CN104663682B - A kind of purposes of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol and preparation method thereof - Google Patents

A kind of purposes of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol and preparation method thereof Download PDF

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CN104663682B
CN104663682B CN201510030554.0A CN201510030554A CN104663682B CN 104663682 B CN104663682 B CN 104663682B CN 201510030554 A CN201510030554 A CN 201510030554A CN 104663682 B CN104663682 B CN 104663682B
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kaurane diterpenoid
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kaurane
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陈佳
高坤
任佳佳
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Ningbo Institute of Technology of ZJU
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • C07C29/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis
    • C07C29/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis the acid being sulfuric acid
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract

The invention discloses a kind of kaurene natural product Ent-kaurane diterpenoid 16 α, purposes of 17,19 triols and preparation method thereof, Ent-kaurane diterpenoid 16 α, 17,19 triols are applied to prepare antibacterial products.The invention provides a kind of kaurene natural product Ent-kaurane diterpenoid 16 α, the new application of 17,19 triols, Ent-kaurane diterpenoid 16 α, the range of application of 17,19 triols are widened, for Ent-kaurane diterpenoid 16 α, the application of 17,19 triols provides more probability；The present invention develops first and obtains Ent-kaurane diterpenoid 16 α, the technique of 17,19 triols with chemistry route, it is provided that obtain Ent-kaurane diterpenoid 16 α, the new way of 17,19 triols.

