CN101376652A - Novel triterpenoid schisanlactone H and extracting and separating method thereof - Google Patents
Novel triterpenoid schisanlactone H and extracting and separating method thereof Download PDFInfo
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- CN101376652A CN101376652A CNA2008102334251A CN200810233425A CN101376652A CN 101376652 A CN101376652 A CN 101376652A CN A2008102334251 A CNA2008102334251 A CN A2008102334251A CN 200810233425 A CN200810233425 A CN 200810233425A CN 101376652 A CN101376652 A CN 101376652A
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- 238000000034 method Methods 0.000 title abstract 2
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 title description 4
- RVEBOCQEYQSGBC-DRBFJGFPSA-N schisanlactone H Natural products COC(=O)CC[C@@]1(C)[C@@H](CC[C@@H]2C1=CC[C@]3(C)[C@H](CC[C@@]23C)[C@H](C)[C@H]4CC=C(C)C(=O)O4)C(C)(C)O RVEBOCQEYQSGBC-DRBFJGFPSA-N 0.000 title description 4
- -1 triterpene compound Chemical class 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 150000002596 lactones Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 235000021028 berry Nutrition 0.000 claims description 10
- 239000003480 eluent Substances 0.000 claims description 9
- 235000008422 Schisandra chinensis Nutrition 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 7
- 240000006079 Schisandra chinensis Species 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 3
- 235000019634 flavors Nutrition 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000013375 chromatographic separation Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 238000000926 separation method Methods 0.000 abstract description 8
- 230000000259 anti-tumor effect Effects 0.000 abstract description 4
- 235000013399 edible fruits Nutrition 0.000 abstract description 4
- 241000736078 Schisandra sphenanthera Species 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 abstract 6
- 230000002411 adverse Effects 0.000 abstract 1
- 230000036436 anti-hiv Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- 241000736075 Schisandra Species 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- 241000758724 Schisandraceae Species 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- QFKYMFWLPPOWOB-MPHJNTCLSA-N (+)-Rubriflordilactone A Chemical compound O([C@@H]1[C@H]2OC=3C4=C(C=5CC[C@H]6C(C)(C)O[C@@H]7CC(=O)O[C@@]76CC=5C=3)CC[C@@H]4[C@@H]2C)C(=O)C(C)=C1 QFKYMFWLPPOWOB-MPHJNTCLSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001506371 Kadsura Species 0.000 description 1
- 241000561709 Kadsura longipedunculata Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NJFOSFIPGRXARF-QYLNPOJUSA-N Nigranoic acid Chemical compound C1C[C@@H](C(C)=C)[C@@]2(CCC(O)=O)C[C@@]32CC[C@]2(C)[C@@H]([C@@H](CCC=C(C)C(O)=O)C)CC[C@@]2(C)[C@@H]31 NJFOSFIPGRXARF-QYLNPOJUSA-N 0.000 description 1
- NJFOSFIPGRXARF-UHFFFAOYSA-N Nigranoin-saeure Natural products C1CC(C(C)=C)C2(CCC(O)=O)CC32CCC2(C)C(C(CCC=C(C)C(O)=O)C)CCC2(C)C31 NJFOSFIPGRXARF-UHFFFAOYSA-N 0.000 description 1
- 229930182624 Rubriflorin Natural products 0.000 description 1
- 241000690369 Schisandra lancifolia Species 0.000 description 1
- 241000558607 Schisandra rubriflora Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JDOHERDAOGEJFF-ASWXAAPUSA-N kadlongilactone A Chemical compound C([C@@]1(O)C[C@@H]23)=C4C=CC(=O)OC(C)(C)[C@@H]4CC[C@H]1[C@]3(C)C[C@@H](O)C1=C2C[C@H]2C=C(C)C(=O)O[C@H]2[C@H]1C JDOHERDAOGEJFF-ASWXAAPUSA-N 0.000 description 1
