CN110452113B - (4 → 2) rearranged clerodane diterpenoid compound and preparation method and application thereof - Google Patents
(4 → 2) rearranged clerodane diterpenoid compound and preparation method and application thereof Download PDFInfo
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
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- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Abstract
The invention discloses a (4 → 2) rearranged clerodane diterpenoid compound and a preparation method and application thereof, the (4 → 2) rearranged clerodane diterpenoid compound is a natural compound, and experiments show that the compound has better anti-inflammatory activity.
Description
Technical Field
The invention relates to a natural plant extract, in particular to a (4 → 2) rearranged clerodane diterpenoid compound and a preparation method and application thereof.
Background
Hainan Artocarpus (PolyalthialauuiMerr.) is a plant of the genus Artocarpus (Polyalthia) of the family Annonaceae, often the species Verticillium. According to Chinese plant record, about 200 plants of the genus are distributed in subtropical regions such as Malaysia, Philippines, India and Sri Lanka, and China is distributed in Yunnan, Guangdong, Guangxi and Hainan. There are 17 species in China and 7 species in Hainan, which are respectively as follows: fine base pills (p.cerasoides), sassafras dark roseo (p.conshanguinea), hainan dark roseo (p.laui), lingering water dark roseo (p.nemoralis), twitch dark roseo (p.plateoneura), xianghua dark roseo (p.rumphei) and dark roseo (p.suberosa). Wherein the Hainan dark Rou and the Shacassao dark Rou are special species of Hainan. Hainan Artocarpus heterophyllus is used as a conventional medicinal material in Hainan Li nationality, and has good curative effects on dysmenorrheal, globus hystericus, qi stagnation and abdominal pain and other diseases.
The clerodane diterpenoid is a representative component of the plants in the genus of darkrocia, and more than 300 have been reported since the first report in 1988. Research shows that the compounds have antitumor activity.
A systematic study on the chemical components of Hippocampus dulcis Roots was carried out, and 8 diterpenoids, polyaldimide A (1), kolavonic acid (2), 2-oxo-kolavonic acid (3), 2-oxo-14, 15-biosner-3, 11E-kolavedion-13-one (4),3, 4-dihydroxylodan-13E-en-15-oic acid (5), longimoide B (6), 16-oxocyclododan-3, 13E-dien-15-oic acid (7), and solidal acid methyl ester (8) were isolated from the chemical components of Hippocampus dulcis Roots (Lexiabao et al, organic chemistry, 2013, 33, 1333-1336). Wherein compound 1 is a novel compound, compound 5 is first isolated from Annonaceae, and all compounds are first isolated from the plant. Compounds 2 and 3 showed weak cytotoxicity to human tumor cells SPCA-1, SGC-7901 and K-562.
5 clerodane diterpenoid compounds are obtained by separation in the research on the chemical components of clerodane diterpenoid in Hainan, dark Roots (Lexiabao et al, organic chemistry, 2017, 37 (10): 2763-2766), and the structures of the clerodane diterpenoid compounds are identified as follows according to the NMR and HRMS data: (4 → 2) rearrangement-2, 13-diformyl-clerodane-2, 12E-bisdouble bond-15-methyl ester (1), clerodane-3, 12E-bisdouble bond-15, 16-dicarboxylic acid (2), 14, 15-nordicarbacroxane-3-bisbond-2, 13-dione (3), clerodane-3, 13Z-bisdouble bond-15, 16-lactone (4), 16-hydroxycclerodane-3, 13Z-bisdouble bond-15, 16-lactone (5). Wherein the compounds 1-2 are new compounds, and the results of screening the in vitro cytotoxic activity of the compounds 1-5 show that the compounds have certain in vitro growth inhibition activity on 4 tumor cell strains (Hela, A549, MCF-7 and HL-60), and IC (integrated Circuit) of the compounds50The value range is 13.22 to 37.16. mu. mol/L.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a (4 → 2) rearranged clerodane diterpenoid compound with an anti-inflammatory effect, and a preparation method and application thereof.
The technical scheme for realizing the aim of the invention is a (4 → 2) rearranged clerodane diterpenoid compound represented by the following formula (I):
a method for preparing the (4 → 2) rearranged clerodane-type diterpenoid compound as described above, comprising the steps of:
pulverizing dried Hainan Artocarpus tissue, soaking and extracting with ethanol, mixing extractive solutions, and concentrating under reduced pressure to obtain crude extract.
And secondly, diluting the crude extract obtained in the step I with water to prepare a suspension, extracting with petroleum ether, combining organic phases, and concentrating under reduced pressure to obtain petroleum ether part extract.
