CN105801445A - Nonprotein amino acid with antibacterial activity and preparation method of nonprotein amino acid - Google Patents
Nonprotein amino acid with antibacterial activity and preparation method of nonprotein amino acid Download PDFInfo
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Abstract
The invention relates to nonprotein amino acid with antibacterial activity and a preparation method of the nonprotein amino acid. The nonprotein amino acid is 7-amino-4-hydroxyoct-2-enoic acid, has the molecular formula of C8H15NO3 and the structural formula shown in the specification. The prepared nonprotein amino acid has a better inhibition effect on bacillus subtilis and can be prepared through fermentation with strain Paecilomyces gunnii, culture medium raw materials are wide in source, the preparation method is simple, and industrial production is easy to implement.
Description
Technical field
The present invention relates to a kind of nonprotein amino acid with antibacterial activity and preparation method thereof, belong to biomedicine field.
Background technology
Macro fungi not only has abundant nutritive value, also abundant active medicinal matter can be produced, as there is antibacterium, promoting multiple bioactive polysaccharide class, polypeptide, antibiotics, the antitumor isoreactivities such as nerve growth factor synthesis, enzyme inhibitor, antifungal, cell toxicant, receptor antagonist and antioxidation.The natural product in macro fungi with antibacterial activity is mainly the compounds such as sesquiterpene, Diterpene glucoside and many acetylenics.Agrocybolacton is the drimane type skeleton sesquiterpene separated from field mushroom, inhibited to gram positive bacteria.Illudin M and illudin
S is the sesquiterpene separated from cup umbrella, and they are rightStaphylococcus aureus、Klebsiella pneumoniae、Mycobacterium tuberculosis
WithMycobacterium smegaDeng the MIC value of pathogen all at 10 below μ g/mL.The Diterpene glucoside erinacine E separated from Hericium erinaceus (Bull. Ex Fr.) Pers. mycelium can suppress methicillin resistant staphylococcus aureus (MRSA), and MIC value is 62.5 μMs.Diatrenenitrile be fromClitocybe diatreta
Three acetylene compounds separated, rightMicrococcus pyogenesHaving stronger inhibitory action, MIC value is only 0.1 μ g/mL.Cinnatriacetin A and cinnatriacetin B is that three acetylene compounds separated from Fistulina hepatica sporophore have antibacterial activity.Therefore macro fungi is the important sources of antibacterial substance.Paecilomyces gunniliang is the phorozoon fungus of Cordyceps gunnii (Berk.) Berk., has many important biological activitys.Bacterial disease is the chief threat of human health, and finding safely and effectively antibacterials is the long-term targets of the mankind.Based on background above, carry out the research of the present invention.
Summary of the invention
It is an object of the invention to provide a kind of nonprotein amino acid with antibacterial activity and preparation method thereof.
Another object of the present invention is to this nonprotein amino acid as antibacterials.
A kind of nonprotein amino acid with antibacterial activity, described nonprotein amino acid is 7-amino-4-hydroxyoct-2-enoic
Acid, molecular formula is C8H15NO3, structural formula is as follows:
。
The precursor of the described nonprotein amino acid with antibacterial activity, described compound precursor molecular formula is C20H30N4O5, structural formula is as follows:
。
The nonprotein amino acid preparation method of novel structure of the present invention includes:
1) fungi liquid fermentation: by fungus paecilomyces gunniliang (Paecilomyces
gunnii) (list of references: paecilomyces gunniliang liquid fermentation liquid organic coarse extract produces quantifier elimination, biotechnology, 2012,22(1): 88-89) after slant strains activation, carrying out liquid submerged fermentation, culture medium prescription is by weight: Rhizoma Solani tuber osi 5-40%, glucose 1-5%, peptone 0.1-3%, surplus is water, in 0.1 Mpa and 121 DEG C of sterilizing 30 min.Using constant-temperature table or various fermentation tank to carry out liquid fermentation, temperature arranges 23-30 DEG C, fermentation time 4-15 days；
2) tunning processes: after liquid fermentation terminates, removes mycelial fermentation liquid and is extracted with ethyl acetate, and extract, through dehydration, concentration, obtains organic coarse extract extractum；
3) separation of the nonprotein amino acid precursor described in: by 2) described in organic coarse extract extractum methanol dissolve, carry out reversed-phase silica gel column chromatography, different gradient methanol or acetone water with methanol or acetone concentration are 10-50% are eluant, and the eluent containing target components is concentrated to give subfraction.With methanol, subfraction is dissolved, carry out gel filtration chromatography, with acetone or methanol solution eluting, it is in charge of collection, the eluent containing described nonprotein amino acid precursor component is merged, then carries out purification on normal-phase silica gel column chromatography, post is filled with chloroform, dry method loading, with containing the chloroform solvent eluting that methanol volume ratio is 1-10%, obtains containing described nonprotein amino acid precursor component.
