CN108821949B - Olikane type compound and extraction method and application thereof - Google Patents

Olikane type compound and extraction method and application thereof Download PDF

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CN108821949B
CN108821949B CN201810442290.3A CN201810442290A CN108821949B CN 108821949 B CN108821949 B CN 108821949B CN 201810442290 A CN201810442290 A CN 201810442290A CN 108821949 B CN108821949 B CN 108821949B
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olivine
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dihydroxy
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黄岛平
林葵
谢集照
黄祖林
张思敏
谢云峰
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GUANGXI ZHUANG AUTONOMOUS REGION CENTER FOR ANALYSIS AND TEST RESEARCH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
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    • A61P31/04—Antibacterial agents
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/08—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing three- or four-membered rings

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Abstract

The invention relates to a method for recovering useful substances from distillation still bottom residual liquid of natural plant star anise extracted spice and application thereof, in particular to an extraction method and application of a compound [1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene ]. The method can not only make full use of the residual liquid at the bottom of the distillation kettle of the star anise, but also obtain the [6,6,3] tricyclic olivine sesquiterpene compound, and the olivine sesquiterpene compound can be used as an antibacterial candidate compound or a natural perfume.

Description

Olikane type compound and extraction method and application thereof
Technical Field
The invention relates to the technical field of extracting useful substances from natural plants, in particular to a method for recovering useful substances from distillation still bottom residual liquid of natural plant star anise from which spices are extracted and application thereof.
Background
Fructus Anisi Stellati (Aniseed tree) belonging to family Magnoliaceae, genus Anise, and having Latin chemical nameIlliciumverum，The aniseed, the marine fennel and the aniseed are commonly called as the aniseed, the marine fennel and the aniseed which are the 'medicinal and edible' varieties published in China since 2002, and researches show that the aniseed only has extremely low toxicity. The method is mainly distributed in provinces such as Guangxi provinces, Guangdong provinces, Yunnan provinces and the like in China, is a special product of spices and traditional Chinese medicines in China, and is also widely planted in southeast Asia countries such as Vietnam, Pakistan and the like. Guangxi as the origin and the most predominant production area of star anise, the existing planting area and yield respectively account for85% and 90% of the country. The fennel oil can be extracted from fruits or branches and leaves of the illicium verum by steam distillation, and the production and processing of the fennel oil are also the Guangxi characteristic industry and are important branch industries in certain mountain counties. The main current process technology is to crush anise, extract fennel oil by steam distillation, separate oil from water, and then introduce the fennel oil into a rectifying still for separation to obtain the anethole. After separation, a liquid which is difficult to volatilize and is sticky is deposited at the bottom of the rectifying still, which is called residual liquid and is generally discarded as waste, and few reports are reported on the research or utilization of the residual liquid.
The olivine sesquiterpene compound with [6,6,3] tricyclic belongs to rare natural products, and due to the complex structure and more chiral sites, the synthesis method of the compound is not reported at present. Limiting the channels and the amount of compounds obtained. But can be obtained from waste, which can greatly reduce the cost of raw materials.
Disclosure of Invention
The invention aims to provide a method for extracting an olivine type sesquiterpene compound with [6,6,3] tricycles from a residual liquid at the bottom of a star anise rectifying still, by adopting the method, the residual liquid at the bottom of the star anise rectifying still can be fully utilized, and the olivine type sesquiterpene compound with [6,6,3] tricycles can be obtained, and the olivine type compound can be used as an antibacterial candidate compound or a natural perfume.
