CN107056856A - A kind of new iridoid glycoside compound and its production and use - Google Patents
A kind of new iridoid glycoside compound and its production and use Download PDFInfo
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- CN107056856A CN107056856A CN201710241881.XA CN201710241881A CN107056856A CN 107056856 A CN107056856 A CN 107056856A CN 201710241881 A CN201710241881 A CN 201710241881A CN 107056856 A CN107056856 A CN 107056856A
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention discloses a kind of new iridoid glycoside compound and its production and use, it is related to pharmaceutical technology field, dried leaf specifically using Verbenaceae callicarpa nudiflora (Callicarpa nudiflora Hook.) is raw material, a kind of new iridoid glycoside compound is separated to through certain preparation process, referred to as callicarpa nudiflora glycosides A1, the compound is to report first, callicarpa nudiflora glycosides A1 is through superconduction NMR spectrum, the multiple means such as mass spectrum detect that it is C to determine its molecular formula24H30O12.Molecular weight is 510, and chemical structural formula is formula (I).The invention discloses callicarpa nudiflora glycosides A1 physicochemical property, optical activity, and external activity screening has been carried out using mtt assay, as a result show there is obvious inhibitory action to human lung adenocarcinoma cell and Proliferation of Human Ovarian Cell, can as the antineoplastic of development of new lead compound, can also be used as the medicine for developing the various common multiple cancers of clinic for the treatment of.。
Description
Technical field
The present invention relates to pharmaceutical technology field, and in particular to isolated a kind of cyclenes ether from callicarpa nudiflora dried leaf
Terpene glycoside compound, containing preparation method and use.
Background technology
Callicarpa nudiflora (Callicarpa nudiflora Hook.) is Verenaceae (Verbenaceae) Callicarpa
(Callicarpa L.) plant, also known as：Nakedflower beautyberry branchlet and leaf, successively red, meal soup leaf, spend tea in vain, cauline leaf or complete stool are used as medicine, and main product is in me
The ground such as state Hainan, Guangdong, Guangxi, Jiangxi, are distributed in by level land to the hillside, valley floor, small stream of 1200 meters of height above sea level in woods or in shrubbery.
Callicarpa nudiflora is a kind of large property authentic medicinal herbs in Hainan, while being also one of Nationality in Hainan Province doctor's medicinal herbs most in use, is stopped with antibacterial
Blood, eliminating inflammation and expelling toxin, eliminating stasis to subdue swelling, wind-expelling and dispelling dampness, immune effect of enhancing is usually used in treatment purulent inflammation, acute infective liver
The disease such as inflammation, pulmonary tuberculosis hemoptysis, gastrointestinal bleeding, respiratory tract and hemorrhage of digestive tract, traumatic bleeding, burn is controlled in external application and wound goes out
The diseases such as blood.
Callicarpa nudiflora middle chemical composition is mainly flavonoids, terpene, Phenylpropanoid Glycosides class, volatile oil etc., and terpenoid is
One of callicarpa nudiflora middle main Types composition, mainly there is iridoids, Diterpenes, triterpenes from structure type.From nakedflower
The iridoids got in Japanses beauty-berry has nudifloside, linearoside, 7-O-E-p-coumaroyl-8-epi-
loganic acid、7-O-E-p-coumaroyl-gardoside。
It is callicarpa nudiflora to begin to carry《Bencao Shiyi》, it is with a long history, widely used, evident in efficacy, the title of Hainan black powder is have, and
The medicinal material is China is distributed more widely, abundance, with good value of exploiting and utilizing, for convenience of patient using the medicinal material
It is processed into a variety of single preparations such as tablet, dispersible tablet, capsule, mixture, granule and suppository.
The content of the invention
Goal of the invention：
It is an object of the present invention to provide obtain a new iridoid glycoside compound from callicarpa nudiflora middle extraction
Callicarpa nudiflora glycosides A1.
It is a further object to provide the callicarpa nudiflora glycosides A1 of above-mentioned iridoid glycoside compound preparation method.
