CN109824749A - Triterpenoid and its preparation method and application - Google Patents
Triterpenoid and its preparation method and application Download PDFInfo
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- CN109824749A CN109824749A CN201910046314.8A CN201910046314A CN109824749A CN 109824749 A CN109824749 A CN 109824749A CN 201910046314 A CN201910046314 A CN 201910046314A CN 109824749 A CN109824749 A CN 109824749A
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Abstract
The present invention relates to a kind of triterpenoid and its preparation method and application, the triterpenoid has the following structure Formulas I, wherein R1, R2, R3 represent hydrogen atom, and R4 represents alkyl.This research not only has found new triterpenoid saponin ingredient from the Siraitia grosvenorii root tuber endangered by root-knot nematode, while finding the cucurbitacine ingredient for being referred to as " plant optimum defense weapon ".Cucurbitacin can both defend most of polytrophic insect, can be with the certain special feeding habits insects of food calling.These compounds will play an important role in Siraitia grosvenorii and root-knot nematode interaction, coevolution.This result of study provides certain scientific basis for the development and utilization of Momordica grosvenori root and using the harm that bioengineering controls Meloidogyne incognita.
Description
Technical field
The present invention relates to technical field of traditional Chinese medicines field, more particularly, to a kind of triterpenoid and preparation method thereof and
Using.
Background technique
Root tuber of the Momordica grosvenori root for cucurbitaceous plant Siraitia grosvenorii (Siraitiae Grosvenorii), bitter, property are micro-
It is cold, there is the effect of clearing heat and expelling damp, remove obstruction in channels to relieve pain, be a kind of civil conventional crude drugs in Guilin area.Research finds Siraitia grosvenorii
Root has anti-oxidant, anticancer, antibacterial, anti-inflammatory to wait physiological activity, and clinical test proves that it is significant in efficacy to rheumatic arthritis.King
Sweet smell et al. is avenged first from the ethyl acetate extract of the ethanol extract of Momordica grosvenori root isolated four new cucurbitane type Fourth Rings
Triterpenic acid, two of them are carbon loss triterpenic acid, are respectively designated as arhat tartaric acid first (siraitic acid A), arhat tartaric acid second
(siraitic acid B), arhat tartaric acid third (siraitic acid C), arhat tartaric acid fourth (siraitic acid D).This
Brave et al. subsequent isolated two new triterpenic acids from Momordica grosvenori root again are built, penta (siraitic of arhat tartaric acid is named as
Acid E) and Siraitic Acid F.Seminar's early period has carried out chemical constitution study to the water-soluble portion of Momordica grosvenori root,
Drop triterpenic acid glucosides arhat tartaric acid second glycosides II (II B of Siraitic acid) and the arhat tartaric acid of isolated structure novel for the first time
Third glycosides II (II C of Siraitic acid).
Siraitia grosvenorii is a kind of crop of hyperinfection root-knot nematode, and all plant bury part (including root and part potato root and stem of certain plants)
It can be seriously endangered.We by the analysis means such as HPLC it was found that, no Siraitia grosvenorii root-knot nematode harm and endangered
Root tuber, chemical component have apparent difference.The secondary metabolism after Siraitia grosvenorii root tuber is endangered by root-knot nematode is illustrated for system to produce
Object changing rule, seminar have carried out the chemical constitution study for being endangered Siraitia grosvenorii root tuber by root-knot nematode, have therefrom isolated at present
Four kinds of different cucurbitacins and a new triterpene saponin componds, enrich triterpene compound database, while being also
The further researches and exploitation of Siraitia grosvenorii plant provides material base.
Summary of the invention
The purpose of the present invention is to provide a kind of novel triterpenoids and its preparation method and application.
In order to achieve the goal above, the technical scheme adopted by the invention is as follows:
A kind of triterpenoid, has the following structure Formulas I:
Wherein, R1, R2, R3 represent hydrogen atom, and R4 represents alkyl.
The molecular formula of the triterpenoid is C in one of the embodiments,41H62O14。
The R4 is selected from following groups: propyl, butyl or amyl in one of the embodiments,.
