CN105399656B - A kind of iso-indoles alkaloid compound and preparation method and application - Google Patents
A kind of iso-indoles alkaloid compound and preparation method and application Download PDFInfo
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- CN105399656B CN105399656B CN201510959586.9A CN201510959586A CN105399656B CN 105399656 B CN105399656 B CN 105399656B CN 201510959586 A CN201510959586 A CN 201510959586A CN 105399656 B CN105399656 B CN 105399656B
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- indoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
Abstract
The invention discloses a kind of iso-indoles alkaloid compound, the iso-indoles alkaloid compound is from the Dai nationality's medicinal plant pulse family wing pod Cassia tora（Cassia alata L.）Bark is isolated, is named as:The ketone of 56 isopentene group iso-indoles of (methylol) 2 methyl 1, the one of 6 prenyl isoindolin of entitled 5 (hydroxymethyl) 2 methyl of English 1, its molecular formula is C15H19NO2, there are following structures：The iso-indoles alkaloid compound preparation method is with wing pod Cassia tora（Cassia alata L.）Bark is raw material, extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography it is isolated.The iso-indoles alkaloid compound shows there is good inhibiting effect to tobacco mosaic virus (TMV) through active testing.The compounds of this invention structure is novel, has preferable poisonous activity, can be as the lead compound of resisting tobacco mosaic virus medicine.
Description
Technical field
The invention belongs to technical field of phytochemistry, and in particular to one kind comes from iso-indoles in the wing pod Cassia tora bark of Yunnan and given birth to
Thing alkaloid compound and preparation method and application.
Background technology
Wing pod Cassia tora（Cassia alataL. ）For the kind of species Cassia subordinate.American torrid zone area is originated in, extensively
Whole world torrid areas is distributed in, Guangdong and south of Yunnan area are distributed in China.The flower color is gorgeous, there is higher view and admire
Value, is commonly used for Landscape Trees.Meanwhile it is also important medicinal plant, have the function that it is antifungal, can be used for control
Skin disease is treated, is perfumed soap, shampoo, one of the conventional raw material of washing lotion.The saponin that its seed contains, which can be used as, drives away intestines
The pest repellant of road parasite；Its leaf decocting liquid is often used to treat hypertension, stomach trouble, fever, asthma, venomous snake bite, venereal disease etc..
At present domestic and foreign scholars wing pod Cassia tora was carried out some research, the chemical composition mainly reported have chromone, flavones,
The class compound such as terpene, steroidal, alkaloid.Isoindoles alkaloid is the important component of composition of alkaloids, such biology
Alkali quantity is more, and structure type is complicated, and medical value protrudes, and has many physiologically actives.To make full use of China's abundant
Resource, new bioactive natural product is further found, we are studied wing pod Cassia tora chemical composition, and are therefrom separated to
One new iso-indoles alkaloid, the compound have obvious activity of resisting tobacco mosaic virus.
The content of the invention
The first aspect of the present invention is to provide a kind of structure novel iso-indoles alkaloid compound, and the second purpose exists
In the preparation method for providing the iso-indoles alkaloid compound；3rd purpose is to provide the iso-indoles alkaloids
Application of the compound in resisting tobacco mosaic virus medicine is prepared.
The first object of the present invention is achieved in that the iso-indoles alkaloid compound, is from wing pod Cassia tora
（Cassia alataL.）It is isolated in bark, it is named as 5- (methylol) -2- methyl -6- isopentene groups-iso-indoles -1-
Ketone, its molecular formula are C15H19NO2, there are following structures：
The second object of the present invention is achieved in that the iso-indoles alkaloid compound with wing pod Cassia tora
(Cassia alataL.) bark is raw material, is extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separating step, specifically
For：
A, medicinal extract extracts：By wing pod Cassia tora（Cassia alataL.）Bark is crushed to 20 ~ 40 mesh, organic with 60 ~ 100%
Solvent soaking simultaneously extracts 2 ~ 4 times, and the h of 12 h ~ 72, merges extract solution, filtering, be concentrated under reduced pressure into medicinal extract every time；
B, silica gel column chromatography：After medicinal extract is dissolved with organic solvent, with 60 ~ 120 mesh silica gel of the medicinal extract weight than 1 ~ 1.6 times of amount
Sample is mixed, then silica gel column chromatography is carried out with 160 ~ 300 mesh silica gel dry column-packings of the medicinal extract weight than 2 ~ 5 times of amounts；With volume proportion 10:
0~5:5 chloroform-methanol progress gradient elution, the 9 of eluent:1 part silica gel column chromatography continues to separate, and is matched somebody with somebody with volume
Than 15:1-2:1 chloroform-acetone solution carries out gradient elution, and its priority is divided into 6 parts, collects each several part eluent
And concentrate；
C. high pressure liquid chromatography separates：The 6 of step B eluent:4 parts are further isolated and purified i.e. with high pressure liquid chromatography
Obtain described isoquinoline alkaloids bases compound.
