CN112194690A - 3 new compounds in madder and extraction and separation method - Google Patents
3 new compounds in madder and extraction and separation method Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 238000000605 extraction Methods 0.000 title claims abstract description 11
- 238000000926 separation method Methods 0.000 title claims abstract description 8
- 241000123069 Ocyurus chrysurus Species 0.000 title abstract 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- 238000004440 column chromatography Methods 0.000 claims description 21
- 238000010898 silica gel chromatography Methods 0.000 claims description 17
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 14
- 241001149655 Rubia tinctorum Species 0.000 claims description 14
- 238000004809 thin layer chromatography Methods 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- 229940126214 compound 3 Drugs 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 10
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 10
- 229940125782 compound 2 Drugs 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 241000317854 Uncinata Species 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000002034 butanolic fraction Substances 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 240000009235 Rubia cordifolia Species 0.000 claims 3
- 241000223218 Fusarium Species 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 10
- 238000012306 spectroscopic technique Methods 0.000 abstract description 4
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- 238000002360 preparation method Methods 0.000 description 7
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- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 241001103643 Rubia Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 238000005520 cutting process Methods 0.000 description 2
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- 239000000539 dimer Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 208000034507 Haematemesis Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 208000001780 epistaxis Diseases 0.000 description 1
- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940124600 folk medicine Drugs 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/244—Anthraquinone radicals, e.g. sennosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Biotechnology (AREA)
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Abstract
The invention discloses 3 new compounds in madder and an extraction and separation method, wherein the new compounds provided by the invention are named as follows: 2-methyl-1, 6-dihydroxy-9, 10-anthraquinone-3-xylose- (1 → 2) -beta-D-glucose (1), 1,3, 6-trihydroxy-2-hydroxymethyl-9, 10-anthraquinone-3-O-beta-D-glucose (2), and 1-hydroxy-2-hydroxymethyl-9, 10-anthraquinone-11-O-beta-D-glucose (3). The present invention uses modern spectroscopic techniques such as1HNMR、13And performing structure identification on the separated monomer compound by using CNMR, two-dimensional nuclear magnetic spectrum, high-resolution mass spectrum and physicochemical property of the compound, deducing the molecular structure of the compound, and providing a material basis for further quality control and pharmacodynamic study of madder.
Description
Technical Field
The invention relates to the field of traditional Chinese medicine extraction and separation, in particular to a novel compound extracted, separated and identified from a madder hook medicinal material and an extraction and separation method thereof.
Background
The madder uncinata is dry root and rhizome of madder uncinata (Rubia hand-Mazz) of Rubia of Rubiaceae (Rubiaceae), is distributed in southwest of Guizhou, northeast to southeast of Yunnan, northwest of Guangxi and southwest of Guangxi, and the like, is collected in Chinese medicinal materials and national medicinal material quality standards of Guizhou province (2003 edition), is a minority national medicine of Guizhou province, has the effects of cooling blood, stopping bleeding, relieving cough, eliminating phlegm and the like, and is used for symptoms such as hematemesis, epistaxis, traumatic injury and the like. Modern researches find that the madder comprises naphthoquinones, anthraquinones, terpenes, dimer compounds and the like as main components.
At present, the chemical components of madder uncinata are researched less, and only the Itokawa Hideji group and the Tan Ninghua group are researched to find that the main components are naphthoquinones, anthraquinones, terpenes and dimer compounds, but the number of the separated and identified compounds is less.
Disclosure of Invention
The invention combines a folk medicine application method (water decoction or wine soaking) to research chemical components of n-butanol extraction parts of a madder medicinal material 70% ethanol extract, provides three new compounds in the madder, and simultaneously provides a simple, convenient and rapid extraction and separation method for the new compounds, so as to realize enrichment of material components of the madder medicinal material and provide a theoretical basis for later-period research on drug effect material basis.
In order to achieve the above purpose of the invention, the technical scheme of the invention is as follows:
the new compound provided by the invention is named as: 2-methyl-1, 6-dihydroxy-9, 10-anthraquinone-3-xylose- (1 → 2) -beta-D-glucose (1), 1,3, 6-trihydroxy-2-hydroxymethyl-9, 10-anthraquinone-3-O-beta-D-glucose (2), 1-hydroxy-2-hydroxymethyl-9, 10-anthraquinone-11-O-beta-D-glucose (3), and the structural formula is as follows:
the invention also provides a method for extracting and separating compounds from madder gibbosa, which comprises the following steps:
step 1, cutting dried roots and rhizomes of madder into small sections, extracting for 3 times by 70% ethanol in a refluxing manner, extracting for 2 hours in a volume which is 10 times that of the first time, extracting for 1.5 hours in a volume which is 8 times that of the second time, extracting for 1.5 hours in a volume which is 8 times that of the third time, combining the extracting solutions for 3 times, recovering ethanol under reduced pressure, and volatilizing until no alcohol smell exists to obtain an extract.