The invention also aims to provide application of the olivine compound extracted from the aniseed rectifying still bottom residual liquid in the aspect of preparing antibacterial drugs and application in the aspect of inhibiting staphylococcus aureus 01-04 and staphylococcus aureus ATCC 25923.
In order to achieve the purpose, the invention adopts the following technical scheme:
an olivine-type compound having the structure:
Figure DEST_PATH_IMAGE001
the chemical name of the compound is 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene.
The olivine-type compound (1, 4-dihydroxy-14 (10 → 1) -transfer-olivine-1 (10) -ene) is extracted from the residual liquid at the bottom of the illicium verum rectifying still, the residual liquid at the bottom of the illicium verum rectifying still is a sticky substance which is settled at the bottom of a rectifier after rectification, and the specific extraction process comprises the following operation steps:
(1) taking the residual liquid at the bottom of the illicium verum rectifying still, separating by silica gel column chromatography, and carrying out gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 10:1 and 1:1 in sequence to obtain 7 fractions A-G;
(2) separating the fraction F by silica gel column chromatography, and performing gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 25:1, 10:1, 5:1, 2:1 and 1:1 in sequence to obtain 17 fractions F1-F17; f14 is separated by sephadex LH-20 sephadex column chromatography, and eluted by mixed solution with the volume ratio of chloroform to methanol =1:1 to obtain 2 fractions F14-1-F14-2;
(3) f14-2 is subjected to open ODS column chromatography, and gradient elution is sequentially carried out by using mixed solution with the volume ratio of methanol to water =30%, 50%, 70%, 90% and 100%, so that 4 fractions F14-2-1-F14-2-4 are obtained; separating F14-2-3 by silica gel column chromatography, and gradient-eluting with mixed solution of cyclohexane and ethyl acetate =10:1, 8:1, 6:1, 4:1, 2:1 and 1:1 in sequence to obtain 3 fractions F14-2-3-1-F14-2-3-3;
(4) f14-2-3-2 is separated by preparative thin layer chromatography, and is developed by using a mixed solution with a volume ratio of chloroform to methanol =10:1 as a developing solvent to obtain the compound 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene.
The olivine type compound extracted from the residual liquid at the bottom of the illicium verum rectifying still has the following structure determination process:
white powder, dissolved in methanol. HR-ESI-MSm/z：259.1670 [M+Na]+ (calcd for C15H24NaO2,259.1674). Bonding of1H-NMR and13C-NMR presumes that the compound has the formula C15H24O2The unsaturation was calculated to be 4.
1H-NMR (600 MHz，CD3OD) in the spectrumδ 1.93 (3H，s)，1.07 (3H，s)，1.17(3H，s)，1.04 (3H，d，J = 7.1 Hz) proton signal for 4 methyl groups;δ4.71 (1H，d，J = 4.2 Hz) andδ4.06 (1H，dd，J = 11.8, 4.9 Hz) is 2 connected-oxygen sp3Proton signal on the hybridized carbon.13C-NMR (150 MHz，CD3OD) combined with DEPT-135 carbon spectrum, the compound has 2 sp2Hybridized quaternary carbon signals (δ146.3, 134.6), 1 sp3Hybridized quaternary carbon signals (δ22.6), 2 connected-oxygen sp3Hybridized tertiary carbon signal (δ75.6, 74.5), 3 sp3Hybridized secondary carbon signal: (δ42.5, 32.4, 22.3), 4 sp3Hybridized tertiary carbon signal (δ40.6, 34.6, 31.5, 22.3), 4 methyl carbon signals: (δ28.6、18.9、16.1、15.7）。
In that1H-1Proton signal in H COSY spectraδ4.71(H-2) andδ1.77 (H-3), 1.40(H-3) proton signal correlation; proton signalδ1.77 (H-3) andδ2.56(H-4) proton signal correlation; proton signalδ2.56(H-4) andδ1.04(H-3), 2.68 (H-5) proton signal correlation; proton signalδ2.68 (H-5) andδ0.59 (H-6) proton signal correlation; proton signalδ0.59 (H-6) andδ0.49 (H-7) proton signal correlation; proton signalδ0.49 (H-7) andδ2.08(H-8), 1.68 (H-8) proton signal correlation; proton signalδ2.08(H-8), 1.68 (H-8) withδ4.06 (H-9) proton signal correlation, fragment A was obtained.
Figure 469540DEST_PATH_IMAGE002
Proton signal in HMBC spectraδ1.93 (Me-12) withδRemote correlation of 74.5 (C-2), 134.6(C-10) carbon signals; proton signalδ4.71(H-2) andδ134.6(C-10), 34.6(C-4) carbon signal remote correlation; proton signalδ4.06 (H-9) withδRemote phase of 146.3 (C-1), 40.6(C-5), 31.5(C-7) carbon signalAlternatively, fragment A may be combined to give fragment B. In HMBC, proton signalδ1.07 (H-15) andδ22.3 (C-6), 31.5(C-7) carbon signal remote correlation; proton signalδ1.17(H-14) andδ22.3 (C-6), 31.5(C-7) carbon Signal remote correlation, Critical HMBC and1H-1the correlation between H COSY signals is as follows. In summary, the structure of the compound is 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene.
Figure DEST_PATH_IMAGE003
