CN109180623A - The preparation method and applications of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine - Google Patents
The preparation method and applications of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine Download PDFInfo
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Abstract
The present invention relates in water cape jasmine 3; the preparation method and applications of the new terpene A of 4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine effectively solve the problem of quickly to prepare two 3 4- driffractive ring cycloartane type triterpenoids compounds with nephrocyte protection activity from water cape jasmine; method is; water cape jasmine is crushed, acetone historrhexis extracts, and is concentrated under reduced pressure; concentrate is suspended with distilled water; petroleum ether, ethyl acetate are sequentially added, solvent is recovered under reduced pressure, obtains water cape jasmine crude extract；Water cape jasmine crude extract uses volume ratio to carry out gradient elution for the methylene chloride-methanol system of 100:1,50:1,30:1 through silica gel column chromatography initial gross separation, and collecting methylene chloride-methanol volume ratio is that 50:1,30:1 elute fraction；Methylene chloride-methanol volume ratio is that 50:1 elution fraction is further separated through silica gel column chromatography, obtains the new terpene A of cape jasmine；Methylene chloride-methanol volume ratio is that 30:1 elution fraction is further separated through ODS column chromatography, obtains the new terpene F of cape jasmine；The method of the present invention is reliable and stable, high-efficient.
Description
Technical field
The present invention relates to medicine, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and cape jasmine in especially a kind of water cape jasmine
The preparation method and applications of new terpene F.
Background technique
Pyemia is the systemic inflammatory response caused by infecting, and usually causes more tissue damages and dysfunction.Currently, purulence
Toxication has become the main reason for intensive care unit (ICU) death, be 1~7 years old infant the seventh-largest cause of death and
The eighth-largest cause of death of 65~75 years old old men.Acute kidney injury (AKI) is most serious during clinical pathogenesis of sepsis, most often
One of complication seen.The disease incidence of AKI can increase with pyemic development, and case fatality rate increases by 1 after pyemia merges AKI
Times, hence it is evident that it is higher than acute renal failure caused by other factors.Clinically widely used nephrocyte protects drug master at present
It to include HMG-COA reductase inhibitor, angiotensin converting enzyme inhibitor (ACEI) and angiotensin-ii-receptor antagonism
Agent (ARB) etc..Effect due to most synthetic drugs based on single target spot is difficult to obtain ideal for the complicated cause of disease of injury of kidney
Therapeutic effect.
Water cape jasmine is Rubiaceae (Rubiaceae) Gardenia Ellis plant water cape jasmine (Gardenia jasminoides
Var.radicans dry mature fruit).History tree works, such as " Thunder God processes opinion ", " eight Fujian lead to will " etc. is related
In water cape jasmine correlation record, civil in China, water cape jasmine root, leaf and fruit can be used as medicine, have antipyretic cool blood, sedation-analgesia,
The wet effect of dispelling wind solution.Water cape jasmine is widely distributed, and multiple provinces and regions on the south China the Changjiang river are distributed or artificial cultivation, mainly
Producing region saves in Hubei, Hunan, Sichuan, Jiangxi, Fujian, Zhejiang etc..Chemical constitution study shows water cape jasmine in addition to containing cyclenes ether
Other than terpene and monoterpenes compound, research discovery water cape jasmine in recent years also contains a large amount of triterpene compound, same to have
There is the bioactivity of multiplicity, it is such as antitumor, inhibit tumour cell angiogenic growth and anti-inflammatory isoreactivity.The present invention uses silicagel column
Chromatography is enriched with target component, then combines preparation liquid phase to isolate and purify with column chromatographies such as silica gel, ODS, establishes in water cape jasmine
The fast preparation method of 3,4- driffractive ring cycloartane type triterpenoids compound the cape jasmine new terpene A and the new terpene F of cape jasmine of two traces.
This method separative efficiency is high, the time is short, and solvent-oil ratio is small, and sample recovery rate is high, obtained target component purity is high.The two
Compound is to have no noval chemical compound reported in the literature.
Applicating history of the Chinese herbal medicine in terms of cytoprotection is long, and the activity with nephrocyte protection is found from Chinese herbal medicine
Substance, developing the small newtype drug of high specificity, toxic side effect has important Social benefit and economic benefit.
Summary of the invention
For above situation, for the defect for overcoming the prior art, the purpose of the present invention is just to provide 3 in a kind of water cape jasmine,
The preparation method and applications of the new terpene A of 4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine can be solved effectively quickly from water Cape jasmine
Preparing two in son has the problem of 3,4- driffractive ring cycloartane type triterpenoids compound of nephrocyte protection activity.