The structure of new iso-indoles alkaloid compound prepared by method described above is to determine to come by the following method
's：
The compounds of this invention is light yellow solid；Ultraviolet spectra（Solvent is methanol）,λ max (logε）：210 (4.05)、
260 (3.68)、296 (3.04)；Infrared spectrum（Pressing potassium bromide troche）νmax：3386、2938、1670、1610、1533、1468、
1355、1267、1131、1074、837、759 cm–1；High resolution mass spectrum（HRESIMS）Show the compounds of this invention quasi-molecular ion
Peakm/z 268.1319 [M+Na]+（Calculated value 268.1313）.Its infrared spectrum, which is shown in compound, hydroxyl (3386 cm-1), carbonyl (1670 cm-1), and aromatic ring (1610,1533,1468 cm-1) signal, ultraviolet spectra is in 210,260,296 nm
There is absorption maximum to also confirm that and aromatic ring structure in compound be present.Compound1H- and13C-NMR spectrums (table -1) show that it contains
There are 15 carbon and 19 hydrogen, including 1 iso-indoles -1- ketone parent nucleus (C-1 ~ C-7a, H-3, H-4 and H-6), an isoamyl
Alkenyl (C-1' ~ C-5', H-1', H-2', H-4' and H-5'), a methylol (C-6', H-6'), and N- methyl (C-7',
H-7').H in compound2- 3 and C-1, C-3a, C-4, C-7a, C-7', H-4 and C-3, H-7 and C-1, H2- 7' and C-1, C-
3 HMBC (figure -3) further confirms iso-indoles -1- ketone parent nucleus be present in compound.The framework types of compound are confirmed
Afterwards, substituting group position further can be determined by HMBC Correlated Spectroscopies；According to H2- 1 ' and C-5, C-6, C-7, H-2 ' and C-6's
HMBC correlations can determine that isopentene group is substituted in C-6 positions；Methylol is substituted in C-5 positions can be by methylol hydrogen (H2- 6 ') and
C-4, C-5, C-6 HMBC are related to be confirmed.Methyl is connected with nitrogen-atoms and by methyl hydrogen (H3And C-1, C-3, and H- -7 ')
3 confirmations related to C-7 HMBC.So far the structure of compound is determined, the compound is named as：5- (methylol) -2-
Methyl -6- isopentene groups-iso-indoles -1- ketone；5-(hydroxymethyl)-2-methyl-6-prenylisoindolin-1-
one。
The third object of the present invention be achieved in that will the iso-indoles alkaloid compound be applied to anti-tobacco
The preparation of mosaic virus medicine.
The compounds of this invention is separated first, is defined as iso-indoles by nuclear magnetic resonance and measuring method of mass spectrum
Alkaloid compound, and characterize its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches
36.8%, there is good activity of resisting tobacco mosaic virus, it is higher than the relative inhibition (31.5%) of positive reference substance Nanning mycin.
The compound that result above discloses the present invention has good application prospect in resisting tobacco mosaic virus medicine is prepared.The present invention
The simple activity of compound structure preferably, can be used for anti-tobacco as the guiding compound of resisting tobacco mosaic virus medicament research and development
Mosaic virus pharmaceutical preparation is researched and developed.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of the compounds of this invention.
Fig. 2 is the proton nmr spectra of the compounds of this invention.
Fig. 3 is the main HMBC relevant indicators of the compounds of this invention.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is further illustrated, but the present invention is not subject in any way
Limitation, based on present invention teach that any conversion or improvement made, each fall within protection scope of the present invention.
The present invention is raw materials used not to be limited by area and kind, the wing pod Cassia tora in any source（Cassia alataL.）
Bark can realize the present invention, below with from the wing pod Cassia tora in Yunnan（Cassia alataL.）Bark is raw material pair
The present invention is described further.
Unless otherwise indicated, the percentage employed in the present invention is mass percent.
