CN1442426A - Diterpene compound of veronicastrum sibiricum and its extraction separation method - Google Patents
Diterpene compound of veronicastrum sibiricum and its extraction separation method Download PDFInfo
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Abstract
A diterpenoid of gaminate speedwell herb is prepared from said geminate speedwell herb through pulverizing, immersing, extracting and chromatography. The said diterpenoid with immunosuppression activity is C18H12O3, C18H14O3, C19H18O3, C19H20O3, C19H20O2 and C19H22O2.
Description
Technical field
The present invention relates to the natural product chemistry field, diterpene-kind compound that extracts from the wheel blade veronica and method belong to the technology of extracting diterpene-kind compound from natural phant.
Background technology
Wheel blade veronica [Veronicastrum sibirica (L.) Pennell.] is the herb of scrophulariaceae brooklime Leptandra sibirica.Scrophulariaceae (Scrophulariaceae) plant about 200 belongs to 3000 kinds, blazons all parts of the world, and China has and 56 belong to (for example: Veronica, come river Calamus, Verbascum, beautiful paulownia to belong to etc.).Veronica (Veronica.) plant is distributed widely in the whole world, and main product is in the Eurasia, about 250 kinds.China produces 61 kinds, and the each province all has (for example: wheel blade veronica, Veronica linariifolia, leatherleaf veronica, Woolly Speedwell, big veronica etc.), and most of kinds originate in southwestern mountain region.Show that through chemical ingredients prerun the underground part of wheel blade veronica contains the iridoid glycoside constituents, root and rhizome may contain iridoid glycoside, coumarin glucoside, flavonoid glycoside, steroid class, condensed tannin, carbohydrate and amino acid etc.
The herb (2kg) of wheel blade veronica [Veronicastrum sibirica (L.) Pennell.] picks up from the Northeast China September calendar year 2001, believed in a religion by Wang Liang and award evaluation.Extraction and separation technology is 95% extraction using alcohol, and the extract petroleum ether extraction is separating the chemical monomer that obtains through various silica gel column chromatographies with the preparative high-performance liquid chromatographic method.The structure of chemical monomer identify be adopt various modern spectroscopic techniques particularly the two dimensional NMR spectroscopic technique unknown natural organic-compound carried out structure identify.
Summary of the invention
The object of the present invention is to provide a kind of diterpene-kind compound and method of from the wheel blade veronica, extracting, in the hope of seeking the strong compound of immunosuppressive activity and illustrating the relevant group of structure-activity with immunosuppressive activity.
Of the present inventionly realized by following technical proposals:
The diterpene-kind compound that extracts first from the wheel blade veronica is characterized in that having the diterpenes new compound of four known diterpene-kind compounds and two the unknowns, and the title of four known compounds and molecular formula are for being respectively: TANSHINONES-I (VSZ2901), C
18H
12O
3Dihydrotanshinone-I (VSZ3504), C
18H
14O
3Cryptotanshinone (VSZ3505), C
19H
18O
3TANSHINONES-II (VSZ3604), C
19H
20O
3Their structural formula is as follows:
Tanshinone I (VSZ2901) dihydrotanshinone I (VSZ3504)
Cryptotanshinone (VSZ3505) Tanshinone I I (VSZ3604)
Two new compounds are respectively: a code name is VSZ3705, molecular formula C
19H
20O
2, molecular weight 280; Another code name is VSZ3707, molecular formula C
19H
22O
2, molecular weight 282.Its structural formula is as follows:
VSZ3705???????????????????????????????????VSZ3707
Above-mentioned All new compounds identify be by various organic Spectrum Analysis (
1H-NMR
13C-NMR DEPT2D-NMR
1H-
1H COSY, HSQC, HMBC, NOESY) and the spectral data of similar compound relatively, identified the structure of its unknown compound.
The spectral data of VSZ3705 is as follows: [α]
D 25+ 16.6 (c 0.2) .UV λ
Max MeOH(log ε): 225nm (4.25), 275nm (3.24), 464nm (3.52) .IR (KBr) ν
Max2962,2927,1722,1662,1626,1465,1428,1258,1232,1147,944,755.