The technical solution that the present invention solves is, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and Cape jasmine in a kind of water cape jasmine
Sub new terpene F, the new terpene A of the triterpene compound cape jasmine and the new terpene F molecular structural formula (chemical structural formula) of cape jasmine are as follows:
Preparation method includes the following steps:
(1) prepare crude extract, method is to crush water cape jasmine, cross 40 meshes, every time with water cape jasmine weight 6-9 times measure
Volumetric concentration be 50% acetone historrhexis extract 3 times, each 1-3min, merge acetone extract, be concentrated under reduced pressure, obtain dense
Contracting object, the distilled water for adding 3-5 times of concentrate bulking value to measure are suspended, and sequentially add the petroleum ether isometric with suspension, acetic acid
Solvent is recovered under reduced pressure in ethyl ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；The weighing body
Product refer to solids in terms of g, liquids are the same below in terms of ml, as concentrate be 1g when, distilled water 3-5ml；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
Through silica gel column chromatography initial gross separation, uses volume ratio to carry out gradient for the methylene chloride-methanol system of 100:1,50:1,30:1 and wash
It is de-, flow velocity 15mlmin-1, every 200ml is 1 fraction, and collecting methylene chloride-methanol volume ratio respectively is that 50:1,30:1 are washed
Separation of flow part；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for
The petroleum ether of 4:1,2:1-acetone system carry out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum
Ether-acetone volume ratio is that 2:1 elutes fraction；Petroleum ether-acetone volume ratio elutes fraction for 2:1 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, obtain the new terpene A of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for
The methanol-water system of 80:10,90:10 carry out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects first
Alcohol-water product ratio is that 90:10 elutes fraction, and methanol-water volume ratio elutes fraction for 90:10 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 75:25, obtain the new terpene F of cape jasmine.
The new terpene A of cape jasmine, the new terpene F of cape jasmine of the method for the present invention preparation, which have, inhibits renal cells NRK 52e apoptosis
Protective effect, realize answering in the drug of injury of kidney caused by the new terpene A of cape jasmine, the new terpene F of cape jasmine treat a variety of causes in preparation
With.
The method of the present invention is reliable and stable, high-efficient, can quick isolated two 3,4- driffractive ring ring pineapple from water cape jasmine
The sweet new terpene A and new terpene F of cape jasmine of alkane type triterpenoid class compound cape jasmine, withers to lipopolysaccharide-induced renal cells NRK 52e
It dies with certain protective effect, the drug of injury of kidney caused by a variety of causes is treated effective for preparation, has opened up water cape jasmine
Medical value and commercial value, economic and social benefit it is significant.
Detailed description of the invention
Fig. 1 is the molecular structure of the new terpene A of the compounds of this invention cape jasmine, the new terpene F of cape jasmine.
Specific embodiment
It elaborates below in conjunction with concrete condition and embodiment to a specific embodiment of the invention.
The present invention in specific implementation, can be provided by following embodiment.
Embodiment 1
In specific implementation, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and cape jasmine are new in a kind of water cape jasmine by the present invention
The preparation method of terpene F, comprising the following steps:
(1) crude extract is prepared, method is to crush water cape jasmine 4.03kg, crosses 40 meshes, uses water cape jasmine weight 9 every time
The acetone historrhexis that the volumetric concentration of amount is 50% again extracts 3 times, each 1min, merges acetone extract, and reduced pressure obtains
Concentrate adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, acetic acid
Solvent is recovered under reduced pressure in ethyl ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
61.3g, after mixing sample with 100~200 mesh silica gel 60g, on the silicagel column containing 100~200 mesh silica gel 600g, use volume ratio for
The methylene chloride-methanol system of 100:1,50:1,30:1 carry out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
Fraction, collecting methylene chloride-methanol volume ratio respectively is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for
The petroleum ether of 4:1,2:1-acetone system carry out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum
Ether-acetone volume ratio is that 2:1 elutes fraction；Petroleum ether-acetone volume ratio elutes fraction for 2:1 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains
The new terpene A (compound 1) of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for
The methanol-water system of 80:20,90:10 carry out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects first
Alcohol-water product ratio is that 90:10 elutes fraction, and methanol-water volume ratio elutes fraction for 90:10 and uses half preparation liquid phase progress pure
Change, volume ratio is used to be eluted for the acetonitrile-water of 75:25, collect eluent, is concentrated and dried, obtains the new terpene F (compound of cape jasmine
2)。
Compound structure identification:
Above-mentioned two compound, by NMR spectrum (1H-NMR、13C-NMR、HSQC、HMBC、1H-1H COSY、
NOESY) and high resolution mass spectrum (HR-ESI-MS) spectral technique identifies its chemical structure:
Compound 1, colorless waxy are soluble in methanol.+30.459(c 0.8036,CH3), OH it is surveyed through HR ESI MS
Surely its quasi-molecular ion peak [M-H] is obtained-M/z:487.3421 (C30H47O5487.3418) calculated value is.
