CN112028958B - A kind of method for preparing dammarane-type triterpenes from marine mangrove silique leaves - Google Patents
A kind of method for preparing dammarane-type triterpenes from marine mangrove silique leaves Download PDFInfo
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- 150000003648 triterpenes Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 25
- 240000002044 Rhizophora apiculata Species 0.000 title claims abstract description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000741 silica gel Substances 0.000 claims abstract description 27
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 27
- OORMXZNMRWBSTK-LGFJJATJSA-N dammarane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@H]([C@H](C)CCCC(C)C)[C@H]4CC[C@@H]3[C@]21C OORMXZNMRWBSTK-LGFJJATJSA-N 0.000 claims abstract description 24
- 239000003208 petroleum Substances 0.000 claims abstract description 19
- 239000000469 ethanolic extract Substances 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012156 elution solvent Substances 0.000 claims abstract description 14
- 238000002953 preparative HPLC Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 229930186864 Cereotagalol Natural products 0.000 claims description 62
- 238000010828 elution Methods 0.000 claims description 27
- 238000001035 drying Methods 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 8
- 238000002481 ethanol extraction Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims 1
- 240000008886 Ceratonia siliqua Species 0.000 abstract 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- 241000256856 Vespidae Species 0.000 description 3
- 241000862497 Ceriops tagal Species 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 241000258957 Asteroidea Species 0.000 description 1
- 101800004637 Communis Proteins 0.000 description 1
- -1 Dammarane Triterpenes Chemical class 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the technical field of medicinal chemistry, and particularly discloses a method for preparing dammarane type triterpenes from marine mangrove hornberry leaves. The method comprises the following steps: (1) extracting folium Caricae with ethanol to obtain ethanol extract; (2) passing the ethanol extract through a silica gel column, eluting with chloroform: eluting with an eluting solvent consisting of methanol to obtain fraction 1; (3) fraction 1 was again applied to a silica gel column and purified with petroleum ether: eluting with an elution solvent consisting of ethyl acetate to obtain fraction 2; (4) separating fraction 2 by preparative HPLC to obtain dammarane type triterpene. The invention provides a brand-new method for preparing dammarane type triterpenes from carob leaves; the method can be used for simultaneously preparing two dammarane type triterpenes, and the obtained two dammarane type triterpenes have high purity.
Description
Technical Field
The invention relates to the technical field of medicinal chemistry, and particularly discloses a method for preparing dammarane type triterpenes from marine mangrove hornberry leaves.
Background
Silique leaves are leaves of the plant cerasus silique of the family mangrove, the latin name of silique is Ceriops tagal (perr.) c.b.rob, another name: shears, flail seeds, starfish seeds (Guangdong, Hainan), Xunao of Guangdong, northeast to south beach of Hainan, Gandronggang of Taiwan, etc.
In previous studies, the inventors isolated two Dammarane-type Triterpenes Cereotagalol C and Cereotagalol D from the Leaves of Cereocarpus communis, which showed certain antitumor activities and had certain application values (see, for example, Xin Wu, Hongbo Liao, Xiaohui Zhu, Hongyu Lu, Xiiaobin Zeng, Liao Cui, Xiaohua Lv, Yanqun Li and Chaohua Zhang. two New Dammarane Triterpenes from the Leaves of Ceriops tagal, Rec. Nat. Prod.10:5(2016)628 and 632.). Although the above documents disclose methods for separating Cereotagalol C and Cereotagalol D, Cereotagalol C and Cereotagalol D in the above documents are obtained by separating through combination of various chromatographic separation techniques such as macroporous resin column chromatography, silica gel column chromatography, ODS column chromatography, preparative high performance liquid chromatography, etc., and have many preparation steps and great preparation difficulty; and the Cereotagalol C and the Cereotagalol D are separated by various chromatographic columns and distributed in different fractions, need to be prepared separately and cannot be prepared in the same fraction at one time, so that the preparation steps and the preparation difficulty are further increased. Therefore, it is of great significance to develop a method for preparing Cereotagalol C and Cereotagalol D with few preparation steps and relative ease.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for preparing dammarane type triterpenes from ocean mangrove hornberry leaves. The method can prepare the dammarane type triterpenes Cereotagalol C and Cereotagalol D in the same fraction; simplifies the preparation steps of the existing preparation method.
