CN108285411B - 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound and preparation method and application thereof - Google Patents

3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound and preparation method and application thereof Download PDF

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CN108285411B
CN108285411B CN201810070700.6A CN201810070700A CN108285411B CN 108285411 B CN108285411 B CN 108285411B CN 201810070700 A CN201810070700 A CN 201810070700A CN 108285411 B CN108285411 B CN 108285411B
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钟添华
曾贤明
张永红
马新华
骆祝华
产竹华
谷力
杨献文
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Abstract

A 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound, a preparation method and application thereof, relating to a compound. The 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound is derived from marine fungi. Preparing a fermentation extract of a strain Alternaria sp 3A 00467; extraction and isolation of the secondary metabolite of the strain Alternaria sp 3A 00467. Experiments prove that the novel 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compounds with antitumor activity have good inhibition effects on U266 (myeloma cells), HepG2 (human hepatoma cells) and A549 (human lung cancer cells), so that the compounds can be used for preparing antitumor drugs.

Description

3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound and preparation method and application thereof
Technical Field
The invention relates to a compound, in particular to a 3, 5-dyhydroxy-1-methoxyl-3 substituted-benzophenone compound with antitumor activity and a preparation method and application thereof.
Background
In recent years, the incidence of cancer in China is rising year by year, the speed is high, the scale is large, all people are shocked, and the rapid development of the cancer generates a series of social problems (1) a new concept of clinical comprehensive treatment of tumors [ M ] the university Press, 2006). The current clinical antitumor drugs mainly comprise alkylating drugs such as nitrogen mustards and metal poise complexes (2 Sunpiyan. consensus suggestion about classification of antitumor drugs [ J ]. evidence-based medicine, 2004,4(3): 190-191). The action mechanism of the medicine is that electron-deficient active intermediates and other compounds with active electrophilic groups are formed in vivo, and are combined with groups with abundant electrons in biological macromolecules (DNA, RNA or enzyme) in an electrophilic covalent manner, so that the macromolecules are inactivated, and the normal physiological functions of the macromolecules are hindered. However, the alkylating agent compounds of the compounds have strong toxic and side effects on cells, can also have an inhibiting effect on rapidly growing normal cells, and are extremely easy to generate drug resistance after long-term use. Therefore, the development of the discovery and invention of the compound with antitumor activity is particularly urgent.
Disclosure of Invention
The invention aims to provide a 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound with good antitumor activity and great potential application value, and a preparation method and application thereof.
The 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound is derived from marine fungi, and the structural general formula of the compound or the addition salt thereof is as follows:
Figure GDA0003005033690000011
in the formula, R1Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R2Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R3Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R4Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R5Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R6Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R7Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
The R groups of the compound or the addition salt thereof are matched as follows:
(1)R1is H: R2Can be H, OH, CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(2) R1 is OH R2 can be H, OH or CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(3) R1 is CH3CH 2: R2 can be H, OH, CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(4) R4 and R5 are H: H, OH and CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
The preparation method of the 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound or the addition salt thereof comprises the following steps:
1) preparing a fermentation extract of a strain Alternaria sp 3A 00467;
in step 1), the specific method for preparing the fermentation extract of the strain Alternaria (Alternaria sp.)3a00467 can be as follows: taking a pipette to suck seed liquid of a bacterial strain Alternaria sp 3A00467, inoculating the seed liquid into a container containing No. 7 solid culture medium for culturing to obtain a solid fermentation product of the bacterial strain Alternaria sp 3A 00467; the composition of the No. 7 solid medium can be as follows: 80g of rice, 2% of maltose, 1% of glucose, 1% of monosodium glutamate and KH2PO4 0.05％，MgSO4·7H20.03 percent of O, 0.3 percent of yeast extract, 0.1 percent of corn steep liquor, 2 percent of mannitol and CaCO32 percent of aged seawater; the container can adopt a 1000ml Erlenmeyer flask, and the culture condition can be static culture for 30d in a constant temperature incubator at 28 ℃; the strain Alternaria sp 3A00467 is from China Marine microorganism culture Collection management center of the third Marine research institute of the national Marine agency, and has the address: the linkage is as follows, Xianming district university No. 178, Xianming province, mansion in Fujian province: telephone: 86(0) -592-2195177, fax: 86(0) -592-219517, electronic mail box: mcc 5177@163. com.
2) Extraction and isolation of the secondary metabolite of the strain Alternaria sp 3A 00467.