- JDOHERDAOGEJFF-UHFFFAOYSA-N kadlongilactone A Natural products C12CC3(O)C=C4C=CC(=O)OC(C)(C)C4CCC3C1(C)CC(O)C1=C2CC2C=C(C)C(=O)OC2C1C JDOHERDAOGEJFF-UHFFFAOYSA-N 0.000 description 1
- GFRDTMTUJTYIJJ-IUSUREMMSA-N lancifodilactone F Chemical compound C([C@@]12[C@H]([C@](C)(O)CO)CC[C@@H]3[C@]4(C)CC[C@@H]([C@]4(CC[C@@H]3C2)C)[C@H](C)C(O)=O)CC(=O)O1 GFRDTMTUJTYIJJ-IUSUREMMSA-N 0.000 description 1
- GFRDTMTUJTYIJJ-UHFFFAOYSA-N lancifodilactone F Natural products C1C2CCC3(C)C(C(C)C(O)=O)CCC3(C)C2CCC(C(C)(O)CO)C21CCC(=O)O2 GFRDTMTUJTYIJJ-UHFFFAOYSA-N 0.000 description 1
- ZQIOPEXWVBIZAV-ZKYCIREVSA-N lanostane Chemical class CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@@H]2[C@]2(C)CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 ZQIOPEXWVBIZAV-ZKYCIREVSA-N 0.000 description 1
- HPMBMZUDXWXFOU-UHFFFAOYSA-N longipedlactone A Natural products C=1CC(C2CCC3C(C)(C)OC(=O)C=CC3=CC2(O)C2)(C)C2C(=C)C=1C(C)C1CC=C(C)C(=O)O1 HPMBMZUDXWXFOU-UHFFFAOYSA-N 0.000 description 1
- NHRSXCUUAIYPDX-UHFFFAOYSA-N longipedlactone B Natural products C1CC(C2CCC3C(C)(C)OC(=O)C=CC3=CC2(O)C2)(C)C2C(=C)C1C(C)C1CC=C(C)C(=O)O1 NHRSXCUUAIYPDX-UHFFFAOYSA-N 0.000 description 1
- ORWYYJLUJLOTPL-UHFFFAOYSA-N longipedlactone C Natural products C1CC(C2CCC3C(C)(C)OC(=O)C=CC3=CC2(O)C2)(C)C2C(=C)C1(O)C(C)C1CC=C(C)C(=O)O1 ORWYYJLUJLOTPL-UHFFFAOYSA-N 0.000 description 1
- SJCQJLRZUFTNFT-UHFFFAOYSA-N longipedlactone F Natural products C=1CC(C2CC(O)C3C(C)(C)OC(=O)C=CC3=CC2(O)C2)(C)C2C(=C)C=1C(C)C1CC=C(C)C(=O)O1 SJCQJLRZUFTNFT-UHFFFAOYSA-N 0.000 description 1
- YMROIYYFBRDJOJ-UHFFFAOYSA-N longipedlactone H Natural products C1CC(C2CC(O)C3C(C)(C)OC(=O)C=CC3=CC2(O)C2)(C)C2C(=C)C1(O)C(C)C1CC=C(C)C(=O)O1 YMROIYYFBRDJOJ-UHFFFAOYSA-N 0.000 description 1
- HPMBMZUDXWXFOU-QSISBBOKSA-N longipedlactone a Chemical compound C([C@@H]1[C@H](C)C=2C([C@H]3[C@@]([C@@H]4CC[C@H]5C(C)(C)OC(=O)C=CC5=C[C@@]4(O)C3)(C)CC=2)=C)C=C(C)C(=O)O1 HPMBMZUDXWXFOU-QSISBBOKSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- TXNBIFNTDYSZNF-UHFFFAOYSA-N nigranoic acid Natural products CC(CCC=C(C)/C(=O)O)C1CCC2(C)C3CCC(C4(C)CC4)C5(CCC(=O)O)CC35CCC12C TXNBIFNTDYSZNF-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 1
- QFKYMFWLPPOWOB-UHFFFAOYSA-N rubriflordilactone A Natural products CC1C2CCC(C=3CCC4C(C)(C)OC5CC(=O)OC54CC=3C=3)=C2C=3OC1C1OC(=O)C(C)=C1 QFKYMFWLPPOWOB-UHFFFAOYSA-N 0.000 description 1
- 229930193284 schisanlactone Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229930184222 wuweizidilactone Natural products 0.000 description 1
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Abstract
The invention provides a new triterpene compound (valerolactone H) and an extraction separating method thereof. The new triterpene compound (valerolactone H) is separated from the fruits of orange magnoliavine fruit, has a novel structure, simple extraction separation process and a relatively higher content, facilitates the further pharmacological research thereof and creates the condition for developing novel anti-tumor and anti-HIV pharmaceuticals with good therapeutic effect and low toxic and adverse effects. The new triterpene compound (valerolactone H) has a structural formula as above.
