CN115838328A - Abietane diterpenoid compound, preparation method, application and antitumor drug - Google Patents
Abietane diterpenoid compound, preparation method, application and antitumor drug Download PDFInfo
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Abstract
The invention relates to the technical field of antitumor compounds, and discloses an abietane diterpenoid compound, a preparation method, an application and an antitumor drug, wherein the compound has a chemical structure shown in a formula I, or a pharmaceutical composition of pharmaceutically acceptable salts, stereoisomers, hydrates, solvates or prodrugs of the compound shown in the formula I,
the invention can extract and prepare the abietane diterpenoid compound from the rice cluster flowers, and the compound has an inhibiting effect on human liver cancer cells.
Description
Technical Field
The invention relates to the technical field of anti-tumor compounds, in particular to an abietane diterpenoid compound, a preparation method, an application and an anti-tumor medicament.
Background
The rice flower is also called sugar flower and bee flower. Shrubs or small trees, the young branches are densely villi. The blade is in the shape of a needle with an ellipse, the length of the blade is 10-23 cm, the width of the blade is 5-9 cm, the top end of the blade is tapered, the base part of the blade is in the shape of a wedge, the edge of the blade is provided with shallow sawteeth or sawteeth, and the back surface of the blade is densely covered with grey or light yellow star-shaped villi and clump curly hair. The cymbidium floribundum floribunda is multi-floribunda and is arranged into a cylindrical spike-shaped inflorescence growing at the top; the bract is kidney-shaped, is full of or has irregular teeth, and is externally coated with stellate villi; the small bract is linear and is about 1mm long, and the villus is dense and is shaped like a star; the calyx is bell-shaped, the outer surface of the calyx is provided with faint yellow star-shaped villi and small saccular protrusions, the inner surface of the calyx has no hair, and the calyx teeth are triangular and about 1.5mm or slightly shorter; white or pink to purple red corolla, hidden or slightly extended crown tube, inner hairless ring, two lips on lip eave, slightly lacking top of upper lip, 3 cracks on lower lip, and larger middle crack. The small nuts are in a long round triangular prism shape, the top ends of the small nuts are truncated, the umbilicus is small, and the small nuts are located at the base parts. The flowering period is 11 months to 3 months in the next year, and the fruit period is 3-5 months. Property and taste: bitter and cool. The plant has effects of clearing away heat and toxic materials, promoting diuresis, relieving swelling, and stopping bleeding.
Abietane diterpenoid compounds have been used in pharmacy, for example, patent with application number CN101633660a discloses a novel abietane diterpenoid compound, and a preparation method and application thereof. The results show that the cyhalofop-butyl has obvious inhibiting effect on mouse sarcoma cells and mouse liver cancer cells, can be used as a lead compound for developing new antitumor drugs, and can also be used as a drug for developing and treating various clinically common multiple cancers.
According to the technical scheme, the abietane diterpenoid compound is extracted from rabdosia rubescens and used as an anti-tumor medicament, but more than 60 chemical components including sesterterpenoids, flavonoids, phenylethanoid glycosides, acyl glycosides, phenols and the like are separated from the Leucosceptrum plants at present, wherein sesterterpenoids and flavonoids are used as main structural types. However, the research of applying the chemical components of the rice flower branches to the antitumor activity is not reported.
Disclosure of Invention
In view of the above, the present invention aims to provide an abietane-type diterpenoid compound, a preparation method, an application and an antitumor drug, wherein the abietane-type diterpenoid compound can be extracted and prepared from the Leucosceptrum micranthum, and has an inhibitory effect on human liver cancer cells.
The invention solves the technical problems by the following technical means:
in a first aspect, the invention provides an abietane-type diterpene compound Leucosceptrum B, the chemical name of which is 3,11,12-trihydroxy-8,11,13,15-abietane tetraen-7-one, and the structure of which is shown as the following formula I:
the invention also provides pharmaceutical compositions of pharmaceutically acceptable salts, stereoisomers, hydrates, solvates or prodrugs of the compounds of formula I.
