CN114031517B - Nitrogen-containing organic acid in purslane and extraction and separation method thereof - Google Patents
Nitrogen-containing organic acid in purslane and extraction and separation method thereof Download PDFInfo
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- CN114031517B CN114031517B CN202111394360.0A CN202111394360A CN114031517B CN 114031517 B CN114031517 B CN 114031517B CN 202111394360 A CN202111394360 A CN 202111394360A CN 114031517 B CN114031517 B CN 114031517B
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- purslane
- separating
- ethanol
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- -1 Nitrogen-containing organic acid Chemical class 0.000 title claims abstract description 35
- 241000219304 Portulacaceae Species 0.000 title claims abstract description 26
- 235000001855 Portulaca oleracea Nutrition 0.000 title claims abstract description 25
- 238000000926 separation method Methods 0.000 title claims abstract description 21
- 238000000605 extraction Methods 0.000 title claims abstract description 19
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000544 cholinesterase inhibitor Substances 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
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- 238000001816 cooling Methods 0.000 claims description 4
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- 238000005303 weighing Methods 0.000 claims description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- 238000010829 isocratic elution Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
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- 238000010183 spectrum analysis Methods 0.000 abstract 1
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- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 3
- 229960001697 physostigmine Drugs 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- NTBLZMAMTZXLBP-UHFFFAOYSA-M 2-acetylsulfanylethyl(trimethyl)azanium;iodide Chemical compound [I-].CC(=O)SCC[N+](C)(C)C NTBLZMAMTZXLBP-UHFFFAOYSA-M 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- FZNMBBPKZSTVOR-UHFFFAOYSA-N 4-hydroxy-5-methylfuran-3-carboxylic acid Chemical compound CC=1OC=C(C(O)=O)C=1O FZNMBBPKZSTVOR-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PCSKKIUURRTAEM-UHFFFAOYSA-N 5-hydroxymethyl-2-furoic acid Chemical compound OCC1=CC=C(C(O)=O)O1 PCSKKIUURRTAEM-UHFFFAOYSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000448435 Acalypha australis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 201000000297 Erysipelas Diseases 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical class CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- WYGMGKPKILJUQX-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)SSC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].[P] Chemical compound [N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)SSC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].[P] WYGMGKPKILJUQX-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- ONBIUAZBGHXJDM-UHFFFAOYSA-J bismuth;potassium;tetraiodide Chemical compound [K+].[I-].[I-].[I-].[I-].[Bi+3] ONBIUAZBGHXJDM-UHFFFAOYSA-J 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
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- 230000036772 blood pressure Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002072 distortionless enhancement with polarization transfer spectrum Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
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- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- CTGNYPVJSIRPLG-UHFFFAOYSA-N trimethyl(2-sulfanylethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CCS CTGNYPVJSIRPLG-UHFFFAOYSA-N 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- 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
Abstract
The invention relates to the field of traditional Chinese medicine extraction and separation, in particular to a method for extracting, separating and identifying a nitrogenous organic acid compound from purslane and an extraction and separation method thereof. Its molecular formula is C 16 H 30 N 2 O 5 Designated 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid. Also provides an extraction and separation method, which sequentially adopts water decoction and extraction, silica gel column chromatography, ethyl acetate extraction, ODS medium pressure column, SI medium pressure column and liquid phase separation. The structure adopts 1 H‑NMR、 13 C-NMR and two-dimensional nuclear magnetic spectrum analysis are determined to be the nitrogenous organic acid compound. The compound has potential anticholinesterase activity, provides a preparation method, and provides a lead and a theoretical basis for developing new drugs and developing new components.
Description
Technical Field
The invention relates to the field of traditional Chinese medicine extraction and separation, in particular to a nitrogenous organic acid compound extracted, separated and identified from purslane medicinal materials and an extraction and separation method thereof.
Background
Herba PortulacaePortulaca oleraceaL.), also known as changcai, acalypha australis, wuxing grass, is an annual fleshy herb of the portulacaceae family. Purslane is drought-resistant and waterlogging-resistant, light-resistant and yin-resistant, wide in distribution and rich in resources. Most of wild plants, rarely planted, are one of 78 medicinal and edible wild plants regulated by the Ministry of health in China, and are listed in the menu of the Beijing Olympic Games in 2008. The dry overground part of the purslane in the pharmacopoeia of the people's republic of China of 2020 edition is used as a medicine, has the effects of clearing heat and detoxicating, cooling blood and stopping bleeding, stopping dysentery and the like, and is used for treating heat toxin bloody dysentery, carbuncle and furuncle, eczema, erysipelas, snake and insect bite, hematochezia, hemorrhoids, metrorrhagia, bleeding and the like.
