CN102796153B - Novel antitumor component Swertiridoid A in swertia phragmitiphylla - Google Patents
Novel antitumor component Swertiridoid A in swertia phragmitiphylla Download PDFInfo
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- CN102796153B CN102796153B CN201210318801.3A CN201210318801A CN102796153B CN 102796153 B CN102796153 B CN 102796153B CN 201210318801 A CN201210318801 A CN 201210318801A CN 102796153 B CN102796153 B CN 102796153B
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- 0 CCC(C1)C[C@@](C*)OC1OC(C(C1CC2OC2O2)C=C)OC=C1C2=O Chemical compound CCC(C1)C[C@@](C*)OC1OC(C(C1CC2OC2O2)C=C)OC=C1C2=O 0.000 description 1
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Abstract
The invention relates to a novel antitumor component Swertiridoid A in swertia phragmitiphylla. The molecular formula of the Swertiridoid A is shown as C16H20O10. The chemical structure of a compound is determined through multiple types of conventional spectrum analysis; the compound is iridoid glycoside of which the aglycone is similar to cantharidin, contains a sugar structure in molecules, and has high water solubility. Meanwhile, as proved by an in-vitro antitumor experiment, the compound has a remarkable inhibiting effect on tumor cell strains. A pilot compound can be provided for the research and development of novel antitumor medicaments, and plays an important role in developing and utilizing special plant medicinal materials on the Qinghai-Tibet Plateau.
Description
Technical field
The present invention relates to medical technical field, relate in particular to antineoplastic component Swertiridoid A new in reed leaf Herba Swertiae bimaculatae.
Background technology
Reed leaf Herba Swertiae bimaculatae (
swertia phragmitiphyllat. N. He et S. W. Liu) be Gentianaceae Swertia plant, originate in the ground such as China Tibet, belong to traditional Tibetan medicine, be the herbal medicine that is used for the treatment of hepatitis among the people, but the research of its chemical composition there is not yet report.
Summary of the invention
Technical problem to be solved by this invention is to provide antineoplastic component Swertiridoid A new in a kind of reed leaf Herba Swertiae bimaculatae.
Another technical problem to be solved by this invention is to provide the preparation method of antineoplastic component Swertiridoid A new in this reed leaf Herba Swertiae bimaculatae.
For addressing the above problem, new antineoplastic component Swertiridoid A in reed leaf Herba Swertiae bimaculatae of the present invention, is characterized in that: its molecular formula is C
16h
20o
10, its chemical structure is as follows:
。
The preparation method of new antineoplastic component Swertiridoid A in reed leaf Herba Swertiae bimaculatae as above, comprises the following steps:
(1) extract: first reed leaf Herba Swertiae bimaculatae is dried in the shade, after herb is broken into pieces, the alcohol immersion that is 95% by 10 ~ 20 times of its weight and volumetric concentration 10 ~ 14 hours, heating and refluxing extraction 2 ~ 4 times at 80 ~ 90 DEG C of temperature, each 2 hours, concentrating under reduced pressure, reclaims after ethanol, obtains mass content and be 20 ~ 25% extract; Then described extract is refrigerated after 36 ~ 60h at 0 ~ 5 DEG C of temperature, through centrifugal, getting supernatant liquor, again to obtain proportion after decompression recycling ethanol be 1.1 ~ 1.3 medicinal extract; Finally, described medicinal extract is scattered in water by the mass volume ratio that is 1:4 ~ 6, and successively with the isopyknic sherwood oil of disperse water, ethyl acetate, n-butanol extraction repeatedly, obtain respectively four part extracts---sherwood oil part, ethyl acetate part, propyl carbinol part, water section;
(2) separation and purification: first adopt D101 macroporous adsorbent resin to carry out the absorption of 2 ~ 4 hours described water section, then adopt successively the aqueous ethanolic solution that water, mass concentration are 5%, the aqueous ethanolic solution that mass concentration is 20%, the aqueous ethanolic solution that mass concentration is 50%, the aqueous ethanolic solution that mass concentration is 95% to carry out wash-out, elution flow rate is 15 mL/min, obtains respectively five components---water elution part, 5% ethanol elution part, 20% ethanol elution part, 50% ethanol elution part, 95% ethanol elution part; Choosing described 5% ethanol elution part, adopt high performance liquid chromatography to separate preparation to it, is C in chromatographic column
18(250 mm × 10 mm, 5 μ m), mass concentration is 30% methanol aqueous solution is that moving phase, volumetric flow rate are 2.0 mLmin for post
-1, to detect wavelength be that 260 nm, column temperature are to carry out isocratic elution under the condition of 25 DEG C, obtains compound S wertiridoid A.
