CN1884246A - Method for extracting diaryl heptane compounds from galangas - Google Patents
Method for extracting diaryl heptane compounds from galangas Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 34
- -1 diaryl heptane compounds Chemical class 0.000 title claims description 21
- 235000013421 Kaempferia galanga Nutrition 0.000 title abstract 4
- 241000985198 Galanga Species 0.000 title 1
- 239000000284 extract Substances 0.000 claims abstract description 95
- 238000000605 extraction Methods 0.000 claims abstract description 74
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 44
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003208 petroleum Substances 0.000 claims abstract description 31
- 239000000706 filtrate Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims abstract description 19
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000004440 column chromatography Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims description 48
- 230000006837 decompression Effects 0.000 claims description 24
- 239000012153 distilled water Substances 0.000 claims description 24
- 238000010828 elution Methods 0.000 claims description 24
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- 238000010298 pulverizing process Methods 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 18
- NKSWRYBLSIGGIU-UHFFFAOYSA-N 5-hydroxy-1-(4-hydroxyphenyl)-7-phenylheptan-3-one Chemical compound C=1C=C(O)C=CC=1CCC(=O)CC(O)CCC1=CC=CC=C1 NKSWRYBLSIGGIU-UHFFFAOYSA-N 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 6
- 229940095731 candida albicans Drugs 0.000 abstract description 5
- 230000001032 anti-candidal effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 244000062241 Kaempferia galanga Species 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 238000002953 preparative HPLC Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010067171 Regurgitation Diseases 0.000 description 1
- 240000007918 Tacca chantrieri Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002279 cholagogic effect Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108010080511 serum sodium transport inhibitor Proteins 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
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Abstract
本发明公开了一种从高良姜中提取二芳基庚烷类化合物的方法，其步骤：将高良姜粉碎用醇提取，滤液浓缩，浸膏用水溶解后用三氯甲烷萃取，将浓缩后的萃取液经硅胶柱层析分离，用石油醚－乙酸乙酯梯度洗脱，得33个组分；将第10、11组分合并，硅胶柱层析，氯仿－甲醇洗脱，通过TLC合并类似流分后，得6个组分，将第3组分进行Toyopearl HW－40C柱层析，得6组分，将第2个组分以反相制备HPLC，95∶5甲醇－水洗脱，分离得到2组分，其中之一为7－(4－羟苯基)－1－苯基－4－烯－3－庚酮，本发明工艺简单，活性成分损失少，高良姜经现代分离方法提取其抗白色念珠菌有效化学成分，为开发新型抗真菌药物奠定了基础。The invention discloses a method for extracting diarylheptane compounds from galangal. The steps include: crushing galangal and extracting with alcohol, concentrating the filtrate, dissolving the extract in water and extracting with chloroform, and extracting the concentrated The extract was separated by silica gel column chromatography, eluted with petroleum ether-ethyl acetate gradient, and 33 fractions were obtained; the 10th and 11th fractions were combined, silica gel column chromatography, eluted with chloroform-methanol, combined by TLC and similar After fractionation, 6 fractions were obtained. The third fraction was subjected to Toyopearl HW-40C column chromatography to obtain 6 fractions. The second fraction was eluted by reverse-phase preparative HPLC, 95:5 methanol-water, Two components are obtained by separation, one of which is 7-(4-hydroxyphenyl)-1-phenyl-4-ene-3-heptanone. The process of the present invention is simple and the loss of active components is small. Galangal is separated by a modern separation method. The extraction of its effective anti-Candida albicans chemical components has laid the foundation for the development of new antifungal drugs.
Description
Technical field
The present invention relates to a kind of method of from Chinese medicine, extracting compound, particularly relate to a kind of method of from Rhizoma Alpiniae Officinarum, extracting the diaryl heptane compounds.
Background technology
The Chinese medicine Rhizoma Alpiniae Officinarum is one of conventional Chinese medicine, the effect of cold, the promoting the circulation of qi of having warm stomach, dispel the wind, loose, pain relieving.The food flavouring that is used in a large number among the people.The clinical treatment of conditions such as the cold pain of gastral cavity abdomen, gastrofrigid vomiting, maldigestion, heating installation acid regurgitation that are usually used in.Modern chemistry and pharmacological research show the Rhizoma Alpiniae Officinarum complex chemical composition, and pharmacologically active is strong, and effects such as stronger antiulcer agent, diarrhea, cholagogic, analgesia, anti-inflammatory, anti-hypoxia, anti-freezing, antithrombotic formation are arranged.Clinical for many years proof, the Rhizoma Alpiniae Officinarum determined curative effect is widely used, and develops multiple formulation in recent years and is applied to clinical and has received curative effect preferably.