Description

A kind of use of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol Way and preparation method thereof
Technical field
The present invention relates to new application of a kind of compound and preparation method thereof, particularly to a kind of kaurene natural product Purposes of Ent-kaurane diterpenoid-16 α, 17,19-triol and preparation method thereof.
Background technology
Ent-kaurane diterpenoid-16 α, 17,19-triol is the earliest from euphorbia plant Ricinocarpos stylosus Isolated (see document: Australian Journal of Chemistry (1964), 17, (8), 915-933), but this The method extraction efficiency of sample is low.Document report also obtains this compound from other plant the most successively, sees document: medicine divides Analysis magazine (2013), 33 (12), 2104-2108.This compound have active anticancer, allelopathy and Selective depression 11 β- The activity of HSD1 enzyme, sees document: (1) Chinese patent (2012), CN 102603519A；(2)Ecletica Quimica (2009),34(1),57-62；(3)European Journal of Medicinal Chemistry(2013),65,403- 414.But have no that Ent-kaurane diterpenoid-16 α, 17,19-triol has the report of antibacterial activity.
Summary of the invention
It is an object of the invention to the new use of a kind of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol On the way, to widen Ent-kaurane diterpenoid-16 α, the range of application of 17,19-triols, for Ent-kaurane diterpenoid-16 α, 17,19-triols Application provide more probability.
Present invention also offers the preparation side of a kind of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol Method, develops first and obtains Ent-kaurane diterpenoid-16 α, the technique of 17,19-triols with chemistry route, it is provided that obtain mapping shellfish The new way of shell China fir alkane-16 α, 17,19-triol.
The technical solution adopted for the present invention to solve the technical problems is:
A kind of kaurene natural product Ent-kaurane diterpenoid-16 α, the purposes of 17,19-triols, Ent-kaurane diterpenoid-16 α, 17,19-triol is applied to prepare antibacterial products.
As preferably, described antibacterial products is antibacterials, antibacterial, disinfection hand cleanser, germicidal soap, disinfecting scrub One in liquid.
As preferably, the fungicidal spectrum of described antibacterial products includes colon bacillus, Bacillus cercus, golden yellow Portugal Grape coccus, Erwinia carotorora and bacillus subtilis.
A kind of antibacterial products, it is by Ent-kaurane diterpenoid-16 α, and 17,19-triols are that active component is made and formed, and this resists Concentration >=62.5 μ the g/mL of Ent-kaurane diterpenoid-16 α, 17,19-triol in antibacterial product.As preferably, described antibacterium produces Product are the one in antibacterials, antibacterial, disinfection hand cleanser, germicidal soap, disinfecting scrub liquid.
Kaurene natural product Ent-kaurane diterpenoid-16 α, the preparation method of 17,19-triols, comprise the steps:
(1) synthesis of intermediate kaurene-16-alkene-19-alcohol
By LiAlH4It is suspended in anhydrous tetrahydro furan, under ice-water bath stirring, adds Ent-kaurane diterpenoid-16-alkene-19- Acid sterling, is stirred at room temperature uniformly afterwards, and concentrating under reduced pressure removes oxolane, by gained reactant acetic acid ethyl dissolution, and uses Saturated NH4Cl solution washing, concentrating under reduced pressure removes ethyl acetate and obtains mixture, mixed by mixture with 200-300 mesh silica gel, warp Silica gel chromatography, elution, obtain Ent-kaurane diterpenoid-16-alkene-19-alcohol；
(2) synthesis of Ent-kaurane diterpenoid-16 α, 17,19-triol
Ent-kaurane diterpenoid-16-alkene-19-alcohol is dissolved in CH2Cl2, lower addition m-CPBA is stirred at room temperature, reacts 24 hours, In reactant liquor, add diluted ethyl acetate afterwards, use saturated NaHCO3Solution washing three times, concentrating under reduced pressure removes organic molten Agent obtains mixture A, and this mixture A is dissolved in CH2Cl2, under ice-water bath stirring, add 2%H2SO4, removing ice-water bath, room temperature is anti- Answer 24 hours, add diluted ethyl acetate afterwards, use saturated NaHCO3Solution washing three times, concentrating under reduced pressure removes organic solvent Obtain mixture B, by mixture B through silica gel chromatography, elution, obtain Ent-kaurane diterpenoid-16 α, 17,19-triols.
The invention has the beneficial effects as follows:
1, provide a kind of kaurene natural product Ent-kaurane diterpenoid-16 α, the new application of 17,19-triols, widen Ent-kaurane diterpenoid-16 α, the range of application of 17,19-triols, for Ent-kaurane diterpenoid-16 α, the application of 17,19-triols carries For more probability.
2, develop first with chemistry route acquisition Ent-kaurane diterpenoid-16 α, the technique of 17,19-triols, it is provided that obtain Take the new way of Ent-kaurane diterpenoid-16 α, 17,19-triol.
Detailed description of the invention
Below by specific embodiment, technical scheme is described in further detail.
In the present invention, if not refering in particular to, the raw material used and equipment etc. are all commercially available or commonly used in the art. Method in following embodiment, if no special instructions, is the conventional method of this area.
Embodiment:
The present invention tests Ent-kaurane diterpenoid-16 α, 17,19-triol pure strain used from instruction plant trilobated leaf Sesarmae dehaani (synthetic method of Ent-kaurane diterpenoid-16-alkene-19-acid sees CN in the Ent-kaurane diterpenoid-16-alkene-19-acid that chrysanthemum is extracted 103086879B) synthesis obtains, and its building-up process is as follows:
By 300mg LiAlH4It is suspended in 50mL anhydrous tetrahydro furan (THF), under ice-water bath stirring, is dividedly in some parts mapping Kaurene-16-alkene-19-acid sterling (604mg), is stirred at room temperature 24 hours afterwards.Reactant liquor concentrating under reduced pressure is removed THF, will Gained reactant 50mL acetic acid ethyl dissolution, and use saturated NH4Cl solution washing 3 times.Concentrating under reduced pressure removes ethyl acetate Obtain mixture.Mixture is mixed with 0.5g 200-300 mesh silica gel, through silica gel (200-300 mesh, 10g) chromatograph, with petroleum ether: second Acetoacetic ester (volume ratio of 8:1) is elution, obtains Ent-kaurane diterpenoid-16-alkene-19-alcohol (400mg).