In step 2), the specific method for extraction and separation may be: soaking a solid fermentation product of the strain Alternaria sp (Alternaria sp.)3A00467 in methanol, repeatedly extracting for 3-4 times, combining extracting solutions, concentrating under reduced pressure until the solid fermentation product does not contain methanol, suspending with water, extracting for 3-4 times by using ethyl acetate with the same volume, combining ethyl acetate extracting solutions, concentrating under reduced pressure until the solid fermentation product is dry to obtain 18.6g of an ethyl acetate extract of the strain Alternaria sp (Alternaria sp.)3A00467, and adopting a separation method such as thin layer chromatography, reverse ODS silica gel column chromatography, sephadex gel column chromatography, normal phase silica gel column chromatography and semi-preparative high performance liquid chromatography.
The invention relates to a novel 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound with anti-tumor activity, which has good inhibition effect on U266 (myeloma cell), HepG2 (human hepatoma cell) and A549 (human lung cancer cell) proved by experiments, thus being used for preparing anti-tumor drugs.
Drawings
FIG. 1 is a schematic diagram of the separation and purification process of compounds according to the embodiment of the present invention.
Detailed Description
The 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound is derived from marine fungi, and the structural general formula of the compound or the addition salt thereof is as follows:
Figure GDA0003005033690000031
in the formula, R1Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R2Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R3Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R4Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R5Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R6Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
R7Represents H, OH, CH3、OCH3、CH2CH3、NH2、NO2、CnH2n-1、CnH2n-1OH；
The R groups of the compound or the addition salt thereof are matched as follows:
(1)R1is H: R2Can be H, OH, CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(2) R1 is OH R2 can be H, OH or CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(3) R1 is CH3CH 2: R2 can be H, OH, CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
(4) R4 and R5 are H: H, OH and CH2CH3，CH2CH2OH，CH3C＝OOCH2CH2And branched or straight chain alkyl groups.
The structure of the 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound or the addition salt thereof is shown in table 1.
TABLE 1
Compound (I) R1 R2 R3 R4 R5 R6 R7
1 CH3 H H OH
2 CH2CH3 H H H
3 CH3 H H H
4 CH3 H H OOCCH3
5 CH2CO(CH2)2CH3 CH2CH3 H OH
6
7 H H CH3
8 H OH (CH2)2CH3
9 H H (CH＝CH2)CH3
10 H NHCH3 CH2CH3
The preparation method of the 3, 5-dihydroxy-1-methoxy-3 substituted-benzophenone compound or the addition salt thereof comprises the following steps:
1) preparation of a fermentation extract of the strain Alternaria sp 3A 00467: taking a pipette to suck seed liquid of the strain Alternaria alternata (Alternaria sp.)3A00467, inoculating the seed liquid into a container containing No. 7 solid culture medium, and culturing to obtain the solid of the strain Alternaria alternata (Alternaria sp.)3A00467A fermentation product; the composition of the No. 7 solid medium can be as follows: 80g of rice, 2% of maltose, 1% of glucose, 1% of monosodium glutamate and KH2PO4 0.05％，MgSO4·7H20.03 percent of O, 0.3 percent of yeast extract, 0.1 percent of corn steep liquor, 2 percent of mannitol and CaCO32 percent of aged seawater; the container can adopt a 1000ml Erlenmeyer flask, and the culture condition can be static culture in a constant temperature incubator at 28 ℃ for 30 d.
2) Extracting and separating secondary metabolites of a strain Alternaria sp 3A00467, soaking solid fermentation products of the strain Alternaria sp 3A00467 in methanol, repeatedly extracting for 3-4 times, combining extracting solutions, concentrating under reduced pressure until the solid fermentation products do not contain methanol, suspending with water, extracting for 3-4 times with equal volume of ethyl acetate, combining ethyl acetate extracting solutions, concentrating under reduced pressure until the extracting solutions are dry to obtain 18.6g of ethyl acetate extract of the strain Alternaria sp 3A00467, and adopting separation methods such as thin layer chromatography, reverse ODS silica gel column chromatography, sephadex gel column chromatography, normal phase silica gel column chromatography and semi-preparative high performance liquid chromatography.
The antitumor activity assay is given below:
taking human tumor cell line in logarithmic growth phase, preparing into proper concentration of about 3 × 10 with complete culture solution4-6×104one/mL, inoculated on a 96-well culture plate, each 100. mu.L, each concentration setting 2 multiple wells, blank group set 4 multiple wells, overnight culture to make it adhere to the wall.
Weighing appropriate amount of medicine, preparing into solution with concentration of 40, 20, 10, 5, 2.5, 1.25 μ g/mL with whole culture solution, sucking original culture solution in 96-well plate, adding above medicine solution with different concentration, each well 100 μ L, acting under conventional culture condition for 48h, adding 20 μ L MTT solution (prepared with PBS, pH 7.4) into each well, culturing for 4h, centrifuging, discarding supernatant, adding dimethyl sulfoxide (DMSO)150 μ L into each well, shaking for 10min, measuring absorbance of each well at OD 490nm with microplate reader (BIO-RAD product), averaging each group, calculating inhibition ratio according to average value, performing statistical analysis with SPSS12.0, and calculating IC50Values, some of which are shown for antitumor activityTable 2.
TABLE 2 (IC)50μg/mL)
Compound (I) U266 HepG2 A549
1 15.48 33.52 >100
2 >100 >100 >100
3 >100 >100 >100
4 70.4 80.6 78.5
5 21.98 25.77 >100
6 24.99 33.16 80.25
7 23.49 15.6 61.15
8 14.78 15.79 20.41
9 13.26 14.69 24.39
10 97 >100 >100
Therefore, the compound of the invention has antitumor activity, and especially the compounds 1, 5, 6, 7, 8 and 9 have stronger antitumor activity.