The position of the absorption peak of the triterpenoid is in 3423cm in one of the embodiments,-1、3157cm-1、
1699cm-1And 1643cm-1。
The triterpenoid includes 41 carbon signals in the carbon spectrum of nuclear magnetic resonance in one of the embodiments,.
41 carbon signals include 6 methyl signals, 15 methine signals, 9 season in one of the embodiments,
Carbon signal and 11 methylene signals.
The triterpenoid includes 4,24- diene cucurbit alkane type triterpenoid skeleton and 2 six in one of the embodiments,
Carbon sugar unit.
The present invention also provides the preparation methods of the triterpenoid, include the following steps:
The Siraitia grosvenorii root tuber sample of crushing is extracted, extracting solution is obtained；
It is concentrated under reduced pressure, is eluted using chromatographic column, obtain concentrating sample；
The concentrating sample is eluted by MCI chromatographic column, by silica gel column chromatography plate, C18 chromatographic column and preparation chromatography
It combines and isolates and purifies to obtain triterpenoid.
It is concentrated under reduced pressure, is eluted using chromatographic column in one of the embodiments, obtain concentrating sample, wherein the layer
Analysis column is HPD-100 macroreticular resin chromatographic column.
The present invention also provides triterpenes obtained by the preparation method of the triterpenoid or the triterpenoid
Application of the compound in prevention and treatment Meloidogyne incognita.
This research not only has found new triterpenoid saponin ingredient, simultaneously from the Siraitia grosvenorii root tuber endangered by root-knot nematode
It was found that being referred to as the cucurbitacine ingredient of " plant optimum defense weapon ".Cucurbitacin can both defend most of polytrophic insect,
It can be with the certain special feeding habits insects of food calling.These compounds will rise important in Siraitia grosvenorii and root-knot nematode interaction, coevolution
Effect.This result of study is the development and utilization of Momordica grosvenori root and is mentioned using the harm that bioengineering controls Meloidogyne incognita
Certain scientific basis is supplied.
Specific embodiment
The invention can be embodied in many other ways as described herein, and those skilled in the art can be not
Similar improvement is done in the case where violating intension of the present invention, therefore the present invention is not limited to the specific embodiments disclosed below.
Unless otherwise defined, all technical and scientific terms used herein and belong to technical field of the invention
The normally understood meaning of technical staff is identical.Term as used herein in the specification of the present invention is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.
1, reagent and instrument
Momordica grosvenori root picks up from Guilin Yongfu county, through Guangxi Plant Inst., Chinese Academy of Sciences, Guangxi Zhuang Autonomous Jiang
Water elemental study person is accredited as the root tuber of cucurbitaceous plant Siraitia grosvenorii.
1200 high performance liquid chromatograph of Agilent: Agilent Technologies, the U.S.；
Brucker Avance 500MHz type NMR spectrometer with superconducting magnet: Brooker (Beijing) Science and Technology Ltd.；
LCMC-IT-TOF type High Performance Liquid Chromatography/Mass Spectrometry: Shimadzu business administration (China) Co., Ltd；
Analytical liquid chromatograph Shimadzu LC-2030C: Shimadzu business administration (China) Co., Ltd；
Electronic balance: Mei Tele-support benefit instrument company；
EYELA 0SB-2200 Rotary Evaporators: Tokyo Physico-chemical Apparatus Co., Ltd.；
Agilent XDB-C18 prepares column (9.4 × 250mm, 5um)；
Agilent SB-C18 analytical column (4.6 × 150mm, 5um)；
HPD-100 macroreticular resin: Cangzhou Bon Adsorption Material Science and Technology Co., Ltd；
Chromatography acetonitrile, methanol: Fisher Scientific Worldwide；
Methylene chloride: Shanghai Titan Chemical Co., Ltd.；
Analyze methanol: western Gansu Province science limited liability company.