The technical problem to be solved by the invention is realized by the following technical scheme:
a method for preparing dammarane type triterpenes from leaves of ocean mangrove hornberries is characterized by comprising the following steps:
(1) extracting folium Caricae with ethanol to obtain ethanol extract;
(2) passing the ethanol extract through a silica gel column, eluting with chloroform: eluting with an eluting solvent consisting of methanol to obtain fraction 1;
(3) fraction 1 was again applied to a silica gel column and purified with petroleum ether: eluting with an elution solvent consisting of ethyl acetate to obtain fraction 2;
(4) separating fraction 2 by preparative HPLC to obtain dammarane type triterpene.
The ocean mangrove hornet leaves of the invention refer to the leaves of the hornet trees growing in the ocean mangrove.
The invention uses chloroform: an elution solvent system consisting of methanol and petroleum ether: performing silica gel column chromatography twice on an elution solvent system consisting of ethyl acetate, and enriching a large amount of Cereotagalol C and Cereotagalol D in the fraction 2 through the silica gel column chromatography twice; further separation by preparative HPLC may allow for the simultaneous preparation of the dammarane-type triterpenes Cereotagalol C and Cereotagalol D in the same fraction. The method can realize the simultaneous preparation of the dammarane type triterpenes Cereotagalol C and Cereotagalol D only by three separation and purification steps; the method simplifies the preparation steps of the triterpenoids Cereotagalol C and Cereotagalol D, and greatly improves the preparation efficiency.
Preferably, the ethanol extraction in the step (1) is to extract with ethanol with a volume fraction of 70-95% for 48-72 h, and concentrate and dry the extract to obtain the ethanol extract.
Most preferably, the ethanol extraction in step (1) is to extract with 95% ethanol by volume for 60h, and concentrate and dry the extractive solution to obtain ethanol extract.
Preferably, the step (2) is performed with chloroform: the specific conditions for eluting with the elution solvent consisting of methanol to obtain fraction 1 are as follows: firstly, using a mixture with the volume ratio of 95: 5 chloroform: eluting with methanol to remove impurities; then, the following steps of 85: 15 chloroform: methanol was eluted and 85: 15 chloroform: concentrating and drying the methanol elution part to obtain fraction 1.
Further preferably, the chloroform used in step (2): the specific conditions for eluting with the elution solvent consisting of methanol to obtain fraction 1 are as follows: firstly, using a volume ratio of 5-8 times of column volume as 95: 5 chloroform: eluting with methanol to remove impurities; then, the volume ratio of 6-10 times of the column volume is 85: 15 chloroform: methanol was eluted and 85: 15 chloroform: concentrating and drying the methanol elution part to obtain fraction 1.
Preferably, the weight consumption of the silica gel in the silica gel column in the step (2) is 20-30 times of that of the ethanol extract; the mesh number of the silica gel is 200-300 meshes.
Preferably, in step (3), the ratio of petroleum ether: the specific conditions for eluting with the elution solvent consisting of ethyl acetate to obtain fraction 2 are as follows: firstly, using a mixture with the volume ratio of 96: 4 petroleum ether: eluting with ethyl acetate to remove impurities, and then carrying out elution with a volume ratio of 92: 8 petroleum ether: eluting with ethyl acetate; and (4) collecting 92: 8 petroleum ether: concentrating and drying the elution part of the ethyl acetate to obtain a fraction 2.
Further preferably, in step (3), the mixture is prepared from petroleum ether: the specific conditions for eluting with the elution solvent consisting of ethyl acetate to obtain fraction 2 are as follows: firstly, using a column with the volume ratio of 6-10 times of column volume as 96: 4 petroleum ether: eluting with ethyl acetate to remove impurities, and then carrying out elution with a volume ratio of 8-12 times of column volume of 92: 8 petroleum ether: eluting with ethyl acetate; and (4) collecting 92: 8 petroleum ether: concentrating and drying the elution part of the ethyl acetate to obtain a fraction 2.