Description
Technical field
The present invention relates to a kind of new triterpene compound thing and extraction and separation method thereof, belong to field of phytochemistry.
Background technology
Have extensive bioactive Lignanoids compounds owing to be rich in Schisandraceae (Schisandraceae) plant, so its research receives much attention.In recent years, the investigator has found a series of triterpene compounds from this section plant, and many triterpene compounds have antitumor and HIV (human immunodeficiency virus)-resistant activity.
From long stalk kadsura longepedunculata (Kadsura longipedunculata), separate Kadlongilactone A and the B that obtains, all can significantly suppress human body K562 growth of tumour cell, its IC
50Value is respectively 1.40 and 1.71 μ gmL
-1, suitable with the activity of positive control cis-platinum; Separation obtains from this plant Longipedlactone A, B, C, F and H are to A549, and HT-29 and K562 all show tangible cytotoxicity, its IC
50Value is at 0.84-11.38 μ gmL
-1Between.
From the shizandra berry that comes into leaves (Schisandra lancifolia), separate the triterpenoid lancifodilactone F and the H that obtain and all show the anti-HIV-1 activity, its EC
50Be respectively 20.69,16.6 μ gmL
-1, have minimum cytotoxicity (CC simultaneously to the C8166 cell
50200 μ gmL
-1).Separating the nigranoic acid that obtains from the cauline leaf of ball stamen shizandra berry (Schisandra sphaerandra), is a triterpenoid with remarkable inhibition HIV-1 reversed transcriptive enzyme, polymerase activity.Separate 6 high oxidation degree that obtain and fall triterpene from shizandra berry (Schisandra chinensis), shizandra berry dilactone (wuweizidilactone) A-F shows anti-HIV-1 activity in various degree, the wherein EC of shizandra berry dilactone A and B
50Be respectively 26.81 and 28.86 μ gmL
-1(the EC of positive control: AZT
50=2.26 μ gmL
-1).From Schisandra sphnanthera (Schisandra rubriflora), separate the rubriflordilactone A obtain and B and show in various degree anti-HIV-1 activity, the former activity relatively a little less than, and the latter can suppress HIV-1 and duplicates its EC
50Value is 9.75 μ gmL
-1, have lower cytotoxicity simultaneously; The triterpenoid rubriflorins A-C that separation obtains from this plant also shows anti-HIV-1 activity in various degree, its EC
50Be respectively 10.0,16.2 and 81.3 μ gmL
-1, while CC
50Value (C8166 cell) is respectively 89.1,100.3, and 200 μ gmL
-1
Up to now, new triterpene compound thing involved in the present invention still finds no patent or bibliographical information.
Summary of the invention
The present invention's purpose is to provide a kind of new triterpene compound thing, specifically is a kind of new triterpene compound thing five lactone H, in the hope of seeking compound antitumor or that HIV (human immunodeficiency virus)-resistant activity is strong.
Another object of the present invention is to provide the extraction and separation method of above-mentioned new triterpene compound thing.
New triterpene compound thing five lactone H provided by the invention (schisanlactone H), its chemical structural formula is as follows:
New triterpene compound thing five lactone H provided by the invention (schisanlactone H) are that extraction separation comes out from the fruit of schisandra chinensis Schisandrasphenanthera, and its processing step is:
A, schisandra raw material pulverized after, by shizandra berry: the mass/volume ratio of aqueous acetone solution=1: 2～4, it is 70% aqueous acetone solution that shizandra berry is put into concentration, after soaking 15～30 hours under the room temperature, get extracting solution, so repeat to extract united extraction liquid 2～3 times;
B, with the underpressure distillation of above-mentioned A step gained extracting solution after do not have acetone flavor, press extracting solution: the volume ratio of ethyl acetate=1: 1, under room temperature, the extracting solution of above-mentioned A step is carried out 2～3 times extraction with ethyl acetate, must ethyl acetate medicinal extract;
C, silicagel column on the ethyl acetate medicinal extract of above-mentioned B step is carried out chromatographic separation, use chloroform: acetone=1～0: the eluent of 1 volume ratio carries out wash-out, remove impurity after, the roughing out thing;
D, with the roughing out thing of above-mentioned C step successively with sherwood oil: eluent, the chloroform of the volume ratio of acetone=30: 1: the eluent of the volume ratio of acetone=50: 1 carries out silica gel column chromatography and wash-out 2～5 times, remove impurity after, compound five lactone H.