Have not yet to see the relevant open report that from Rhizoma Alpiniae Officinarum, extracts the anti-candida albicans active chemical.
Summary of the invention
The object of the invention is to provide a kind of method of extracting diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone from Rhizoma Alpiniae Officinarum.
Second purpose of the present invention provides a kind of method of extracting diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone from Rhizoma Alpiniae Officinarum.
The 3rd purpose of the present invention provides a kind of diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, method of 5-dihydroxy heptane extracted from Rhizoma Alpiniae Officinarum.
Technical scheme of the present invention is summarized as follows:
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone, comprise the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 is 7-(4-hydroxyphenyl)-1-phenyl 4-alkene-3-heptanone.
The preferred extracting method of diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone step (1) is:
With the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components.
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, comprise the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out with described AO0508, separates to obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, with volume ratio is 3: 2 petroleum ether-ethyl acetate wash-out, obtains compd A O2210, and described AO2210 is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
The preferred extracting method of diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone step (1) is:
With the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components.
Extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane comprises the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, get AO1601-AO1605 totally 5 components, with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out with AO1605, purifying, obtain compd A O1703, described AO1703 is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
Diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the preferred extracting method of 5-dihydroxy heptane step (1) is:
With the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components.
The invention has the advantages that extraction process is simple, active ingredient loss is less, traditional Rhizoma Alpiniae Officinarum medicine materical crude slice through modern separation method, is extracted its anti-candida albicans active chemical, for the development of new antifungal drug is laid a good foundation.
Embodiment
Below in conjunction with specific embodiment invention is further described.
Embodiment 1
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl 4-alkene-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials (in March, 2004 available from Tianjin prepared slices of Chinese crude drugs factory, identify by pharmacognosy teaching and research room of Medical University Of Tianjin), add 4 kilograms of concentration expressed in percentage by volumes and be 95% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, and extracts 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, the dissolved in distilled water that adds 4 times of described medicinal extract quality is used chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure, extraction liquid after concentrating is separated through silica gel column chromatography, with volume ratio is 4: 1,3: 1, and 2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution got AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 compares through various organic wave spectrum analysis and data in literature, and authenticating compound is 7-(4-hydroxyphenyl)-1-phenyl 4-alkene-3-heptanone.
AO2105
Embodiment 2
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 6 kilograms of concentration expressed in percentage by volumes and be 75% aqueous ethanolic solution, reflux 5 hours, extracting solution filters, extract 3 times, relative density was 1.05 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 5 times of described medicinal extract quality, with chloroform extraction 2 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 is 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone.
Embodiment 3
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl 4-alkene-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2 kilograms of concentration expressed in percentage by volumes and be 98% aqueous ethanolic solution, reflux 7 hours, extracting solution filters, extract 1 time, relative density was 1.20 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 3 times of described medicinal extract quality, with chloroform extraction 4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 is 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone.
Embodiment 4
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 8 kilograms of concentration expressed in percentage by volumes and be 60% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 6 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO010l-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 is 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone.