And 2, dissolving and dispersing the extract by using water, and then sequentially and respectively extracting by using petroleum ether, ethyl acetate and n-butanol to respectively obtain a petroleum ether part, an ethyl acetate part, an n-butanol part and a water part.
And 3, taking the n-butanol section, separating by normal phase silica gel column chromatography, carrying out gradient elution by dichloromethane-methanol (50: 1-1:1), detecting by thin layer chromatography, and combining similar components by different color development modes to obtain 7 components Fr.1-Fr.7.
And 4, subjecting the Fr.2 to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol (15:1-1:1), and detecting by thin layer chromatography to combine the same components to obtain a plurality of components. Subjecting one of the fractions to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol (8:1) to obtain different sub-fractions, and subjecting one of the sub-fractions to normal phase silica gel column chromatography, dichloromethane: methanol (8:1-4:1) was eluted in a gradient and chromatographed on a Toyopearl HW-40F column, eluting with methanol, chloroform: methanol (1:1) to obtain the compound 1.
And 5, subjecting the Fr.4 to Sephadex LH-20 column chromatography, methanol elution and thin-layer chromatography, and combining the same fractions to obtain a plurality of components. Subjecting one of the fractions to Toyopearl HW-40F column chromatography, eluting with methanol to obtain different sub-fractions, subjecting one of the sub-fractions to MCI column chromatography, eluting with methanol-water, eluting with Toyopearl HW-40F column chromatography, and eluting with methanol to obtain compound 2.
And step 6, subjecting Fr.6 to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol (15:1-1:1), detecting by thin layer chromatography, and mixing the same fractions to obtain multiple components. Subjecting one component to Sephadex LH-20 column chromatography, chloroform: methanol (1:1) elution gave different subfractions. And then passing a certain sub-component through Sephadex LH-20 column chromatography, eluting with methanol to obtain a plurality of small components, and then passing the components through Sephadex LH-20 column chromatography, chloroform: methanol (1:1) to obtain 2 fractions, and performing normal phase silica gel column chromatography, ethyl acetate-methanol (15:1-1:1) elution, Toyopearl HW-40F column chromatography, and methanol elution to obtain compound 3.
The invention has the following technical effects: the present invention uses modern spectroscopic techniques such as1H NMR、13And performing structure identification on the separated monomer compound by using C NMR, two-dimensional nuclear magnetic spectrum, high-resolution mass spectrum and physicochemical property of the compound, deducing the molecular structure of the compound, and providing a material basis for further quality control and pharmacodynamic study of madder.
Drawings
FIG. 1 HR-ESI-MS of novel Compound 1 of the present invention;
FIG. 2 HR-ESI-MS of novel Compound 2 of the present invention;
FIG. 3 HR-ESI-MS of novel Compound 3 of the present invention;
FIG. 4 Process for preparing novel Compound 1 of the present invention1H-NMR chart (DMSO);
FIG. 5 Process for preparing novel Compound 1 of the present invention13C-NMR chart (DMSO);
FIG. 6 preparation of Compound 21H-NMR chart (DMSO);
FIG. 7 preparation of Compound 21H-NMR chart (DMSO);
figure 8 HMBC map (DMSO) of compound 2;
FIG. 9 preparation of Compound 31H-NMR chart (DMSO);
FIG. 10 preparation of Compound 313C-NMR chart (DMSO);
figure 11 HMBC map (DMSO) of compound 3;
figure 12 HMQC picture (DMSO) of compound 3.
Detailed Description
The technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. The technical features mentioned in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other. The ingredients or materials involved in the following processes, unless otherwise specified, are commercially available. The related experimental methods are conventional methods in the technical field if not specifically stated. The numerical values or numerical proportions, if not indicated, are mass values or mass proportions.
Example 1:
step 1: cutting dried root and rhizome of Rubia harorum into small pieces of about 1-2cm, extracting with 70% ethanol under reflux for 3 times, 10 times of the first time for 2 hr, 8 times of the second time for 1.5 hr, and 8 times of the third time for 1.5 hr, mixing the extractive solutions for 3 times, recovering ethanol under reduced pressure, and volatilizing to remove ethanol smell to obtain extract.