1H-NMR (CDCl
3): δ 7.87 (1H, d, J=10.2Hz, H-1), 7.50 (1H, d, J=7.8Hz, H-6), 7.12 (1H, d, J=7.8Hz, H-7), 7.09 (1H, s, H-12), 6.33 (1H, m, H-2), 3.02 (1H, sept, J=6.9Hz, H-15), 2.28 (2H, dd, J=4.5,1.8Hz, H-3), 1.29 (6H, s, H
3-16,17), 1.17 (6H, d, J=6.9Hz, H
3-18,19)
13C-NMR (CDCl
3): δ 183.2 (C-11), 181.5 (C-14), 148.0 (C-5), 144.9 (C-13), 139.9 (C-12), 139.5 (C-9), 137.2 (C-10), 134.4 (C-2), 134.2 (C-8), 130.6 (C-6), 129.2 (C-7), 124.7 (C-1), 38.0 (C-3), 34.0 (C-4), 28.3 (C-16,17), 26.9 (C-15), 21.5 (C-18,19) .EIMS:m/z 280 (5), and 252 (54), 237 (100), 222 (12), 179 (22), 149 (90), 71 (12), 57 (13), 41 (12).
The spectral data of VSZ3707 is as follows: [α]
D 25+ 7.8 (c 0.2) .UV λ
Max MeOH(log ε): 220nm (4.17), 260nm (3.99), 450nm (3.22) .IR (KBr) ν
Max2962,2932,1728,1660,1563,1462,1390,1260,1143,938,756.
1H-NMR (CDCl
3): δ 7.59 (1H, d, J=7.9Hz, H-7), 7.11 (1H, d, J=7.9Hz, H-6), 7.07 (1H, s, H-12), 3.17 (2H, t, J=6.4Hz, H-1), 3.02 (1H, sept, J=6.9Hz, H-15), 1.80 (2H, m, H-2), 1.65 (2H, m, H-3), 1.30 (6H, s, H
3-16,17), 1.16 (6H, d, J=6.9Hz, H
3-18,19)
13C-NMR (CDCl
3): δ 182.4 (C-11), 181.5 (C-14), 149.6 (C-5), 145.0 (C-13), 144.5 (C-9), 139.9 (C-12), 134.4 (C-10), 133.7 (C-17), 133.4 (C-8), 127.9 (C-6), 37.8 (C-3), 34.5 (C-4), 31.7 (C-16,17), 29.7 (C-2), 26.9 (C-15), 21.5 (C-18,19), 19.0 (C-1) .EIMS:m/z 282 (13), and 255 (53), 239 (100), 224 (14), 165 (12), 115 (4), 89 (4), 41 (6).
Six diterpene-kind compounds that above-mentioned C ring has o-quinone or para-quinoid structure have immunosuppressive activity.
Above-mentioned diterpene-kind compound with immunosuppressive activity extracts the preparation method from the wheel blade veronica, its feature comprises the following steps:
1. with the wheel blade veronica medicinal material of pulverizing, to soak 5-7 hour 45-55 ℃ of temperature with 95% ethanol of medicinal material 5-7 times weight, filtration is soaked with 95% an ethanol 45-55 ℃ temperature of 5-7 times of weight again, so extracts three times, and merging filtrate is evaporated to and soaks paste.
2. the paste that step 1 is obtained distributes in separating funnel with distilled water/sherwood oil (3: 2), uses petroleum ether extraction 3-4 time then, and the extraction liquid concentrating under reduced pressure gets ligroin extraction.
3. above-mentioned petroleum ether layer extraction enriched material is separated with silica gel column chromatography, with 7: 1,5: 1,3: 1,1: 1,1: 3 sherwood oil-ethyl acetate solvent system, then with 100% ethyl acetate, 19: 1,10: 1, the ethyl acetate of 100% methyl alcohol-each 2000ml of methanol solvate system carries out gradient elution, gets 21 of components (with VSZ 0201-VSZ0221 name).
4. above-mentioned column chromatography component being passed through silica gel column chromatography, hydroxypropyl dextrane gel (LH-20) more respectively separates with the preparative high-performance liquid chromatographic method and obtains each monomeric compound.
Characteristics of the present invention are: extraction separation and proves that through pharmacological testing these diterpene-kind compounds all have stronger immunosuppressive activity to diterpene-kind compound from the wheel blade veronica first, and its preparation process is quick, easy.