Antineoplastic component Swertiridoid A new in reed leaf Herba Swertiae bimaculatae as above is in the application of preparing in antitumor drug, it is characterized in that: described antineoplastic component Swertiridoid A is equipped with medicinal stone and acceptable carrier pharmaceutically or on physiology, is prepared into any formulation in pharmaceutics with conventional preparation technology.
The present invention compared with prior art has the following advantages:
1, the present invention extracts and separates a kind of new iridoid Swertiridoid A the Tibetan medicine material reed leaf Herba Swertiae bimaculatae from being grown in Tibet, and this Swertiridoid A is white powder (95% ethanol), fusing point 191-193 DEG C, [α]
d 20:-196 (H
2o), λ
max meOH(nm): 245.After multiple present spectroscopic analysis, determine the chemical structure of this compound, this compound is the aglycon iridoid glycoside similar to Cantharidin, contains sugared structure in its molecule, has good water-soluble.
Molecular formula C
16h
20o
10;
1h(500Hz, DMSO-d6),
13c(300Hz, DMSO-d6) nuclear magnetic resonance spectrum data are in table 1.
Table 1 Swertiridoid A's
1h and
13c NMR data (ppm)
Note: solvent is DMSO-d
6.
2, Swertiridoid A of the present invention is carried out to anticancer experiment in vitro, show that it has the effect of obvious inhibition tumour.Testing cell strain used is international tumor cell line---liver cancer cell HepG2, rectum cancer cell LOVO.
Experimental technique adopts international MTT measuring method to carry out: first, inoculate 2 × 104 liver cancer cell HepG2, rectum cancer cell LOVO logarithmic phase cell on 24 porocyte culture plates, 3 multiple holes, after cell attachment; Add again different concns product to be tested, 8 drug level gradients are set altogether, are respectively 0.1%DMSO, 0.625 μ mol/L Swertiridoid A DMSO, 1.25 μ mol/L Swertiridoid A DMSO, 2.5 μ mol/L Swertiridoid A DMSO, 5 μ mol/L Swertiridoid A DMSO, 10 μ mol/L Swertiridoid A DMSO, 20 μ mol/L Swertiridoid A DMSO and 40 μ mol/L Swertiridoid A DMSO; After drug treating 48h, adding new preparation final concentration is the MTT[3-(4 of 1 mg/mL, 5-dimethylthiazole-2)-2,5-phenylbenzene tetrazole bromine salt] solution in 37 DEG C of incubation 3 h.Use the long microplate reader of all-wave to detect the absorbancy at 570nm wavelength, with the negative contrast of 0.1%DMSO, calculate inhibiting rate and the half-inhibition concentration IC of product to be tested cell growth
50.Every kind of sample revision test 3 times.The IC of liver cancer
50be 18.93 (μ g/ml)=51nM/ml; The IC of the rectum cancer
50be 16.96 (μ g/ml)=45.71nM/ml.Experimental result shows, this compound all has obvious restraining effect to tumor cell line, provides new lead compound for developing new antitumor drug, significant to developing China's Resources of Tibetan Medicine in China.
3, the present invention is owing to adopting the material and facilities such as macroporous adsorbent resin, silica gel column chromatography, high performance liquid chromatography, agents useful for same is recyclable recycling all, avoided silica gel separation simultaneously, stop the use of the organic solvent such as chloroform, benzene, greatly reduce the pollution to environment, therefore, preparation method is simple, with low cost.
