CN1295225C - Bibenzyl compound plagiochin E and its extraction separation method and application - Google Patents
Bibenzyl compound plagiochin E and its extraction separation method and application Download PDFInfo
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- CN1295225C CN1295225C CN 200410036045 CN200410036045A CN1295225C CN 1295225 C CN1295225 C CN 1295225C CN 200410036045 CN200410036045 CN 200410036045 CN 200410036045 A CN200410036045 A CN 200410036045A CN 1295225 C CN1295225 C CN 1295225C
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Abstract
The present invention relates to a compound plagiochin E in a general formula (I), an extraction and separation method for the compound and the application of the compound in preparing antifungal medications. The compound exploits a new path for developing and applying antifungal medications with natural sources in a new generation.
Description
Technical field
The present invention relates to a kind of bibenzyl compound and extraction and separation method and application, relate in particular to a kind of bibenzyl compound Plagiochin E (Plagiochin E) and by the method for extraction separation in the Hepaticae marchantia marchantia and its application in the preparation antifungal drug.
Background technology
The bibenzyl compound is more common in the bryophyte, structurally with C
6-C
2-C
6Parent nucleus and dimer thereof exist, and are divided into different types of structure with mode of connection difference between the phenyl ring, name according to plant origin usually; Because of the difference of benzene ring substitution group produces numerous compounds, name successively according to affiliated structure type, as the plain B-H of marchantia, J-L, jungermanniaceae C, (Susanne F. such as different jungermanniaceae C, Ulrich HM., Brigirle DN., et al Biosynthesis ofCyclic Bisbibenzyls in Marchantia polymorpha.Phytochemistry, 2001,50 (4): 589-598.).Up till now for extremely, more than 80 of bibenzyl compounds from liverwort, have been obtained, wherein plumage tongue element (Plagiochin) structure type person is only four, i.e. plain A～D (Hashimoto, T. of plumage tongue, M.Tori, Y.Asakawa, Y.Fukazawa.Plagiochins A, B, C, D.New type of macrocycl ic bis (bibenzyls) .Having a biphenyl methylenes; From the liverwort plagiochila acanthophyllasubsp.japonica.Tetrahedron Letters, 1987,28:6295).
At present, because the antifungal compound of natural origin is less, people are at developing new drug and utilize natural matter to extract and done many work aspect the new drug, attempt to find and have stronger antifungic action, overcome that synthesising bacteria anti-reflecting medicine is chemical sproof, the novel cpd of novel structure, but, in many reports of retrieval, yet there are no the report of relevant Plagiochin E (Plagiochin E).
Summary of the invention
At the deficiencies in the prior art, the problem to be solved in the present invention provides a kind of bibenzyl compound Plagiochin E (Plagiochin E) and by the method for extraction separation in the Hepaticae marchantia marchantia and its application in the preparation antifungal drug.
Compound of the present invention is represented with following general formula (I):
Compound called after Plagiochin E of the present invention (Plagiochin E), molecular formula is C
28H
240
4, molecular weight is 424; Fusing point is 194～196 ℃; Be colourless block crystallization; Silica gel thin-layer chromatography shows Rf=0.3～0.6, and spray iron trichloride-Tripotassium iron hexacyanide developer shows blue; HREI-MS:[M]
+424.1685, calculated value 424.1675; EI-MS (Rel.Int): 424 (100), 301 (2), 225 (7), 211 (68), 197 (8), 165 (5), 152 (2), 107 (13), 105 (6), 91 (8), 77 (5); 28 carbon atoms signal distributions on the carbon spectrum is 24 in δ 110-δ 160 districts, and 4 in δ 36-δ 39 districts present the characteristic feature of duplex benzyl compounds.