The present invention has following advantage and effect: compound structure novelty provided by the invention, extraction and separation method is simple and easy, and the gained compounds content is higher relatively, help it is carried out further pharmacological research, created condition for developing good effect and little new antitumoral and the inverase of toxic side effect.
Description of drawings
Fig. 1 is the structure of five lactone H (1);
Fig. 2 is the HMBC figure of five lactone H;
Embodiment
Embodiment
With schisandra chinensis (Schisandra sphenanthera) fruit (dry weight 8kg) is raw material, by shizandra berry: the mass/volume ratio of aqueous acetone solution=1: 3, be that 70% acetone water liquid leaves standstill in room temperature and extracts three times with concentration, each 24 hours, the acetone consumption is 25L * 3, merge No. three times extracting solution, be evaporated to no acetone flavor; Press extracting solution: the volume ratio of ethyl acetate=1: 1, with ethyl acetate extracting solution is carried out 3 extractions, after the recovery medicinal extract 145.9g; On the medicinal extract behind the silica gel column chromatography, use chloroform: acetone is respectively: 1: 0, and 9: 1,8:: 2,7: 3,6: 4,5:: the eluent of 5,0: 1 volume ratio, carry out seven gradient elutions, obtain eight polarity sections of A-H respectively, the B section (promptly use chloroform: the part of acetone=9: 1 wash-out) successively with sherwood oil: eluent, the chloroform of the volume ratio of acetone=30: 1: the eluent of the volume ratio of acetone=50: 1 carries out silica gel column chromatography, compound five lactone H (18mg).
Five lactone H (schisanlactone H) are white powder.HR-ESI-MS measures its [M+Na]
+(C
31H
48O
5Na
+) molecular weight at peak is 523.3398 (calculated value is 523.3399), thereby determines that its molecular formula is C
31H
48O
5, degree of unsaturation is 8.From compound 1
1Can observe in the H-NMR spectrum: Zhong Jiaji (δ 0.98, d, J=6.4Hz), six uncle's methyl (δ 0.69,0.72,1.29,1.26,1.21,1.92), two alkene protons (δ 5.39,6.61) and a methoxyl group (δ 3.70) signal.Compound 1
13C-NMR, DEPT and HSQC data disclose in the molecule and contain a carboxymethyl, a α, beta-unsaturated carbonyl, six quaternary carbons (comprising oxygen containing and two alkene carbon), seven methynes (comprise two undersaturated), eight methylene radical, and seven methyl.The nuclear magnetic resonance data of synthesization compound 1, except that two two keys and two carbonyls, causing undersaturated other factors of this compound should be a tetra-atomic ring skeleton.Careful control compounds 1 and five lactones (schisanlactone) F's
1H-and
13The C-NMR data find that these two compounds have identical D ring and E ring, and the A of two compounds ring has all experienced the oxidation scission between C-3 and C-4 position simultaneously.To compound 1
1H-
1HCOSY, the analysis of HSQC and HMBC data has further confirmed above deduction.Therefore think that compound 1 belongs to 3, the lanostane derivative of 4-fracture.
(δ 1.92, and s) and C-24, the HMBC of C-25 and C-26 is relevant, and the fragment m/z111[C among the positively charged ion FAB-MS for Me-27
6H
7O
2 +] disclosed hexa-atomic Alpha-Methyl-α in the molecule, the existence of β-unsaturated-delta-lactone ring.Me-30 (δ 1.26, s) and C-4, the relevant and Me-29 of the HMBC between C-5 and the C-29 (δ 1.29, s) and C-4, C-5, the HMBC between the C-30 is relevant, require Me-29 and Me-30 be connected in same contain the oxygen quaternary carbon (δ 75.5, s, C-4) on.Methoxyl group (δ 3.70, s) and H-2 (δ 2.44, m, H-2a; 2.35, m, H-2b) with C-3 between HMBC relevant, and the fragment m/z440[M-HCOOCH among the positively charged ion FAB-MS
3] illustrate that carboxymethyl links to each other with C-2.δ 5.41 (proton signal H-11) shows and C-9 for d, J=5.8Hz, C-12, and the HMBC of C-10 and C-13 is relevant, illustrates that double bond position is between C-9 and C-11.This point is by Me-19, and the HMBC relevant peaks between H-12 and H-7 and the C-9 further confirms.