Embodiment
New antineoplastic component Swertiridoid A in reed leaf Herba Swertiae bimaculatae, its molecular formula is C
16h
20o
10, its chemical structure is as follows:
。
embodiment 1the preparation method of new antineoplastic component Swertiridoid A in this reed leaf Herba Swertiae bimaculatae, comprises the following steps:
(1) extract: first reed leaf Herba Swertiae bimaculatae is dried in the shade, after herb is broken into pieces, the alcohol immersion that is 95% by 10 times of its weight and volumetric concentration 10 hours, heating and refluxing extraction 2 times at 80 DEG C of temperature, each 2 hours, under 0 ~ 0.08MPa condition, through concentrating under reduced pressure, reclaim after ethanol, obtain mass content and be 20 ~ 25% extract; Then extract is refrigerated after 36h at 0 ~ 5 DEG C of temperature, carry out centrifugally with the speed of 0 ~ 10000 rev/min, getting supernatant liquor, under 0 ~ 0.08MPa condition, after decompression recycling ethanol, to obtain proportion be 1.1 ~ 1.3 medicinal extract; Finally, medicinal extract is scattered in water by the mass volume ratio (kg/mL) that is 1:4, and successively with the isopyknic sherwood oil of disperse water, ethyl acetate, n-butanol extraction repeatedly, obtain respectively four part extracts---sherwood oil part, ethyl acetate part, propyl carbinol part, water section.
(2) separation and purification: first adopt D101 macroporous adsorbent resin to carry out the absorption of 2 hours water section, then adopt successively the aqueous ethanolic solution that water, mass concentration are 5%, the aqueous ethanolic solution that mass concentration is 20%, the aqueous ethanolic solution that mass concentration is 50%, the aqueous ethanolic solution that mass concentration is 95% to carry out wash-out, elution flow rate is 15 mL/min, obtains respectively five components---water elution part, 5% ethanol elution part, 20% ethanol elution part, 50% ethanol elution part, 95% ethanol elution part; Choosing 5% ethanol elution part, adopt high performance liquid chromatography to separate preparation to it, is C in chromatographic column
18(250 mm × 10 mm, 5 μ m), mass concentration is 30% methanol aqueous solution is that moving phase, volumetric flow rate are 2.0 mLmin for post
-1, to detect wavelength be that 260 nm, column temperature are to carry out isocratic elution under the condition of 25 DEG C, obtains compound S wertiridoid A.
embodiment 2the preparation method of new antineoplastic component Swertiridoid A in this reed leaf Herba Swertiae bimaculatae, comprises the following steps:
(1) extract: first reed leaf Herba Swertiae bimaculatae is dried in the shade, after herb is broken into pieces, the alcohol immersion that is 95% by 20 times of its weight and volumetric concentration 14 hours, heating and refluxing extraction 4 times at 90 DEG C of temperature, each 2 hours, under 0 ~ 0.08MPa condition, through concentrating under reduced pressure, reclaim after ethanol, obtain mass content and be 20 ~ 25% extract; Then extract is refrigerated after 60h at 0 ~ 5 DEG C of temperature, carry out centrifugally with the speed of 0 ~ 10000 rev/min, getting supernatant liquor, under 0 ~ 0.08MPa condition, after decompression recycling ethanol, to obtain proportion be 1.1 ~ 1.3 medicinal extract; Finally, medicinal extract is scattered in water by the mass volume ratio (kg/mL) that is 1:6, and successively with the isopyknic sherwood oil of disperse water, ethyl acetate, n-butanol extraction repeatedly, obtain respectively four part extracts---sherwood oil part, ethyl acetate part, propyl carbinol part, water section.