1H NMR(500MHz,CD3OD in), occur 2 hydrogen width unimodals at δ 4.81 and 4.74, prompt this 2 hydrogen for end
Two hydrogen signals on terminal double bond；δ 4.08 (1H, br d, J=11.5Hz, H-21a), 3.50 (1H, d, J=11.2Hz, H-
26a), 3.47 (1H, dd, J=11.5,2.2Hz, H-21b), 3.42 (1H, d, J=11.2Hz, H-26b) and 3.35 (1H, dd, J
=10.8,2.4Hz, H-24) it is the hydrogen signal connected on oxygen carbon；δ 0.76 (1H, d, J=4.4Hz, H-19a) and 0.44 (1H, d, J
=4.4Hz, H-19b) it is cyclopropylmethylene hydrogen signal；At δ 1.70 (3H, s, H-29), 1.11 (3H, s, H-27), 1.05
4 methyl hydrogen signals are shown at (3H, s, H-30) and 0.99 (3H, s, H-18).
13C NMR(125MHz,CD3OD occur 30 carbon signals in) altogether, and most is fatty carbon, prompts the compound can
Can be a triterpene compound, δ 177.8 be carbonyl carbon signals, δ 150.8 and 112.2 be terminal double bond carbon signal, δ 82.5,
75.3,71.6 and 68.0 be even oxygen carbon signal.Pass through analysis1H-1There are 5 Spin Systems in H COSY spectrum discovery molecular structure,
Respectively S1:C-1 (δ 30.4)/C-2 (δ 32.5)；S2:C-5 (δ 47.2)/C-6 (δ 29.0)/C-7 (δ 26.2)/C-8 (δ
49.5)；S3:C-11 (δ 28.1)/C-12 (δ 33.7)；S4:C-15 (δ 36.7)/C-16 (δ 28.3)/C-17 (δ 43.7)/C-20
(δ37.2)/(C-21)/C-22(δ28.3)/C-23(δ21.8)/C-24(δ82.5)；S5:C-28(δ112.2)/C-4(δ
150.8)/C-29(δ20.1)。
In HMBC spectrum, H-19 (δ 0.76 and 0.44) and C-1, C-5, C-8 and C-11 have it is long-range related, prompt S1 C-1 and
The C-5 of S2 is connected on the C-10 ring of the cyclopropane where C-19, and the C-9 of the C-8 and S3 of S2 are connected on the C-9 of cyclopropane；By
H-18 and C-12, C-14 (δ 50.3) have long-range related to C-17, and H-30 (δ 1.05) and C-8, C-13 (δ 46.0) and C-15 have far
Cheng Xiangguan determines that the C-8 of S2, C-15, C-17 of the C-12 and S4 of S3 are connected on C-13；H-1 (δ 2.04 and 1.37) and C-3
(δ 177.8) has long-range correlation, and carboxyl is prompted to be connected on C-2；H-28 (δ 4.08 and 3.51) have to C-5 it is long-range related, prompt should
Isopropenyl is connected on C-5；H-21 (δ 4.81 and 4.74) and C-20, C-22, C-24 have long-range correlation, illustrate C-21 and C-24
It is connected together by oxygen atom；In addition, H-24 (δ 3.35) and C-25 (δ 75.3), C-26 (δ 68.0) and C-27 (δ 20.2) have far
Cheng Xiangguan prompts a 2- propylene-glycol-based to be connected on C-24.By being analyzed above it is found that the compound is that 3,4- splits ring-ring spinach
Trailing plants honey alkane type triterpenoid derivative, C-21 and C-24 are at ether, and C-25 and C-26 are connected with hydroxyl.