Modern pharmacological researches of purslane show that it has the functions of resisting inflammation, relieving pain, resisting bacteria and viruses, reducing blood pressure, reducing blood fat, resisting oxidation and cancer, relaxing skeletal and smooth muscles, regulating immune function and the like. The researches show that the purslane has a plurality of chemical components which provide a material basis for various pharmacological actions, and the main chemical components of the purslane comprise flavonoids, coumarins, terpenes, steroids, organic acids, volatile oil, alkaloids, amino acids, various pigments, minerals and the like. The organic acids are main chemical components in purslane, and the organic acids reported at present comprise 4-hydroxy-5-methylfuran-3-carboxylic acid, 5-hydroxymethyl furoic acid, L-pyroglutamic acid, salicylic acid, vanillic acid, p-hydroxybenzoic acid, stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid and the like.
Most of the chemical components separated from purslane are known at present, and the structural novelty is low, so that development and separation of new compounds in purslane are needed.
Disclosure of Invention
In order to solve the problems, the invention provides a method for extracting a nitrogenous organic acid compound from purslane, which is researched and found to have anticholinesterase effect and simultaneously provides a simple, rapid, environment-friendly and high-purity extraction and separation method for the novel alkali compound.
In order to achieve the above purpose, the present invention provides the following technical solutions.
The invention provides a nitrogenous organic acid compound separated from purslane medicinal materials, which is characterized in that the molecular formula is C 16 H 30 N 2 O 5 Designated 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid. The chemical structural formula is as follows:
the invention also provides an extraction and separation method of the nitrogen-containing organic acid compound in the purslane, which comprises the following specific steps:
and 5, performing HPLC separation on the concentrate obtained in the step 4, and taking acetonitrile-water-0.1% formic acid as a mobile phase, wherein the detection wavelength is 210nm and 280nm, so as to prepare the nitrogenous organic acid compound. The purity of the product is higher than 98% by high performance liquid chromatography.
Further, the pretreatment process of ODS in the step 3 and SI in the step 4 is that methanol is soaked for 24 hours, the mixture is put on a column, and the mixture is washed by methanol until the mixture is dropped into water to avoid turbidity, and then the mixture is balanced by an initial mobile phase.
Further, in the step 2, silica gel chromatography is sequentially performed with a volume ratio of 5: 1. 4: 1. 3:1 and 2:1 in ethyl acetate-ethanol gradient.
Further, the polyamide column separation in the step 2 adopts a volume ratio of 1: 100. 50: 50. 70:30 and 90: ethanol of 10: and (5) water gradient elution.
Further, the volume ratio of methanol to water in the gradient elution of the methanol to water used in the step 3 is 50:50, 70:30 and 90:10; the filler particle size of the ODS column is 20-40 μm.
Further, the elution conditions in the step 3 are as follows: the mixture was pressurized at room temperature to a flow rate of 1mL/min.
Further, the ethyl acetate elution procedure used in step 4 was isocratic.
Further, the volume ratio of acetonitrile to water in the isocratic elution of acetonitrile to 0.1% formic acid used in the step 5 is 10:90.
The invention also provides an application of the nitrogenous organic acid compound separated from the purslane medicinal material in preparing anticholinesterase drugs.
Compared with the prior art, the invention has the beneficial effects.
The separation and pharmacological activity research of the purslane nitrogen-containing organic acid compound in the invention are not reported by the existing journal of papers; the invention provides a nitrogen-containing organic acid compound from purslane and an extraction and separation method aiming at the novel compound, which sequentially adopts 50% ethanol reflux extraction, silica gel column chromatography, polyamide column chromatography, ODS medium pressure column, SI medium pressure column and HPLC for separation and purification and preparation and successful extraction and separation to obtain the nitrogen-containing organic acid compound.
Drawings
FIG. 1 is a high resolution mass spectrum of the nitrogen-containing organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention.
FIG. 2 is a schematic diagram of the nitrogen-containing organic acid compound 5- (diethyl-Mino) -2- (3- (diethyl-Mino) -3-oxoopyl) -2-hydroxy-5-oxopentanoic acid according to the present invention 1 H-NMR spectrum.
FIG. 3 is a schematic diagram of the nitrogen-containing organic acid compound 5- (diethyl-Mino) -2- (3- (diethyl-Mino) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention 13 C-NMR spectrum.