A further object of the present invention be to provide the callicarpa nudiflora glycosides A1 of above-mentioned iridoid glycoside compound prepare cancer and/
Or the application in antineoplastic.
2nd, technical scheme：The present invention extracts separation first from callicarpa nudiflora (Callicarpa nudiflora Hook.)
A kind of iridoid glycoside, entitled callicarpa nudiflora glycosides A1 are obtained, its molecular formula is C24H30O12, its chemical structural formula is as follows：
A kind of callicarpa nudiflora glycosides A1 of iridoid glycoside compound preparation method, its step is successively：
(1) ethanol heating and refluxing extraction：Dry callicarpa nudiflora leaf, uses ethanol heating and refluxing extraction after crushed, filtering,
Obtain ethanol extract；
(2) ethanol extract is concentrated：Ethanol extract is concentrated under reduced pressure to obtain ethanol extract；
(3) extraction and concentration：Ethanol extract distilled water dissolves, and is extracted, protected with ethyl acetate, water-saturated n-butanol successively
Water-saturated n-butanol extraction phase is stayed, water-saturated n-butanol extract is obtained, water-saturated n-butanol extract is concentrated under reduced pressure, positive fourth is obtained
Alcohol medicinal extract；
(4) medicinal extract rough segmentation：It is fitted into n-butanol medicinal extract and silica gel mixed sample in apparatus,Soxhlet's, successively with ethyl acetate, second
Acetoacetic ester-acetone (1:1), acetone, acetone-methanol (1:1), methanol heating and refluxing extraction, acetone extract is concentrated under reduced pressure, and is obtained
Acetone medicinal extract；
(5) column chromatography for separation：By acetone medicinal extract and silica gel mixed sample, chromatographic column, the mesh of silica gel granularity 200~300, with two are transferred to
Chloromethanes-meoh eluate elution, thin layer detection is carried out by eluent, and concentration merges similar eluting fraction, obtains 15 cuts, the
4 cuts and C18Sample is mixed, middle pressure reversed phase column chromatography is transferred to, with acetonitrile-water eluent gradient elution, eluent is subjected to thin layer inspection
Survey, concentration merges similar eluting fraction, obtains callicarpa nudiflora glycosides A1 crude products；
(6) purifying of monomeric compound：Callicarpa nudiflora glycosides A1 crude products obtain the callicarpa nudiflora of the present invention through recrystallization purifying
Glycosides A1.
Ethanol volumetric concentration is 80% in above-mentioned processing step (1).
Eluant, eluent is methylene chloride-methanol in above-mentioned processing step (5), and chloroform is with methanol volume proportion：15:1 or 10:
1 or 6:1 or 4:1 or 2:1；In acetonitrile-water eluant, eluent, acetonitrile volumetric concentration is 20%~40%.
Recrystallization solvent is ethyl acetate, acetone or methanol in above-mentioned processing step (6).
Product of the present invention is detected through multiple means such as superconduction NMR spectrum, mass spectrums, it is determined that callicarpa nudiflora glycosides A1's
Molecular formula C24H30O12, chemical structural formula：
Product is callicarpa nudiflora, and glycosides A1 is pale yellow powder, is dissolved in ethyl acetate, acetone, n-butanol, pyridine, methanol etc. organic
Reagent, fusing point is 196~197 DEG C, optical activity [α]20 D- 46 (c 0.1, MeOH), UV (CH3OH)λmax228nm and 312nm.
Experiment proves callicarpa nudiflora glycosides A1 1 × 10-8Mol/L~1 × 10-5To human lung adenocarcinoma cell and people's ovum during mol/L
Nest cancer cell has obvious inhibitory action, IC50Respectively 0.27 μM and 0.14 μM.
Brief description of the drawings
Fig. 1 is callicarpa nudiflora glycosides A1 preparation technology schematic flow sheet, has illustrated callicarpa nudiflora glycosides A1 preparation step
Suddenly it is：(1) alcohol reflux is extracted；(2) ethanol extract is concentrated；(3) ethyl acetate, extracting n-butyl alcohol and concentration；(4) medicinal extract is thick
Point；(5) column chromatography for separation；(6) purify.