The signals of the nuclear magnetic resonance spectrum of the compound are assigned in table 1:
Figure 205284DEST_PATH_IMAGE004
through tests, the inventor finds that the olivine type compound [1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene ] has better in-vitro antibacterial activity, can be applied to the production of medicines for inhibiting staphylococcus aureus 01-04 and staphylococcus aureus ATCC25923, and can be applied to the preparation of antibacterial medicines.
The invention has the following beneficial effects:
the invention extracts 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene from the residual liquid at the bottom of the illicium verum rectifying still, which not only can fully utilize the residual liquid at the bottom of the illicium verum rectifying still to greatly reduce the cost, but also the extracted 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene has better in vitro antibacterial activity, can be used for antibacterial candidate compounds, is applied to the aspect of preparing antibacterial drugs, or is used as natural perfume, and is worthy of development and utilization.
Drawings
FIG. 1 is a drawing showing 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene1H-NMR；
FIG. 2 is a representation of 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene13C-NMR；
FIG. 3 is HMBC of 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene;
FIG. 4 is the HSQC of 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene;
FIG. 5 is HR-ESI-MS of 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene;
FIG. 6 is a scheme showing the isolation of 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
(1) Taking 950G of residual liquid at the bottom of the illicium verum rectifying still, separating by silica gel column chromatography, and carrying out gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 10:1 and 1:1 in sequence to obtain 7 fractions A-G;
(2) separating the fraction F (43.05 g) by silica gel column chromatography, and performing gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 25:1, 10:1, 5:1, 2:1 and 1:1 in sequence to obtain 17 fractions F1-F17; f14 (1.61 g) is separated by sephadex LH-20 sephadex column chromatography, and is eluted by a mixed solution with the volume ratio of chloroform to methanol =1:1 to obtain 2 fractions F14-1-F14-2;
(3) f14-2 (530 mg) was subjected to open ODS column chromatography, and gradient-eluted sequentially with a mixed solution of methanol to water =30%, 50%, 70%, 90%, 100% by volume to give 4 fractions F14-2-1 to F14-2-4; f14-2-3 (109 mg) is separated by silica gel column chromatography, and is sequentially subjected to gradient elution by using mixed solution with the volume ratio of cyclohexane to ethyl acetate =10:1, 8:1, 6:1, 4:1, 2:1 and 1:1 to obtain 3 fractions F14-2-3-1-F14-2-3-3;
(4) f14-2-3-2 (14 mg) was separated by preparative thin layer chromatography, and developed with a mixed solution of chloroform: methanol =10:1 in volume ratio as a developing solvent to give compound 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene (6.9 mg).
Application example 1
In vitro antibacterial Activity test
Adopting staphylococcus aureus (01-04) and staphylococcus aureusThe strain ATCC25923 is respectively transferred to a solid slant culture medium to carry out slant activation of the strain. And (3) adding some activated bacteria to be tested into a test tube filled with 10 mL of physiological saline, and shaking to fully mix the bacteria to be tested to obtain a test bacteria suspension. Accurately sucking 1.0 mL of the test bacterial suspension, diluting in another sterile test tube containing 9.0 mL of physiological saline in advance, performing bacterial count by McLeod's turbidimetry, and adjusting concentration to 107～108Bacterial suspension per mL for subsequent use.
The compound 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene extracted by the invention is diluted by agar plate double dilution method, bacteria is inoculated by an instrument in multiple points, and the Minimum Inhibitory Concentration (MIC) is measured. The experimental strain is inoculated into culture medium plates containing compounds with different concentrations, and cultured in an incubator at 37 ℃ for 18-24 hours, wherein the MIC value is the minimum drug concentration for inhibiting the growth of bacteria.
The experimental results are as follows: 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene has MIC values of 26.3 mu g/mL for staphylococcus aureus (01-04) and staphylococcus aureus (ATCC 25923) and 2.4 mu g/mL for amoxicillin as a positive control drug. The results show that 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene has better in vitro antibacterial activity.