The preparation method of compound Plagiochin E of the present invention, this method may further comprise the steps:
(1) preparation ether total extract: dried marchantia (Marchantia polymorpa L.) is pulverized, added the ether of 5～10 times of marchantia volumes, under 20 ℃～35 ℃ conditions, soaked 4～7 days, normal pressure filters, collect ether extracted liquid I, repeat united extraction liquid I 3～6 times; With the dregs of a decoction after extracting with the methyl alcohol of its 2～4 times of amounts under 20 ℃～35 ℃ conditions, soak 3～5 times, each 2～3 days, normal pressure filtered, and collected methanol extract liquid, merge, 50 ℃～70 ℃ of Rotary Evaporators, under the vacuum tightness 0.09Mpa condition, concentrating under reduced pressure gets methyl alcohol medicinal extract, with the extracted with diethyl ether medicinal extract that is equivalent to 2～5 times of amounts of medicinal extract 2～4 times, collect, merge ether extraction liquid II; Above-mentioned I, II two portions ether solution are merged, be distilled to fluid extract, volatilize naturally, get the ether total extract in 50 ℃～70 ℃ conditions;
(2) separate: 200～300 purpose silica gel mixed samples of above-mentioned ether total extract with its 1～3 times of amount, carry out silica gel column chromatography (200～300 orders, 6 * 15cm), with sherwood oil-acetone system ratio gradient elution (100% sherwood oil～50% sherwood oil) routinely, at sherwood oil: acetone is that 90～98: 2～10 wash-outs part detects with silica gel thin-layer chromatography, and wherein developping agent is a sherwood oil: acetone=6: 4; Developer is iron trichloride-potassium ferricyanide solution, merges to collect Rf=0.3～0.6 same stream part, concentrates with ordinary method and separates out crystallization, the dry Plagiochin E that gets.
Wherein, above-mentioned iron trichloride-potassium ferricyanide solution is 1% iron trichloride and 2% potassium ferricyanide solution equal-volume mixing solutions.
Wherein, the described sherwood oil of step (2): acetone is preferably 95: 5.
The application of compound Plagiochin E of the present invention in the preparation antibacterials especially relates to the application in the preparation antifungal drug.
Adopting compound Plagiochin E of the present invention to carry out antibacterial activity test shows: this compound has stronger antifungic action, and because its novel structure has the applications well prospect in natural new drug development.
The Plagiochin E that utilization the present invention relates to adopts TLC (thin-layer chromatography) bioautography to carry out the anti-microbial activity test: under the aseptic condition, with getting collarium Candida albicans (Candida allbicans) is inoculated in conventional broth agar culture medium (peptone, sodium-chlor, extractum carnis, nutrient agar medium), constant temperature culture is to test concentrations (about 10
7CFU/mL).Sample TLC method is launched, treat that solvent on the thin layer plate volatilizes fully after, the ultraviolet sterilization spreads upon bacteria culture fluid on the thin plate uniformly, constant temperature culture is observed its antibacterial spot.After 5 minutes, observe its antibacterial spot with the colour developing of MTT (tetrazolium salts) solution.The result shows that Plagiochin E shows strong anti-microbial activity.
Compound of the present invention is new bibenzyl compound, utilize of the present invention from the marchantia plant method of extraction separation compound Plagiochin E, the extraction productive rate is higher, the compound purity that obtains reaches more than 98%, antibacterial activity test shows that this compound has stronger antifungic action, though it is active not as good as the synthetic antibacterial drug miconazole nitrate, but the antifungal compound of natural origin is more rare, cause that drug-fast possibility is less, under present synthesising bacteria anti-reflecting medicine resistance serious environmental, adopt compound Plagiochin E of the present invention to have excellent development, utilize and development prospect, also provide lead compound to open up a new approach simultaneously for researching and developing new antibacterials.