By H-21 α (dd, J=11.5,2.2Hz), H-21 β (d, J=11.5Hz) and H-24 (dd, J=10.8,2.4Hz)
Coupling constant can deduce the two sides that H-20 and H-24 is respectively at ring.In NOE spectrum, H-20 and H-21 β, H-21 α and H-
24 have NOE relationship respectively, demonstrate this supposition.In summary it analyzes, can obtain the structure of compound, be 21,24 epoxies-
25,26- dihydroxy -3,4- driffractive ring cycloartanes -4 (28)--3 carboxylic acid of alkene, literature search are found to be a noval chemical compound, name
For the new terpene A of cape jasmine (gardenpic A).
Compound 2, white amorphous powder are soluble in methanol.+45.571(c 0.1120,CH3OH), through HR ESI
MS measures to obtain quasi-molecular ion peak [M+Na]+M/z:527.3712 (C31H52O5527.3707) Na calculated value is.
1H NMR(500MHz,CD3OD in), δ 5.28 (1H, t, J=7.0Hz, H-24) is the hydrogen signal in double bond；δ4.07
(2H, dd, J=15.4,12.6Hz, H-26), 3.69 (1H, dd, J=11.0,3.3Hz, H-21a) and 3.48 (1H, dd, J=
11.0,6.3Hz, H-21b) it is the hydrogen signal connected on oxygen carbon；δ 3.62 (3H, s) is methoxyl group hydrogen signal；δ 0.71 (1H, d, J=
4.6Hz, H-19a) and 0.52 (1H, d, J=4.6Hz, H-19b) be cyclopropyl on methylene hydrogen signal；In δ 1.75 (3H, s, H-
27) 5 are shown at, 1.20 (3H, s, H-28), 1.19 (3H, s, H-29), 1.01 (3H, s, H-18) and 0.98 (3H, s, H-30)
Methyl hydrogen signal.
13C NMR(125MHz,CD3OD occur 31 carbon signals in) altogether, and most is fatty carbon, prompts the compound can
It can be a triterpene compound, δ 176.7 is carbonyl carbon signals, and δ 135.4 and 129.5 is double bond carbon signal, δ 76.8,62.7
It is even oxygen carbon signal with 61.4.The compound with 1 nuclear magnetic resonance data it is closely similar, both prompt skeleton class having the same
Type, difference are that the isopropenyl double bond for being connected in 5 is saturated, oxo forms isopropyl alcohol radical and 17 side chain open loops are formed
Chain structure.Analysis1H-1H COSY spectrum, discovery structure contain C-21 (δ 62.7)/C-20 (δ 43.5)/C-22 (δ 30.9)/C-23
(δ 25.1)/C-24 (δ 129.5) structure fragment, wherein C-21 is to connect oxygen carbon, and C-24 is double key carbon.By comparing C- with document
26 chemical shift (E configuration: δ 69.0~70.0；Z configuration: δ 60.0~62.0) it can determine that 24 (25) double bonds are Z configuration.
HMBC spectrum in, H-26, H-27 have to C-24 and C-25 it is long-range related, prompt there is a methyl and a methylol to be connected in C-25
On；δ 3.62 (3H, s) has long-range related, the carboxyl formation methyl esters in prompt 3 to C-3.In summary it analyzes, it can be deduced that change
The structure of object is closed, is (24Z) -4,21,26- trihydroxy -3,4- driffractive ring cycloartanes -24 (25)-alkene -3- carboxylate methyl ester, warp
Literature search is found to be a noval chemical compound, is named as the new terpene F of cape jasmine.
The nuclear magnetic data of 1 compound 1 and 2 of table
a NMR spectroscopic data were recorded in CD3OD at 500MHz(1H NMR)and
125MHz(13CNMR)
Above-mentioned two compound belongs to two two 3,4- driffractive ring ring spinach with nephrocyte protection activity in water cape jasmine
The trailing plants honey alkane type triterpenoid class compound cape jasmine new terpene A and new terpene F of cape jasmine.