Fig. 2 is ultra performance liquid chromatography-quadrupole time-of-flight mass spec-trometry (UPLC-Q-TOF-MS) figure, illustrates that nakedflower is purple
Pearl glycosides A1 molecular weight；
Fig. 3 is nuclear magnetic resonance1H NMR spectras, illustrate hydrogen in callicarpa nudiflora glycosides A1 structures (H-C=C-H ,-C=C-H ,-
CH3,-CH2OH-, Glc-H etc.) ownership；
Fig. 4 is nuclear magnetic resonance13C NMR spectras, illustrate carbon (- C=C- ,-CH in callicarpa nudiflora glycosides A1 structures2- O- ,-O-
CH-O- ,-CH-OH etc.) ownership；
Fig. 5 is nuclear magnetic resonance hsqc spectrum figure, illustrates the ownership of carbon related in callicarpa nudiflora glycosides A1 structures and hydrogen；
Fig. 6 is nuclear magnetic resonance HMBC spectrograms, illustrates glucose and aglycon and caffeoyl in callicarpa nudiflora glycosides A1 structures
The link position of base and glucose；
Fig. 7 is nuclear magnetic resonance NOESY spectrograms, illustrates the relative structure of 1 and 6 hydroxyl in callicarpa nudiflora glycosides A1 structures
Type.
Embodiment
With reference to embodiment, the present invention is further elaborated.The following embodiments of mandatory declaration are to be used to illustrate the present invention
Rather than limitation of the present invention.The simple modifications carried out according to the essence of the present invention to the present invention belong to application claims and protected
The scope of shield.
Hydraulic fluid phase preparative chromatograph (Switzerland in the series of high efficiency liquid chromatograph of Shimadzu 2010 (Japanese Shimadzu Corporation), BUCHi
BUCHI Labortechnik AG), Waters series of high efficiency liquid chromatograph (including Waters 600Control, PAA2996 type diode arrays
Detector, Waters 717Plus automatic samplers, Empower chem workstations) (Waters, US), Agilent 1200
The preparative high-performance liquid chromatographic instrument of type half, Sartoris BP211A types electronic balance (German Sai Tuolisi groups), EYELA SB-
1000 Rotary Evaporators (Japanese EYELA companies), electric-heated thermostatic water bath (Shanghai leap medical apparatus and instruments factory), UV-260 light splitting light
Degree meter (Japanese Shimadzu Corporation), the NMR spectrometer with superconducting magnet of Varian UNITY INOVA 600 (Varian companies of the U.S.), Xevo
G2Q-Tof time of-flight mass spectrometers (Waters, US), Autopol IV-T/V polarimeters (AKSH companies of the U.S.), RY-
1G melting point detectors (Chinese Tianjin daylight optical instrument Co., Ltd), C18Reverse phase filler is YMC productions, column chromatography silica gel, thin
Layer chromatographic silica gel produces for Haiyang Chemical Plant, Qingdao.
Acetonitrile is chromatographically pure, and water is Wahaha Pure Water, and other reagents are that analysis is pure.
Embodiment 1：The callicarpa nudiflora callicarpa nudiflora glycosides A1 of middle iridoid glycoside compound extraction separation method：
It is callicarpa nudiflora to pick up from Wuzhishan Mountain in Hainan city in September, 2014, detect Guiping master research institute Yuan through Jiangxi Province's medicine
Pharmacist is appointed to be accredited as the callicarpa nudiflora Callicarpa nudiflora Hook. of Verbenaceae leaf, sample is retained in Jiangxi
Save medicine detection research institute Specimen Room (sample number：LHZZ20140926).
