CN107082767A - Phloroglucinol derivatives noval chemical compound of separation and Extraction and preparation method thereof in Samson St Johswort - Google Patents

Phloroglucinol derivatives noval chemical compound of separation and Extraction and preparation method thereof in Samson St Johswort Download PDF

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CN107082767A
CN107082767A CN201610989988.8A CN201610989988A CN107082767A CN 107082767 A CN107082767 A CN 107082767A CN 201610989988 A CN201610989988 A CN 201610989988A CN 107082767 A CN107082767 A CN 107082767A
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johswort
samson
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张勇慧
薛永波
朱虎成
陈春梅
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Huazhong University of Science and Technology
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Abstract

The present invention relates to phloroglucinol derivatives noval chemical compound of separation and Extraction in Samson St Johswort and preparation method thereof.The invention belongs to pharmaceutical technology field, and in particular to the activity and structure of the isolated noval chemical compound with Anti-tumor angiogenesis and anti-HIV activity (one) are extracted from the aerial part of Guttiferae hypericum Samson St Johswort.(2) preparation method for separating and purifying and related activity of the good compound 16 20 of antitumor activity, structural formula is as shown in Equation 1.(3) preparation method for separating and purifying and related activity of the compound 1 and 2 with anti-HIV activity, structural formula is as shown in Equation 1.The present invention provides compound candidate for the new antitumor and anti-hiv drug of exploitation, and the exploitation to Garcinia maingayii have very important significance.