FIG. 4 is a chart showing the nuclear magnetic resonance carbon spectrum (DEPT) of the nitrogen-containing organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention.
FIG. 5 shows the nuclear magnetic resonance of the nitrogen-containing organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention 1 H- 1 HCOSY spectrogram.
FIG. 6 is a chart showing the nuclear magnetic resonance HMBC spectrum of the nitrogen-containing organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention.
FIG. 7 is a nuclear magnetic resonance HSQC spectrum of the nitrogen-containing organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention.
FIG. 8 is a nuclear magnetic resonance NOESY spectrum of 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid of the present invention.
Detailed Description
The following examples will aid in the understanding of the present invention, but are merely illustrative of the invention and the invention is not limited thereto. The methods of operation in the examples are all conventional in the art.
Example 1.
The invention provides a nitrogenous organic acid compound with a molecular formula of C 16 H 30 N 2 O 5 Designated 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyyl) -2-hydroxy-5-oxopentanoic acid. The chemical structural formula is as follows:
the nitrogen-containing organic acid compound is named as 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxoopyl) -2-hydroxy-5-oxopentanoic acid according to the structure, and the nuclear magnetic data of the nitrogen-containing organic acid compound are shown in Table 1: 1 H-NMR 13 C-NMR at MeOD-d 4 Is a kind of medium.
Table 1: nuclear magnetic data of the nitrogen-containing organic acid compound of the present invention
The structure identification and deduction of the nitrogenous organic acid compound 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxopropyl) -2-hydroxy-5-oxopentanoic acid are carried out.
The obtained compound is light yellow powdery substance, and is easily dissolved in methanol. HRESI (-) TOFMS gives m/z:230.1397[ M-H ]] - The molecular weight of the excimer ion peak is 330.2155. After spotting on a silica gel thin layer plate, spraying dilute bismuth potassium iodide test solution to spot and display orange. Bonding of 1 H-NMR， 13 C-NMR and DEPT data, it is presumed that the compound may have the formula C 16 H 30 N 2 O 5 The unsaturation was 6.
13 C-NMR spectrum, HMBC spectrum and DEPT spectrum showed 9 carbon signals of 4 CH respectively 2 （δ C 44.5, 44.7, 62.0, 63.0, overlap), 2 CH 3 （δ C 14.5, 14.6, overlap), 2 carbonyl carbons (delta) C 171.5、175.1，δ C 171.5 overlap), 1 quaternary carbon (delta) C 74.7). At the position of 1 In the H NMR spectrum, delta H 1.23（t，3H，J=7.2 Hz, overlap), δ H 1.28（t，3H，J=7.2 Hz, overlap) demonstrates the presence of 4 methyl groups. Delta H 2.75（t，2H，J=15.36 Hz, overlap), δ H 2.91（dd，2H，J 1 =15.24Hz，J 2 =7.74 Hz, overlap), δ H 4.11（dd，2H，J 1 =14.28Hz，J 2 =7.14 Hz, overlap), δ H 4.22（dd，2H，J 1 =14.28Hz，J 2 =7.14 Hz, overlap) demonstrates the presence of 8 methylene groups. By passing through 13 C-NMR spectrum revealed C-1 ʹ ʹ (delta) H 62.0），C-5ʹʹ（δ H 62.0 And C-3 ʹ ʹ (delta) H 63.0），C-7ʹʹ（δ H 63.0 With low field chemical sitesShift according to delta H 4.11（dd，2H），δ H 4.22 The signals and formulas at (dd, 2H) may illustrate that C-1 ʹ ʹ, C-5 ʹ ʹ and C-3 ʹ ʹ, C-7 ʹ ʹ are attached to the N atom. 1 H- 1 In the H COSY spectrum, H-1 ʹ ʹ (delta) H 4.11）, H-5ʹʹ（δ H 4.11 And H-2 ʹ ʹ (delta) H 1.23），H-6ʹʹ（δ H 1.23），H-3ʹʹ（δ H 4.22），H-7ʹʹ（δ H 4.22 And H-4 ʹ ʹ (delta) H 1.28），H-8ʹʹ（δ H 1.28 Shows a clear correlation according to C-5 (delta) C 171.5），C-3ʹ（δ C 171.5 Along with the HMBC correlation from H-1 ʹ ʹ, H-3 ʹ ʹ to C-5 and H-5 ʹ ʹ, H-7 ʹ ʹ to C-3 ʹ, two symmetrical N, N-diethylcarboxamides can be presumed to exist. 13 Delta in C-NMR spectra C 171.5 (C-1) shows the signal of carboxyl group, delta C 74.7 (C-2) biasing towards Low field, H-3 (delta) in HMBC spectra H 2.75 From C-1, C-2, C-4, C-5,H-1 ʹ (. Delta.) H 2.75 C-1, C-2 ʹ, C-3 ʹ and H-4 (. Delta.) H 2.91 From C-1, C-2, C-3, C-5,H-2 ʹ (. Delta.) H 2.91 From C-1, C-2, C-1 ʹ, C-3 ʹ shows a correlation signal, and from the above information, the structure of the nitrogen-containing organic acid compound 5- (diethyl-amine) -2- (3- (diethyl-amine) -3-oxoopyl) -2-hydroxy-5-oxopentanoic acid can be determined.