Iso-indoles alkaloid compound of the present invention, it is from wing pod Cassia tora（Cassia alata L.）In bark
It is isolated, 5- (methylol) -2- methyl -6- isopentene groups-iso-indoles -1- ketone is named as, its molecular formula is C15H19NO2,
With following structures：
The preparation method of iso-indoles alkaloid compound of the present invention, be with wing pod Cassia tora (Cassia alata
L.) bark is raw material, is extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separating step, is specially：
A, medicinal extract extracts：By wing pod Cassia tora（Cassia alataL.）Bark is crushed to 20 ~ 40 mesh, organic with 60 ~ 100%
Solvent soaking simultaneously extracts 2 ~ 4 times, and the h of 12 h ~ 72, merges extract solution, filtering, be concentrated under reduced pressure into medicinal extract every time；
B, silica gel column chromatography：After medicinal extract is dissolved with organic solvent, with 60 ~ 120 mesh silica gel of the medicinal extract weight than 1 ~ 1.6 times of amount
Sample is mixed, then silica gel column chromatography is carried out with 160 ~ 300 mesh silica gel dry column-packings of the medicinal extract weight than 2 ~ 5 times of amounts；With volume proportion 10:
0~5:5 chloroform-methanol progress gradient elution, the 9 of eluent:1 part silica gel column chromatography continues to separate, and is matched somebody with somebody with volume
Than 15:1-2:1 chloroform-acetone solution carries out gradient elution, and its priority is divided into 6 parts, collects each several part eluent
And concentrate；
C. high pressure liquid chromatography separates：The 6 of step B eluent:4 parts are further isolated and purified i.e. with high pressure liquid chromatography
Obtain described isoquinoline alkaloids bases compound.
Organic solvent is the mixture of ethanol, methanol or acetone and water in the step A.
The weight of organic solvent and bark ratio is 1.5 ~ 4 in the step A:1.
The organic solvent of the step B is pure methanol, straight alcohol or pure acetone.
Chloroform-methanol volume proportion in the step B is 10:0、9:1、8:2、7:3、6:4 and 5:5.
It is using the mm of 21.2 mm × 250 5 that the step C mesohigh liquid chromatogram, which isolates and purifies,μM C18Chromatogram
Post, mobile phase are 52 wt% methanol aqueous solution, and flow rate of mobile phase is 15 mL/min, and UV-detector Detection wavelength is
295nm, each sample introduction 60 ~ 150μL, 22.8 min chromatographic peak is collected, is evaporated after repeatedly adding up.
The step C mesohigh liquid chromatogram refers to the reversed-phase preparative chromatography for making service pressure in 5-15 Mpa.
Material after the step C mesohigh liquid chromatogram isolates and purifies is dissolved with methanol again, then using methanol solution as
Mobile phase, separated with gel filtration chromatography, further to isolate and purify.
Application of the iso-indoles alkaloid compound of the present invention in resisting tobacco mosaic virus medicine is prepared.
Embodiment 1
Wing pod Cassia tora bark used is adopted in Yunnan Dehong.Bark is sampled into 3.2 kg crushing and extracts 3 with 70% acetone/water
It is secondary, 24 h are extracted every time, and extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains the g of medicinal extract 158.Medicinal extract is with weight than 180 g
Pure methanol dissolving after use 200 g the thick silica gel mixed sample of 80 mesh, 1.0 kg 160 mesh silica gel dress post carry out silica gel column chromatography, use
Volume proportion is 10:0、9:1、8:2、7:3、6:4、5:5 chloroform-methanol gradient elution, will volume proportion be wherein 9:1 chlorine
Imitation-carbinol elution fraction is further with 15:1-2:A series of 1 chloroform-acetone solutions carry out gradient elution, and its priority is divided
Into 6 parts, wherein 6:4 elution fractions pacify the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half separation, water-soluble with 52% methanol
Liquid is mobile phase, Zorbax SB-C18 It is stationary phase that (21.2 × 250 mm, 5 μm), which prepare post, flow rate of mobile phase 15
ML/min, UV-detector Detection wavelength are 295 nm, each μ L of sample introduction 125, collect the chromatogram that the residence time is 22.8 min
Peak, it is evaporated after repeatedly adding up, produces iso-indoles alkaloid compound crude product of the present invention；In order to further purify, also
Products therefrom can be dissolved with methanol solution, then using methanol solution as mobile phase, with Sephadex LH-20 gel filtration chromatographies
Separation, produce the noval chemical compound of higher purity.