Claims (4)

1. An olivine-type compound characterized by the following structure:
Figure 938634DEST_PATH_IMAGE001
the chemical name of the compound is 1, 4-dihydroxy-14 (10 → 1) -migratory-olivine-1 (10) -ene.
2. The method for extracting an olivine-type compound according to claim 1, wherein the compound is extracted from the bottom residue of the distillation still of Illicium verum, by the following steps:
(1) taking the residual liquid at the bottom of the illicium verum rectifying still, separating by silica gel column chromatography, and carrying out gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 10:1 and 1:1 in sequence to obtain 7 fractions A-G;
(2) separating the fraction F by silica gel column chromatography, and performing gradient elution by using mixed solutions with the volume ratios of cyclohexane to ethyl acetate =1:0, 50:1, 25:1, 10:1, 5:1, 2:1 and 1:1 in sequence to obtain 17 fractions F1-F17; f14 is separated by sephadex LH-20 sephadex column chromatography, and eluted by mixed solution with the volume ratio of chloroform to methanol =1:1 to obtain 2 fractions F14-1-F14-2;
(3) f14-2 is subjected to open ODS column chromatography, and gradient elution is sequentially carried out by using mixed solution with the volume ratio of methanol to water =30%, 50%, 70%, 90% and 100%, so that 4 fractions F14-2-1-F14-2-4 are obtained; separating F14-2-3 by silica gel column chromatography, and gradient-eluting with mixed solution of cyclohexane and ethyl acetate =10:1, 8:1, 6:1, 4:1, 2:1 and 1:1 in sequence to obtain 3 fractions F14-2-3-1-F14-2-3-3;
(4) f14-2-3-2 is separated by preparative thin layer chromatography, and is developed by using a mixed solution with a volume ratio of chloroform to methanol =10:1 as a developing solvent to obtain the compound 1, 4-dihydroxy-14 (10 → 1) -migration-olivine-1 (10) -alkene.
3. The method for extracting an olivine-type compound according to claim 2, wherein the residual liquid at the bottom of the rectifying still of illicium verum is a viscous substance which settles at the bottom of the rectifying still after rectification.
4. Use of the olivine-type compounds according to claim 1 for inhibiting Staphylococcus aureus (01-04), Staphylococcus aureus
Use of cocci ATCC25923 in the preparation of medicaments.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102031196A (en) * 2010-12-02 2011-04-27 北京航空航天大学 Method for extracting effective ingredients in industrial residue of Chinese anise
CN104628546A (en) * 2015-02-13 2015-05-20 广西壮族自治区分析测试研究中心 4-hydroxyl-3-(1, 2-dimethyl-2-propylene) benzaldehyde and use
CN105315145A (en) * 2015-02-13 2016-02-10 广西壮族自治区分析测试研究中心 Method for extracting alpha and beta-unsaturated ketone from illicium verum rectifying kettle residual liquor

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Publication number Priority date Publication date Assignee Title
US7232795B2 (en) * 2005-11-23 2007-06-19 International Flavors & Fragrances Inc. Derivatives of decahydro-cycloprop[e]indene compounds and their use in perfume compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102031196A (en) * 2010-12-02 2011-04-27 北京航空航天大学 Method for extracting effective ingredients in industrial residue of Chinese anise
CN104628546A (en) * 2015-02-13 2015-05-20 广西壮族自治区分析测试研究中心 4-hydroxyl-3-(1, 2-dimethyl-2-propylene) benzaldehyde and use
CN105315145A (en) * 2015-02-13 2016-02-10 广西壮族自治区分析测试研究中心 Method for extracting alpha and beta-unsaturated ketone from illicium verum rectifying kettle residual liquor

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