Step 2: dissolving the extract in water, dispersing, sequentially extracting with petroleum ether, ethyl acetate and n-butanol to obtain petroleum ether fraction (55g), ethyl acetate fraction (65g), n-butanol fraction (215g) and water fraction (257 g).
And step 3: taking the n-butanol section, separating by normal phase silica gel column chromatography, gradient eluting with dichloromethane-methanol (50: 1-1:1), detecting by thin layer chromatography and different color development modes to see that the components are similar, and combining the similar components to obtain 7 components Fr.1-Fr.7.
And 4, step 4: subjecting Fr.2(44.08g) to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol (15:1-1:1), and detecting by thin layer chromatography to obtain 9 fractions (Fr.2.1-Fr.2.9). Subjecting Fr.2.4 to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol (8:1) to obtain 5 fractions (Fr.2.4.1-Fr.2.4.5), wherein Fr.2.4.5 is subjected to normal phase silica gel column chromatography, dichloromethane: methanol (8:1-4:1) was eluted in a gradient and chromatographed on a Toyopearl HW-40F column, eluting with methanol, chloroform: methanol (1:1) was eluted to give Compound 1(10 mg).
And 5: subjecting Fr.4(10.72g) to Sephadex LH-20 column chromatography, eluting with methanol, detecting with thin layer chromatography, and mixing the same fractions to obtain 6 fractions (Fr.4.1-Fr.4.6). Subjecting Fr.4.4 to Toyopearl HW-40F column chromatography, eluting with methanol to obtain 3 fractions (Fr.4.4.1-Fr.4.4.3), subjecting Fr.4.4.2 to MCI column chromatography, eluting with methanol-water, subjecting to Toyopearl HW-40F column chromatography, and eluting with methanol to obtain compound 2(9 mg).
Step 6: subjecting Fr.6(14.00g) to normal phase silica gel column chromatography, gradient eluting with ethyl acetate-methanol (15:1-1:1), and detecting by thin layer chromatography to combine the same fractions to obtain 5 components (Fr.6.1-Fr.6.5). Subjecting Fr.6.3 to Sephadex LH-20 column chromatography, chloroform: methanol (1:1) to obtain 6 components (Fr.6.3.1-Fr.6.3.6). Then, the Fr.6.3.1 is subjected to Sephadex LH-20 column chromatography and methanol elution to obtain 6 components (Fr.6.3.1.1-Fr.6.3.1.6), and then the Fr.6.3.1.4 is subjected to Sephadex LH-20 column chromatography, chloroform: eluting with methanol (1:1) to obtain 2 components (Fr.6.3.1.4.1-Fr.6.3.1.4.2), wherein Fr.6.3.1.4.1 is subjected to normal phase silica gel column chromatography, gradient elution with ethyl acetate-methanol (15:1-1:1), chromatography with Toyopearl HW-40F column, and elution with methanol to obtain compound 3(8.7 mg).
Conditions for TLC detection according to the present invention: and (3) color developing agent a: observing fluorescence under an ultraviolet lamp (254nm, 365 nm); and (3) color developing agent b: iodine color development; and (3) a color developing agent c: 10% sulfuric acid ethanol.
And (3) structural identification: using modern spectroscopic techniques such as1H NMR、13And carrying out structural identification on the separated monomer compound by using C NMR, two-dimensional nuclear magnetic spectrum and high-resolution mass spectrum.
Compound 1: pale yellow amorphous powder. HR-ESI-MS M/z 563.1400[ M-H ]]–(calculated value: 563.1399) and molecular formula C26H28O14The compound is determined to be 2-methyl-1, 6-dihydroxy-9, 10-anthraquinone-3-xylose- (1 → 2) -beta-D-glucose by the spectral technique. The nuclear magnetic data are shown in Table 1.
Compound 2: pale yellow amorphous powder. HR-ESI-MS M/z 447.0920[ M-H ]]-(calculated value: 447.0921) and molecular formula C21H20O11The compound is determined to be 1,3, 6-trihydroxy-2-hydroxymethyl-9, 10-anthraquinone-3-O-beta-D-glucose by a spectroscopic technique. The nuclear magnetic data are shown in Table 2.
Compound 3: pale yellow amorphous powder. HR-ESI-MS M/z 415.1025[ M-H ]]-(calculated value: 415.1023) and molecular formula C21H20O9The compound is determined to be 1-hydroxy-2-hydroxymethyl-9, 10-anthraquinone-11-O-beta-D-glucose by the spectral technique. The nuclear magnetic data are shown inTable 3.