Embodiment 2
Wing pod Cassia tora bark derives from In Xishuangbanna of Yunnan, and bark is sampled into 3.6 kg choppings, 3 are extracted with 95% ethanol
It is secondary, 48 h are extracted every time, and extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains the g of medicinal extract 140.Medicinal extract is with weight than 2.0 times
Silica gel column chromatography is carried out with the 150 g thick silica gel mixed sample of 80 mesh, 0.9 kg 200 mesh silica gel dress post after the pure methanol dissolving of amount,
It is 10 with volume proportion:0、9:1、8:2、7:3、6:4、5:5 chloroform-methanol gradient elution, will be 9 wherein with volume proportion:1
Chloroform-methanol elution successively be divided into 6 parts, wherein 6:4 elution fractions pacify prompt logical sequence 1,100 half and prepare high-efficient liquid phase color
Spectrum separation, using 52% methanol aqueous solution as mobile phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μm) prepare post and are
Stationary phase, flow rate of mobile phase are 15 mL/min, and UV-detector Detection wavelength is 295 nm, and each μ L of sample introduction 100, collection stops
The chromatographic peak that the time is 22.8 min is stayed, is evaporated after repeatedly adding up, produces iso-indoles alkaloid compound of the present invention.
In order to further purify, products therefrom can also be dissolved with methanol solution, then using methanol solution as mobile phase, use Sephadex
LH-20 gel filtration chromatographies separate, and produce the noval chemical compound of higher purity.
Embodiment 3
Compound prepared by Example 1, is light yellow solid.
The structure of new iso-indoles alkaloid compound prepared by the present invention is to determine to come by the following method：
The compounds of this invention is light yellow solid；Ultraviolet spectra（Solvent is methanol）,λ max (logε）：210 (4.05)、260
(3.68)、296 (3.04)；Infrared spectrum（Pressing potassium bromide troche）νmax：3386、2938、1670、1610、1533、1468、1355、
1267、1131、1074、837、759 cm–1；High resolution mass spectrum（HRESIMS）Show the compounds of this invention quasi-molecular ion peakm/z
268.1319[M+Na]+（Calculated value 268.1313）.Its infrared spectrum, which is shown in compound, hydroxyl (3386 cm-1), carbonyl
(1670 cm-1), and aromatic ring (1610,1533,1468 cm-1) signal, ultraviolet spectra has maximum in 210,260,296 nm
Absorption, which also confirms that, has aromatic ring structure in compound.Compound1H- and13C-NMR spectrums (table -1) show that it contains 15
Individual carbon and 19 hydrogen, including 1 iso-indoles -1- ketone parent nucleus (C-1 ~ C-7a, H-3, H-4 and H-6), an isopentene group (C-
1' ~ C-5', H-1', H-2', H-4' and H-5'), a methylol (C-6', H-6'), and a N- methyl (C-7', H-7').
H in compound2- 3 and C-1, C-3a, C-4, C-7a, C-7', H-4 and C-3, H-7 and C-1, H2- 7' and C-1, C-3's
HMBC (figure -3) further confirms iso-indoles -1- ketone parent nucleus be present in compound.After the framework types of compound are confirmed,
Substituting group position further can be determined by HMBC Correlated Spectroscopies；According to H2- 1 ' and C-5, C-6, C-7, H-2 ' and C-6's
HMBC correlations can determine that isopentene group is substituted in C-6 positions；Methylol is substituted in C-5 positions can be by methylol hydrogen (H2- 6 ') and
C-4, C-5, C-6 HMBC are related to be confirmed.Methyl is connected with nitrogen-atoms and by methyl hydrogen (H3And C-1, C-3, and H- -7 ')
3 confirmations related to C-7 HMBC.So far the structure of compound is determined, the compound is named as：5- (methylol) -2-
Methyl -6- isopentene groups-iso-indoles -1- ketone.
Embodiment 4
Compound prepared by Example 2, is light yellow solid.Assay method is same as Example 3, confirms embodiment 2
The compound of preparation is described iso-indoles alkaloid compound --- 5- (methylol) -2- methyl -6- isopentene groups-different Yin
Diindyl -1- ketone.