Embodiment 2
In specific implementation, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and cape jasmine are new in a kind of water cape jasmine by the present invention
The preparation method of terpene F, comprising the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 5.11kg, crosses 40 meshes, uses water cape jasmine weight 7 every time
The acetone historrhexis that the volumetric concentration of amount is 50% again extracts 3 times, each 2min, merges acetone extract, and reduced pressure obtains
Concentrate adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, acetic acid
Solvent is recovered under reduced pressure in ethyl ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
77.86g, after mixing sample with 100~200 mesh silica gel 80g, on the silicagel column containing 100~200 mesh silica gel 800g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for
The petroleum ether of 4:1,2:1-acetone system carry out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum
Ether-acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio elutes fraction for 2:1 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains
The new terpene A (compound 1) of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for
The methanol-water system of 80:20,90:10 carry out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects first
Alcohol-water product ratio is that 90:10 elutes fraction, and methanol-water volume ratio elutes fraction for 90:10 and uses half preparation liquid phase progress pure
Change, volume ratio is used to be eluted for the acetonitrile-water of 75:25, collect eluent, is concentrated and dried, obtains the new terpene F (compound of cape jasmine
2)。
The Structural Identification of compound
Above two powder by nuclear magnetic resonance (1H-NMR, 13C-NMR, HSQC, HMBC,1H-1H COSY, NOESY) and
The spectroscopy technologies such as high resolution mass spec (HR-ESI-MS) are identified (structure of the qualification process with the compound in embodiment 1
Identification), it is respectively to belong to two two 3,4- driffractive ring cycloartane types three with nephrocyte protection activity in water cape jasmine
The new terpene A of the terpenoid cape jasmine and new terpene F of cape jasmine.
Embodiment 3
In specific implementation, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and cape jasmine are new in a kind of water cape jasmine by the present invention
The preparation method of terpene F, comprising the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 4.11kg, crosses 40 meshes, uses water cape jasmine weight 8 every time
The acetone historrhexis that the volumetric concentration of amount is 50% again extracts 3 times, each 3min, merges acetone extract, and reduced pressure obtains
Concentrate adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, acetic acid
Solvent is recovered under reduced pressure in ethyl ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
57.91g, after mixing sample with 100~200 mesh silica gel 60g, on the silicagel column containing 100~200 mesh silica gel 600g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for
The petroleum ether of 4:1,2:1-acetone system carry out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum
Ether-acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio elutes fraction for 2:1 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains
The new terpene A (compound 1) of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for
The methanol-water system of 80:20,90:10 carry out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects first
Alcohol-water product ratio is that 90:10 elutes fraction, and methanol-water volume ratio elutes fraction for 90:10 and uses half preparation liquid phase progress pure
Change, volume ratio is used to be eluted for the acetonitrile-water of 75:25, collect eluent, is concentrated and dried, obtains the new terpene F (compound of cape jasmine
2)。
The Structural Identification of compound
Above two powder by nuclear magnetic resonance (1H-NMR, 13C-NMR, HSQC, HMBC,1H-1H COSY, NOESY) and
The spectroscopy technologies such as high resolution mass spec (HR-ESI-MS) are identified (structure of the qualification process with the compound in embodiment 1
Identification), it is respectively to belong to two two 3,4- driffractive ring cycloartane types three with nephrocyte protection activity in water cape jasmine
The new terpene A of the terpenoid cape jasmine and new terpene F of cape jasmine.
Embodiment 4
In specific implementation, the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and cape jasmine are new in a kind of water cape jasmine by the present invention
The preparation method of terpene F, comprising the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 5.14kg, crosses 40 meshes, uses water cape jasmine weight 6 every time
The acetone historrhexis that the volumetric concentration of amount is 50% again extracts 3 times, each 2min, merges acetone extract, and reduced pressure obtains
Concentrate adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, acetic acid
Solvent is recovered under reduced pressure in ethyl ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify, and method is: the medicinal extract of Ethyl acetate fraction
78.04g, after mixing sample with 100~200 mesh silica gel 80g, on the silicagel column containing 100~200 mesh silica gel 800g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for
The petroleum ether of 4:1,2:1-acetone system carry out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum
Ether-acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio elutes fraction for 2:1 and uses half preparation liquid phase progress pure
Change, uses volume ratio to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains
The new terpene A (compound 1) of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for
The methanol-water system of 80:20,90:10 carry out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects first
Alcohol-water product is than being that 90:10 elutes fraction.Methanol-water volume ratio elutes fraction for 90:10 and uses half preparation liquid phase progress pure
Change, volume ratio is used to be eluted for the acetonitrile-water of 75:25, collect eluent, is concentrated and dried, obtains the new terpene F (compound of cape jasmine
2)。
The Structural Identification of compound
Above two powder by nuclear magnetic resonance (1H-NMR, 13C-NMR, HSQC, HMBC,1H-1H COSY, NOESY) and
The spectroscopy technologies such as high resolution mass spec (HR-ESI-MS) are identified (structure of the qualification process with the compound in embodiment 1
Identification), it is respectively to belong to two two 3,4- driffractive ring cycloartane types three with nephrocyte protection activity in water cape jasmine
The new terpene A of the terpenoid cape jasmine and new terpene F of cape jasmine.