Embodiment
Specific embodiment:
Wheel blade veronica medicinal material 2kg with pulverizing soaked 6 hours 50 ℃ of temperature with 12kg95% ethanol, filtered, and soaked with 50 ℃ of temperature of ethanol of 10kg95% again, so extracted three times, and merging filtrate is evaporated to and soaks paste 0.5kg.Petroleum ether layer extraction enriched material 0.5kg separates (800g silica gel with silica gel column chromatography, chromatography column: 60 * 1200mm), with sherwood oil-ethyl acetate solvent system (7: 1,5: 1,3: 1,1: 1,1: 3), then with ethyl acetate-methyl alcohol (100% ethyl acetate, 19: 1,10: 1,100% methyl alcohol) each 2000ml carries out gradient elution, 21 of components (with the VSZ0201-VSZ0221 name).
VSZ0215 is carried out silica gel column chromatography (silica gel 60g), respectively with chloroform: normal hexane (9: 1) → chloroform: methyl alcohol (98: 2) wash-out, behind the similar flow point of thin-layer chromatography detection merging, get 3 components (VSZ2901-VSZ2903), with VSZ2901 with recrystallizing methanol after, chemical monomer VSZ2901 (91.6mg).
VSZ2902 with after the acetonitrile dissolving and filtering, is prepared HPLC (Hibar RT 250-25, LiChrosorb with solute usefulness, RP-18, acetonitrile) carries out separation and purification, carry out each chromatographic peak according to UV, RI detector and collect, get chemical monomer VSZ3504 (7.0mg) and VSZ3505 (17.3mg).
VSZ0211 and VSZ0212 (1.8g) are merged, carry out wash-out by silica gel column chromatography (silica gel 300g, chromatography column: 40 * 800mm, chloroform/methanol 99: 1 → 95: 5 → 9: 1), thin-layer chromatography gets 6 components (VSZ2201-VSZ2206) after detecting and merging similar flow point.
With VSZ2203 (250mg), carry out hydroxypropyl dextrane gel (LH-20, MeOH) column chromatography, get 5 components (VSZ2301-VSZ2305), wherein VSZ2305 is with HPLC reverse-phase chromatography (Hibar RT 250-25, LiChrosorb, RP-18, acetonitrile) further separates, carry out each chromatographic peak according to UV, RI detector and collect, get chemical monomer VSZ3604 (27mg).
VSZ0209 (0.7g) is dissolved in methyl alcohol, carry out Sephadex LH-20 (MeOH) column chromatography, get 4 components (VSZ0901-VSZ0904), with wherein VSZ0903 (392mg) with further separation and purification of silica gel column chromatography (silica gel 60g), with chloroform/normal hexane (9: 1) wash-out, get 7 components (VSZ1001-VSZ1007), VSZ1006 is with HPLC reverse-phase chromatography (Hibar RT 250-25, LiChrosorb, RP-18, acetonitrile) further separates, carry out each chromatographic peak according to the RI detector and collect, get new compound VSZ3705 (63mg) and VSZ3707 (8mg).
The lymphocyte transformation experiment of above-mentioned each monomeric compound is as follows:
Lymphocyte receptor ConA stimulates the back that lymphoblastic transformation takes place, and the OD value is by 0.203 to 0.261.Each administration group and Con+cell control group more all show the LT effect of stronger inhibition.Five dosage group OD values of its Chinese traditional medicine 1# (Vsz3604), 3# (Vsz3504), 4# (Vsz3707) reduce with the increase of dosage, show tangible dose-dependently, and 2# (Vsz3705), 5# (Vsz3505), 6# (Vsz2901) respectively organizes the OD value than Con+cell control group OD value tangible reduction also, but the variable gradient of dose-effect relationship more not obvious (the results are shown in Table).Positive drug Dexamethasone group 50 μ g/ml, the OD value is 0.075 obviously to reduce than Con+cell control group OD value.Six diterpene-kind compounds of above presentation of results have stronger immunosuppressive activity.
