CN105622379B - 2,4- diacetyl phloroglucins are similar to thing and its preparation method and application - Google Patents

2,4- diacetyl phloroglucins are similar to thing and its preparation method and application Download PDF

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CN105622379B
CN105622379B CN201610147829.3A CN201610147829A CN105622379B CN 105622379 B CN105622379 B CN 105622379B CN 201610147829 A CN201610147829 A CN 201610147829A CN 105622379 B CN105622379 B CN 105622379B
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龚亮
谭海波
蒋跃明
段学武
杨宝
张丹丹
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South China Botanical Garden of CAS
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    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
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    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic

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Abstract

The invention discloses 2,4 diacetyl phloroglucins similar to thing and its preparation method and application.2,4 diacetyl phloroglucins are shown similar to thing, its structure such as formula (1) or formula (2)：Wherein R is C2‑C15Alkyl, R1、R2For C1‑C15Alkyl, and R1And R2It is different.Have the 2 of preferable anti-Penicillium italicum bacterium, citrus common green mold bacterium, citrus sour rot bacterium or banana crown rot bacterium activity the present invention provides a kind of; 4 diacetyl phloroglucins are similar to thing; and provide a kind of synthesis above-mentioned 2; short-cut method of the 4 diacetyl phloroglucins similar to thing; due to the 2 of the present invention; 4 diacetyl phloroglucins have preferable anti-Penicillium italicum bacterium, citrus common green mold bacterium, citrus sour rot bacterium or banana crown rot bacterium activity similar to thing; therefore it can be used for preparing antibacterials, especially applied on prevention citrus and banana Major Diseases.