Embodiment 5
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 4 kilograms is 95% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate and obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, is 3: 2 petroleum ether-ethyl acetate wash-out with volume ratio, obtains compd A O2210, described AO2210 compares through various organic wave spectrum analysis and data in literature, and authenticating compound is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
AO2210
Embodiment 6
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 6 kilograms is 75% aqueous ethanolic solution, reflux 7 hours, extracting solution filters, extract 1 time, relative density was 1.05 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 5 times of described medicinal extract quality, with chloroform extraction 2 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out with described AO0508, separates to obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, with volume ratio is 3: 2 petroleum ether-ethyl acetate wash-out, obtains compd A O2210, and described AO2210 is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
Embodiment 7
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 2 kilograms is 98% aqueous ethanolic solution, reflux 5 hours, extracting solution filters, extract 3 times, relative density was 1.20 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 6 times of described medicinal extract quality, with chloroform extraction 4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out with described AO0508, separates to obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, with volume ratio is 3: 2 petroleum ether-ethyl acetate wash-out, obtains compd A O2210, and described AO2210 is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
Embodiment 8
From Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, comprise the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 8 kilograms is 60% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 3 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out with described AO0508, separates to obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, with volume ratio is 3: 2 petroleum ether-ethyl acetate wash-out, obtains compd A O2210, and described AO2210 is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
Embodiment 9
Extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane comprises the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 4 kilograms is 95% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, AO1601-AO1605 totally 5 components, with AO1605 with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out, purifying obtains compd A O1703, and described AO1703 compares through various organic wave spectrum analysis and data in literature, authenticating compound is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
AO1703
Embodiment 10
Extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane comprises the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 6 kilograms is 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 1 time, relative density was 1.20 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 5 times of described medicinal extract quality, with chloroform extraction 4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, get AO1601-AO1605 totally 5 components, with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out with AO1605, purifying, obtain compd A O1703, described AO1703 is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
Embodiment 11
Extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane comprises the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 2 kilograms is 98% aqueous ethanolic solution, reflux 7 hours, extracting solution filters, extract 3 times, relative density was 1.05 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 3 times of described medicinal extract quality, with chloroform extraction 2 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, get AO1601-AO1605 totally 5 components, with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out with AO1605, purifying, obtain compd A O1703, described AO1703 is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
Embodiment 12
Extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane comprises the steps:
(1) with 1 kilogram of Rhizoma Alpiniae Officinarum pulverizing medicinal materials, the concentration expressed in percentage by volume that adds 8 kilograms is 60% aqueous ethanolic solution, reflux 5 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 6 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, get AO1601-AO1605 totally 5 components, with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out with AO1605, purifying, obtain compd A O1703, described AO1703 is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
Embodiment 13
The bacteriostatic activity of each compound
More than each monomeric compound studies show that all have anti-candida albicans (Candidaalbicans) activity through external paper disk method bacteriostatic experiment, (MIC) is as follows for its minimum inhibitory concentration:
| Compound | MIC(mg/mL) |
| AO2105 AO2210 AO1703 | 0.1～1 0.01～0.1 0.01～0.1 |
Reference:
(1)Hideh Itokawa，Hiroshi Morita，Ikuko Midorikawa.Diarylheptanoids from the Rhizome ofAlpinia officinarum Hance.Chem.Pharm.Bull.，1985，33(11)：4889～4893
(2)Katharina Bratt，Kerstin Sunnerheim.Synthesis and digestibility inhibitin ofdiarylheptanoids：structure-activity.J.Chem.Eco.，1999，25(12)：2703～2713
(3)Akihito Yokosuka，Yoshihiro Mimaki，Hiroshi Sakagami，et al.New diarylheptanoids anddiarylheptanoid glucosides from the Rhizomes of Tacca chantrieri and their cytotoxicactivity.J.Nat.Prod.，2002，65(3)：283～289
Claims (6)
1. from Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone, it is characterized in that comprising the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with described AO0508 with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out, separate obtaining AO2105-AO2104 totally 2 components, described AO2105 is 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone.
2. a kind of method of from Rhizoma Alpiniae Officinarum, extracting diaryl heptane compounds 7-(4-hydroxyphenyl)-1-phenyl-4-alkene-3-heptanone according to claim 1, it is characterized in that described step (1) is: with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, the dissolved in distilled water that adds 4 times of described medicinal extract quality is used chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure, extraction liquid after concentrating is separated through silica gel column chromatography, with volume ratio is 4: 1,3: 1, and 2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution got AO0101-AO0133 totally 33 components.
3. from Rhizoma Alpiniae Officinarum, extract the method for diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone, it is characterized in that comprising the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0110 and AO0111 are merged, silica gel column chromatography, it with volume ratio 98: 2 chloroform-methanol wash-out, after merging similar flow point by TLC, get AO0501-AO0506 totally 6 components, described AO0503 is carried out Toyopearl HW-40C column chromatography, get AO0507-AO0512 totally 6 components, with anti-phase preparation HPLC, volume ratio is 95: 5 a methanol-water wash-out with described AO0508, separates to obtain AO2105-AO2104 totally 2 components, described AO2104 is with positive HPLC purifying, with volume ratio is 3: 2 petroleum ether-ethyl acetate wash-out, obtains compd A O2210, and described AO2210 is 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone.