Embodiment 5
Prepared by Example 1-3 appoints sesquiterpenoids to carry out activity of resisting tobacco mosaic virus experiment, test situation
It is as follows：
Using half leaf method, anti-Tobacco mosaic is carried out to the compounds of this invention when the mass concentration of medicament is 50 mg/L
Virus activity determines.On the plant of 5~6 age flue-cured tobaccos, the blade (leaf row is normal, disease-free no worm) suitable for test is chosen, first
Blade is uniformly sprinkled into fine emery powder, with writing brush by standby tobacco mosaic virus (TMV) source (3.0 × 10-3) be uniformly put on sprinkled with Buddha's warrior attendant
On the blade of sand, connect after the blade of all middle choosings after poison terminates, be immediately placed in the culture dish for fill decoction and handle 20 min, take
Go out, wipe the globule and decoction on blade, the recovery of two and half leaves is emitted on and is covered with the glass jar of toilet paper moisturizing, and covers glass
Glass lid, temperature control (23 ± 2) DEG C are placed on greenhouse natural light irradiation, and 2~3 d are that each processing sets second half leaf to visible withered spot
For control, 1 group of processing for commodity Ningnanmycin is additionally provided with as a comparison, press formula and calculate relative inhibition.
XI%=(CK-T)/CK × 100%
X：Relative inhibition (%), CK：The withered spot number (individual) that half in clear water connects malicious leaf is soaked in, T is soaked in decoction
Half connects the withered spot number (individual) of malicious leaf.
As a result the relative inhibition of bright compound be 36.8%, more than control Ningnanmycin relative inhibition 31.5%,
Illustrate that compound has good activity of resisting tobacco mosaic virus.
Claims (2)
1. a kind of iso-indoles alkaloid compound, it is characterised in that the iso-indoles alkaloid compound is from wing pod Cassia tora
（Cassia alataL.）It is isolated in bark, it is named as 5-（Methylol）- 2- methyl -6- isopentene groups-iso-indoles -1-
Ketone, its molecular formula are C15H19NO2, there are following structures：
。
A kind of 2. application of the iso-indoles alkaloid compound in resisting tobacco mosaic virus medicine is prepared described in claim 1.
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| CN105884588B (en) * | 2016-04-19 | 2018-01-05 | 秦瑞欣 | One kind drop sesquiterpenoids and preparation method and application |
| CN106146383B (en) * | 2016-07-04 | 2018-07-17 | 云南中烟工业有限责任公司 | A kind of iso-indoles alkaloid compound, preparation method and application in tobacco |
| CN110452170B (en) * | 2019-08-29 | 2022-11-08 | 云南中烟工业有限责任公司 | Isoquinoline alkaloid compound and preparation method and application thereof |
| CN111574492B (en) * | 2020-06-08 | 2022-05-20 | 云南民族大学 | Compound for resisting tobacco mosaic virus, preparation method and application thereof, and tobacco mosaic virus inhibitor containing compound |
| CN111518070B (en) * | 2020-06-08 | 2022-12-09 | 云南民族大学 | Rotavirus-resistant compound in cassia wingnut, preparation method and application thereof |
| CN111747881B (en) * | 2020-07-01 | 2023-02-28 | 济南大学 | Two isopentenyl substituted indole alkaloids with alpha-glucosidase inhibition effect, and preparation method and application thereof |
| CN113087664B (en) * | 2021-03-22 | 2022-03-11 | 云南中烟工业有限责任公司 | Quinoline alkaloid compound and preparation method and application thereof |
| CN113057168B (en) * | 2021-03-22 | 2022-02-11 | 云南中烟工业有限责任公司 | Seed disinfection preparation, preparation method, use method and application thereof |
| CN114456102A (en) * | 2022-01-27 | 2022-05-10 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
| CN114751911B (en) * | 2022-05-10 | 2023-07-14 | 云南中烟工业有限责任公司 | Indole alkaloid compound, and preparation method and application thereof |
| CN115286561B (en) * | 2022-08-01 | 2023-06-16 | 云南中烟工业有限责任公司 | Indole alkaloid compound in gene editing tobacco, and preparation method and application thereof |
| CN115124505B (en) * | 2022-08-01 | 2023-07-18 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
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| WO2011062864A2 (en) * | 2009-11-17 | 2011-05-26 | Emory University | Inhibitors of nox enzymes and methods of use thereof |
| US9365512B2 (en) * | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN102827118B (en) * | 2012-09-08 | 2014-06-11 | 云南民族大学 | Siamaurone B compound and preparation method and application thereof |
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