Preferably, the weight consumption of the silica gel in the silica gel column in the step (3) is 40-60 times of that of the ethanol extract; the mesh number of the silica gel is 300-400 meshes.
The choice of the composition of the elution solvent and the ratio of the elution solvent for the two silica gel column chromatographies described above plays a crucial role in whether Cereotagalol C and Cereotagalol D can be enriched in fraction 2. The improper composition or proportion of the elution solvent in the two silica gel column chromatographies can cause that the fraction 2 can not be simultaneously enriched into Cereotagalol C and Cereotagalol D; and even none of them can be enriched. A large number of experimental researches prove that the fraction 2 rich in Cereotagalol C and Cereotagalol D can be obtained under the condition of the two silica gel column chromatographies. Provides decisive conditions for the subsequent preparative HPLC to be capable of preparing the dammarane type triterpenes Cereotagalol C and Cereotagalol D simultaneously.
Preferably, the specific conditions for separation by preparative HPLC are: a preparative C18 chromatographic column and an ultraviolet detector are adopted, and the detection wavelength is 230-254 nm; performing gradient elution by taking acetonitrile as a mobile phase A and water as a mobile phase B; the gradient elution is as follows: the volume change of the mobile phase A is 0-12% in 0-5 min; 5-15 min, wherein the volume change of the mobile phase A is 12-26%; keeping the volume of the mobile phase A unchanged at 26 percent for 15-35 min; collecting the elution parts corresponding to chromatographic peaks of 24.1min and 30.8min respectively, concentrating and drying to obtain the dammarane type triterpene Cereotagalol C and Cereotagalol D.
Although enrichment after two silica gel column chromatographies yielded fraction 2 containing Cereotagalol C and Cereotagalol D. However, it is also a technical problem how to separate Cereotagalol C and Cereotagalol D from fraction 2. And the preparative HPLC is adopted for separation, and the selection of the mobile phase and the elution condition of the mobile phase play a decisive role in whether Cereotagalol C and Cereotagalol D can be separated. The elution conditions of the mobile phase were not properly selected and Cereotagalol C and Cereotagalol D could not be separated from fraction 2. Through a large number of experimental researches, the invention obtains that the Cereotagalol C and Cereotagalol D can be successfully separated under the specific separation condition of the preparative HPLC.
Has the advantages that: the invention provides a brand-new method for preparing dammarane type triterpenes from ocean mangrove hornberry leaves.
The method can realize the simultaneous preparation of the dammarane type triterpenes Cereotagalol C and Cereotagalol D only by three separation and purification steps; the silica gel column chromatography is carried out twice under the silica gel column chromatography condition, the Cereotagalol C and the Cereotagalol D can be enriched at the same part, and the dammarane type triterpenes Cereotagalol C and the Cereotagalol D can be simultaneously prepared by one-time HPLC separation. Compared with the prior art, the method simplifies the preparation steps of the triterpenoids Cereotagalol C and Cereotagalol D, and greatly improves the preparation efficiency.
Detailed Description
The present invention is further explained below with reference to specific examples, but the scope of protection described herein is not limited to the scope of the examples.