Description of drawings
Fig. 1 Plagiochin E
1The HNMR spectrogram
Fig. 2 Plagiochin E
13The CNMR spectrogram
Fig. 3 Plagiochin E
1H-
1The HCOSY spectrogram
The HMBC spectrogram of Fig. 4 Plagiochin E
The HMQC collection of illustrative plates of Fig. 5 Plagiochin E
The EI-MS spectrogram of Fig. 6 Plagiochin E
Fig. 7 TLC bioautography is carried out anti-microbial activity test minimal inhibitory concentration (MID) test-results:
Wherein: A figure is a miconazole nitrate, antibacterial spot occurs since the 3rd point, shows that MID is 0.01 μ g;
B figure is a Plagiochin E, antibacterial spot occurs since the 3rd point, shows that MID is 0.25 μ g.
Embodiment
Embodiment 1:
To pick up from the geographic marchantia of Mt.E'mei, Sichuan Province height above sea level 1000-1500 rice (Marchantia polymorpa L.) dry in the shade naturally pulverize 8.95Kg, ether with 8 times of marchantia volumes soaked 5 days for 28 ℃, and normal pressure filters, and collects ether extracted liquid I, repeat united extraction liquid I 4 times.The dregs of a decoction after extracting are for the last time soaked 4 times for 28 ℃ with 3 times of amount methyl alcohol, each 3 days, normal pressure filtered, and collected methanol extract liquid, merge, 60 ℃ of Rotary Evaporators, decompression (vacuum tightness 0.09Mpa) concentrate methyl alcohol medicinal extract, with the extracted with diethyl ether medicinal extract that is equivalent to 3 times of amounts of medicinal extract 3 times, collect, merge ether extraction liquid II, I, II two portions ether solution are merged the back be distilled to fluid extract, volatilize naturally, get the ether total extract in 60 ℃ of conditions.With 200～300 purpose silica gel mixed samples of above-mentioned ether total extract with its 2 times of amounts, carry out silica gel column chromatography (Qingdao Haiyang Chemical Manufacture 200～300 orders, 6 * 15cm), sherwood oil-acetone system convention ratio gradient elution (100% sherwood oil～50% sherwood oil), partly use silica gel thin-layer chromatography (developping agent, sherwood oil: acetone=6: 4 at sherwood oil one acetone (95: 5) wash-out; Developer, iron trichloride-potassium ferricyanide solution) detect, merge and collect Rf=0.3～0.6 same stream part, concentrate with ordinary method and separate out crystallization, the dry Plagiochin E 4.117g that gets.
The crystallization of above-claimed cpd Plagiochin E is colourless block crystallization, mp:194.8-195.8 ℃, (sherwood oil: Rf=0.56 acetone=6: 4), iron trichloride-potassium ferricyanide solution (described iron trichloride-potassium ferricyanide solution is 1% iron trichloride and 2% potassium ferricyanide solution equal-volume mixing solutions) show blue to TLC.
HREI-MS:[M]
+424.1685, calculated value 424.1675, molecular formula is C
28H
24O
4The carbon spectrum shows 28 carbon atoms, and δ 110-δ 160 has 24, and δ 36-δ 39 has 4, points out this compound may be duplex benzyl compounds.
1What HNMR demonstrated that 13 fragrant hydrogen signals possess fragrant hydrogen on four kinds of different substituted benzene rings splits branch feature (formula A～D structure fragment as follows), and the coupled relation of saturation region proton signal shows two groups of adjacent methylene radical features.