4) preparation of the nonprotein amino acid described in: by 3) prepare the nonprotein amino acid precursor acid of gained or alkali is degraded, then carry out chromatographic separation and purification and obtain described nonprotein amino acid.
5) application on antibiosis of the nonprotein amino acid described in.
Nonprotein amino acid prepared by the present invention has good inhibiting effect to bacillus subtilis, it is possible to use bacterial strainPaecilomyces gunniiFermentation prepares, culture medium raw material wide material sources, and preparation method is simple, easily realizes industrialized production.
Accompanying drawing explanation
The chemical constitution of compound precursor described in Fig. 1.
The stereochemical structure of compound precursor described in Fig. 2.
Compound 7-amino-4-hydroxyoct-2-enoic described in Fig. 3
The chemical constitution of acid.
The antibacterial activity of compound described in Fig. 4.Wherein 1,2,3,4,5,6 represent that the concentration of described compound is respectively 0.25,0.2,0.15,0.1,0.05,0.025 μ g/uL；7,8,9,10 represent methanol (10 μ L/ hole), penicillin (0.02 μ g/uL), lysine (8 μ g/uL) respectively, connect the culture medium of 10 uL bacterium solution；11 is the culture medium not connecing bacterium.
Detailed description of the invention
The invention will be further described for following example.
Embodiment
1
By fungus paecilomyces gunniliang (Paecilomyces
gunnii) slant strains is inoculated in the triangular flask equipped with 150 mL Rhizoma Solani tuber osi fluid mediums activation, activation condition is rotating speed 230 r/min, cultivation temperature 28 DEG C, incubation time 6 days, carrying out large batch of liquid fermentation 30 L again, employing culture medium prescription is: the g Han Rhizoma Solani tuber osi 200, glucose 20 g in every liter of water, peptone 5 g, pH is natural, 0.1 Mpa, 121 DEG C of sterilizing 3 0min, it is placed in 28 DEG C, 230 r/min constant-temperature tables are cultivated.After fermenting 11 days, by centrifuging by mycelium and separation of fermentative broth.Fermentation liquid extracts by isopyknic ethyl acetate, gained extract anhydrous sodium sulfate dehydration, then is concentrated in vacuo under the conditions of 40 DEG C with Rotary Evaporators, obtains organic coarse extract extractum (6.34 g).
The organic coarse extract extractum (6.34 g) that will obtain in previous step, dissolve with methanol, carry out anti-phase silicon (170 g) column chromatography, with 30% methanol-water eluting 2 L, flow velocity is 15 mL/min, and often 280 mL collected by pipe, after concentrating with rotavapor under vacuum, separately sampled carry out thin layer chromatography analysis merging (developing solvent is chloroform: methanol=10:1, and developer is iodine, 10% sulphuric acid ethanol or bismuth potassium iodide), obtain the component (852.3 mg) containing target compound precursor.
The component (852.3 mg) obtained from previous step, dissolve by proper amount of methanol, carry out gel (120g, Sephadex LH-20) column chromatography, methanol-eluted fractions, flow velocity is about 12 s/drop, and often 4 mL collected by pipe, obtains the component (213.6 mg) containing target compound precursor according to thin layer chromatography combining data detection.
The component (213.6 mg) obtained from previous step, dissolve by proper amount of acetone, carry out gel (120 g, Sephadex LH-20) column chromatography, acetone eluting, flow velocity is about 12 s/drop, and often 4 mL collected by pipe, obtains the component (61 mg) of target compound precursor according to thin layer chromatography combining data detection.
The component (61 mg) obtained from previous step carries out purification on normal-phase silica gel chromatography (5.2 g silica gel), chloroform dress post, dry method loading, flowing is chloroform mutually: methanol (60:1), elution volume is 300 mL, and thin layer chromatography combining data detection obtains target compound precursor (39.4 mg).
By the compound precursor of previous step gained, carry out NMR (Nuclear Magnetic Resonance) spectrum (1H-NMR、13C-NMR、HSQC、HMBC、1H-1H COSY and NOESY), mass spectrum (EI), high resolution mass spectrum (HREI-MS), optically-active ([α]), ultraviolet spectra (UV), infrared spectrum (IR) and X-ray single crystal diffraction measure, and determine described compound precursor structure (Fig. 1).