The invention also provides an extraction and separation method of the nitrogenous organic acid compound, which comprises the following specific steps:
step 1: weighing 150kg of dry purslane, reflux-extracting with 50% ethanol, wherein the dosage of 50% ethanol is 8-16 times of that of the purslane, reflux-extracting twice, each time for 2 hours, recovering ethanol under reduced pressure, and cooling to room temperature to obtain a liquid medicine for later use;
step 2: separating the concentrated solution in the step 1 by silica gel column chromatography, wherein silica gel is 100-200 meshes, sequentially eluting with ethyl acetate-ethanol (5/1, 4/1, 3/1, 2/1, v/v) gradient to obtain 4 parts, evaporating 3/1 part to obtain 2.6kg of extract, separating the extract by polyamide column, eluting with ethanol-water (1/100, 50/50, 70/30, 90/10, v/v) gradient, and evaporating 70% ethanol part to obtain extract;
step 3: separating the pretreated ODS obtained in step 2 by medium pressure column chromatography, wherein the filler particle size is 20-40 μm, eluting with methanol-water (50/50, 70/30, 90/10 v/v) (pressurizing to flow rate of 1mL/min, and temperature of room temperature), concentrating 50/50 part under reduced pressure below 40deg.C until it is dry for use. The pretreatment process of the ODS comprises the steps of soaking the ODS in methanol for 24 hours, loading the ODS on a column, washing the ODS with the methanol until the ODS is not turbid in dripping water, and balancing the ODS with an initial mobile phase;
step 4: separating the obtained product in step 3 by SI medium pressure column chromatography, eluting with ethyl acetate isocratically to obtain 6 parts (i.e. eluting to obtain 6 bottles of 200mL each), detecting by thin layer chromatography, and concentrating the first part under reduced pressure below 50deg.C until it is dry for use. The pretreatment process of SI is that methanol is soaked for 24 hours, the mixture is put on a column, and is washed by methanol until the mixture is dripped into water without turbidity, and then the mixture is balanced by an initial mobile phase;
step 5: separating and preparing the product obtained in the step 4 by HPLC, taking acetonitrile-water-0.1% formic acid (10/90, v/v) as a mobile phase, and measuring the wavelength to be 210nm and 280nm to obtain the nitrogenous organic acid compound, wherein the purity measured by a normalization method is 90-99%.
Example 2 anticholinesterase action of nitrogen-containing organic acid compounds of the present invention.
1. The main material.
1.1, medicines and reagents: the nitrogenous organic acid compounds used in the experiments were prepared by the above method with purity of 90-99%, sodium dihydrogen phosphate, disodium hydrogen phosphate (national pharmaceutical sciences chemical Co., ltd.), physostigmine (Han Xiang Biotechnology), phosphorus 5,5' -dithiobis (2-nitrobenzoic acid) (Dithiobisnitrobenzoic acid, DTNB, shanghai jinnian Biotechnology Co., ltd.), acetylcholinesterase (AChE) and thiocholine iodide (Acetylthiocholine iodide, ATCI, dalian Mei Lun Biotechnology Co., ltd.).
1.2, grouping: the negative control group, the positive control group and the experimental group are divided into one group.
2. Experimental methods.
2.1 sample preparation, precisely weighing 1mg of the sample and 1mg of physostigmine respectively, and preparing five gradient concentrations of lmg/mL, 0.5mg/mL, 0.1mg/mL, 0.05mg/mL and 0.01mg/mL by taking methanol as a solvent respectively. 7.098g of sodium dihydrogen phosphate and 5.999g of disodium hydrogen phosphate are respectively weighed precisely, distilled water is used for constant volume to 50mL, 3.40mL of sodium dihydrogen phosphate and 46.6mL of disodium hydrogen phosphate are taken, and 50mL of PBS (0.1M pH=8.0) is prepared; 0.0594g of DTNB is precisely weighed, 10mL of PBS is added to prepare a DTNB solution (15 mmol/L); precisely weighing 0.01g AChE, adding 10mLPBS, and preparing AChE solution (0.2 u/mL); 0.044g of ATCI was precisely weighed, and distilled water was used to determine the volume to 10mL to prepare an ATCI solution (15 mmol/L).