A method for preparing dammarane type triterpenes from leaves of marine mangrove hornberries comprises the following steps:
(1) extracting the air-dried marine mangrove hornet fruit tree leaves with 5 times of 95% ethanol by volume for 60h, standing the extracting solution for 48h, concentrating and drying to obtain an ethanol extract;
(2) applying the ethanol extract to a silica gel column (the weight of the silica gel in the silica gel column is 25 times of that of the ethanol extract, the mesh number of the silica gel is 200-300 meshes), and firstly, using a silica gel column with the volume ratio of 6 times of the column volume of 95: 5 chloroform: eluting with methanol to remove impurities; then, the column was again packed in a volume ratio of 8 column volumes of 85: 15 chloroform: methanol was eluted and 85: 15 chloroform: concentrating and drying the methanol elution part to obtain fraction 1;
(3) and (3) putting the fraction 1 on a silica gel column again (the weight of the silica gel in the silica gel column is 50 times of that of the fraction 1, the mesh number of the silica gel is 300-400 meshes), and performing column chromatography by using a column chromatography column with the volume ratio of 8 times of the column volume of 96: 4 petroleum ether: eluting with ethyl acetate to remove impurities, and then performing elution with a column volume ratio of 10 times of 92: 8 petroleum ether: eluting with ethyl acetate; and (4) collecting 92: 8 petroleum ether: concentrating and drying the elution part of the ethyl acetate to obtain a fraction 2;
(4) separating fraction 2 by preparative HPLC to obtain dammarane type triterpene; the specific conditions for separation by preparative HPLC were: adopting a preparative C18 chromatographic column and an ultraviolet detector, wherein the detection wavelength is 245 nm; performing gradient elution by taking acetonitrile as a mobile phase A and water as a mobile phase B; the gradient elution is as follows: the volume change of the mobile phase A is 0-12% (the volume change of the mobile phase B is 100-88%) in 0-5 min; 5-15 min, the volume change of the mobile phase A is 12-26% (the volume change of the mobile phase B is 88-74%); keeping the volume of the mobile phase A unchanged at 26 percent (keeping the volume of the mobile phase B unchanged at 74 percent) for 15-35 min; collecting the elution parts corresponding to chromatographic peaks of 24.1min and 30.8min respectively, concentrating and drying to obtain the dammarane type triterpene Cereotagalol C and Cereotagalol D.
The structure of the compound obtained by concentrating and drying the elution part corresponding to the chromatographic peak of 24.1min is characterized by mass spectrum and nuclear magnetism, and the result shows that the molecular formula of the compound is determined by high-resolution mass spectrum as follows: m/z 483.3856. The 1H NMR spectrum showed: Δ H1.69 (1H, m),0.98(1H, m),1.61(1H, m),3.63(1H, t,8.5),1.34(1H, m),1.49(1H, m),1.32(1H, m),1.51(1H, m),1.25(1H, m),0.88(1H, m),1.52(1H, m),1.25(1H, m),1.52(1H, m),1.44(1H, m),1.62(1H, m),1.44(1H, m),1.05(1H, m),1.84(1H, m),1.24(1H, m),1.73(1H, m),0.96(3H, s),0.88(3H, s),1.14(3H, s),1.47(2H, 8H, m), 1.42 (1H, m), 1.42H, 1.42 (1H, m), 1.42 (1H, m), s),0.88(3H, s). The 13C NMR spectrum showed: δ C38.7, 26.9,76.6,41.9,50.6,18.3,34.9,40.3,50.4,36.9,21.5,24.7,42.2,50.3,31.1,27.5,49.8,15.5,16.4,75.3,25.4,40.4,22.5,124.7,131.6,25.7,17.7,71.9,11.3, 16.5.
The structure of the compound obtained by concentrating and drying the elution part corresponding to the chromatographic peak of 30.8min is characterized by mass spectrum and nuclear magnetism, and the result shows that the molecular formula of the compound is determined by high-resolution mass spectrum as follows: m/z 481.3692, 1H NMR spectrum showed: 1.76(1H, m),1.06(1H, m),1.62(1H, m),3.76(1H, dd,11.7,4.6),1.29(1H, m),1.49(1H, m),1.32(1H, m),1.57(1H, m),1.23(1H, m),1.43(1H, m),1.53(1H, m),1.27(1H, m),1.52(1H, m),1.44(1H, m),1.63(1H, m),1.44(1H, m),1.06(1H, m),1.84(1H, m),1.23(1H, m),1.74(1H, m),0.96(3H, s),0.89(3H, s),1.14(3H, s),1.47 (1H, 2 s), 1.23 (1.74 (1H, m),0.96(3H, s),0.89(3H, s),1.14(3H, 2 s),1.47, 2H, 1.05, 1.9, 1H, m), 1.9H, 1.9, 1.05, 1.9H, m). The 13C NMR spectrum showed: δ C38.6, 26.4,71.8,55.5,48.9,21.0,34.6,40.8,50.6,36.1,21.6,24.8,42.2,50.3,31.1,27.4,49.8,15.5,16.4,75.4,25.5,40.4,22.5,124.6,131.7,25.7,17.7,207.0,8.6, 16.4.