Described compound precursor, white, dissolve in methanol, [α]+19.7
(c=0.07, MeOH)；UV-vis (MeOH),λ/ nm:207；HREI MS:406.2202([M+], C20H30N4O5;
calc. 406.2216)；IR (KBr) νmax: 3428,2925,2855,1720,1384 cm-1；Its monocrystalline fusing point is 197-200 DEG C. combines1H and13C H NMR spectroscopy data (table 1) determine that the molecular formula of compound is C20H30N4O5.Analyze1H and13C NMR and DEPT composes, and shows that described compound precursor contains 3 methyl, 4 methylene, 7 methines (wherein 4 azines or oxygen, 2 is olefinic carbon), 6 quaternary carbons (wherein 3 acylamino-s, 2 is olefinic carbon).According to C5 (δC164.4s), C13 (δC 170.6s), C15(δC165.7s), and C2 (δCChemical displacement value 97.8s), and in single crystal diffraction, record N3-C5 (1.354), N12-C13 (1.329), N16-C15 (1.365) and the bond distance of N1-C2 (1.464), and in infrared spectrum, observe 1384 cm-1INFRARED ABSORPTION, described compound precursor can be deduced and contain three acylamino-groups.Methyl H is it was experimentally observed that according to from HMBC320 and C3/C2, H19 and C13/14/3/2 and H14 with C19/C14a/C18a/C13 hydrocarbon the most relevant, and from1H-1Hydrogen hydrogen between H19 to H14 that H COSY it was experimentally observed that is relevant, and C14a (δC97.0s) with C18a (δCChemical displacement value 164.1s) can deduce a structure fragment of compound1a(C3/C2/C19/C14/C13/C14a/C18a)
(Fig. 1).Methyl H is it was experimentally observed that also according to from HMBC322 and C11/C10, H6/7 and C5/8 and H10 with C11 hydrocarbon the most relevant, and from1H-1Relevant another structure fragment that can deduce compound of hydrogen hydrogen between H10 to H11 and H8 and H9 that H COSY it was experimentally observed that1b (C5/C6/C7/C8/C9/C10/C22)
(Fig. 1).Again according to the methyl H that it was experimentally observed that from HMBC321 hydrocarbon remotely the most relevant to C18, and from1H-1Relevant another structure fragment that can deduce compound of hydrogen hydrogen between H17 to H18 that H COSY it was experimentally observed that1c(C21/C17/C18) (Fig. 1).Comprehensive data above, can deduce the basic structure (Fig. 1) of described compound precursor.At room temperature, the monocrystalline of described compound precursor can be obtained from the methanol aqueous solution of compound, the spatial configuration (Fig. 2) of described compound precursor can be obtained according to X-ray single crystal diffraction.
NMR spectra data (the DMSO-of table 1 compound precursord6, 500M)
Take described compound precursor (10.0 mg) and be dissolved in 0.5 ml DMSO, it is placed on miniature whirlpool instrument mixing, it is 30% adding 30 μ L NaOH(concentration) mix and react, react and carried out reverse phase silica gel (30 g) column chromatography, with 30% methanol-eluted fractions 300 ml, flow speed control is 15 mL/min, is in charge of collection, every test tube sampling carries out thin layer chromatography, and combining data detection obtains described compound (2.1 mg).
By the compound of previous step gained, carry out mass spectrum (EI), high resolution mass spectrum (HREI-MS), optically-active ([α]), ultraviolet spectra (UV), infrared spectrum (IR) and NMR (Nuclear Magnetic Resonance) spectrum (1H-NMR、13C-NMR、HSQC、HMBC、1H,1H-COSY and NOESY) measure, and determine described compound structure (Fig. 3).