1H-
1HCOSY as can be known δ 7.22 (1H, t, J=7.8Hz), δ 7.01 (1H, dd, J=7.8Hz, J=1.05Hz).(J=7.8Hz's δ 6.80 J=1.05Hz) intercouples for 1H, dd, and three hydrogen are connected on three continuous carbon of phenyl ring as can be known.Link to each other with the carbon of δ 129.99, δ 123.17, δ 114.42 respectively as can be known by HMQC.δ 7.01, δ 6.80 have remote couplings with δ 126.65 among the HMBC, the carbon of prompting δ 126.65 position between δ 123.17 and δ 114.42.δ 7.22 and δ 145.61 and δ 156.18 have remote couplings, and the carbon potential of prompting δ 145.61 and δ 156.18 is the position between δ 129.99.The carbon of δ 156.18 has bigger low field displacement with respect to the carbon of normal phenyl ring, and prompting links to each other with oxygen.The low field displacement of δ 145.61 is also bigger, but is not so good as the big of δ 156.18, therefore should link to each other with carbon.δ 7.15 places have the carbon of 1 hydrogen and δ 114.42, δ 126.65, δ 156.18 that remote couplings is arranged among the HMBC, and the carbon that in HMQC, is not attached thereto, prompting should be one-OH herein.Therefore can release following formula A structure fragment, in like manner in conjunction with HMBC, HMQC,
1H-
1HCOSY can release following formula B structure fragment and C-structure segment;
1Four broad peaks of residue among the HNMR, among the HMQC respectively with δ 130.91, δ 130.65, δ 123.71, four wide carbon signals of δ 123.40 are relevant, also remain the carbon atom of δ 141.93, δ 154.96.By EI-MS as can be known molecular weight be 424, can know by inference and also remain a phenyl ring, be connected with four hydrogen atoms, a carbon, an oxygen.Chemical displacement value according to carbon in the carbon spectrum can be released following formula D structure fragment.
1H-
1δ 2.69 (2H), δ 2.71 (1H), δ 2.60 (1H) intercouple among the HCOSY, can know following formula E structure fragment by inference in conjunction with HMQC, in like manner also can release following formula F structure fragment.
δ 2.69 has remote couplings with δ 118.48, δ 123.40, δ 134.29 among the HMBC.δ 2.60 and δ 2.68 and δ 118.41, δ 139.29, δ 121.82, δ 143.28 remote couplings can release following formula G structure fragment, in like manner also can release following formula H structure fragment.δ 6.85 has remote couplings with δ 126.65 among the HMBC, can know A, B ring by inference directly links to each other, the high field of 3 ' hydrogenation displacement study value δ 5.46 in the C segment, general Wave Spectrum feature according to the bibenzyl compound, can draw the D ring and C ring both links to each other by 1,2 ' ether-oxygen bond and draws following formula one-piece construction I.
EI-MS(Rel.Int)：424(100)，301(2)，225(7)，211(68)，197(8)，165(5)，152(2)，107(13)，105(6)，91(8)，77(5)。Each fragmention can both obtain proper explanations, and its possible lytic pathway is shown below.
Through consulting documents and materials, described compound parent nucleus is a plumage tongue element, and pertinent literatures such as retrieval CA are not found the record of this compound, determine that this compound is a new compound, called after Plagiochin E (Plagiochin E).The MS that the The compounds of this invention Plagiochin E relates in identifying,
1HNMR,
13CNMR,
1H-HCOSY, HMBC, HMQC collection of illustrative plates are seen accompanying drawing 1-6.
1The H-NMR data see Table 1,
13The C-NMR data see Table 2.