The relative steric configuration that the ROESY data of compound 1 are disclosed is consistent with compound five lactone F.Table 1 has been listed compound 1
1H-and
13The C-NMR data.
Table 1. five lactone H's
1H-NMR (400MHz) and
13C-NMR (100MHz) data (ppm, in CDCl
3)
Claims (2)
1. new triterpene compound thing five lactone H, its chemical structural formula is as follows:
2. preparation method of compound according to claim 1 is characterized in that through the following step:
A, schisandra raw material pulverized after, by shizandra berry: the mass/volume ratio of aqueous acetone solution=1: 2～4, it is 70% aqueous acetone solution that shizandra berry is put into concentration, after soaking 15～30 hours under the room temperature, get extracting solution, so repeat to extract united extraction liquid 2～3 times;
B, with the underpressure distillation of above-mentioned A step gained extracting solution after do not have acetone flavor, press extracting solution: the volume ratio of ethyl acetate=1: 1, under room temperature, the extracting solution of above-mentioned A step is carried out 2～3 times extraction with ethyl acetate, must ethyl acetate medicinal extract;
C, silicagel column on the ethyl acetate medicinal extract of above-mentioned B step is carried out chromatographic separation, use chloroform: acetone=1～0: the eluent of 1 volume ratio carries out wash-out, remove impurity after, the roughing out thing;
D, with the roughing out thing of above-mentioned C step successively with sherwood oil: eluent, the chloroform of the volume ratio of acetone=30: 1: the eluent of the volume ratio of acetone=50: 1 carries out silica gel column chromatography and wash-out 2～5 times, remove impurity after, compound five lactone H.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101708215B (en) * | 2009-11-27 | 2011-09-21 | 辽宁晟麦实业股份有限公司 | Method for extracting triterpenes from schisandra chinansis |
| CN104430560A (en) * | 2014-12-08 | 2015-03-25 | 北京农学院 | Schisandra chinensis extract and application thereof in bacteriostasis |
| CN106265930A (en) * | 2016-08-30 | 2017-01-04 | 青海民族大学 | Herba Lycopodii AntiHIV1 RT activity 1 virus effective site and preparation method and application |
| CN108165496A (en) * | 2017-12-01 | 2018-06-15 | 国家海洋局第三海洋研究所 | Fu Keer sclerotinite 3A00494 and its fermented cpds application in preparation of anti-tumor drugs |
| CN112592293A (en) * | 2020-12-16 | 2021-04-02 | 云南大学 | Synthesis and application of tetracyclic triterpene derivative |
-
2008
- 2008-10-10 CN CNA2008102334251A patent/CN101376652A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101708215B (en) * | 2009-11-27 | 2011-09-21 | 辽宁晟麦实业股份有限公司 | Method for extracting triterpenes from schisandra chinansis |
| CN104430560A (en) * | 2014-12-08 | 2015-03-25 | 北京农学院 | Schisandra chinensis extract and application thereof in bacteriostasis |
| CN104430560B (en) * | 2014-12-08 | 2017-07-07 | 北京农学院 | A kind of Schisandra chinens P.E and its application in antibacterial |
| CN106265930A (en) * | 2016-08-30 | 2017-01-04 | 青海民族大学 | Herba Lycopodii AntiHIV1 RT activity 1 virus effective site and preparation method and application |
| CN106265930B (en) * | 2016-08-30 | 2019-11-12 | 青海民族大学 | Herba Lycopodii anti-HIV-1 virus active component and preparation method and application |
| CN108165496A (en) * | 2017-12-01 | 2018-06-15 | 国家海洋局第三海洋研究所 | Fu Keer sclerotinite 3A00494 and its fermented cpds application in preparation of anti-tumor drugs |
| CN108165496B (en) * | 2017-12-01 | 2020-09-08 | 国家海洋局第三海洋研究所 | Application of sclerotinia Rickettii 3A00494 and fermentation compound thereof in preparation of antitumor drugs |
| CN112592293A (en) * | 2020-12-16 | 2021-04-02 | 云南大学 | Synthesis and application of tetracyclic triterpene derivative |
| CN112592293B (en) * | 2020-12-16 | 2023-06-16 | 云南大学 | Synthesis and application of tetracyclic triterpene derivative |
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