Described compound, white, dissolve in methanol, [α]-8.9 (c=0.071, MeOH)；UV-vis
(MeOH,λ/ nm): 205；HREI MS: 173.1050 ([M+],
C8H15NO3; calc. 173.1052)；IR (KBr)
νmax: 3406,2925,1563,1423 cm-1；In conjunction with1H and13C H NMR spectroscopy data (table 2) determine that the molecular formula of compound is C8H15NO3.Analyze1H and13C NMR and DEPT composes, and shows that compound contains 1 methyl, 2 methylene, and 4 methines (wherein 2 olefinic carbons, 1 company's oxygen, 1 azine), 1 is ester group carbon.Methyl H be can be observed from HMBC tests38 and C7/C6, H7 and C5, H26 and C7/C8/C5/C4, H25 and C7/C6/C4/C3, H4 and C2/C3/C5, H3 and C5/C4/C2/C1, and H2 to C4/C1 hydrocarbon remotely the most relevant, from1H-1H2 and H3, H3 and H4, H4 and H be can be observed in H COSY experiment25, H25 and H26, H26 and H7, and H7 and H3Hydrogen hydrogen between 8 is correlated with, and can deduce the basic structure of compound.Rhizoma Nelumbinis according to H2 Yu H3 close constant (J=15.5) double bond that can deduce C2-C3 is cis-structure.Deriving from precursor due to described compound again, therefore its solid type can be speculated (Fig. 3) by precursor, for (4S, 7S, E)-7-amino-4-hydroxyoct-2-enoic
acid。
Table 2 compound 7-amino-4-hydroxyoct-2-enoic
NMR spectra data (the DMSO-of acidd6, 500M)
Embodiment
2
96 well plate method are used to carry out the MIC bacteriostatic test of described compound.Under sterile working, (1% Carnis Bovis seu Bubali cream, 1% peptone, 0.5% sodium chloride, be settled to 1000 mL to add 100 μ L bacteria culture medias in every hole of 96 orifice plates
, pH 7.2-7.5,121 DEG C of autoclaving 30 min), 10 μ L bacillus subtilis bacterium solution are (containing bacterium number about 2.0 × 106), with the sample that 10 μ L contain compound described in variable concentrations, the final concentration of described compound 0.25,0.2,0.15,0.1,0.05 and 0.025 μ g/ μ L respectively, if 3 parallel, set interpolation 10 μ L methanol as solvent control simultaneously, if penicillin is positive control (concentration is 0.02 μ g/ μ L), separately set lysine as negative control ((concentration is 8 μ g/ μ L), separately set fluid medium (1% Carnis Bovis seu Bubali cream, 1% peptone, 0.5% sodium chloride, is settled to 1000 mL
, pH 7.2-7.5) and it is blank.24 h, perusal bacillus subtilis growing state is cultivated in putting 37 DEG C of calorstats.During it is observed that described compound is 0.15 μ g/ μ L, bacillus subtilis does not grows (Fig. 4), shows that compound described in ancient Buddhist nun's propylhomoserin has antibacterial activity, and minimum inhibitory concentration is 0.87 mM.
The foregoing is only presently preferred embodiments of the present invention, all impartial changes done according to scope of the present invention patent and modification, all should belong to the covering scope of the present invention.
Claims (4)
1. a nonprotein amino acid with antibacterial activity, it is characterised in that: described nonprotein amino acid is 7-amino-4-hydroxyoct-2-enoic
Acid, molecular formula is C8H15NO3, structural formula is as follows:
。
2. the preparation method of a nonprotein amino acid as claimed in claim 1, it is characterised in that: by fermentation culture paecilomyces gunniliangPaecilomyces gunnii, obtain fermented product, then from fermented product isolated and purified go out this compound or this compound precursor, then compound precursor is carried out acidolysis or alkaline hydrolysis obtains described nonprotein amino acid.
3. the precursor of a nonprotein amino acid as claimed in claim 1 with antibacterial activity, it is characterised in that: described compound precursor molecular formula is C20H30N4O5, structural formula is as follows:
。
4. the nonprotein amino acid as claimed in claim 1 purposes in preparation antibacterials.
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| CN109575040A (en) * | 2019-01-17 | 2019-04-05 | 福建师范大学 | A kind of compound and preparation method thereof with antibacterial activity |
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| US20020006960A1 (en) * | 2000-02-22 | 2002-01-17 | Stefan Abrecht | Process for the preparation fo 4,5-diamino shikimic acid derivatives |
| CN104059038A (en) * | 2014-07-08 | 2014-09-24 | 福建师范大学 | Sesquiterpene compounds and application thereof |
| CN104059040A (en) * | 2014-07-08 | 2014-09-24 | 福建师范大学 | Sesquiterpene compounds with antitumor activity and preparation method of sesquiterpene compounds |
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| US20020006960A1 (en) * | 2000-02-22 | 2002-01-17 | Stefan Abrecht | Process for the preparation fo 4,5-diamino shikimic acid derivatives |
| CN104059038A (en) * | 2014-07-08 | 2014-09-24 | 福建师范大学 | Sesquiterpene compounds and application thereof |
| CN104059040A (en) * | 2014-07-08 | 2014-09-24 | 福建师范大学 | Sesquiterpene compounds with antitumor activity and preparation method of sesquiterpene compounds |
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| 李军进 等: "古尼拟青霉液体发酵液有机粗提物产量的研究", 《生物技术》 * |
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| CN109575040A (en) * | 2019-01-17 | 2019-04-05 | 福建师范大学 | A kind of compound and preparation method thereof with antibacterial activity |
| CN109575040B (en) * | 2019-01-17 | 2021-03-26 | 福建师范大学 | Compound with antibacterial activity and preparation method thereof |
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