Table 1 Plagiochin E
1The H-NMR data (Acetone, 600MHz)
| Sequence number | 1H(ppm) | Sequence number | 1H(ppm) |
| 2 3 5 6 7 8 10 11 12 14 13-OH | 6.78(m) 6.94(m) 7.04(m) 6.78(m) 2.92(m) 2.91(m)，2.79(m) 7.01(dd，J＝7.8，1.8Hz) 7.22(d，J＝7.8Hz) 6.80(dd，J＝7.8，1.8Hz) 7.15(s) | 2′ 3′ 5′ 6′ 7′ 8′ 10′ 11′ 12′ 14′ 1′-OH 13′-OH | 5.46(d，J＝1.80Hz) 6.74(dd，J＝7.8，1.8Hz) 6.86(d，J＝7.8Hz) 2.70(2H，m) 2.68(m)，2.60(m) 6.85(d，J＝7.8Hz) 6.33(m) 6.33(m) 7.68(s) 7.68(s) |
Table 2 Plagiochin E
13The C-NMR data (Acetone, 150MHz)
| Sequence number | 13C(ppm) | Sequence number | 13C(ppm) |
| 1 2 3 4 5 6 7 8 9 10 11 12 13 14 | 154.96 123.71 130.91 141.93 130.65 123.40 39.10 36.29 145.61 123.17 129.99 114.47 156.18 126.65 | 1′ 2′ 3′ 4′ 5′ 6′ 7′ 8′ 9′ 10′ 11′ 12′ 13′ 14′ | 145.94 148.95 118.48 134.29 123.40 117.29 38.11 39.08 143.28 121.82 134.18 121.74 155.65 118.41 |
Embodiment 2:
To pick up from the geographic marchantia of Mt.E'mei, Sichuan Province height above sea level 1000-1500 rice (Marchantia polymorpa L.) dry in the shade naturally pulverize 9.50Kg, ether with 5 times of marchantia volumes soaked 4 days for 23 ℃, and normal pressure filters, and collects ether extracted liquid I, repeat united extraction liquid I 6 times; The dregs of a decoction after extracting are for the last time soaked 5 times for 35 ℃ with 2 times of amount methyl alcohol, each 2 days, normal pressure filtered, and collected methanol extract liquid, merge, 70 ℃ of Rotary Evaporators, decompression (vacuum tightness 0.09Mpa) concentrate methyl alcohol medicinal extract, with the extracted with diethyl ether medicinal extract that is equivalent to 2 times of amounts of medicinal extract 4 times, collect, merge ether extraction liquid II, I, II two portions ether solution are merged the back be distilled to fluid extract, volatilize naturally, get the ether total extract in 70 ℃ of conditions.With the 200 purpose silica gel mixed samples of above-mentioned ether total extract with its 1 times of amount, with silica gel column chromatography (200 orders, 6 * 15cm) sherwood oils-acetone system convention ratio gradient elution (100% sherwood oil～50% sherwood oil), partly use silica gel thin-layer chromatography (developping agent, sherwood oil: acetone=6: 4 at sherwood oil-acetone (98: 2) wash-out; Developer, iron trichloride-potassium ferricyanide solution) detect, merge and collect Rf=0.3～0.6 same stream part, concentrate with ordinary method and separate out crystallization, the dry Plagiochin E 4.275g that gets.
Embodiment 3:
With the marchantia of adopting (Marchantia polymorpa L.) dry in the shade naturally pulverize 8.25Kg, soaked 7 days for 35 ℃ with the ether of 10 times of marchantia volumes, normal pressure filters, and collects ether extracted liquid I, repeats united extraction liquid I 3 times.The dregs of a decoction after extracting are for the last time measured the methyl alcohol soaking at room temperature 3 times with 4 times, each 2 days, normal pressure filtered, and collected methanol extract liquid, merge, 50 ℃ of Rotary Evaporators, decompression (vacuum tightness 0.09Mpa) concentrate methyl alcohol medicinal extract, with the extracted with diethyl ether medicinal extract that is equivalent to 5 times of amounts of medicinal extract 2 times, collect, merge ether extraction liquid II, I, II two portions ether solution are merged the back be distilled to fluid extract, volatilize naturally, get the ether total extract in 50 ℃ of conditions.With the 300 purpose silica gel mixed samples of above-mentioned ether total extract with its 3 times of amounts, with silica gel column chromatography (300 orders, 6 * 15cm) sherwood oils-acetone system convention ratio gradient elution (100% sherwood oil～50% sherwood oil), partly use silica gel thin-layer chromatography (developping agent, sherwood oil: acetone=6: 4 at sherwood oil-acetone (90: 10) wash-out; Developer, iron trichloride-potassium ferricyanide solution) detect, merge and collect Rf=0.3～0.6 same stream part, concentrate with ordinary method and separate out crystallization, the dry 3.547g Plagiochin E that gets.