In a second aspect, the invention also provides a preparation method of the abietane-type diterpene compound, which adopts the following technical scheme:
taking air-dried branches of the rice cluster flowers as raw materials, crushing, extracting with an organic solvent, and concentrating under reduced pressure at low temperature to obtain an extract;
mixing the extract with water to obtain a suspension, adding ethyl acetate for extraction, and carrying out low-temperature reduced pressure concentration to obtain an ethyl acetate extract phase;
step (3), separating an ethyl acetate extract phase by silica gel column chromatography, performing gradient elution by using petroleum ether-ethyl acetate as an eluent, wherein the volume ratio of petroleum ether to ethyl acetate is 9.8-10.2;
and (4) separating the primary component F44 by preparative liquid chromatography, and isocratic eluting with acetonitrile and water as an eluent to obtain the abietane-type diterpene compound Leucosceptrum B shown in the formula I.
Further, in the step (1), the organic solvent is ethanol with volume fraction not less than 90%, and the volume-to-mass ratio of the organic solvent to the rice-roll flower branches is 10-20 mL:1g of a compound; the leaching temperature is 65-75 ℃, and the leaching is carried out for 2-3 times, 4-6 h each time.
Furthermore, the temperature of low-temperature decompression concentration in the step (1) and the step (2) is 40-50 ℃, and the vacuum degree is 0.07-0.09 MPa.
Further, in the step (2), the mass ratio of the extract to the water is 1:1-3, the volume ratio of the ethyl acetate to the suspension is 0.8-1:1, and the extraction is carried out for 2-4 times.
Furthermore, the volume fraction of acetonitrile in the eluent in the step (4) is 30-40%, and the balance is water.
The abietane diterpenoid compound Leucosceptrum B is obtained by taking branches of the Leucosceptrum indicum as raw materials and performing crushing, leaching, reduced pressure concentration, extraction and multiple separation and purification. When the method is used, dried rice ball flower branches are selected or used after being dried, so that the branches can be conveniently crushed. The method comprises the following steps of taking an eluent with the same volume of petroleum ether and ethyl acetate as a target separation system, and simultaneously, eluting with a single concentration to obtain an abietane diterpenoid Leucosceptrum B due to more impurity components in the Leucosceptrum; and unreasonable concentration gradient setting, and too large or too small concentration gradient setting may cause the abietane-type diterpenoid Leucosceptrum B not to be sufficiently eluted. There is considerable uncertainty in treating the bouquet minor and obtaining Leucosceptrum B therefrom in the absence of a reference material providing an indication that the abietane-type diterpene compound Leucosceptrum B is extractable.
In a third aspect, the invention also provides an application of a pharmaceutical composition containing the abietane-type diterpenoid compound, or a pharmaceutically acceptable salt, a stereoisomer, a hydrate, a solvate or a prodrug thereof in preparing an antitumor drug.
Furthermore, the tumor cells corresponding to the tumor are human liver cancer SMMC7721 cells.
In a fourth aspect, the invention also provides an antitumor drug, which comprises a pharmaceutically acceptable carrier and the compound, or a pharmaceutical composition of the pharmaceutically acceptable salt, stereoisomer, hydrate, solvate or prodrug of the compound.
The invention has the following beneficial effects:
the abietane diterpenoid Leucosceptrum B is a natural anti-tumor compound extracted from the Leucosceptrum micranthum branches, has the biological activity of inhibiting tumor cells, and has obvious cell inhibition effect on human liver cancer SMMC7721, and the half inhibition concentration IC50 value is smaller than that of a broad-spectrum anti-tumor medicament cis-platinum on the market, so that the abietane diterpenoid B has very strong anti-tumor activity, has very large application prospect in preparing anti-tumor medicaments, and has important effect on improving the medical and economic values of Leucosceptrum micranthum.
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FIG. 1 is a scheme for preparing an abietane-type diterpene compound Leucosceptrum B.
Detailed Description
The invention will be described in detail below with reference to examples and the accompanying drawings:
the materials used in the present invention are commercially available or commonly used in the art unless otherwise specified, and the methods in the following examples are conventional in the art unless otherwise specified.
Example 1: physicochemical property test of abietane diterpenoid Leucoseptrum B
1.1 determination of molecular Structure
The NMR used was a Bruker AVANCE III 500 NMR apparatus manufactured by Bruker corporation, a deuterated CDCl3 (deuterated chloroform) reagent was used for NMR, and the hydrogen spectrum and carbon spectrum data of the obtained abietane-type diterpene compound Leucoseptrum B are shown in Table 1 below.