The method of the present invention is reliable and stable, extracts the isolated new terpene A of cape jasmine and the new terpene F of cape jasmine and is tested, be can be effectively suppressed
The apoptosis of the rat renal tubular epithelial cells (NRK 52e) of lipopolysaccharides (LPS) induction can be effectively used for preparation treatment a variety of causes
The drug of caused injury of kidney, and obtained sufficiently proving through experiment, related experimental data is as follows:
1. rat renal tubular epithelial cells NRK 52e is cultivated
NRK 52e cell culture is cultivated in 37 DEG C, the incubator containing 5%CO2, and culture medium is DMEM high glucose medium
(contain 10% fetal calf serum, 100 Uml-1Penicillin and 100 μ gml-1Streptomysin), it changes the liquid once within two days.When cell is grown
To when being enough to cover the most surfaces of bottom of bottle wall, with 0.25% trypsin digestion, pass on.
Protective effect of the 2.MTT method detection compound to lipopolysaccharide-induced rat renal tubular epithelial cells
Cell is dispersed with culture medium, becoming density is 2 × 104 cell·ml-1Single cell suspension, and with every hole
0.2 ml is inoculated in 96 orifice plates, after cultivating 24 h, cell is divided into control group, model group and different medication groups, normal group adds
Enter equivalent solvent, it is 1mgml that concentration, which is added, in model group-1LPS solution (final concentration of 1 μ gml-1), different medication groups add
Entering untested compound that concentration is 0.1,1,10,50,100 μM and concentration is 1 μ gml-1Lipopolysaccharides.Every hole adds after culture for 24 hours
Enter MTT solution (5 mgml-1) 20 μ l, 37 DEG C are continued culture 4 hours, and carefully exhaust culture solution, and 150 μ l DMSO are added in every hole,
Concussion 10 minutes, is completely dissolved crystal.It is returned to zero with DMSO, measures the absorbance value in each hole at 490nm with microplate reader
(A), drug is calculated to the inhibiting rate of cell with following formula, SPSS is passed through according to the inhibiting rate for each concentration being calculated
18.0 softwares handle to obtain medium effective concentration (EC50), it retest 3 times, is averaged as final result.
3. experimental result
Influence of the new terpene A and new terpene F of cape jasmine of cape jasmine to the LPS NRK 52e Apoptosis induced, EC are detected by mtt assay50
Value is respectively 38.4 μM and 26.8 μM, achieves identical or similar result through repetition test (10 times or more).
Experiment shows the NRK that the new terpene A of cape jasmine that the present invention prepares and the new terpene F of cape jasmine can effectively inhibit LPS to induce
52e Apoptosis treats the drug of injury of kidney caused by a variety of causes effective for preparation, opens water cape jasmine for nephrocyte
The new application of protective effect drug is the innovation on the drug of injury of kidney caused by treating a variety of causes, opens water cape jasmine
Medicinal new way and commercial value have significant economic and social benefit.
Claims (6)
1. the new terpene A of 3, the 4- driffractive ring cycloartane type cape jasmine and new terpene F of cape jasmine, the triterpene compound in a kind of water cape jasmine
The new terpene A of cape jasmine and the new terpene F molecular structural formula of cape jasmine are as follows:
Preparation method includes the following steps:
(1) crude extract is prepared, method is to crush water cape jasmine, 40 meshes is crossed, every time with 6-9 times of body measured of water cape jasmine weight
The acetone historrhexis that product concentration is 50% extracts 3 times, each 1-3min, merges acetone extract, is concentrated under reduced pressure, must be concentrated
Object, the distilled water for adding 3-5 times of concentrate bulking value to measure are suspended, and sequentially add the petroleum ether isometric with suspension, acetic acid second
Solvent is recovered under reduced pressure in ester, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；The bulking value
Refer to solids in terms of g, liquids are the same below in terms of ml, as concentrate be 1g when, distilled water 3-5ml；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is that the medicinal extract of Ethyl acetate fraction is through silicon
Rubber column gel column chromatography initial gross separation uses volume ratio to carry out gradient elution for the methylene chloride-methanol system of 100:1,50:1,30:1,
Flow velocity is 15mlmin-1, every 200ml is 1 fraction, collects methylene chloride-methanol volume ratio respectively as 50:1,30:1 elution
Fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for 4:1,
The petroleum ether of 2:1-acetone system carries out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum ether-
Acetone volume ratio is that 2:1 elutes fraction；Petroleum ether-acetone volume ratio is that 2:1 elution fraction is purified using half preparation liquid phase,
Volume ratio is used to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, obtain the new terpene A of cape jasmine；
Methylene chloride-methanol volume ratio be 30:1 elute fraction further separated through ODS column chromatography, use volume ratio for 80:10,
The methanol-water system of 90:10 carries out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects methanol-water
Volume ratio is that 90:10 elutes fraction, and methanol-water volume ratio is that 90:10 elution fraction is purified using half preparation liquid phase, is used
Volume ratio is that the acetonitrile-water of 75:25 is eluted, and obtains the new terpene F of cape jasmine.