(2) separation and purification: first adopt D101 macroporous adsorbent resin to carry out the absorption of 4 hours water section, then adopt successively the aqueous ethanolic solution that water, mass concentration are 5%, the aqueous ethanolic solution that mass concentration is 20%, the aqueous ethanolic solution that mass concentration is 50%, the aqueous ethanolic solution that mass concentration is 95% to carry out wash-out, elution flow rate is 15 mL/min, obtains respectively five components---water elution part, 5% ethanol elution part, 20% ethanol elution part, 50% ethanol elution part, 95% ethanol elution part; Choosing 5% ethanol elution part, adopt high performance liquid chromatography to separate preparation to it, is C in chromatographic column
18(250 mm × 10 mm, 5 μ m), mass concentration is 30% methanol aqueous solution is that moving phase, volumetric flow rate are 2.0 mLmin for post
-1, to detect wavelength be that 260 nm, column temperature are to carry out isocratic elution under the condition of 25 DEG C, obtains compound S wertiridoid A.
embodiment 3the preparation method of new antineoplastic component Swertiridoid A in this reed leaf Herba Swertiae bimaculatae, comprises the following steps:
(1) extract: first reed leaf Herba Swertiae bimaculatae is dried in the shade, after herb is broken into pieces, the alcohol immersion that is 95% by 15 times of its weight and volumetric concentration 12 hours, heating and refluxing extraction 3 times at 85 DEG C of temperature, each 2 hours, under 0 ~ 0.08MPa condition, through concentrating under reduced pressure, reclaim after ethanol, obtain mass content and be 20 ~ 25% extract; Then extract is refrigerated after 48h at 0 ~ 5 DEG C of temperature, carry out centrifugally with the speed of 0 ~ 10000 rev/min, getting supernatant liquor, under 0 ~ 0.08MPa condition, after decompression recycling ethanol, to obtain proportion be 1.1 ~ 1.3 medicinal extract; Finally, medicinal extract is scattered in water by the mass volume ratio (kg/mL) that is 1:5, and successively with the isopyknic sherwood oil of disperse water, ethyl acetate, n-butanol extraction repeatedly, obtain respectively four part extracts---sherwood oil part, ethyl acetate part, propyl carbinol part, water section.
(2) separation and purification: first adopt D101 macroporous adsorbent resin to carry out the absorption of 3 hours water section, then adopt successively the aqueous ethanolic solution that water, mass concentration are 5%, the aqueous ethanolic solution that mass concentration is 20%, the aqueous ethanolic solution that mass concentration is 50%, the aqueous ethanolic solution that mass concentration is 95% to carry out wash-out, elution flow rate is 15 mL/min, obtains respectively five components---water elution part, 5% ethanol elution part, 20% ethanol elution part, 50% ethanol elution part, 95% ethanol elution part; Choosing 5% ethanol elution part, adopt high performance liquid chromatography to separate preparation to it, is C in chromatographic column
18(250 mm × 10 mm, 5 μ m), mass concentration is 30% methanol aqueous solution is that moving phase, volumetric flow rate are 2.0 mLmin for post
-1, to detect wavelength be that 260 nm, column temperature are to carry out isocratic elution under the condition of 25 DEG C, obtains compound S wertiridoid A.
Above-mentioned
embodiment 1 ~ 3in the reed leaf Herba Swertiae bimaculatae of gained, new antineoplastic component Swertiridoid A is in the application of preparing in antitumor drug: antineoplastic component Swertiridoid A is equipped with medicinal stone and acceptable carrier pharmaceutically or on physiology, is prepared into any formulation in pharmaceutics with conventional preparation technology.