TABLE 1 Hydrogen 1H-NMR (500 MHz) and carbon 13C-NMR (125 MHz) data for Leucosceptrum B
Note: chemical shifts are denoted by δ; s represents a single peak; br s represents a broad singlet; m represents a multiplet; dd denotes the doublet of two peaks.
1.2 molecular weight measurement
The accurate molecular weight of the compound is measured by adopting high resolution mass spectrum HR-ESI-MS, and the HR-ESI-MS [ M-H ] -M/z is 329.1753. According to the nuclear magnetic NMR data and mass spectrum data in the table 1, the molecular formula of the abietane diterpenoid compound Leucosceptrum B is C20H26O4, the molecular weight is 330, the unsaturation degree is 8, the chemical name is 3,11,12-trihydroxy-8,11,13,15-abietane-7-ketone, and the structure is shown in the formula I.
1.3 melting Point test
The melting point instrument is a WRS-1C type melting point instrument made by Shanghai object light; the melting point of the abietane diterpenoid Leucosceptrum B is m.p.252-254 ℃ through testing.
Example 2:
this example is a preparation of an abietane-type diterpene compound Leucosceptrum B
The method for preparing the compound Leucosceptrum B is shown in figure 1 and comprises the following steps:
(1) Air-drying and crushing 5kg of the branches of the rice dumpling flowers, adding the crushed branches into ethanol with the volume fraction of 95%, and leaching according to the mass of the rice dumpling flowers and the volume of the ethanol of 1g: adding 10mL of ethanol, and leaching for 5 hours for 3 times at 70 ℃; filtering insoluble substances, mixing filtrates, and evaporating at vacuum degree of 0.08MPa and temperature of 45 deg.C under reduced pressure to obtain extract;
(2) Uniformly mixing the obtained extract with water according to the mass ratio of 1:2 to prepare suspension, extracting for 3 times by using equal volume of ethyl acetate, combining extract liquor, and performing reduced pressure evaporation at a low temperature of 45 ℃ under the vacuum degree of 0.08MPa to obtain an ethyl acetate extract phase;
(3) Uniformly stirring the obtained ethyl acetate extract phase with silica gel of equal mass, then placing the mixture into the silica gel column for chromatography, performing gradient elution by using petroleum ether-ethyl acetate as an eluent, wherein the volume ratio of gradient elution of the petroleum ether to the ethyl acetate is 10, 5:1, 3:1 and 1:1, collecting eluent when the volume ratio of the petroleum ether to the ethyl acetate is 1:1, analyzing by thin layer chromatography, and combining similar components to obtain different initial components F41-F44;
(4) And separating the collected primary component F44 by preparative liquid chromatography, wherein the mass ratio of acetonitrile: isocratically eluting with water at a volume ratio of 35.
Example 3:
this example is a preparation of an abietane-type diterpene compound Leucosceptrum B
The method for preparing the compound Leucosceptrum B comprises the following steps:
(1) Air-drying and crushing branches of 5kg of rice cluster flowers, adding the crushed branches into ethanol with the volume fraction of 90%, and leaching for 3 times, 4 hours each time, at the leaching temperature of 65 ℃, wherein the added amount of the ethanol is 20mL/g of the rice cluster flowers; filtering insoluble substances, mixing filtrates, and evaporating at vacuum degree of 0.07MPa and temperature of 50 deg.C under reduced pressure to obtain extract;
(2) Uniformly mixing the obtained extract with water according to a mass ratio of 1:1 to prepare a suspension, extracting for 4 times by using equal volume of ethyl acetate, combining extract liquor, and evaporating at a low temperature of 50 ℃ under reduced pressure at a vacuum degree of 0.07MPa to obtain an ethyl acetate extract phase;
(3) Uniformly mixing the obtained ethyl acetate extract phase with silica gel with equal mass, then placing the mixture into a silica gel column for chromatography, performing gradient elution by using petroleum ether-ethyl acetate as an eluent, wherein the volume ratio of the petroleum ether to the ethyl acetate in each gradient elution is 9.8;
(4) And separating the collected chromatographic separation initial component F44 by preparative liquid chromatography, wherein the chromatographic separation initial component is prepared from acetonitrile: water (volume ratio 30.