2. the system of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine according to claim 1
Preparation Method, which comprises the following steps:
(1) crude extract is prepared, method is to crush water cape jasmine 4.03kg, 40 meshes is crossed, every time with 9 times of water cape jasmine weight amounts
Volumetric concentration be 50% acetone historrhexis extract 3 times, each 1min, merge acetone extract, be concentrated under reduced pressure, must be concentrated
Object adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, ethyl acetate,
Solvent is recovered under reduced pressure, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
61.3g, after mixing sample with 100~200 mesh silica gel 60g, on the silicagel column containing 100~200 mesh silica gel 600g, use volume ratio for
The methylene chloride-methanol system of 100:1,50:1,30:1 carry out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
Fraction, collecting methylene chloride-methanol volume ratio respectively is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio be 50:1 elute fraction further separated through silica gel column chromatography, use volume ratio for 4:1,
The petroleum ether of 2:1-acetone system carries out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum ether-
Acetone volume ratio is that 2:1 elutes fraction；Petroleum ether-acetone volume ratio is that 2:1 elution fraction is purified using half preparation liquid phase,
Volume ratio is used to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains cape jasmine
New terpene A；
Methylene chloride-methanol volume ratio is that 30:1 elution fraction is further separated through ODS column chromatography, uses volume ratio for 80:20,
The methanol-water system of 90:10 carries out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects methanol-water
Volume ratio is that 90:10 elutes fraction, and methanol-water volume ratio is that 90:10 elution fraction is purified using half preparation liquid phase, is used
Volume ratio is that the acetonitrile-water of 75:25 is eluted, and collects eluent, is concentrated and dried, obtains the new terpene F of cape jasmine.
3. the system of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine according to claim 1
Preparation Method, which comprises the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 5.11kg, crosses 40 meshes, every time with 7 times of water cape jasmine weight amounts
Volumetric concentration be 50% acetone historrhexis extract 3 times, each 2min, merge acetone extract, be concentrated under reduced pressure, must be concentrated
Object adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, ethyl acetate,
Solvent is recovered under reduced pressure, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
77.86g, after mixing sample with 100~200 mesh silica gel 80g, on the silicagel column containing 100~200 mesh silica gel 800g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio is that 50:1 elution fraction is further separated through silica gel column chromatography, uses volume ratio for 4:1,
The petroleum ether of 2:1-acetone system carries out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum ether-
Acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio is that 2:1 elution fraction is purified using half preparation liquid phase,
Volume ratio is used to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains cape jasmine
New terpene A；
Methylene chloride-methanol volume ratio is that 30:1 elution fraction is further separated through ODS column chromatography, uses volume ratio for 80:20,
The methanol-water system of 90:10 carries out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects methanol-water
Volume ratio is that 90:10 elutes fraction, and methanol-water volume ratio is that 90:10 elution fraction is purified using half preparation liquid phase, is used
Volume ratio is that the acetonitrile-water of 75:25 is eluted, and collects eluent, is concentrated and dried, obtains the new terpene F of cape jasmine.
4. the system of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine according to claim 1
Preparation Method, which comprises the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 4.11kg, crosses 40 meshes, every time with 8 times of water cape jasmine weight amounts
Volumetric concentration be 50% acetone historrhexis extract 3 times, each 3min, merge acetone extract, be concentrated under reduced pressure, must be concentrated
Object adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, ethyl acetate,
Solvent is recovered under reduced pressure, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify: method is the medicinal extract of Ethyl acetate fraction
57.91g, after mixing sample with 100~200 mesh silica gel 60g, on the silicagel column containing 100~200 mesh silica gel 600g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio is that 50:1 elution fraction is further separated through silica gel column chromatography, uses volume ratio for 4:1,
The petroleum ether of 2:1-acetone system carries out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum ether-
Acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio is that 2:1 elution fraction is purified using half preparation liquid phase,
Volume ratio is used to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains cape jasmine
New terpene A；
Methylene chloride-methanol volume ratio is that 30:1 elution fraction is further separated through ODS column chromatography, uses volume ratio for 80:20,
The methanol-water system of 90:10 carries out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects methanol-water
Volume ratio is that 90:10 elutes fraction, and methanol-water volume ratio is that 90:10 elution fraction is purified using half preparation liquid phase, is used
Volume ratio is that the acetonitrile-water of 75:25 is eluted, and collects eluent, is concentrated and dried, obtains the new terpene F of cape jasmine.