Ent-kaurane diterpenoid-16-alkene-19-alcohol (288mg) is dissolved in 20mL CH2Cl2, lower addition m-CPBA is stirred at room temperature (metachloroperbenzoic acid) 500mg, reacts 24 hours.50mL diluted ethyl acetate is added, with saturated afterwards in reactant liquor NaHCO3Solution washing three times, concentrating under reduced pressure removes ethyl acetate and obtains mixture A.This mixture A is dissolved in 20mL CH2Cl2, Under ice-water bath stirring, it is dividedly in some parts 2%H2SO4(10mL), remove ice-water bath, room temperature reaction 24 hours, add in reactant liquor afterwards Enter 20mL diluted ethyl acetate, use saturated NaHCO3Solution washing three times, concentrating under reduced pressure removes organic solvent and obtains mixture B. By mixture B through silica gel (200-300 mesh, 10g) chromatograph, with petroleum ether: ethyl acetate (volume ratio of 5:1) is that eluent is washed De-, obtain Ent-kaurane diterpenoid-16 α, 17,19-triols (50mg).
The Structural Identification of product: white powdery solids；Mass spectrum EI-MS provides its molecular ion peak [M+H]+M/z= 323；In conjunction with13C NMR and DEPT, it may be determined that the molecular formula of this compound is C20H34O3, degree of unsaturation 4, illustrate this molecule is deposited At 4 rings；20 carbon signals: wherein 2 methyl, 11 methylene, 3 methines and 4 quaternary carbons；1H H NMR spectroscopy 4.12 (1H, D, J=10.2Hz), 4.04 (1H, d, J=12.8Hz), 4.01 (1H, d, J=10.2Hz) and 3.60 (d, J=12.8Hz) display In molecule exist 2 methylols, 1.18 (3H, s) He 1.05 (3H, s) display molecule in existence 2 angular methyls, show this chemical combination Thing is the structure of Ent-kaurane diterpenoid diterpene.Comprehensively1H NMR、13C NMR and DEPT modal data, further consulting literatures compares to be sent out The now spectral data of this compound and Ent-kaurane diterpenoid-16 α, the spectral data of 17,19-triols is completely the same, so far, product Structure determined.
Its spectral data is as follows:1H NMR(400MHz,CDCl3): δH4.12 (1H, d, J=10.2Hz, 17a)；4.04 (1H, d, J=12.8Hz, 19a)；4.01 (1H, d, J=10.2Hz, 17b)；3.60 (d, J=12.8Hz, 19b)；1.18(3H, s,CH3-18)；1.05(3H,s,CH3-20).13C NMR(100MHz,CDCl3):δC40.7(C-1)；18.7(C-2)；36.2 (C-3)；39.4(C-4)；57.0(C-5)；21.1(C-6)；43.1(C-7)；45.0(C-8)；57.4(C-9)；39.6(C-10)； 18.9(C-11)；26.8(C-12)；46.1(C-13)；37.7(C-14)；53.9(C-15)；81.6(C-16)；66.4(C-17)； 28.1(C-18)；64.1(C-19)；18.6(C-20)；EI-MS:[M+H]+M/z=323.
The Determination of Antibacterial Activity of compound Ent-kaurane diterpenoid-16 α, 17,19-triol
1. for examination antibacterial: colon bacillus (Escherichia coli), Bacillus cercus (Bacillus Cereus), staphylococcus aureus (Staphyloccocus aureus), Erwinia carotorora (Erwinia And bacillus subtilis (Bacillus subtili) carotovora).
2. test method: draw gently with inoculating loop and take a ring strain bacterium colony to 50mL LB culture medium (peptone 0.5g, chlorine Change sodium 0.25g, Carnis Bovis seu Bubali cream 0.15g, deionized water 50mL, pH=7.0 ± 0.1) in, 220r/min training on 37 DEG C of constant-temperature tables Support to OD600=0.5, take 10 μ L concentration and be respectively 125,62.5,31.3,15.5,7.8,3.9,1.9,0.9,0.5 μ g/mL mappings Kaurene-16 α, 17,19-triol DMSO sample solutions, take OD600The bacteria suspension of=0.5 is in 10 μ L, in 80 μ L nutrient broths Mixing concussion is uniformly placed in 37 DEG C of incubators cultivation 24h, then according to turbidimetry principle, measures OD by microplate reader600Obtain Low Mlc (MIC), the sample solution of each concentration of each strain is parallel does 3 tests.Ampicillin is positive right According to.
3. result of the test: compound Ent-kaurane diterpenoid-16 α, 17,19-triol is to colon bacillus, wax-like spore bar Bacterium, staphylococcus aureus, Erwinia carotorora, the minimum inhibitory concentration MIC test result of bacillus subtilis are shown in Table 1.Sun Property comparison for ampicillin.
The antibacterial activity of table 1 compound Ent-kaurane diterpenoid-16 α, 17,19-triol
Table 1 shows, Compound Compound Ent-kaurane diterpenoid-16 α, 17,19-triols are to colon bacillus (E.coli), Bacillus cercus (B.cereus), staphylococcus aureus (S.aureus), Erwinia carotorora (E.carotovora), bacillus subtilis (B.subtilis) has the strongest inhibitory action, ratio positive control ampicillin Activity will get well.Antibacterial tests shows, Ent-kaurane diterpenoid-16 α, and 17,19-triols may be used for preparing antibacterials, or Person prepares antibacterial, or is used for preparing anti-bacterial hand lotion or antibacterial medicated soap or antimicrobial cleaning liquid.
Embodiment described above is the one preferably scheme of the present invention, not makees the present invention any pro forma Limit, on the premise of without departing from the technical scheme described in claim, also have other variant and remodeling.

Claims (2)

1. kaurene natural product Ent-kaurane diterpenoid-16 α, the purposes of 17,19-triols, it is characterised in that: mapping shellfish Shell China fir alkane-16 α, 17,19-triols are applied to prepare antibacterial products, and the fungicidal spectrum of described antibacterial products is: E Bacterium, Bacillus cercus, staphylococcus aureus, Erwinia carotorora and bacillus subtilis；Ent-kaurane diterpenoid-16 α, 17,19-triol structural formula is:。
Purposes the most according to claim 1, it is characterised in that: described antibacterial products is antibacterials, antibacterial, sterilization One in handwashing liquid, germicidal soap, disinfecting scrub liquid.
CN201510030554.0A 2015-01-22 2015-01-22 A kind of purposes of kaurene natural product Ent-kaurane diterpenoid-16 α, 17,19-triol and preparation method thereof Expired - Fee Related CN104663682B (en)

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天然贝壳杉烷二萜类物质的生物活性;李大喜;《国外医药植物药分册》;19981231;第13卷(第4期);147-152 *

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