Callicarpa nudiflora glycosides A1 preparation process is as follows successively：
(1) ethanol heating and refluxing extraction：Callicarpa nudiflora dried leaf (15.0Kg) is crushed, and is heated to reflux carrying with 80% ethanol
Take 3 times, filter, obtain 80% ethanol extract；
(2) 80% ethanol extract is concentrated：80% ethanol extract is concentrated under reduced pressure to obtain ethanol extract 2200g, in decompression
Ethanol is reclaimed in concentration process；
(3) extraction and concentration：80% ethanol extract is dissolved in distilled water, then 3 times, water saturation is extracted with ethyl acetate
Extracting n-butyl alcohol 3 times, obtains water-saturated n-butanol extract, and water-saturated n-butanol extract is concentrated under reduced pressure to obtain n-butanol medicinal extract
486g, reclaims n-butanol during being concentrated under reduced pressure；
(4) medicinal extract rough segmentation：It is fitted into n-butanol medicinal extract and silica gel mixed sample in apparatus,Soxhlet's, successively with ethyl acetate, second
Acetoacetic ester-acetone (1:1), acetone, acetone-methanol (1:1), methanol heating and refluxing extraction, acetone extract is concentrated under reduced pressure, and is obtained
Acetone medicinal extract 87g, reclaims acetone during being concentrated under reduced pressure；
(5) column chromatography for separation：By acetone medicinal extract and silica gel mixed sample, chromatographic column, the mesh of silica gel granularity 200~300, with two are transferred to
Chloromethanes-meoh eluate gradient elution, dichloromethane is 3 with methanol volume ratio:1, eluent is subjected to thin layer detection, concentration
Merge similar eluting fraction, obtain 15 cuts, the 4th cut and C18Sample is mixed, middle pressure reversed phase column chromatography is transferred to, is washed with acetonitrile-water
De- liquid gradient elution, acetonitrile volumetric concentration is 20%~40%, and eluent is carried out into thin layer detection, and concentration merges similar elution and evaporated
Point, obtain callicarpa nudiflora glycosides A1 crude products；
(6) purifying of monomeric compound：Callicarpa nudiflora glycosides A1 crude product re-crystallizing in ethyl acetate, obtains nakedflower of the invention purple
Pearl glycosides A1 (58mg).
Embodiment 2：Iridoid glycoside compound is callicarpa nudiflora glycosides A1 Structural Identifications
Callicarpa nudiflora glycosides A1 physicochemical property is as follows：Pale yellow powder, be dissolved in ethyl acetate, acetone, n-butanol, pyridine,
The organic reagents such as methanol, fusing point is 196~197 DEG C, optical activity [α]20 D- 46 (c 0.1, MeOH), UV (CH3OH)λmax
228nm and 312nm.Ultra performance liquid chromatography-quadrupole time-of-flight mass spec-trometry provides the [M of quasi-molecular ion peak m/z 533.1635
+Na]+(calcd for C24H30O12Na, 533.1635), with reference to1H-NMR and13C-NMR spectrums determine that its molecular formula is
C24H30O12。1H with13C NMR datas are shown in Table 1, meanwhile, by determining two dimension H-C Correlated Spectroscopies (HSQC), the long-range Correlated Spectroscopies of H-C
(HMBC) and rotating coordinate system NOE (ROESY), it is determined that all carbon atoms and the signals assignment of hydrogen atom and the compound
Chemical constitution.Chemical structural formula is as follows：
Table 1 is callicarpa nudiflora glycosides A1 hydrogen spectrum and carbon modal data table (δ in ppm, J in Hz)
Note：INOVA 600MHz；δ chemical shift unit ppm,1H-NMR and13C-NMR test solvents are DMSO；Nuclear-magnetism is total to
The ownership of signal of shaking is completed on the basis of the two-dimensional spectrums such as HSQC, HMBC.
Embodiment 3：Iridoid glycoside compound is callicarpa nudiflora glycosides A1 anti tumor activity in vitro test
Growth of tumour cell inhibiting rate (%)=(1- experimental ports measured value/control wells measured value) × 100%
Test philosophy：Mtt assay：Existed in the mitochondria of living cells with NAAP (nicotinamide-adenine dinucleotide phosphate,
Codehydrogenase Ⅱ) related dehydrogenase, can be by the tetrazolium bromide MTT (3- (4,5-Aimethylthiazo-2-yl) -2,5- of yellow
Aiphenyl tetrazolium bromiAe) it is reduced to this enzyme in insoluble bluish violet formazan (Formanzan), dead cell
Disappear, MTT is not reduced.Optical density (OA), light can be detected at 570nm with ELIASA after being dissolved with DMSO (dimethyl sulfoxide (DMSO))
Density value is directly proportional to viable count.