Example 4:
this example is a preparation of an abietane-type diterpene compound Leucosceptrum B
The method for preparing the compound Leucosceptrum B comprises the following steps:
(1) Air-drying and crushing branches of 5kg of rice cluster flowers, adding the crushed branches into ethanol with volume fraction of 95%, and leaching for 2 times, 4 hours each time, at the leaching temperature of 75 ℃, wherein the added amount of the ethanol is 15mL/g of the rice cluster flowers; filtering insoluble substances, combining filtrates, and evaporating to dryness at vacuum degree of 0.09MPa and temperature of 40 deg.C under reduced pressure to obtain extract;
(2) Uniformly mixing the obtained extract with water according to a mass ratio of 1:3 to prepare a suspension, extracting for 2 times by using equal volume of ethyl acetate, combining extract liquor, and evaporating at a low temperature of 40 ℃ under reduced pressure at a vacuum degree of 0.09MPa to obtain an ethyl acetate extract phase;
(3) Uniformly mixing the obtained ethyl acetate extract phase with silica gel with equal mass, then placing the mixture into the silica gel column for chromatography, performing gradient elution by using petroleum ether-ethyl acetate as an eluent, wherein the volume ratio of the petroleum ether to the ethyl acetate in each gradient elution is (10.2);
(4) And separating the collected chromatographic separation initial component F44 by preparative liquid chromatography, wherein the chromatographic separation initial component is prepared from acetonitrile: water (40.
Example 5: antitumor performance test of abietane diterpenoid Leucoseptrum B
The abietane-type diterpene compound Leucosceptrum B prepared in example 2 was used as an antitumor activity test in the following procedure:
in vitro tumor cell proliferation inhibition assay: taking tumor cells in logarithmic growth phase, adjusting the concentration of cell suspension (50000-100000 cells/ml), inoculating 100 mu L of cell suspension into a 96-well cell culture plate, inoculating for 24h, then administering (100 mu L/well), respectively setting a blank control group, a cell control group and 6 concentrations (3.12,6.25, 12.5, 25, 50, 100 mu mol/L) of a tested drug group, wherein the drug in the cell control group is cis-platinum, continuously culturing for 72h, then adding 100 mu L of MTT (1 mg/ml, dissolved by DMEM culture solution) into each well, incubating for 4h at 37 ℃, discarding the liquid in each well, adding 150 mu L of acidified isopropanol (containing 0.04mol/L HCl), placing for 30min in a dark place, measuring the absorbance at 570nm by an enzyme labeling instrument, calculating the proliferation inhibition rate of the tested drug to the tumor cells, calculating the half inhibition concentration (IC 50) of the test drug to the tumor cells proliferation (72 h), and reducing the influence caused by error, and making three parallel experiments for each time, wherein the results are as follows.
5.1 human hepatoma SMMC7721 cells
(1) The control group shows the inhibition effect of cisplatin on SMMC7721 cells, which is shown in tables 2, 3 and 4.
TABLE 2 inhibition of SMMC7721 cells by cisplatin results were tested in parallel
IC50=21.97 was obtained from Graphpad Prism 6.0.
TABLE 3 inhibition of SMMC7721 cells by cisplatin two results were tested in parallel
IC50=22.68 was obtained from Graphpad Prism 6.0.
TABLE 4 inhibition of SMMC7721 cells by cisplatin three results were tested in parallel
IC50=18.72 was obtained from Graphpad Prism 6.0.
From the above data, one can find: the IC50=21.12 ± 2.11 for cisplatin.
(2) The inhibitory effect of the compound Leucosceptrum B on SMMC7721 cells is shown in tables 5, 6 and 7.
TABLE 5 inhibitory Effect of Leucosceptrum B on SMMC7721 cells in parallel
IC50=19.93 was obtained from Graphpad Prism 6.0.
TABLE 6 inhibition of SMMC7721 cells by Leucosceptrum B compound
IC50=15.95 was obtained from Graphpad Prism 6.0.
TABLE 7 inhibitory Effect of the Compound Leucosceptrum B on SMMC7721 cells three results were tested in parallel
IC50=16.04 was determined from Graphpad Prism 6.0.
From the above data, one can find: IC50=17.31 ± 2.27 for Leucosceptrum B.
5.2Leucosceptrum B and cisplatin the half maximal inhibitory concentration IC50 (μmol/L) of SMMC7721 cells for 72 hours is shown in Table 8.
