP5274431B2 (en) * | 2009-11-11 | 2013-08-28 | 株式会社 資生堂 | Tie2 activator, vascular maturation, normalization or stabilization agent, lymphatic vessel stabilizer, wrinkle prevention / improving agent and swelling improvement / prevention agent |
| CN102372721A (en) * | 2010-08-26 | 2012-03-14 | 苏州宝泽堂医药科技有限公司 | Preparation method for magnolin |
| WO2012101746A1 (en) * | 2011-01-24 | 2012-08-02 | 株式会社資生堂 | Tie-2 activator, agent for maturation, normalization, or stabilization of blood vessels, lymph vessel stabilizing agent, wrinkle prevention/improvement agent, and edema improvement/prevention agent |
| CN103040805B (en) * | 2012-12-28 | 2014-04-09 | 上海中医药大学 | Medical application of fargesin |
| CN103525557B (en) * | 2013-09-25 | 2015-01-28 | 广西芳香植物开发应用有限公司 | Ecological flower growing method applied before extracting magnolia aroma substance |
| EP2962679A1 (en) * | 2014-06-30 | 2016-01-06 | Symrise AG | Use of tetrahydrofuranlignans |
| KR101826229B1 (en) * | 2015-10-07 | 2018-02-06 | 최봉근 | A Composition comprising extracts, fractions or isolated compounds of Magnolia flower for preventing and treating of periodentitis as an active ingredient |
| CN106632378A (en) * | 2016-12-23 | 2017-05-10 | 上海中医药大学 | Compound capable of inhibiting mast cell degranulation and preparation method and application thereof |
| CN111826234A (en) * | 2019-04-16 | 2020-10-27 | 江苏苏中药业集团股份有限公司 | Extraction method of cassia twig and magnolia flower mixed volatile oil |
| CN114557933A (en) * | 2022-03-09 | 2022-05-31 | 上海珈凯生物科技有限公司 | Magnolia biondii flower extract and preparation method and application thereof |
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| CN1289835A (en) * | 2000-06-13 | 2001-04-04 | 芦建仁 | Tiannu Magnolia oil |
| CN1493351A (en) * | 2003-09-18 | 2004-05-05 | 江苏扬子江药业集团有限公司 | Chinese medicine compound spraying agent for treating acute, chronic nasitis and its preparation method |
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| CN1289835A (en) * | 2000-06-13 | 2001-04-04 | 芦建仁 | Tiannu Magnolia oil |
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