4. a kind of method of from Rhizoma Alpiniae Officinarum, extracting diaryl heptane compounds 5-hydroxyl-1-(4-hydroxyphenyl)-7-phenyl-3-heptanone according to claim 3, it is characterized in that described step (1) is: with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, the dissolved in distilled water that adds 4 times of described medicinal extract quality is used chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure, extraction liquid after concentrating is separated through silica gel column chromatography, with volume ratio is 4: 1,3: 1, and 2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution got AO0101-AO0133 totally 33 components.
5. extract diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 from Rhizoma Alpiniae Officinarum, the method for 5-dihydroxy heptane is characterized in that comprising the steps:
(1) with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 2-8 quality concentration expressed in percentage by volume doubly is the aqueous ethanolic solution of 60%-98% at every turn, reflux 5-7 hour, extracting solution filters, extract 1-3 time, relative density was the medicinal extract of 1.05-1.20 when filtrate decompression was concentrated into 50 ℃, added described medicinal extract quality 3-6 dissolved in distilled water doubly, with chloroform extraction 2～4 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components;
(2) described AO0121 and AO0122 are merged, carry out silica gel column chromatography, with volume ratio is 96: 4,93: 7,9: 1 chloroform-methanol wash-outs, get AO1401-AO1405 totally 5 components, described AO1404 is separated with Toyopearl HW-40C, get AO1601-AO1605 totally 5 components, with anti-phase preparation HPLC, volume ratio is 9: 1 a methanol-water wash-out with AO1605, purifying, obtain compd A O1703, described AO1703 is 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3, the 5-dihydroxy heptane.
6. a kind of diaryl heptane compounds 1-(4-hydroxy 3-methoxybenzene base)-7-(4-hydroxyphenyl)-3 that from Rhizoma Alpiniae Officinarum, extracts according to claim 5, the method of 5-dihydroxy heptane, it is characterized in that described step (1) is: with the Rhizoma Alpiniae Officinarum pulverizing medicinal materials, add 4-6 quality concentration expressed in percentage by volume doubly at every turn and be 75% aqueous ethanolic solution, reflux 6 hours, extracting solution filters, extract 2 times, relative density was 1.10 medicinal extract when filtrate decompression was concentrated into 50 ℃, added the dissolved in distilled water of 4 times of described medicinal extract quality, with chloroform extraction 3 times, the extraction liquid concentrating under reduced pressure separates the extraction liquid after concentrating through silica gel column chromatography, be 4: 1 with volume ratio, 3: 1,2: 1,1: 1,1: 2,1: 3 petroleum ether-ethyl acetate gradient elution gets AO0101-AO0133 totally 33 components.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529733A (en) * | 2015-01-05 | 2015-04-22 | 海南医学院 | Separated single body in galangal and antineoplastic application thereof |
| CN106806361A (en) * | 2016-12-28 | 2017-06-09 | 中国科学院成都生物研究所 | The new application of Diarylheptanoids |
| CN114533711A (en) * | 2022-03-08 | 2022-05-27 | 海南医学院 | Application of diphenyl heptanone compound in preparation of lipid metabolism improving drugs and compound preparation method |
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2006
- 2006-06-29 CN CN 200610014484 patent/CN1884246A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529733A (en) * | 2015-01-05 | 2015-04-22 | 海南医学院 | Separated single body in galangal and antineoplastic application thereof |
| CN104529733B (en) * | 2015-01-05 | 2016-04-06 | 海南医学院 | The monomer be separated in a kind of Rhizoma Alpiniae Officinarum and for anticancer usage |
| CN106806361A (en) * | 2016-12-28 | 2017-06-09 | 中国科学院成都生物研究所 | The new application of Diarylheptanoids |
| CN106806361B (en) * | 2016-12-28 | 2020-03-06 | 中国科学院成都生物研究所 | Use of diarylheptane compounds |
| CN114533711A (en) * | 2022-03-08 | 2022-05-27 | 海南医学院 | Application of diphenyl heptanone compound in preparation of lipid metabolism improving drugs and compound preparation method |
| CN114533711B (en) * | 2022-03-08 | 2024-01-30 | 海南医学院 | Application of diphenyl heptanone compounds in preparation of drugs for improving lipid metabolism and preparation method of compounds |
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