Description

2,4- diacetyl phloroglucins are similar to thing and its preparation method and application
Technical field：
The invention belongs to preservation field, and in particular to 2,4- diacetyl phloroglucins are similar to thing and preparation method thereof and answer With.
Background technology：
2,4- diacetyl phloroglucins (2,4-Diacetylphloroglucinol, 2,4-DAPG, in formula (5) MP10), it is a kind of phenolic compound, the secondary metabolite produced for Pseudomonas fluorescens.Studies have found that, this kind of metabolism Product has antibiosis to plant pathogen, be the important function factor of Pseudomonas biocontrol microorganisms (Haas et al., Annu.Rev.Phytopathol.2003,41:117-153)。
The content of the invention：
First purpose of the present invention is to provide suppresses Penicillium italicum bacterium, citrus common green mold bacterium, citrus with significant The 2,4- diacetyl phloroglucins of the mycelial growth of sour germ and banana crown rot bacterium are similar to thing.
2, the 4- diacetyls phloroglucin of the present invention is shown similar to thing, its structure such as formula (1) or formula (2)：
Wherein R is C2-C15Alkyl, R1、R2For C1-C15Alkyl, and R1And R2It is different.
The 2,4- diacetyls phloroglucin is similar to any compound that thing is preferably in formula (3)：
Further preferably, 2, the 4- diacetyls phloroglucin is any compound in formula (4) similar to thing：
Second object of the present invention is to provide preparation method of one kind 2,4- diacetyls phloroglucin similar to thing, it is special Sign is that its building-up process is as follows：
The compound shown in formula (1) is obtained with phloroglucin and alkyl acyl chloride reaction under the catalysis of methanesulfonic acid (MSA), its Middle R is C2-C15Alkyl；
The change shown in formula (2) is obtained with monoacyl phloroglucin and alkyl acyl chloride reaction under the catalysis of methanesulfonic acid (MSA) Compound, wherein R1、R2For C1-C15Alkyl, and R1And R2It is different.
Third object of the present invention is to provide above-mentioned 2,4- diacetyls phloroglucin and is preparing antibacterials similar to thing In application.
The antibacterials are anti-Penicillium italicum bacterium, citrus common green mold bacterium, citrus sour rot bacterium or banana crown rot The medicine of bacterium.
The 2,4- diacetyls phloroglucin is similar to any compound that thing is in formula (4)：
Fourth object of the present invention is to provide above-mentioned 2,4- diacetyls phloroglucin and is preparing citrus or perfume (or spice) similar to thing Application in any of several broadleaf plants antistaling agent, or prevention citrus sour rot medicine.
The 2,4- diacetyls phloroglucin is similar to any compound that thing is in formula (4)：
The present invention provides one kind to have preferable anti-Penicillium italicum bacterium, citrus common green mold bacterium, citrus sour rot bacterium or perfume (or spice) 2, the 4- diacetyl phloroglucins of any of several broadleaf plants crown rot bacterium activity provide a kind of synthesize between above-mentioned 2,4- diacetyls similar to thing The short-cut method of benzenetriol analog, since 2, the 4- diacetyls phloroglucin of the present invention has preferable anti-citrus similar to thing Mould germ, citrus common green mold bacterium, citrus sour rot bacterium or banana crown rot bacterium activity, therefore can be used for preparing antimicrobial Thing, is especially applied on prevention citrus and banana Major Diseases.
Embodiment：
Following embodiments are to further explanation of the invention, rather than limitation of the present invention.
Embodiment 1：Preparation method of the 2,4- diacetyls phloroglucin similar to thing：
The 2,4- diacetyls phloroglucin of the present invention is as follows similar to the building-up process of thing：
With phloroglucin and alkyl acyl chloride under the catalysis of methanesulfonic acid (MSA), by heating 3 it is small when react to obtain formula (1) Shown compound, wherein R are C1-C15Alkyl；
Reacted with monoacyl phloroglucin with alkyl acyl chloride under the catalysis of methanesulfonic acid (MSA), by heating 3 it is small when obtain Compound shown in formula (2), wherein R1、R2For C1-C15Alkyl, and R1And R2It is different.
Comprise the following steps that：