2.2 modified Ellman method to determine anticholinesterase activity 140 μl of LPBS (0.1M ph=8.0), 10 μl of LDTNB (15 mmol/L), 15 μl of LAChE (0.2 u/mL) and 20 μl of sample solution were added sequentially to 96-well elisa plates. The negative control experiments replaced the sample with methanol, and the positive control experiments replaced the sample with physostigmine. After incubation at 37℃for 10min, 10. Mu. LATCI (15 mmol/L) was added. After incubation at 20℃for 10min, the absorbance was measured at 410nm using a microplate reader. Inhibition ratio (%) = (blank-sample)/blank×100% was calculated according to the following formula.
3. Experimental results.
Experimental results show that the nitrogenous organic acid compound has anticholinesterase effect. The experimental results are shown in table 2.
Table 2: the anticholinesterase activity of the invention
Claims (8)
1. A nitrogenous organic acid compound separated from purslane medicinal materials is characterized by having a molecular formula: c (C) 16 H 30 N 2 O 5 And according to the structural designation 5- (diethyl amine) -2- (3- (diethyl amine) -3-oxopropyl) -2-hydroxy-5-oxopentanoic acid, the chemical structural formula is as follows:
2. the method for extracting and separating the compound according to claim 1, which comprises the following specific steps:
step 1: weighing 150kg of dry purslane, reflux-extracting with 50% ethanol, wherein the dosage of 50% ethanol is 8-16 times of that of the purslane, reflux-extracting twice, each time for 2 hours, recovering ethanol under reduced pressure, and cooling to room temperature to obtain a liquid medicine for later use;
step 2: separating the concentrated solution in the step 1 by silica gel column chromatography, and sequentially using the following components in volume ratio of 5: 1. 4: 1. 3:1 and 2:1 in total, 4 fractions were obtained by gradient elution with ethyl acetate-ethanol, 3: evaporating the part 1 to obtain 2.6kg of extract, separating the extract by a polyamide column, wherein the volume ratio of the extract to the polyamide column is 1: 100. 50: 50. 70:30 and 90:10, ethanol-water gradient elution, and evaporating 70% ethanol part for later use;
step 3: separating the pretreated ODS obtained in the step 2 by medium-pressure column chromatography, eluting with methanol-water with volume ratio of 50:50, 70:30 and 90:10, and eluting with 50: concentrating 50 parts under reduced pressure below 40deg.C to dry;
step 4: separating the obtained product in step 3 by SI medium pressure column chromatography, eluting with ethyl acetate isocratically to obtain 6 parts, eluting to obtain 6 bottles of 200mL each, detecting by thin layer chromatography, concentrating the first part under reduced pressure below 50deg.C until it is dry;
step 5: and (3) separating and preparing the product obtained in the step (4) by HPLC, taking acetonitrile-water-0.1% formic acid as a mobile phase, and detecting the wavelength of 210nm and 280nm to obtain the nitrogenous organic acid compound, wherein the purity of the nitrogenous organic acid compound measured by a normalization method is 90-99%.
3. The extraction and separation method as claimed in claim 2, wherein the pretreatment process of ODS in step 3 and SI in step 4 is that methanol is soaked for 24 hours, the mixture is put on a column, washed with methanol until the mixture is dropped into water without turbidity, and then the mixture is balanced by an initial mobile phase.
4. The extraction and separation method as claimed in claim 2, wherein the packing particle size of the ODS column in the step 3 is 20-40. Mu.m.
5. The extraction and separation method according to claim 2, wherein the elution conditions in step 3 are: the mixture was pressurized at room temperature to a flow rate of 1mL/min.
6. The extraction and separation method according to claim 2, wherein the ethyl acetate elution procedure used in step 4 is isocratic elution.
7. The method according to claim 2, wherein the volume ratio of acetonitrile to water in the isocratic elution of acetonitrile to 0.1% formic acid used in step 5 is 10:90.
8. The use of the nitrogen-containing organic acid compound isolated from purslane herb as claimed in claim 1 in the preparation of anticholinesterase drugs.
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