The characterization data of the mass spectrum and the nuclear magnetic structure show that the compound obtained after concentrating and drying the elution part corresponding to the chromatographic peak at 24.1min is Cereotagalol C; the compound obtained after concentrating and drying the elution part corresponding to the chromatographic peak at 30.8min is Cereotagalol D. The method successfully realizes the simultaneous preparation of the dammarane type triterpenes Cereotagalol C and Cereotagalol D; and the preparation steps are simple, and the preparation efficiency of Cereotagalol C and Cereotagalol D is greatly improved.
Claims (4)
1. A method for preparing dammarane-type triterpenes from leaves of the marine mangrove hornberry trees, wherein the dammarane-type triterpenes are Cereotagalol C and Cereotagalol D, and the method is characterized by comprising the following steps:
(1) extracting folium Caricae with ethanol to obtain ethanol extract;
(2) passing the ethanol extract through a silica gel column, eluting with chloroform: eluting with an eluting solvent consisting of methanol to obtain fraction 1;
(3) fraction 1 was again applied to a silica gel column and purified with petroleum ether: eluting with an elution solvent consisting of ethyl acetate to obtain fraction 2;
(4) separating fraction 2 by preparative HPLC to obtain dammarane type triterpene;
the ethanol extraction in the step (1) is to extract the extract by using ethanol with the volume fraction of 70-95%, wherein the extraction time is 48-72 h, and the extract is concentrated and dried to obtain an ethanol extract;
the chloroform used in the step (2): the specific conditions for eluting with the elution solvent consisting of methanol to obtain fraction 1 are as follows: firstly, using a volume ratio of 5-8 times of column volume as 95: 5 chloroform: eluting with methanol to remove impurities; then, the volume ratio of 6-10 times of the column volume is 85: 15 chloroform: methanol was eluted and 85: 15 chloroform: concentrating and drying the methanol elution part to obtain fraction 1;
in the step (3), petroleum ether is used: the specific conditions for eluting with the elution solvent consisting of ethyl acetate to obtain fraction 2 are as follows: firstly, using a column with the volume ratio of 6-10 times of column volume as 96: 4 petroleum ether: eluting with ethyl acetate to remove impurities, and then carrying out elution with a volume ratio of 8-12 times of column volume of 92: 8 petroleum ether: eluting with ethyl acetate; and (4) collecting 92: 8 petroleum ether: concentrating and drying the elution part of the ethyl acetate to obtain a fraction 2;
the specific conditions for separation by preparative HPLC were: a preparative C18 chromatographic column and an ultraviolet detector are adopted, and the detection wavelength is 230-254 nm; performing gradient elution by taking acetonitrile as a mobile phase A and water as a mobile phase B; the gradient elution is as follows: the volume change of the mobile phase A is 0-12% in 0-5 min; 5-15 min, wherein the volume change of the mobile phase A is 12-26%; keeping the volume of the mobile phase A unchanged at 26 percent for 15-35 min; collecting elution parts corresponding to chromatographic peaks of 24.1min and 30.8min respectively, concentrating and drying to obtain dammarane type triterpene Cereotagalol C and Cereotagalol D;
the structural formulas of the dammarane type triterpenes Cereotagalol C and Cereotagalol D are shown as follows:
2. the method according to claim 1, wherein the ethanol extraction in step (1) is performed by extracting with 95% ethanol by volume for 60h, concentrating the extractive solution, and drying to obtain ethanol extract.
3. The method according to claim 1, wherein the amount of the silica gel in the silica gel column in the step (2) is 20 to 30 times of the weight of the ethanol extract; the mesh number of the silica gel is 200-300 meshes.
4. The method according to claim 1, wherein the amount of the silica gel in the silica gel column in the step (3) is 40 to 60 times of the weight of the ethanol extract; the mesh number of the silica gel is 300-400 meshes.
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| CN112028958A (en) | 2020-12-04 |
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