| ??Number ????of ??Trial | ?Number?of ?compound | ?????????????????????????????????????????????Values?ofOD | ||||
| ????81μg/ml | ???40.5μg/ml | ????20μg/ml | ???13.5μg/ml | ???4.5μg/ml | ||
| ????1# | ??Vsz3604 | ??0.109±0.0064 | ??0.122±0.0036 | ??0.132±0.0020 | ??0.134±0.0042 | ??0.251±0.0042 |
| ????2# | ??Vsz3705 | ??0.119±0.0036 | ??0.128±0.0037 | ??0.138±0.0049 | ??0.187±0.0043 | ??0.227±0.0180 |
| ????3# | ??Vsz3504 | ??0.104±0.0055 | ??0.132±0.0038 | ??0.147±0.0036 | ??0.185±0.0061 | ??0.259±0.0125 |
| ????4# | ??Vsz3707 | ??0.098±0.0053 | ??0.116±0.0040 | ??0.132±0.0039 | ??0.166±0.0121 | ??0.178±0.0074 |
| ????5# | ??Vsz3505 | ??0.118±0.0037 | ??0.125±0.0025 | ??0.129±0.0026 | ??0.143±0.0041 | ??0.169±0.0054 |
| ????6# | ??Vsz2901 | ??0.128±0.0025 | ??0.137±0.0043 | ??0.159±0.0028 | ??0.167±0.0052 | ??0.190±0.0081 |
O
Ddecacortin＝0.075，OD
con+Cell＝0.203，OD
Blank＝0.017，n＝12
Claims (3)
1. the diterpene compound that extracts from the wheel blade veronica is characterized in that having the diterpenes new compound of four known diterpene-kind compounds and two the unknowns, and the title of four known compounds and molecular formula are for being respectively: TANSHINONES-I (VSZ2901), C
18H
12O
3Dihydrotanshinone-I (VSZ3504), C
18H
14O
3Cryptotanshinone (VSZ3505), C
19H
18O
3TANSHINONES-II (VSZ3604), C
19H
20O
3Their structural formula is as follows:
Tanshinone I (VSZ2901) dihydrotanshinone I (VSZ3504)
Cryptotanshinone (VSZ3505) Tanshinone I I (VSZ3604)
Two new compounds are respectively: a code name is VSZ3705, molecular formula C
19H
20O
2, molecular weight 280; Another code name is VSZ3707, molecular formula C
19H
22O
2, molecular weight 282; Structural formula is as follows:
VSZ3705??????????????????????????????????VSZ3707
The spectral data of VSZ3705 is as follows: [α]
D 25+ 16.6 (c0.2) .UV λ
Max MeOH(log ε): 225nm (4.25), 275nm (3.24), 464nm (3.52). IR (KBr) ν
Max2962,2927,1722,1662,1626,1465,1428,1258,1232,1147,944,755.
1H-NMR (CDCl
3): δ 7.87 (1H, d, J=10.2Hz, H-1), 7.50 (1H, d, J=7.8Hz, H-6), 7.12 (1H, d, J=7.8Hz, H-7), 7.09 (1H, s, H-12), 6.33 (1H, m, H-2), 3.02 (1H, sept, J=6.9Hz, H-15), 2.28 (2H, dd, J=4.5,1.8Hz, H-3), 1.29 (6H, s, H
3-16,17), 1.17 (6H, d, J=6.9Hz, H
3-18,19)
13C-NMR (CDCl
3): δ 183.2 (C-11), 181.5 (C-14), 148.0 (C-5), 144.9 (C-13), 139.9 (C-12), 139.5 (C-9), 137.2 (C-10), 134.4 (C-2), 134.2 (C-8), 130.6 (C-6), 129.2 (C-7), 124.7 (C-1), 38.0 (C-3), 34.0 (C-4), 28.3 (C-16,17), 26.9 (C-15), 21.5 (C-18,19). EIMS:m/z 280 (5), and 252 (54), 237 (100), 222 (12), 179 (22), 149 (90), 71 (12), 57 (13), 41 (12).
The spectral data of VSZ3707 is as follows: [α]
D 25+ 7.8 (c 0.2) .UV λ
Max MeOH(log ε): 220nm (4.17), 260nm (3.99), 450nm (3.22). IR (KBr) ν
Max2962,2932,1728,1660,1563,1462,1390,1260,1143,938,756.