Description

Phloroglucinol derivatives noval chemical compound of separation and Extraction and preparation method thereof in Samson St Johswort
Present patent application is the divisional application of the application for a patent for invention of Application No. 2014106745446, The applying date of No. 2014106745446 patent applications is on November 21st, 2014, and its is entitled：Have in Samson St Johswort anti-swollen The compound and separation preparation and use of knurl and HIV-resistant activity.
Technical field
The invention belongs to pharmaceutical technology field, it is related to compound 1-30 method for separating and preparing and purposes.Specifically related to divide From purge process, structural identification, anti-tumour cell proliferative effect and anti-HIV activity etc..
Background technology
Samson St Johswort is Guttiferae (Guttiferae) Hypericum (Hypericum) plant Samson St Johswort (Hypericumsampsonii Hance), alias hancock swallowwort herb, lateral-flower milkwort herb, Ye Baozhi, common canscora herb etc..The plant is perennial grass This, it is high about 0.2-0.8 meter, it is all hairless.Stem is single or minority, cylinder, no gland point, top branch.Leaf is to life, stockless, its The complete symphysis of base portion is integrated and the stem heart therethrough.6-15 millimeters of flower diameter, bennet is about 2-3 millimeters.The wide ovum pearl shape of capsule It is long 6-9 millimeters to wide or narrow ovum pearl cone, it is wide 4-5 millimeters, it is scattered with ovum pearl yellowish-brown cryptomere body of gland.Seed Yellowish-brown, long ovum cylindricality is about 1 millimeter, and both sides are without keel, and top is without adjunct, and there is obvious fine cells line on surface. 5-June of florescence, 7-August of fruiting period.Samson St Johswort is widely distributed in China, originates in Shaanxi to south of the River each province.Typically it is born in roadside, mountain Slope, meadow, shrubbery, Tian Bian, limes marginis etc., 0-1200 meter of height above sea level.Japan, Vietnam (the north), Burma (east), India (northeast Portion) it is also distributed, but it is less.Among the people with Samson St Johswort all herbal medicine as Chinese traditional herbs, the medical instrument has cooling blood and hemostasis, clear Thermal detoxification, promoting blood circulation for regulating menstruation, the effect of dispelling wind and removing obstruction in the meridians.Available for treatment haematemesis, spitting of blood, traumatic bleeding, enteritis, dysentery, acute mastitis, carbuncle Swollen serious case of furuncle, scald, snake bite, irregular menstruation, arthralgia pain due to rheumatism etc..
Researcher has carried out more careful research to the plant chemical ingredient, and these results of study show, Samson St Johswort Chemical composition mainly includes polycyclic many isopentene group phloroglucin derivatives (PPAPs), dianthrone, mouth mountain ketone, flavones and hexichol First ketone compounds, in addition with phytosterol, benzoic acid, caffeic acid, volatile oil etc..The chemical combination for having separated identification at these In thing, include nearly 40 PPAPs, be the main chemical composition of Samson St Johswort.The activity research of these compounds is shown, he There is antitumor, antibacterial, the multiple pharmacological effect such as antiviral.
In recent years, cancer and AIDS patient are continuously increased, it has also become threaten the topmost of animals and humans life security Reason.The medicine for finding safely and effectively treating cancer and AIDS virus is one of study hotspot of natural products, therefore, from Guttiferae Being found in hypericum Samson St Johswort, there is antitumor and anti AIDS virus new natural products to have very important significance.
The content of the invention
It is an object of the invention to provide the new phloroglucinol derivatives compound with antitumor and anti-HIV activity Source and isolation and purification method and its potential using value.
The phloroglucinol derivatives compound of the present invention, its structural formula such as formula (1)；
The present inventor is isolated and purified by the ethanol extract to Guttiferae hypericum Samson St Johswort, obtains 30 Individual noval chemical compound.With a variety of analysis method by use of spectrum and other means, it is phloroglucinol derivatives compound to determine its structure, specific knot Shown in structure such as formula (1).By the antitumor activity evaluation to all noval chemical compounds, find compound 16-20 to leukaemia HL-60, human liver cancer cells Hep G2, human lung carcinoma cell A-549, human breast cancer cell line Bcap-37, human colon cancer cell SW480 In part cells show go out good activity, can be used as treatment antitumor cell drug development lead compound.Pass through Anti-HIV activity test to compound 1 and 2, it is found that compound 1 and 2 pairs of HIV-1 (LAI) strains show good suppression System activity, can be developed as the lead compound for the treatment of AIDS virus.
Second object of the present invention is to provide applications of the compound 1-30 in antineoplastic is prepared shown in formula (1).
Third object of the present invention is to provide compound 1 and 2 shown in formula (1) and is preparing the application of anti-hiv drug.
Brief description of the drawings
Fig. 1：The experiment ECD and calculating ECD comparison diagrams of compound 13；
Fig. 2：The ECD comparison diagrams of compound 13 and 16-20.
Embodiment
Embodiment 1：Noval chemical compound 16-20 preparation and Structural Identification.
(1) as shown in formula (1) compound 16-20 preparation
1. extract separation
Dry Samson St Johswort aerial part, is extracted after chopping with multi-function extractor with 95% ethanol, 100 liters or so every time In being extracted 10 hours at 45 DEG C, repeat to extract 4 times, solvent is recovered under reduced pressure and obtains total medicinal extract.Total medicinal extract is suspended in water, used successively Petroleum ether part and chloroform extract is obtained by extraction in petroleum ether and chloroform.Petroleum ether part progress silica gel column chromatography (100-200 mesh, 5kg), petroleum ether：Acetone gradient elution (100:0→0:100), with TLC combining data detection similar portions, 6 components are obtained.Part III draws section with silica gel, alternately and repeatedly using silica gel, ODS, Sephadex LH-20 and reverse HPLC-purified obtains compound afterwards 16.Section is drawn in part IV with silica gel, alternately and repeatedly using silica gel, ODS, Sephadex LH-20 and reverse HPLC-purified obtains afterwards Compound 17-18.Section is drawn in part V with ODS, and silica gel, ODS, Sephadex LH-20 and reversed-phase HPLC are alternately and repeatedly used afterwards Purifying obtains compound 19.Chloroform extract carries out silica gel column chromatography (100-200 mesh, 6kg), petroleum ether：Acetone gradient elution (100:0→0:100), with TLC combining data detection similar portions, 6 components (I-VI) are obtained, part II draws section with silica gel, afterwards Alternately and repeatedly using silica gel, ODS, Sephadex LH-20 and reverse HPLC-purified obtain compound 20.
Compound 16-20 Structural Identifications as shown in Equation 1
Mass spectrum, ultraviolet spectra, infrared spectrum, optically-active, nuclear magnetic resonance (see Tables 1 and 2), circle are carried out to compound 16-20 The data test such as two chromatograms and calculating circular dichroism spectra, so that it is determined that the structure of compound.
Compound 16:Colorless oil,UV(CH3OH)λmax(log ε)= 204(4.22),248(3.95),and 275(3.88)nm；IRνmax=3421,1722,1696, and 1626cm–1；for1H NMR(400MHz)and13C NMR(100MHz)data see Tables1and 2；HRESIMS[M+Na]+m/z 641.3431 (calcd C38H50O7Na for 641.3454) compounds 16 absolute configuration determination be by calculate ECD and compare ECD come Determine, as depicted in figs. 1 and 2.
Compound 17:Colorless oil,UV(CH3OH)λmax(log ε)= 205(4.01),247(3.73),and 277(3.65)nm；IRνmax=3454,1728,1697, and 1626cm–1；for1H NMR(400MHz)and13C NMR(100MHz)data see Tables1and 2；HRESIMS[M+Na]+m/z 641.3431 (calcd C38H50O7Na for 641.3454) absolute configurations of compounds 17 is by coming true with the ECD of compound 13 contrast Fixed, as depicted in figs. 1 and 2.
Compound 18:Colorless oil,UV(CH3OH)λmax(log ε)= 205(4.46),248(4.17),and 277(4.15)nm；IRνmax=3518,1728,1698, and 1627cm–1；for1H NMR(400MHz)and13C NMR(100MHz)data see Tables1and 2；HRESIMS[M+Na]+m/z 641.3429 (calcd C38H50O7Na for 641.3454) absolute configurations of compounds 18 is by coming true with the ECD of compound 13 contrast Fixed, as depicted in figs. 1 and 2.
Compound 19:Colorless oil,UV(CH3OH)λmax(log ε)= 203(4.25),247(4.00),and 274(3.88)nm；IRνmax=3419,1734, and 1700cm–1；for1H NMR (400MHz)and 13C NMR(100MHz)data see Table 1and 2；HRESIMS[M+Na]+m/z 657.3380 (calcd C38H50O8Na for 657.3403) absolute configurations of compounds 19 is by coming true with the ECD of compound 13 contrast Fixed, as depicted in figs. 1 and 2.
Compound 20:Colorless oil,UV(CH3OH)λmax(log ε)=203 (4.39),248(4.04),and 277(3.95)nm；IRνmax=3423,1728,1697, and 1626cm–1；for1H NMR (400MHz)and13C NMR(100MHz)data see Tables 1and 2；HRESIMS[M+Na]+m/z 657.3383 (calcd C38H50O8Na for 657.3403) absolute configurations of compounds 20 is by coming true with the ECD of compound 13 contrast Fixed, as depicted in figs. 1 and 2.
Embodiment 2：Compound 16-20 is to leukaemia HL-60, human liver cancer cells Hep G2, human lung carcinoma cell A- 549, human breast cancer cell line Bcap-37, the inhibitory activity of human colon cancer cell SW480 competent cells.
Compound 16-20 antitumor activity is by MTS methods to leukaemia HL-60, human liver cancer cell SMMC- 7721, human lung carcinoma cell A-549, human breast cancer cell line Bcap-37, five kinds of human body tumour cells of human colon cancer cell SW480 are carried out Evaluate.As a result it is as shown in table 3：
Embodiment 3：The inhibitory activity of compound 1 and 2 pairs of HIV-1 types.
From HIV-1 (LAI) strain, the method that HIV core protein P24 antigens are detected using ELISA, Zidovudine (AZT) it is positive drug, preliminary HIV-resistant activity screening (single hole, 6 concentration) has been carried out to noval chemical compound 1,2 and 5, the results are shown in Table 4.Wherein compound 1 and 2 has preferable antiviral activity and selection index, and we have carried out secondary screening to it, and (3 holes, 12 is dense Degree).As a result it is as shown in table 4：
Hydrogen modal data (the Table 1. of the compound 16-20 of table 1.1H NMR Datafor Compounds 16–20)
400MHz nuclear-magnetisms are surveyed in deuterochloroform, chemical shift unit ppm (Record in CDCl3,400MHz for 1H,δ in ppm)
Carbon modal data (the Table 2. of the compound 16-20 of table 2.13C NMR Datafor Compounds 16–20)
100MHz nuclear-magnetisms are surveyed in deuterochloroform, chemical shift unit ppm (Record in CDCl3,400MHz for 1H,δ in ppm)
The cytotoxic activity of 3. compound of table 1-30 (Table 3Cytotoxic activities of compounds1- 30)
The compound 1 of table 4. and 2 HIV-resistant activities (Table 4.Anti-HIV activities of compounds 1and 2)