Cell line used is：A549 (human lung adenocarcinoma cell) and A2780 (Proliferation of Human Ovarian Cell).
Test method：Mtt assay：Take the logarithm growth period cell, single cell suspension is fully blown and beaten into after digestion, diluted after counting
Into 1 × 104Cell/mL, is inoculated in 96 well culture plates, 100 μ L/ holes.Each 4-5 concentration rank of sample design, Ran Hou
Add the culture medium of 100 μ L various concentrations rank samples in experimental port, parallel 3 hole of each concentration rank.The bodies such as control group addition
Product solvent.96 well culture plates are placed in 37 DEG C, 5%CO2After being cultivated 96 hours in saturated humidity incubator, nutrient solution is discarded, often
Hole is added at the MTT containing 0.20mg/mL of fresh configuration serum free medium, 37 DEG C continue to cultivate 4 hours after, centrifuge, remove
Supernatant.150 μ L DMSO dissolving Formazan precipitations are added per hole, putting concussion on micro oscillator makes it fully molten for 5 minutes
Solution.Rate mapping processed at 570nm is determined on the type ELIASAs of BIORAA 550 to obtain measuring curve, and the half of medicine is read from curve
Number inhibition concentration (IC50) value.
The inhibitory action of table 2 is callicarpa nudiflora glycosides A1 to A549 (human lung adenocarcinoma cell)
| Sample | Concentration (mol/L) | Inhibiting rate (%) | IC50(μM) |
| Taxol (positive) | 1×10-5 | 95.3 | 0.073 |
| 1×10-6 | 91.8 | ||
| 1×10-7 | 77.3 | ||
| 1×10-8 | 23.6 | ||
| Callicarpa nudiflora glycosides A1 | 1×10-5 | 90.4 | 0.27 |
| 1×10-6 | 74.0 | ||
| 1×10-7 | 23.3 | ||
| 1×10-8 | 10.5 |
The inhibitory action of table 3 is callicarpa nudiflora glycosides A1 to A2780 (Proliferation of Human Ovarian Cell)
Summarize：Callicarpa nudiflora glycosides A1 has inhibitory action to human lung adenocarcinoma cell and Proliferation of Human Ovarian Cell, available for developing
The medicine for the treatment of cancer or tumour.
Claims (7)
1. it is separated to one kind from Verbenaceae callicarpa nudiflora (Callicarpa nudiflora Hook.) dried leaf
New iridoid glycoside compound, entitled callicarpa nudiflora glycosides A1, molecular formula is C24H30O12, its chemical structural formula is as follows：
。
2. according to the preparation method of the callicarpa nudiflora glycosides A1 described in claim 1, it is characterized in that preparation process is as follows successively：
(1) ethanol heating and refluxing extraction：Dry callicarpa nudiflora leaf, uses ethanol heating and refluxing extraction after crushed, filtering, obtains second
Alcohol extract；
(2) ethanol extract is concentrated：Ethanol extract is concentrated under reduced pressure to obtain ethanol extract；
(3) extraction and concentration：Ethanol extract distilled water dissolves, and is extracted successively with ethyl acetate, water-saturated n-butanol, retains water
Saturation extracting n-butyl alcohol phase, obtains water-saturated n-butanol extract, and water-saturated n-butanol extract is concentrated under reduced pressure, and obtains n-butanol leaching
Cream；
(4) medicinal extract rough segmentation：It is fitted into n-butanol medicinal extract and silica gel mixed sample in apparatus,Soxhlet's, successively with ethyl acetate, acetic acid second
Ester-acetone (1:1), acetone, acetone-methanol (1:1), methanol heating and refluxing extraction, acetone extract is concentrated under reduced pressure, and obtains acetone
Medicinal extract；
(5) column chromatography for separation：By acetone medicinal extract and silica gel mixed sample, chromatographic column is transferred to, the mesh of silica gel granularity 200~300 uses dichloromethane
Alkane-meoh eluate elution, thin layer detection is carried out by eluent, and concentration merges similar eluting fraction, obtains 15 cuts, the 4th
Cut and C18Sample is mixed, middle pressure reversed phase column chromatography is transferred to, with acetonitrile-water eluent gradient elution, eluent is subjected to thin layer detection,
Concentration merges similar eluting fraction, obtains callicarpa nudiflora glycosides A1 crude products；
(6) purifying of monomeric compound：Callicarpa nudiflora glycosides A1 crude products obtain the callicarpa nudiflora glycosides of the present invention through recrystallization purifying
A1。
3. preparation method according to claim 2, it is characterized in that ethanol volumetric concentration is 60%~95% in step (1).