TABLE 8 72-hour half maximal inhibitory concentration IC50 (μmol/L) of Leucosceptrum B and cisplatin on SMMC7721 cells
As can be seen from the tables 5 to 8, the compound Leucosceptrum B with different concentrations has an inhibitory effect on human liver cancer SMMC7721, the IC50 value of Leucosceptrum B after 72 hours reaches 17.31 +/-2.27 mu mol/L, and the IC50 value is lower than that of a cis-platinum control group, namely 21.12 +/-2.11 mu mol/L, which indicates that Leucosceptrum B has a very significant inhibitory effect on SMMC7721 cells.
Although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted without departing from the spirit and scope of the invention as defined in the appended claims. The techniques, shapes, and configurations not described in detail in the present invention are all known techniques.
Claims (10)
1. An abietane-type diterpene compound which is characterized in that: the compound is a chemical structure of formula I, or a pharmaceutical composition of pharmaceutically acceptable salt, stereoisomer, hydrate, solvate or prodrug of the compound of formula I,
2. a preparation method of abietane diterpenoid compounds is characterized by comprising the following steps: comprises the following steps of (a) carrying out,
taking air-dried branches of the rice cluster flowers as raw materials, crushing, extracting with an organic solvent, and concentrating at low temperature under reduced pressure to obtain an extract;
step (2), mixing the extract with water to obtain a suspension, adding ethyl acetate for extraction, and concentrating at low temperature under reduced pressure to obtain an ethyl acetate extract phase;
step (3), separating an ethyl acetate extract phase by silica gel column chromatography, and performing gradient elution by using petroleum ether-ethyl acetate as an eluent, wherein the volume ratio of the petroleum ether to the ethyl acetate is (9.8-10.2): 1, (4.8-5.2): 1, (2.8-3.2): 1, (0.8-1.2): 1; collecting corresponding eluent when the volume ratio of petroleum ether to ethyl acetate is (0.8-1.2) to 1, then carrying out thin layer chromatography analysis, and combining similar components to obtain different initial components F41-F44;
and (4) separating the primary component F44 by preparative liquid chromatography, and isocratic eluting with acetonitrile and water as eluents to obtain the abietane diterpene compound.
3. The method for producing an abietane-type diterpene compound according to claim 2, which is characterized by comprising the steps of: the volume-mass ratio of the organic solvent to the air-dried branches of the rice cluster flowers in the step (1) is 10-20 mL:1g; the leaching temperature is 65-75 ℃, and the leaching is carried out for 2-3 times, 4-6 h each time.
4. The method for producing an abietane-type diterpene compound according to claim 3, which is characterized by comprising: the temperature of low-temperature decompression concentration in the step (1) and the step (2) is 40-50 ℃, and the vacuum degree is 0.07-0.09 MPa.
5. The method for producing an abietane-type diterpene compound according to claim 4, which is characterized by comprising: in the step (2), the mass ratio of the extract to the water is 1:1-3, the volume ratio of the ethyl acetate to the suspension is 0.8-1:1, and the extraction is carried out for 2-4 times.
6. The method for producing an abietane-type diterpene compound according to claim 5, which is characterized by comprising: the volume fraction of acetonitrile in the eluent in the step (4) is 30-40%, and the balance is water.
7. An application of the abietane-type diterpene compound as described in claim 1 in the preparation of antitumor drugs.
8. Use of a pharmaceutical composition of a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate or prodrug of the compound of claim 1 for the preparation of an anti-tumor medicament.
9. Use according to claim 7 or 8, characterized in that: the anti-tumor cell is a human liver cancer SMMC7721 cell.
10. An antitumor agent characterized by: the antitumor drug comprises a pharmaceutically acceptable carrier and the compound as claimed in claim 1, or a pharmaceutical composition of the pharmaceutically acceptable salt, stereoisomer, hydrate, solvate or prodrug of the compound.
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| CN115448827A (en) * | 2022-10-20 | 2022-12-09 | 杭州师范大学 | Abietane diterpenoid compound containing terminal double bond and preparation method and application thereof |
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| CN115448827A (en) * | 2022-10-20 | 2022-12-09 | 杭州师范大学 | Abietane diterpenoid compound containing terminal double bond and preparation method and application thereof |
| CN115448827B (en) * | 2022-10-20 | 2024-01-30 | 杭州师范大学 | Abietane diterpenoid compound containing terminal double bond, and preparation method and application thereof |
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