2, the preparation method of triterpenoid
A kind of preparation method of triterpenoid includes the following steps:
Siraitia grosvenorii root tuber is acquired, soil is cleaned, thinly slices, room temperature is dried in the shade, and is crushed；
Siraitia grosvenorii root tuber sample 4.75kg, three times, 7 days every time, combined extract was concentrated under reduced pressure into 75% alcohol steep
1000mL crosses HPD-100 macroreticular resin chromatographic column, successively uses pure water, and 20%, 40%, 60%, 80%, 100% methanol gradient is washed
It is de-, wherein 100% meoh eluate is concentrated and dried, obtain 20.86g concentrating sample；
Above-mentioned concentrating sample is using MCI chromatographic column, using above-mentioned identical elution process, through thin layer of silicone analysis plate inspection
It surveys, collects 60%-100% methanol-water eluent, be concentrated under reduced pressure and be dried to obtain 3 sample segments, respectively Fr41 (2.5785g),
Fr42 (2.9038g), Fr43 (4.5948g).The method separate fraction Fr42 combined with C18 chromatographic column and preparation chromatography, obtains
To triterpenoid.
Using nuclear magnetic resonance to obtained 29-nor-3,11-dioxo-cucurbit-4,24-diene-27-oic acid
27-O- β-D-glucopyranosyl- (1 → 6)-β-D-glucopyranoside is analyzed, obtain nuclear magnetic resonance spectroscopy and
The results are shown in Table 1 for carbon spectrum.
Table 1
Above compound amorphous powder, is dissolved in pyridine.UV (acetonitrile), λ max/nm:230nm or 254n.HR-ESI-MS
It shows quasi-molecular ion peak m/z:823.4050 [M+HCOO]-, molecular formula C41H62O14(calculated value).It is composed according to HR-ESI-MS
As a result, can calculate its degree of unsaturation is 11.IR spectrum display compound is having 3423cm-1、3157cm-1、1699cm-1、
1643cm-1There is strong absworption peak in place, illustrates that compound may contain hydroxyl, carbonyl and double bond functional group.Further analyze 1H-
NMR discovery, has 6 methyl signals (respectively δ H0.76, s, H-18 in high field region；δ H0.84, d, J=6.42, H-21；δ
H1.9, s, H-28；δ H1.92, s, H-26；δ H1.11, s, H-19；δ H1.16, s, H-30), in conjunction with splitting point for chemical shift and peak
Situation, it can be seen that wherein 1 methyl connects on tertiary carbon, and 5 connect on quaternary carbon, and containing ethylene linkage proton signal (δ 7.09,
T, H-24).13C-NMR and DEPT (C5D5N, 125MHz) spectrum shows 41 carbon signals (6 methyl signals, 15 methines altogether
Signal, 9 quaternary carbon signals, 11 methylene signals), wherein 2 sugared end group carbon signals (δ c96.63,105.7), 3 carbonyls letters
Number (δ c214.81,197.89,167.47), 3 sp2 quaternary carbon signals (δ c157.27,132.94,127.88), 1 sp2 olefinic carbon
Signal (δ c144.95).In summary information, thus it is speculated that the compound contains 4,24 diene cucurbit alkane type triterpenoid skeletons and 2 six carbon
Sugar unit, HMBC spectrum find out one of glycosyl and δ c167.47 strong correlation, are inferred to it and are connected by ester bond；Another glycosyl
With 6 δ c69.88 strong correlations of glycosyl, it is inferred between two sugar be connected by 1 → 6.Finally compare the chemistry of 13C-NMR
Chemical shift and the substitute mode of displacement and 1H-NMR, find the compound and known compound 9,29-nor-3,11-dioxo-
cucurbit-4,24-diene-27-oic acid 27-O-β-D-glucopyranosyl-(1→6)-β-D-
The nuclear magnetic data of glucopyranoside is quite similar, only than its more methyl, and on HMBC the methyl (δ c23.22) with
8,9,10,11 strong correlations, and 9 are quaternary carbon, thereby determine that the methyl is connected to 9 of aglycon.In conclusion identifying the change
The structure for closing object is 29-nor-3,11-dioxo-cucurbit-4,24-diene-27-oic acid 27-O- β-D-
Glucopyranosyl- (1 → 6)-β-D-glucopyranoside is noval chemical compound.