Claims (2)

1. phloroglucinol derivatives noval chemical compound of the structural formula 22 with formula 1 into structural formula 30 shown in any structure formula：
2. the preparation method of the phloroglucinol derivatives noval chemical compound described in claim 1, comprises the following steps：
Step (1)：Dry Samson St Johswort aerial part, is extracted after chopping with multi-function extractor with 95% ethanol, 100 liters every time Left and right repeats to extract 4 times, solvent is recovered under reduced pressure and obtains total medicinal extract in being extracted 10 hours at 45 DEG C；
Step (2)：After the total medicinal extract of step (1) is suspended with water, is extracted successively with petroleum ether and chloroform, solvent is recovered under reduced pressure, obtains To petroleum ether and the total extract of chloroform portion；
Step (3)：Gained petroleum ether and chloroform total extract in step (2), through chromatographic isolation, are obtained into new chemical combination shown in formula 1 Thing 22-30；The chromatography separating method includes normal phase silica gel column chromatography, reversed-phase silica gel column chromatography, gel column chromatography, efficient liquid phase Chromatogram.
CN201610989988.8A 2014-11-21 2014-11-21 Phloroglucinol derivatives noval chemical compound of separation and Extraction and preparation method thereof in Samson St Johswort Pending CN107082767A (en)

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CN112939759B (en) * 2019-12-10 2023-12-19 中国医学科学院药物研究所 Application of phloroglucinol compound in preparation of liver protection drugs

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