Embodiment 4:
Under the aseptic condition, with getting collarium Candida albicans (Candida allbicans) is inoculated in conventional broth agar culture medium (peptone, sodium-chlor, extractum carnis, nutrient agar medium), in 30 ℃ of 1 weeks of constant temperature culture, bacteria concentration reaches 10
7CFU/mL.With the serial gradient concentration of Plagiochin E preparation as table 3, with miconazole nitrate (table 4) product in contrast, sample Plagiochin E (Plagiochin E) launches (sherwood oil: acetone=6: 4) through TLC, after treating that solvent on the thin plate volatilizes fully, ultraviolet sterilization 30 minutes spreads upon bacteria culture fluid on the thin plate uniformly, 30 ℃ of constant temperature culture 36 hours, with the MTT solution colour developing of 2.5mg/mL, after 5 minutes, observe its antibacterial spot.
Experimental result: the MID of Plagiochin E (Plagiochin E) anti-candida albicans is 0.25 μ g, and the MID of positive control miconazole nitrate is 0.01 μ g.(seeing accompanying drawing 7).
Table 3 Plagiochin E point sample amount
| E 1 | E 2 | E 3 | E 4 | E 5 | E 6 | |
| C (μ g/ μ l) point sample amount (μ g) | 0.0375 0.075 | 0.075 0.15 | 0.125 0.25 | 0.1825 0.375 | 0.25 0.5 | 0.375 0.75 |
Table 4 miconazole nitrate point sample amount
| A 1 | A 2 | A 3 | A 4 | A 5 | A 6 | |
| C (μ g/ μ l) point sample amount (μ g) | 0.0025 0.005 | 0.00375 0.0075 | 0.005 0.01 | 0.00625 0.0125 | 0.0125 0.025 | 0.025 0.05 |
Claims (6)
1. the compound of following general formula (I):
2. the preparation method of the described compound of claim 1, this method may further comprise the steps:
(1) preparation ether total extract: dried marchantia (Marchantia polymorpa L.) is pulverized, added the ether of 5～10 times of marchantia volumes, under 20 ℃～35 ℃ conditions, soaked 4～7 days, normal pressure filters, collect ether extracted liquid I, repeat united extraction liquid I 3～6 times; With the dregs of a decoction after extracting with the methyl alcohol of its 2～4 times of amounts under 20 ℃～35 ℃ conditions, soak 3～5 times, each 2～3 days, normal pressure filtered, and collected methanol extract liquid, merge, 50 ℃～70 ℃ of Rotary Evaporators, under the vacuum tightness 0.09Mpa condition, concentrating under reduced pressure gets methyl alcohol medicinal extract, with the extracted with diethyl ether medicinal extract that is equivalent to 2～5 times of amounts of medicinal extract 2～4 times, collect, merge ether extraction liquid II; Above-mentioned I, II two portions ether solution are merged, be distilled to fluid extract, volatilize naturally, get the ether total extract in 50 ℃～70 ℃ conditions;
(2) separate: 200～300 purpose silica gel mixed samples of above-mentioned ether total extract with its 1～3 times of amount, carry out silica gel column chromatography, with sherwood oil-acetone system ratio gradient elution routinely, at sherwood oil: acetone is that 90～98: 2～10 wash-outs part detects with silica gel thin-layer chromatography, and wherein developping agent is a sherwood oil: acetone=6: 4; Developer is iron trichloride-potassium ferricyanide solution, merges Rf=0.3～0.6 same stream part, concentrates with ordinary method and separates out crystallization, dry formula (I) compound that gets.
3. the preparation method of compound as claimed in claim 2 is characterized in that, described iron trichloride-potassium ferricyanide solution is 1% iron trichloride and 2% potassium ferricyanide solution equal-volume mixing solutions.
4. the preparation method of compound as claimed in claim 2 is characterized in that, the described sherwood oil of step (2): acetone is 95: 5.
5. the application of the described compound of claim 1 in the preparation antibacterials.
6. application as claimed in claim 5, it is used to prepare antifungal drug.
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| CN113549046B (en) * | 2021-06-23 | 2022-10-18 | 山东大学 | Bisbecklonin S derivative and preparation method and application thereof |
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