Claims (9)

1. A benzophenone compound has the following structural formula:
Figure FDA0003136775960000011
2. the process for producing phenones according to claim 1, which comprises the steps of:
1) preparing a fermentation extract of a strain Alternaria sp 3A 00467;
2) extraction and isolation of the secondary metabolite of the strain Alternaria sp 3A 00467.
3. The method for preparing phenones according to claim 2, wherein in step 1), the specific method for preparing fermented extract of the strain Alternaria sp 3A00467 is: taking a pipette to suck seed liquid of the strain Alternaria alternata (Alternaria sp.)3A00467, and inoculating the seed liquid into a container containing No. 7 solid culture medium for culturing to obtain a solid fermentation product of the strain Alternaria alternata (Alternaria sp.)3A 00467.
4. The method for producing phenones according to claim 3, wherein the composition of the solid medium containing No. 7 is: 80g of rice, 2% of maltose, 1% of glucose, 1% of monosodium glutamate and KH2PO4 0.05％，MgSO4·7H20.03 percent of O, 0.3 percent of yeast extract, 0.1 percent of corn steep liquor, 2 percent of mannitol and CaCO32 percent of aged seawater.
5. The method for producing phenones according to claim 3, wherein the container is a 1000ml Erlenmeyer flask.
6. The method for producing phenones according to claim 3, wherein the conditions for the cultivation are static cultivation in a constant temperature incubator at 28 ℃ for 30 days.
7. The method for preparing phenones compounds according to claim 3, wherein the strain Alternaria sp 3A00467 is derived from China Marine microorganism culture Collection, national institute of oceanographic, third Marine research institute.
8. The method for preparing phenones compound according to claim 2, wherein in step 2), the specific method of extraction and separation is: soaking a solid fermentation product of the strain Alternaria sp (Alternaria sp.)3A00467 in methanol, repeatedly extracting for 3-4 times, combining extracting solutions, concentrating under reduced pressure until the solid fermentation product does not contain methanol, suspending with water, extracting for 3-4 times by using ethyl acetate with the same volume, combining ethyl acetate extracting solutions, concentrating under reduced pressure until the solid fermentation product is dry to obtain 18.6g of an ethyl acetate extract of the strain Alternaria sp (Alternaria sp.)3A00467, and performing thin layer chromatography, reverse ODS (oxide dispersion chromatography) silica gel column chromatography, sephadex gel column chromatography, normal phase silica gel column chromatography and semi-preparative high performance liquid chromatography.
9. The use of the phenones compounds as claimed in claim 1 in the preparation of anti-tumor drugs, wherein the tumors are myeloma cell U266, human hepatoma cell HepG2 or human lung carcinoma cell A549.
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WO1997048279A1 (en) * 1996-06-21 1997-12-24 University Of Alberta Agents with antifungal activity and methods of use thereof
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CN104987316A (en) * 2015-04-27 2015-10-21 中山大学 Marine fungus-derived polyketone compound and application thereof in treatment of type 2 diabetes

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