(1) phloroglucin (315mg, 2.5mmol) and acyl chlorides (5.0mmol) are placed in the round-bottomed flask of 10mL dryings, It is heated to 80 DEG C.Stirring after ten minutes, pyrovinic acid (25mmol, 1.6Ml) is slowly added dropwise into reaction system.After continuation of insurance Stirring 3 hours of reaction system at a temperature of are held, are then cooled to room temperature.Reaction mixture is poured into 25mL frozen water, is used in combination Ethyl acetate (25mL) extracts 3 times, merges organic phase, and use 25mL saturated sodium bicarbonates and brine It respectively.Organic phase Filtered after being dried over anhydrous sodium sulfate, gained filtrate is spin-dried in reduced pressure.Remaining oily mixture passes through rapid column chromatography (n-hexane：Ethyl acetate=5:1) separate, obtain corresponding acyl phloroglucinol compound.
The acyl chlorides
When R is iPr, gained compound is the MP1 in formula (5)；
When R is C8H17During straight chained alkyl, gained compound is the MP2 in formula (5)；
When R is C3H7Straight chained alkyl (CH3CH2CH2-) when, gained compound is the MP4 in formula (5)；
When R is C7H15During straight chained alkyl, gained compound is the MP5 in formula (5)；
When R is iBu, gained compound is the MP7 in formula (5)；
When R is cyclopropyl, gained compound is the MP8 in formula (5)；
When R is PhC2H4When, gained compound is the MP9 in formula (5)；
When R is CH3When, gained compound is the MP10 in formula (5)；
When R is C11H21During straight chained alkyl, gained compound is the MP11 in formula (5)；
When R is C4H9During straight chained alkyl, gained compound is the MP12 in formula (5)；
When R is C5H11During straight chained alkyl, gained compound is the MP13 in formula (5)；
When R is phenyl, gained compound is the MP14 in formula (5)；
When R is C2H5When, gained compound is the MP15 in formula (5).
(2) round bottom that acetyl group phloroglucin (336mg, 2.0mmol) and acyl chlorides (3.0mmol) are placed in 10mL dryings is burnt In bottle, 80 DEG C are heated to.Stirring after ten minutes, pyrovinic acid (15mmol, 1.0mL) is slowly added dropwise into reaction system. 3 hours of reaction system are stirred at a temperature of being continually maintained in, are then cooled to room temperature.Reaction mixture is poured into 25mL frozen water In, and extracted 3 times with ethyl acetate (25mL), merge organic phase, and use 25mL saturated sodium bicarbonates and brine It respectively. Organic phase filters after being dried over anhydrous sodium sulfate, and gained filtrate is spin-dried in reduced pressure.Remaining oily mixture is by quick Column chromatography (n-hexane：Ethyl acetate=5:1) separate, obtain corresponding acyl phloroglucinol compound.
The acyl chlorides
The R2For C5H11Straight chained alkyl (CH3CH2CH2CH2CH2-) when, gained compound is the MP3 in formula (5)；
The R2For C3H7Straight chained alkyl (CH3CH2CH2-) when, gained compound is the MP6 in formula (5).
The nuclear magnetic data of compound MP1-MP15 is as follows：
1st, compound MP10
1,1'-(2,4,6-trihydroxy-1,3-phenylene)diethanone MP10
1H NMR(500MHz,CD3OH+CDCl3):δ=5.75 (s, 1H), 2.60 (s, 6H)；13C NMR(125MHz, CDCl3):δ=203.2,170.6,168.2,103.0,93.8,31.3.
2nd, compound MP15
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(propan-1-one)MP15
1H NMR(500MHz,CDCl3):δ=5.83 (s, 1H), 3.16 (q, J=7.2Hz, 3H), 1.20 (t, J= 7.2Hz,5H)；13C NMR(125MHz,CDCl3):δ=171.8,95.3,37.4,31.0,8.5.
3rd, compound MP6
1-(3-acetyl-2,4,6-trihydroxyphenyl)hexan-1-one MP6
1H NMR(500MHz,CDCl3):δ=5.83 (d, J=3.4Hz, 1H), 3.10 (t, J=7.2Hz, 2H), 2.72 (s, 3H), 1.72 (q, J=7.4Hz, 2H), 1.02 (t, J=7.4Hz, 3H)；13C NMR(125MHz,CDCl3):δ=204.2, 172.0,95.2,46.0,32.8,18.0,13.9.
4th, compound MP4
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(butan-1-one)MP4
1H NMR(500MHz,CDCl3):δ=5.87 (s, 1H), 3.08 (t, J=9.2Hz, 4H), 1.73 (3,4H), 1.01 (t, J=7.4Hz, 6H)；13C NMR(125MHz,CDCl3):δ=207.1,172.0,104.1,95.3,46.0,18.0, 13.9.
5th, compound MP3
1-(3-acetyl-2,4,6-trihydroxyphenyl)hexan-1-one MP3
1H NMR(500MHz,CDCl3):δ=5.86 (s, 1H), 3.10 (t, J=7.5Hz, 2H), 2.72 (s, 3H), 1.70 (m,2H),1.37(m,4H),0.99(m,3H)；13C NMR(125MHz,CDCl3):δ=207.3,204.4,172.1,104.1, 95.3,44.1,32.8,31.6,24.3,22.6,14.0.
6th, compound MP1
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(2-methylpropan-1-one)MP1
1H NMR(500MHz,CDCl3):δ=5.87 (s, 1H), 3.96 (t, J=6.7Hz, 1H), 1.21 (d, J= 6.7Hz,1H)；13C NMR(125MHz,CDCl3):δ=211.5,182.4,172.2,103.6,95.6,39.3,19.2.
7th, compound MP8
(2,4,6-trihydroxy-1,3-phenylene)bis(cyclopropylmethanone)MP8
1H NMR(500MHz,CDCl3):δ=5.78 (s, 1H), 4.17 (s, 2H), 2.0-2.5 (m, 8H)；13C NMR (125MHz,CDCl3):δ=169.6,95.3,45.0,24.7,21.2.
8th, compound MP12
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(pentan-1-one)MP12
1H NMR(500MHz,CDCl3):δ=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J= 15.0,7.5Hz, 4H), 1.42 (dd, J=15.0,7.5Hz, 4H), 0.97 (t, J=7.5Hz, 6H)13C NMR(125MHz, CDCl3):δ=207.3,172.0,95.4,43.9,26.8,24.5,14.0.
9th, compound MP7
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(3-methylbutan-1-one)MP7