Claims (3)
1. antineoplastic component Swertiridoid A in reed leaf Herba Swertiae bimaculatae, is characterized in that: its molecular formula is C
16h
20o
10, its chemical structure is as follows:
。
2. the preparation method of antineoplastic component Swertiridoid A in reed leaf Herba Swertiae bimaculatae as claimed in claim 1, comprises the following steps:
(1) extract: first reed leaf Herba Swertiae bimaculatae is dried in the shade, after herb is broken into pieces, the alcohol immersion that is 95% by 10 ~ 20 times of its weight and volumetric concentration 10 ~ 14 hours, heating and refluxing extraction 2 ~ 4 times at 80 ~ 90 DEG C of temperature, each 2 hours, concentrating under reduced pressure, reclaims after ethanol, obtains mass content and be 20 ~ 25% extract; Then described extract is refrigerated after 36 ~ 60h at 0 ~ 5 DEG C of temperature, through centrifugal, getting supernatant liquor, again to obtain proportion after decompression recycling ethanol be 1.1 ~ 1.3 medicinal extract; Finally, described medicinal extract is scattered in water by the mass volume ratio that is 1:4 ~ 6, and successively with the isopyknic sherwood oil of disperse water, ethyl acetate, n-butanol extraction repeatedly, obtain respectively four part extracts---sherwood oil part, ethyl acetate part, propyl carbinol part, water section;
(2) separation and purification: first adopt D101 macroporous adsorbent resin to carry out the absorption of 2 ~ 4 hours described water section, then adopt successively the aqueous ethanolic solution that water, mass concentration are 5%, the aqueous ethanolic solution that mass concentration is 20%, the aqueous ethanolic solution that mass concentration is 50%, the aqueous ethanolic solution that mass concentration is 95% to carry out wash-out, elution flow rate is 15 mL/min, obtains respectively five components---water elution part, 5% ethanol elution part, 20% ethanol elution part, 50% ethanol elution part, 95% ethanol elution part; Choosing described 5% ethanol elution part, adopt high performance liquid chromatography to separate preparation to it, is C in chromatographic column
18the methanol aqueous solution that post, mass concentration are 30% is that moving phase, volumetric flow rate are 2.0 mLmin
-1, to detect wavelength be that 260 nm, column temperature are to carry out isocratic elution under the condition of 25 DEG C, obtains compound S wertiridoid A.
In reed leaf Herba Swertiae bimaculatae as claimed in claim 1 antineoplastic component Swertiridoid A in the application of preparing in antitumor drug, it is characterized in that: described antineoplastic component Swertiridoid A is equipped with medicinal stone and acceptable carrier pharmaceutically or on physiology, is prepared into any formulation in pharmaceutics with conventional preparation technology.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999536A (en) * | 2006-12-29 | 2007-07-18 | 中国科学院长春应用化学研究所 | Process of simultaneously extracting and detecting cornus cyclic olefine ether terpinyl side like extractive |
| EP1837027A1 (en) * | 2006-03-08 | 2007-09-26 | Council of Scientific and Industrial Research | Iridoid glycoside composition |
| CN100344643C (en) * | 2005-07-21 | 2007-10-24 | 中国科学院昆明植物研究所 | Method for preparing gentiamarin |
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2012
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100344643C (en) * | 2005-07-21 | 2007-10-24 | 中国科学院昆明植物研究所 | Method for preparing gentiamarin |
| EP1837027A1 (en) * | 2006-03-08 | 2007-09-26 | Council of Scientific and Industrial Research | Iridoid glycoside composition |
| CN100999536A (en) * | 2006-12-29 | 2007-07-18 | 中国科学院长春应用化学研究所 | Process of simultaneously extracting and detecting cornus cyclic olefine ether terpinyl side like extractive |
Non-Patent Citations (2)
| Title |
|---|
| Kenzo Chiba，等.New physiological function of secoiridoids: neuritogenic activity in PC12h cells.《J Nat Med》.2010,第65卷第186–190页. * |
| 周永福,等.川西獐牙菜的化学成分研究(Ⅱ).《云南民族大学学报(自然科学版)》.2011,第20卷(第1期),第14-16页. * |
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Effective date of registration: 20200603 Address after: No. 6, Jianye Road, Xinwei Industrial Park, Weishi County, Kaifeng City, Henan Province 475000 Patentee after: Henan Bifu Pharmaceutical Co., Ltd Address before: 810001 Qinghai province Xining City West Street No. 59 Patentee before: Northwest Institute of Plateau Biology, Chinese Academy of Sciences |