1H-NMR (CDCl
3): δ 7.59 (1H, d, J=7.9Hz, H-7), 7.11 (1H, d, J=7.9Hz, H-6), 7.07 (1H, s, H-12), 3.17 (2H, t, J=6.4Hz, H-1), 3.02 (1H, sept, J=6.9Hz, H-15), 1.80 (2H, m, H-2), 1.65 (2H, m, H-3), 1.30 (6H, s, H3-16,17), (1.16 6H, d, J=6.9Hz, H3-18,19)
13C-NMR (CDCl
3): δ 182.4 (C-11), 181.5 (C-14), 149.6 (C-5), 145.0 (C-13), 144.5 (C-9), 139.9 (C-12), 134.4 (C-10), 133.7 (C-17), 133.4 (C-8), 127.9 (C-6), 37.8 (C-3), 34.5 (C-4), 31.7 (C-16,17), 29.7 (C-2), 26.9 (C-15), (21.5 C-18,19), 19.0 (C-1).EIMS：m/z?282(13)，255(53)，239(100)，224(14)，165(12)，115(4)，89(4)，41(6).
2. by the described diterpene compound that extracts from the wheel blade veronica of claim 1, it is characterized in that: the diterpene-kind compound that the C ring has o-quinone or para-quinoid structure has immunosuppressive activity.
By claim 1 described from the wheel blade veronica method of extraction separation diterpene compound: it is characterized in that carrying out as follows:
(1). with the wheel blade veronica medicinal material of pulverizing, soaked 5-7 hour 45-55 ℃ of temperature with 95% ethanol of medicinal material 5-7 times weight, filtration is soaked with 95% an ethanol 45-55 ℃ temperature of 5-7 times of weight again, so extracts three times, and merging filtrate is evaporated to and soaks paste;
(2). the paste that step 1 is obtained distributes in separating funnel with distilled water/sherwood oil (3: 2), uses petroleum ether extraction 3-4 time then, and the extraction liquid concentrating under reduced pressure gets ligroin extraction;
(3). above-mentioned petroleum ether layer extraction enriched material is separated with silica gel column chromatography, with 7: 1,5: 1,3: 1,1: 1,1: 3 sherwood oil-ethyl acetate solvent system, then with 100% ethyl acetate, 19: 1,10: 1, the ethyl acetate of 100% methyl alcohol-each 2000ml of methanol solvate system carries out gradient elution, gets 21 of components;
(4). above-mentioned column chromatography component is passed through silica gel column chromatography, hydroxypropyl dextrane gel (LH-20) more respectively separate with the preparative high-performance liquid chromatographic method and obtain each monomeric compound.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104140404A (en) * | 2014-07-16 | 2014-11-12 | 中国药科大学 | Compounds with effect of directly inhibiting thrombin and applications |
| CN104478832A (en) * | 2015-01-05 | 2015-04-01 | 富阳鸿祥技术服务有限公司 | Diterpene compound, pharmaceutical composition containing same and preparation method and usage thereof |
| CN108379273A (en) * | 2018-03-08 | 2018-08-10 | 广州神农生物技术有限公司 | Dihydrotanshinone I is preparing application and preparation method in treating multidrug-resistant carcinoma drug |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100494215C (en) * | 2007-03-07 | 2009-06-03 | 中国药科大学 | Structure of siRNA for target survivin gene and antineoplastic use |
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2003
- 2003-04-15 CN CNB031095712A patent/CN1194985C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104140404A (en) * | 2014-07-16 | 2014-11-12 | 中国药科大学 | Compounds with effect of directly inhibiting thrombin and applications |
| CN104478832A (en) * | 2015-01-05 | 2015-04-01 | 富阳鸿祥技术服务有限公司 | Diterpene compound, pharmaceutical composition containing same and preparation method and usage thereof |
| CN104478832B (en) * | 2015-01-05 | 2016-04-20 | 项敬来 | Diterpene compound, containing its pharmaceutical composition and its preparation method and application |
| CN108379273A (en) * | 2018-03-08 | 2018-08-10 | 广州神农生物技术有限公司 | Dihydrotanshinone I is preparing application and preparation method in treating multidrug-resistant carcinoma drug |
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