The present invention also provides triterpenes obtained by the preparation method of the triterpenoid or the triterpenoid
Application of the compound in prevention and treatment Meloidogyne incognita.
Following test confirms new triterpene compound object to the control efficiency of Meloidogyne incognita.However, the triterpenoid
The pest controling effect of offer is not limited to these kinds.
Embodiment 1
In order to evaluate the prevention and treatment of root-knot nematode in Siraitia grosvenorii, the above-mentioned new triterpene compound object of Siraitia grosvenorii seed is handled.
Seed is seeded in the plot 10 × 30ft that root-knot nematode infects big Tanaka.
Comparative example 1
Siraitia grosvenorii seed is directly seeded in the plot 10 × 30ft that root-knot nematode infects big Tanaka.
Test result is as shown in table 2, from Table 2, it can be seen that treated that Siraitia grosvenorii seed can with new triterpene compound object
To prevent and treat root-knot nematode significantly.
Table 2
| Test group | The root-knot nematode death rate (%) |
| Embodiment 1 | 75 |
| Comparative example 1 | 5 |
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of triterpenoid, which is characterized in that have the following structure Formulas I:
Wherein, R1, R2, R3 represent hydrogen atom, and R4 represents alkyl.
2. triterpenoid according to claim 1, which is characterized in that the molecular formula of the triterpenoid is
C41H62O14。
3. triterpenoid according to claim 1, which is characterized in that the R4 be selected from following groups: propyl, butyl or
Amyl.
4. triterpenoid according to claim 1, which is characterized in that the position of the absorption peak of the triterpenoid exists
3423cm-1、3157cm-1、1699cm-1And 1643cm-1。
5. according to the triterpenoid as claimed in claim 2, which is characterized in that the triterpenoid is in nuclear magnetic resonance
It include 41 carbon signals in carbon spectrum.
6. triterpenoid according to claim 5, which is characterized in that 41 carbon signals include 6 methyl signals,
15 methine signals, 9 quaternary carbon signals and 11 methylene signals.
7. triterpenoid according to claim 1, which is characterized in that the triterpenoid includes 4,24- diene calabash
Reed alkane type triterpenoid skeleton and 2 hexose units.
8. the preparation method of triterpenoid as described in any one of claim 1 to 7, which comprises the steps of:
The Siraitia grosvenorii root tuber sample of crushing is extracted, extracting solution is obtained；
It is concentrated under reduced pressure, is eluted using chromatographic column, obtain concentrating sample；
The concentrating sample is eluted by MCI chromatographic column, is mutually being tied by silica gel column chromatography plate, C18 chromatographic column with preparation chromatography
Conjunction isolates and purifies to obtain triterpenoid.
9. preparation method according to claim 8, which is characterized in that be concentrated under reduced pressure, elute, obtain dense using chromatographic column
Contracting sample, wherein the chromatographic column is HPD-100 macroreticular resin chromatographic column.
10. such as the described in any item triterpenoids of claim 1-7 or the described in any item preparation method institutes of claim 8-9
Application of the triterpenoid obtained in prevention and treatment Meloidogyne incognita.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018933A (en) * | 2019-12-26 | 2020-04-17 | 杨凌萃健生物工程技术有限公司 | Fructus momordicae extract product and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104273127A (en) * | 2014-10-25 | 2015-01-14 | 佛山市盈辉作物科学有限公司 | Nematode-killing pesticide composition containing lantana allyl methyl element and amino oligosaccharins |
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2019
- 2019-01-18 CN CN201910046314.8A patent/CN109824749A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104273127A (en) * | 2014-10-25 | 2015-01-14 | 佛山市盈辉作物科学有限公司 | Nematode-killing pesticide composition containing lantana allyl methyl element and amino oligosaccharins |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018933A (en) * | 2019-12-26 | 2020-04-17 | 杨凌萃健生物工程技术有限公司 | Fructus momordicae extract product and preparation method and application thereof |
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