5. the system of the new terpene A of 3,4- driffractive ring cycloartane type cape jasmine and the new terpene F of cape jasmine in water cape jasmine according to claim 1
Preparation Method, which comprises the following steps:
(1) prepare crude extract: method is to crush water cape jasmine 5.14kg, crosses 40 meshes, every time with 6 times of water cape jasmine weight amounts
Volumetric concentration be 50% acetone historrhexis extract 3 times, each 2min, merge acetone extract, be concentrated under reduced pressure, must be concentrated
Object adds the distilled water of 5 times of concentrate bulking value amounts to be suspended, sequentially adds the petroleum ether isometric with suspension, ethyl acetate,
Solvent is recovered under reduced pressure, obtains the medicinal extract of Ethyl acetate fraction, as water cape jasmine crude extract；
(2) column chromatographys such as silica gel, ODS combine preparation liquid phase to isolate and purify, and method is: the medicinal extract of Ethyl acetate fraction
78.04g, after mixing sample with 100~200 mesh silica gel 80g, on the silicagel column containing 100~200 mesh silica gel 800g, using volume ratio
Methylene chloride-methanol system for 100:1,50:1,30:1 carries out gradient elution, flow velocity 15mlmin-1, every 200ml is 1
A fraction, collecting methylene chloride-methanol volume ratio is that 50:1 and 30:1 elutes fraction；
Methylene chloride-methanol volume ratio is that 50:1 elution fraction is further separated through silica gel column chromatography, uses volume ratio for 4:1,
The petroleum ether of 2:1-acetone system carries out gradient elution, flow velocity 5mlmin-1, every 20ml is 1 fraction, collects petroleum ether-
Acetone volume ratio is that 2:1 elutes fraction, and petroleum ether-acetone volume ratio is that 2:1 elution fraction is purified using half preparation liquid phase,
Volume ratio is used to be eluted for the acetonitrile-water of 80:20, flow velocity 3mlmin-1, eluent is collected, is concentrated and dried, obtains cape jasmine
New terpene A；
Methylene chloride-methanol volume ratio is that 30:1 elution fraction is further separated through ODS column chromatography, uses volume ratio for 80:20,
The methanol-water system of 90:10 carries out gradient elution, flow velocity 17mlmin-1, every 170ml is 1 fraction, collects methanol-water
Volume ratio is that 90:10 elutes fraction.Methanol-water volume ratio is that 90:10 elution fraction is purified using half preparation liquid phase, is used
Volume ratio is that the acetonitrile-water of 75:25 is eluted, and collects eluent, is concentrated and dried, obtains the new terpene F of cape jasmine.
6. the new terpene A of cape jasmine and the new terpene F of cape jasmine of the method preparation of any one of claims 1 or 2-5 treat renal tubule in preparation
Application in injury of kidney drug caused by epithelial cell NRK 52e apoptosis.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113292427A (en) * | 2020-02-24 | 2021-08-24 | 暨南大学 | Split-ring-altane-type triterpenoid, preparation method and application thereof, and medicine |
| CN113368090A (en) * | 2020-03-09 | 2021-09-10 | 南方科技大学 | Application of 3, 4-secocycloartenane tetracyclic triterpene compound or pharmaceutically acceptable salt thereof in preparation of anti-cancer drugs |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113292427A (en) * | 2020-02-24 | 2021-08-24 | 暨南大学 | Split-ring-altane-type triterpenoid, preparation method and application thereof, and medicine |
| CN113368090A (en) * | 2020-03-09 | 2021-09-10 | 南方科技大学 | Application of 3, 4-secocycloartenane tetracyclic triterpene compound or pharmaceutically acceptable salt thereof in preparation of anti-cancer drugs |
| CN113368090B (en) * | 2020-03-09 | 2023-12-19 | 南方科技大学 | Application of 3, 4-seco cycloartenane type tetracyclic triterpene compound or pharmaceutically acceptable salt thereof in preparation of anticancer drugs |
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