1H NMR(500MHz,CDCl3):δ=5.87 (s, 1H), 2.99 (d, J=6.7Hz, 4H), 2.27 (m, 2H), 1.00 (d, J=6.7Hz, 6H)；13C NMR(125MHz,CDCl3):δ=206.8,179.2,172.1,104.3,95.4,43.1, 25.6,22.8.
10th, compound MP13
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(hexan-1-one)MP13
1H NMR(500MHz,CDCl3):δ=5.83 (s, 1H), 3.10 (t, J=7.4Hz, 4H), 1.71 (m, 4H), 1.37 (m,8H),0.93(m,6H)；13C NMR(125MHz,CDCl3):δ=171.9,95.4,44.1,31.6,24.4,22.6, 14.0.
11st, compound MP14
(2,4,6-trihydroxy-1,3-phenylene)bis(cyclohexylmethanone)MP14
1H NMR(500MHz,CDCl3):δ=5.79 (s, 1H), 4.44 (s, 4H)；13C NMR(125MHz,CDCl3):δ= 204.1,172.1,134.7,129.9,128.5,126.9,95.7,50.1.
12nd, compound MP5
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(octan-1-one)MP5
1H NMR(500MHz,CDCl3):δ=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J= 15.0,7.5Hz, 4H), 1.31 (m, 16H), 0.90 (t, J=7.5Hz, 6H)13C NMR(125MHz,CDCl3):δ=207.3, 172.0,95.4,44.5,31.8,29.5,29.2,29.1,25.1,14.1.
13rd, compound MP2
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(octan-1-one)MP2
1H NMR(500MHz,CDCl3):δ=5.83 (s, 1H), 3.11 (t, J=7.5Hz, 4H), 1.69 (dt, J= 15.0,7.5Hz, 4H), 1.31 (m, 20H), 0.90 (t, J=7.5Hz, 6H)13C NMR(125MHz,CDCl3):δ=207.3, 172.0,95.4,44.3,31.8,29.6,29.5,29.2,29.1,25.0,14.1.
14th, compound MP9
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(2-phenylethanone)MP9
1H NMR(500MHz,CDCl3):δ=7.20-7.40 (m, 10H), 5.79 (s, 1H), 4.44 (s, 4H)；13C NMR (125MHz,CDCl3):δ=204.1,172.1,134.7,129.9,128.5,126.9,95.7,50.1.
15th, compound MP11
1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(dodecan-1-one)MP11
1H NMR(500MHz,CDCl3):δ=5.81 (s, 1H), 3.10 (t, J=7.4Hz, 4H), 1.70 (m, 4H), 1.31 (m, 32H), 0.90 (t, J=7.5Hz, 6H)13C NMR(125MHz,CDCl3):δ=171.9,95.4,44.2,31.9, 29.6,29.6,29.5,29.3,29.2,29.1,24.7,22.7,14.1.
Embodiment 2：
Medicament (compound MP4, compound MP6 or compound MP10) is dissolved in DMSO, is diluted to in PDA culture medium 25 μ g/ml, are subsequently placed in the culture dish of 9cm, culture dish center inoculation citrus green mold bacterium, observe 7 days, using solvent group as Control, inhibiting rate is calculated according to the following formula.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length × 100%
The result shows that：Compound MP6 and compound MP4 is 80% and 84% respectively to the inhibiting rate of citrus green mold, significantly Higher than the inhibiting rate of maternal (2,4-DAPG, i.e. compound MP10) 29.7%.
Embodiment 3：
Medicament (compound MP4, compound MP6 or compound MP10) is dissolved in DMSO, further with PDA culture medium 25 μ g/ml are diluted to, are subsequently placed in the culture dish of 9cm, in culture dish center inoculation citrus Penicillium notatum, are observed 7 days, with solvent Group calculates inhibiting rate as control according to the following formula.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length × 100%
The result shows that：Compound MP6 and compound MP4 is 59.3% and 63% respectively to the inhibiting rate of citrus Penicillium notatum, It is significantly higher than the inhibiting rate of maternal (2,4-DAPG, i.e. compound MP10) 40.7%.
Embodiment 4：
Medicament (compound MP1 or compound MP10) is dissolved in DMSO, further with being diluted to 25 μ in PDA culture medium G/ml, is subsequently placed in the culture dish of 9cm, culture dish center inoculation banana crown rot bacterium, observe 7 days, using solvent group as Control, inhibiting rate is calculated according to the following formula.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length × 100%；
The result shows that：Compound MP1 is 75.4% to the inhibiting rate of banana crown rot bacterium, is significantly higher than female parent (2,4- DAPG) 51.8% inhibiting rate.
Embodiment 5：
Medicament (compound MP14 or compound MP10) is dissolved in DMSO, further with being diluted to 25 μ in PDA culture medium G/ml, is subsequently placed in the culture dish of 9cm, culture dish center inoculation citrus sour rot bacterium, observe 7 days, using solvent group as Control, inhibiting rate is calculated according to the following formula.
Inhibiting rate=(control group mycelial growth length-treatment group mycelial growth length)/control group mycelial growth length × 100%；
The result shows that：Compound MP14 is 69.4% to the inhibiting rate of citrus sour rot bacterium, is significantly higher than female parent (2,4- DAPG) 31.8% inhibiting rate.

Claims (2)

1. applications of the compound MP4 or MP6 in the medicine for preparing anti-Penicillium italicum bacterium or citrus common green mold bacterium, the change The structure of compound MP4 and MP6 are as follows：
2. applications of the compound MP1 in the medicine for preparing anti-banana crown rot bacterium, the following institute of structure of the compound MP1 Show：
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