Subjecting the petroleum ether part extract obtained in the step two to silica gel column chromatography, performing gradient elution by using a petroleum ether-ethyl acetate mixed solvent according to a ratio of 10: 1-1: 10(V/V), and combining the same fractions to obtain Fr.1-Fr.8;
the Fr.4 fraction was subjected to silica gel column chromatography, and gradient elution was carried out using methylene chloride and acetone as solvents, and two column volumes were collected for each gradient and divided into 6 fractions Fr.1 to Fr.6 according to the polarity.
And fourthly, carrying out normal phase silica gel column chromatography on Fr.2 obtained by eluting dichloromethane and acetone in the third step, wherein an eluent is petroleum ether: eluting 2-5 column volumes with a mixed solvent of ethyl acetate 10: 1-1: 1, concentrating under reduced pressure, performing Sephadex LH-20 gel column chromatography, eluting 3-6 column volumes with MeOH as an eluent, concentrating under reduced pressure, and performing HPLC (high performance liquid chromatography) separation to obtain the target extract (4 → 2) rearrangement clerodane diterpenoid compound.
In the first step, the volume fraction of the ethanol solution is 75-95%; heating the ethanol solution to 50-60 ℃ during each soaking and extraction.
In the third step, when dichloromethane and acetone solvent are used for gradient elution, the elution gradient is respectively 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90 and 0: 100.
In the fourth step, when the HPLC separation is adopted, the chromatographic column is Waters C189.4X 250mm, 4.6 μm, flow rate of 2mL/min, mobile phase MeCN: H2O＝25:75。
The use of a compound of formula (I) in the manufacture of an anti-inflammatory medicament.
The inflammation includes systemic inflammatory reaction, bronchitis, gastritis, enteritis, pneumonia and hepatitis.
The invention has the positive effects that: the invention extracts and obtains (4 → 2) rearrangement clerodane diterpenoid compounds from the Hainan darkroco, and the position 6 of the right B ring of the compounds is connected with a hydroxyl group, which is rare in the clerodane diterpenoid compounds.
Experiments prove that the (4 → 2) rearranged clerodane diterpenoid compound has obvious inhibition effect on the release of TNF-alpha inflammatory factors from RAW264.7 cells induced by LPS and IC50The value was only 7.70. mu.g.mL-1。
Drawings
FIG. 1 shows the NMR spectrum of (4 → 2) rearranged clerodane-type diterpenoid compound of the present invention.
FIG. 2 shows the NMR spectrum of (4 → 2) rearranged clerodane-type diterpenoid compound of the present invention.
FIG. 3 shows the nuclear magnetic resonance undistorted polarization transfer enhanced spectrum (DEPT) of the (4 → 2) rearranged clerodane-type diterpenoid of the present invention.
FIG. 4 shows a hydrogen-hydrogen correlation spectrum (H-H-COSY spectrum) of the (4 → 2) rearranged clerodane-type diterpenoid compound of the present invention.
FIG. 5 is an HSQC spectrum of (4 → 2) rearranged clerodane-type diterpenoid compounds of the present invention.
FIG. 6 is an HMBC spectrum of a (4 → 2) rearranged clerodane-type diterpenoid of the present invention.
FIG. 7 is a NOESY spectrum of (4 → 2) rearranged clerodane-type diterpenoid compounds of the present invention.
FIG. 8 is a high resolution electrospray ionization mass spectrometry (HR-ES-IMS) chart of (4 → 2) rearranged clerodane-type diterpenoid of the present invention.
Detailed Description
(example 1)
The molecular formula of the (4 → 2) rearranged clerodane diterpenoid compound is C20H32O5Molecular weight is 353.2322, the appearance is colorless oil, and the oil is easy to dissolve in methanol and chloroform;the structural formula is shown as the following formula (I):
the preparation method of the (4 → 2) rearranged clerodane diterpenoid compound shown in the formula (I) comprises the following steps:
firstly, 10.0kg of dried Hainan Ardisia crassipes is crushed, soaked and extracted for 2-4 times (4 times in the embodiment) by using ethanol solution with volume fraction of more than 75% (75-95%), the ethanol solution is used for 1-3 hours (2 hours in the embodiment) each time, the dosage of the ethanol solution is 25.0L each time, and the ethanol solution is heated to 50-60 ℃ each time.
The extracts were combined and concentrated under reduced pressure to give a crude extract (about 1800 g).
② diluting the crude extract obtained in the step I with 6.0L of water to prepare suspension, extracting with petroleum ether (5 multiplied by 7.2L), combining organic phases, and concentrating under reduced pressure to obtain 300g of petroleum ether part extract.