TABLE 1 preparation of Compound 11H-NMR (DMSO,400MHz) and13C-NMR (DMSO,100MHz) data
TABLE 2 preparation of Compound 21H-NMR (DMSO,400MHz) and13C-NMR (DMSO,100MHz) data
TABLE 3 preparation of Compound 31H-NMR (DMSO,400MHz) and13C-NMR(DMSO,100MHz)
although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that various changes in the embodiments and modifications of the invention can be made, and equivalents of some features of the invention can be substituted, and any changes, equivalents, and improvements made without departing from the spirit and principles of the invention are intended to be included within the scope of the invention.
Claims (5)
1. 3 new compounds in madder uncinata are characterized in that the chemical names of the compounds are as follows: 2-methyl-1, 6-dihydroxy-9, 10-anthraquinone-3-xylose- (1 → 2) -beta-D-glucose (1), 1,3, 6-trihydroxy-2-hydroxymethyl-9, 10-anthraquinone-3-O-beta-D-glucose (2), 1-hydroxy-2-hydroxymethyl-9, 10 anthraquinone-11-O-beta-D-glucose (3); the structural formula is as follows:
2. 3 novel compounds of rubia cordifolia according to claim 1, characterized in that: the three new compounds are all anthraquinone derivatives.
3. The method for extracting and separating 3 new compounds from madder gibberella as claimed in claim 1, characterized in that the method comprises the following steps:
step 1: repeatedly reflux-extracting radix Rubiae with ethanol, mixing extractive solutions, and concentrating to obtain extract;
step 2: sequentially extracting the extract obtained in the step 1 with petroleum ether, ethyl acetate and n-butanol to respectively obtain a petroleum ether part, an ethyl acetate part, a n-butanol part and a water part;
and step 3: taking the n-butanol fraction obtained in the step 2, carrying out normal phase silica gel column chromatography for coarse separation, carrying out thin layer chromatography detection, developing, and combining the developed elution fractions to obtain 7 components Fr.1-Fr.7;
and 4, step 4: subjecting Fr.2 obtained in step 3 to normal phase column chromatography, eluting with ethyl acetate-methanol, detecting with thin layer chromatography, and mixing the same fractions to obtain several components; wherein a certain component is separated by normal phase silica gel column chromatography and Toyopearl HW-40F column chromatography to obtain a compound 1;
and 5: subjecting Fr.4 obtained in step 3 to Sephadex LH-20 column chromatography, methanol elution, and thin layer chromatography, and mixing the same fractions to obtain multiple fractions; repeatedly eluting a certain component by Toyopearl HW-40F column chromatography, MCI and Toyopearl HW-40F column chromatography to obtain a compound 2;
step 6: subjecting Fr.6 obtained in step 3 to normal phase silica gel column chromatography, eluting with ethyl acetate-methanol, detecting with thin layer chromatography, and mixing the same fractions to obtain several components; wherein a certain component is repeatedly eluted by Sephadex LH-20 column chromatography and normal phase silica gel column chromatography to obtain a compound 3.
4. The method for preparing three new compounds in rubia cordifolia according to claim 3, characterized in that: in the step 1, 70% ethanol is adopted for reflux extraction for 3 times, the first extraction is carried out for 2 hours in 10 times of volume, the second extraction is carried out for 1.5 hours in 8 times of volume, and the third extraction is carried out for 1.5 hours in 8 times of volume.
5. The method for preparing three new compounds in rubia cordifolia according to claim 3, characterized in that: when the silica gel column chromatography separation in the steps 3, 4 and 6 is carried out, 100-sand 300-mesh silica gel is selected.
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| CN1397541A (en) * | 2001-07-20 | 2003-02-19 | 中国人民解放军军事医学科学院放射医学研究所 | Trijuganone and its derivative, and its preparing process and application |
| CN103550237A (en) * | 2013-11-11 | 2014-02-05 | 南京中医药大学 | Composition of active ingredients of rubia cordifolia as well as application of composition in medicines |
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2020
- 2020-10-10 CN CN202011078958.4A patent/CN112194690B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1397541A (en) * | 2001-07-20 | 2003-02-19 | 中国人民解放军军事医学科学院放射医学研究所 | Trijuganone and its derivative, and its preparing process and application |
| CN103550237A (en) * | 2013-11-11 | 2014-02-05 | 南京中医药大学 | Composition of active ingredients of rubia cordifolia as well as application of composition in medicines |
Non-Patent Citations (2)
| Title |
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| ZHE WANG 等: "Rubipodanones A-D, naphthohydroquinone dimers from the roots and rhizomes of Rubia podantha" * |
| 王素贤 等: "茜草总蒽醌类成分的研究" * |
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