4. preparation method according to claim 2, it is characterized in that eluant, eluent is methylene chloride-methanol, dichloro in step (5)
Methane is with methanol volume proportion：15:1 or 10:1 or 6:1 or 4:1 or 2:1；Gradient elution agent is acetonitrile-water, and acetonitrile volume is dense
Spend for 20%~40%.
5. preparation method according to claim 2, it is characterized in that recrystallization solvent is ethyl acetate, acetone in step (6)
Or methanol.
6. according to the purposes of the callicarpa nudiflora glycosides A1 described in claim 1, it is characterized in that preparing Antilung gland cancer medicine or anti-ovum
Application in nest cancer drug.
7. callicarpa nudiflora glycosides A1 according to claim 6 is in Antilung gland cancer cell cancer or ovarian cancer resistance medicine medicine is prepared
Using it is characterized in that callicarpa nudiflora glycosides A1 is 1 × 10-8Mol/L~1 × 10-5To human lung adenocarcinoma cell and people's ovum during mol/L
Nest cancer cell shows cytotoxic activity, IC50Respectively 0.27 μM and 0.14 μM.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112194692A (en) * | 2020-09-15 | 2021-01-08 | 诚简科技(深圳)有限公司 | Nudicatalpol A and Nudicatalpol B compounds and application thereof |
| CN113797240A (en) * | 2021-10-21 | 2021-12-17 | 河南省纳普生物技术有限公司 | Application of total polyphenol extract of tung tree in preparation of calcium ion channel inhibiting medicine |
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| CN101486743A (en) * | 2008-01-18 | 2009-07-22 | 北京卓凯生物技术有限公司 | Novel iridoid compound with anti-Alzheimer's disease function |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112194692A (en) * | 2020-09-15 | 2021-01-08 | 诚简科技(深圳)有限公司 | Nudicatalpol A and Nudicatalpol B compounds and application thereof |
| CN113797240A (en) * | 2021-10-21 | 2021-12-17 | 河南省纳普生物技术有限公司 | Application of total polyphenol extract of tung tree in preparation of calcium ion channel inhibiting medicine |
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Effective date of registration: 20201230 Address after: 330000 No. 490 Xinqi Zhou Sanghai South Road, North Suburb of Nanchang City, Jiangxi Province Patentee after: Jiangxi Xinglin Baima Pharmaceutical Co.,Ltd. Address before: 330029 No. 1566, Beijing East Road, Jiangxi, Nanchang Patentee before: JIANGXI INSTITUTE FOR DRUG CONTROL |
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Address after: No. 231, Guoyao North Avenue, Xinqi Zhou Management Office, Ganjiang New District, Nanchang City, Jiangxi Province 330000 Patentee after: Jiangxi Xinglin Baima Pharmaceutical Co.,Ltd. Address before: 330000 No. 490 Xinqi Zhou Sanghai South Road, North Suburb of Nanchang City, Jiangxi Province Patentee before: Jiangxi Xinglin Baima Pharmaceutical Co.,Ltd. |
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