And thirdly, subjecting the petroleum ether part extract obtained in the second step to silica gel column chromatography, adopting a petroleum ether-ethyl acetate mixed solvent as an eluent, performing gradient elution according to the ratio of 10: 1-1: 10(V/V, the same below), detecting by TLC, and combining the same fractions to obtain Fr.1-Fr.8.
Separating the Fr.4 fraction with silica gel column chromatography, eluting with dichloromethane and acetone at different volume ratios with elution gradients of 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, and 0:100, collecting two column volumes per gradient, and separating into 6 fractions according to polarity, namely Fr.1-Fr.6.
And fourthly, carrying out normal phase silica gel column chromatography on Fr.2 obtained by eluting dichloromethane and acetone solvent in the third step, wherein the eluent is petroleum ether: eluting 2-5 column volumes with a mixed solvent of ethyl acetate 10: 1-1: 1, concentrating under reduced pressure, performing Sephadex LH-20 gel column chromatography, eluting 3-6 column volumes with MeOH as eluent, concentrating under reduced pressure, and performing HPLC (high performance liquid chromatography), wherein the chromatographic column is Waters C189.4X 250mm, 4.6 μm, a flow rate of 2mL/min, and a mobile phase ofMeCN:H2O25: 75, to give 8.5mg of the target extract (4 → 2) rearranged clerodane-type diterpenoid, as a colorless oil in appearance.
The structure of the target extract (4 → 2) rearranged clerodane diterpenoid is identified as follows:
(4 → 2) NMR spectrum of rearranged clerodane-type diterpenoid (model 400MHz NMR instrument AV-III manufactured by Bruker, Beijing science and technology Ltd., solvent MeOD, 400Hz) is shown in FIG. 1.
(4 → 2) nuclear magnetic resonance carbon spectrum (solvent MeOD, 100MHz) of rearranged clerodane-type diterpenoid compound is shown in FIG. 2.
(4 → 2) rearrangement of clerodane-type diterpenoid compounds1H and13the C NMR data are shown in Table 1([400MHz ], (C NMR)1H)， 100MHz(13C) The solvent: MeOD])。
TABLE 1 preparation of compound I1H-NMR and13C-NMR data [ delta (ppm), J (Hz)]
(4 → 2) Nuclear magnetic resonance undistorted polarization transfer enhanced (DEPT) spectrum of rearranged clerodane-type diterpenoid is shown in FIG. 3, solvent MeOD, 100 MHz.
(4 → 2) the hydrogen-hydrogen correlation spectrum (H-H-COSY spectrum) of the rearranged clerodane-type diterpenoid is shown in FIG. 4, solvent MeOD, 400 MHz.
(4 → 2) HSQC spectra of rearranged clerodane-type diterpenoid compound are shown in FIG. 5, solvent MeOD, 400 MHz.
(4 → 2) HMBC spectra of rearranged clerodane-type diterpenoid compounds are shown in FIG. 6, solvent MeOD, 400 MHz.
(4 → 2) NOESY spectrum of rearranged clerodane-type diterpenoid compound is shown in FIG. 7, solvent MeOD, 400 MHz.
(4 → 2) HR-ESI-MS spectra of the rearranged clerodane-type diterpenoid is shown in FIG. 8.
By HRESI (+) MS (M/z 353.2315[ M + Na ]]+Theoretical value 353.2322) determined to have the molecular formula C20H32O5。
According to1H，13And C and two-dimensional nuclear magnetic resonance data determine the structure of the compound, the framework type is clerodane diterpene, and the compound is named as (4 → 2) -abeo-6, 16-dihydroxyleroda-2, 13Z-dien-15-oic acid.
(test example 1, evaluation of in vitro anti-inflammatory Activity)
1.1 Experimental materials
Cell: mouse mononuclear macrophage raw264.7.
Cell culture solution: DMEM medium containing 10% Fetal Bovine Serum (FBS), Lipopolysaccharide (LPS) carbohydrate.
The NO detection kit is an ELISA kit.
1.2 Experimental methods
The anti-inflammatory activity in vitro screening adopts a mouse mononuclear macrophage Raw264.7 model, which comprises the following specific steps: raw264.7 cells were cultured in DMEM medium containing 10% FBS at 37 ℃ in 5% CO2Culturing in an incubator by a conventional method. The cells are arranged at 1X 105The samples were inoculated in 96-well plates at 200. mu.L/well, and a blank control group, an LPS-induced group, and high, medium, and low (50,25, 12.5. mu.g. mL) test drugs were placed in the wells, respectively-1) Dose groups, at 37 ℃ and 5% CO2Adherence in a cell culture box for 24 h. Except for blank control group, each component is added with corresponding tested drug and the final concentration is 1 mug.mL-1LPS, and the culture is continued for 24 h.
50 μ L of cell culture supernatant was aspirated to detect TNF-. alpha.levels according to ELISA kit protocol, and then 10 μ L (5 mg. multidot.mL) was added to each well-1) MTT is continuously cultured for 4h, supernatant is discarded, 150 mu L DMSO is respectively added, shaking is carried out for 10min, and OD value is measured at 570nm by adopting an enzyme-labeling instrument.
The anti-inflammatory activity results are shown in table 2.
TABLE 2 anti-inflammatory Activity of Compounds on RAW264.7 cells
Note: the ratio of the number of the blank spaces to the number of the blank spaces,***P<0.001, in relation to LPS,###P<0.001,##P<0.01,#P<0.05。
as can be seen from Table 2, the OD value of LPS group was significantly increased (P) compared with the blank<0.001), indicating that LPS-induced RAW264.7 cells obviously proliferate and generate inflammatory reaction. The OD value of compound I is significantly reduced compared to that of LPS group (P)<0.001,P<0.01,P<0.05), obviously inhibiting the generation of inflammation. Computing IC50The value was 7.70. mu.g.mL-1。
In addition, the TNF-. alpha.inhibitory effect is shown in Table 3.
TABLE 3 TNF-alpha secretion from LPS-induced mouse macrophages by Compound I
Note: in comparison to the LPS ratio,###P<0.001,##P<0.01,#P<0.05。
as can be seen from Table 3, compound I significantly reduced the levels of TNF- α (P <0.001, P <0.01, P <0.05) compared to LPS group.
Claims (7)
1. A (4 → 2) rearranged clerodane-type diterpenoid compound represented by the following formula (I):
2. a method for the preparation of (4 → 2) rearranged clerodane-type diterpenoid compounds according to claim 1, characterized by comprising the steps of:
pulverizing dried Hainan Ardisia Roxburghii, soaking and extracting with ethanol, mixing the extractive solutions, and concentrating under reduced pressure to obtain crude extract;
diluting the crude extract obtained in the step I with water to prepare a suspension, extracting with petroleum ether, combining organic phases, and concentrating under reduced pressure to obtain petroleum ether part extract;
subjecting the petroleum ether part extract obtained in the step two to silica gel column chromatography, performing gradient elution by adopting a mixed solvent of petroleum ether and ethyl acetate according to the ratio of 10: 1-1: 10, and combining the same fractions to obtain Fr.1-Fr.8;
separating the Fr.4 component by silica gel column chromatography, performing gradient elution with dichloromethane and acetone solvent, collecting two column volumes in each gradient, and dividing into 6 components Fr.1-Fr.6 according to polarity;
and fourthly, carrying out normal phase silica gel column chromatography on Fr.2 obtained by eluting dichloromethane and acetone in the third step, eluting 2-5 column volumes by using a mixed solvent of petroleum ether and ethyl acetate in a ratio of 10: 1-1: 1, carrying out Sephadex LH-20 gel column chromatography after carrying out reduced pressure concentration, eluting 3-6 column volumes by using an MeOH solvent, and carrying out High Performance Liquid Chromatography (HPLC) separation after carrying out reduced pressure concentration to obtain the target extract (4 → 2) rearrangement clerodane diterpenoid compound.
3. The method for the preparation of (4 → 2) rearranged clerodane-type diterpenoid compounds according to claim 2, characterized in that: in the first step, the volume fraction of the ethanol solution is 75-95%; heating the ethanol solution to 50-60 ℃ during each soaking and extraction.
4. The method for the preparation of (4 → 2) rearranged clerodane-type diterpenoid compounds according to claim 2, characterized in that: in the third step, when dichloromethane and acetone solvent are used for gradient elution, the elution gradient is respectively 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90 and 0: 100.
5. The method for the preparation of (4 → 2) rearranged clerodane-type diterpenoid compounds according to claim 2, characterized in that: in the fourth step, when the HPLC separation is adopted, the chromatographic column is Waters C189.4X 250mm, 4.6 μm, flow rate of 2mL/min, the mobile phase is MeCN: H2O＝25:75。
6. The use of a compound of formula (i) as claimed in claim 1 in the manufacture of an anti-inflammatory medicament.
7. Use of a compound of formula (i) according to claim 6 for the preparation of an anti-inflammatory agent, characterized in that: the inflammation includes systemic inflammatory reaction, bronchitis, gastritis, enteritis, pneumonia and hepatitis.
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