CN104059040A - Sesquiterpene compounds with antitumor activity and preparation method of sesquiterpene compounds - Google Patents
Sesquiterpene compounds with antitumor activity and preparation method of sesquiterpene compounds Download PDFInfo
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Abstract
The invention relates to sesquiterpene compounds with antitumor activity and a preparation method of the sesquiterpene compounds, belonging to the field of biological medicines. The sesquiterpene compounds have the structural formula as the specification. The compounds are obtained from (Pleurotus cystidiosus) ZYB2013, and the sesquiterpene compounds are used as antitumor drugs or tumor cell proliferation inhibiting drugs. The sesquiterpene compounds provided by the invention are novel in structure and strong in antitumor activity. The sesquiterpene compounds are found to have a relatively strong inhibiting effect for prostate cancer cells DU-145, C42B and LNCaP through measuring the antitumor activities of the compounds. A result shows that the sesquiterpene compounds have antitumor activity so as to be applied to preparation of antitumor drugs or other biological activity primers.
Description
Technical field
The present invention relates to a kind of sesquiterpenoids with anti-tumor activity and preparation method thereof, belong to biomedicine field.
Background technology
Sesquiterpene (sesquiterpenes) refers to the natural terpenes compounds containing 15 carbon atoms in molecule.Sesquiterpenoids is distributed more widely, the abundantest in Magnoliales (magnoliales), rue order (rutales), Cornales (cornales) and chrysanthemum order (asterales) plant.In plant materials, being often present in volatile oil with alcohol, ketone, lactone etc. form, is the chief component of high-boiling fration in volatile oil.Have stronger fragrance and biological activity, be the important source material of medicine, food, cosmetic industry more.
The inventor studies and learns, wild Pleurotus abalonus (
pleurotus cystidiosus) ZYB2013(is preserved in Chinese Typical Representative culture collection center on June 15th, 2014, deposit number is CCTCC M 2014256), solid culture mycelia in early stage is pure white, and late stage of culture mycelia can produce black point secretion.Then the activeconstituents of tunning is studied.Shown in research discovery, sesquiterpenoids has anti-tumor activity, and the report of the proliferation inhibition activity of sesquiterpenoids shown in having not yet to see to tumour cell, therefore also there is not yet medicine related to this on market.
Summary of the invention
The object of the present invention is to provide a kind of sesquiterpenoids being produced by fungi fermentation and preparation method thereof.
Another object of the present invention is to this sesquiterpenoids as antitumor drug or Cytostatic to tumor cell medicine.
Fungi involved in the present invention be wild Pleurotus abalonus (
pleurotus cystidiosus) ZYB2013, this bacterial strain has been preserved in Chinese Typical Representative culture collection center, and the deposit number of registering on the books is CCTCC M 2014256, and the culture title of preservation and dated diagnostic characteristics are wild Pleurotus abalonus
pleurotus cystidiosus, preservation day is on June 15th, 2014.
The chemical structural formula of sesquiterpenoid of the present invention is as follows:
。
The preparation method of sesquiterpenoid of the present invention, by the wild Pleurotus abalonus of fermentation culture (
pleurotus cystidiosus) ZYB2013, obtain fermented product, then from fermented product, separation and purification goes out this compound, described wild Pleurotus abalonus (
pleurotus cystidiosus) ZYB2013, being preserved in Chinese Typical Representative culture collection center on June 15th, 2014, deposit number is CCTCC M 2014256.
Concrete steps are:
1) fungus solids cultivate: by deposit number be CCTCC M 2014256 wild Pleurotus abalonus (
pleurotus cystidiosus) carry out solid culture fermentation after ZYB2013 slant strains activation, the culture medium prescription of solid fermentation is by weight: potato 10-30%, glucose 1-3%, agar powder 0.5-2%, surplus is water, pH nature, 0.1 Mpa, 121 DEG C of sterilizing 30 min, be placed in 25-30 DEG C of constant incubator and cultivate 20-50 days;
2) tunning processing: after fermentation ends, mycelium and fermented substrate are cut into small pieces, with several mixing in the acetic acid of 1～3 times of volume, methyl alcohol, acetone, ethyl acetate, wherein acetic acid volume accounts for 1-5%, lixiviate is more than 1～5 time, filter and collect organic vat liquor, be evaporated to paste at 40～50 DEG C, paste extracts 1～8 time by pure water and ethyl acetate (volume of pure water and ethyl acetate is 1:1), ethyl acetate is evaporated to paste at 40～50 DEG C, obtains ethyl acetate extract medicinal extract;
3) by 2) described ethyl acetate extract medicinal extract dissolve with methanol, (reverse phase silica gel adopts RP18 to carry out reversed-phase silica gel column chromatography, consumption is 40～400 times of sample quality), first use 5～10 column volumes of pure water wash-out, then with methanol-water gradient, be in charge of collection, each pipe is in 40～50 DEG C of difference concentrating under reduced pressure, according to thin-layer chromatography (taking chloroform: methyl alcohol=10:1 as developping agent, taking 10% sulfuric acid ethanol as developer) result, the collection tube that contains target compound is merged into component Fr.1;
4) Fr.1 is carried out to reversed-phase silica gel column chromatography, taking methanol-water as eluent, be in charge of collection, thin-layer chromatography is carried out in every test tube sampling, merges similar component and obtains Fr.C1 and Fr.C2.Fr.C1 is through Sephadex LH-20 dextrane gel column chromatography, and acetone wash-out, follows through reversed-phase silica gel column chromatography, 40% methanol-eluted fractions, then through purification on normal-phase silica gel column chromatography, chloroform: methyl alcohol (200:1) wash-out obtains compound
1.By Fr.C2 through Sephadex LH-20 dextrane gel column chromatography, acetone wash-out, purification on normal-phase silica gel column chromatography, chloroform: methyl alcohol (200:1) wash-out, then through Sephadex LH-20 dextrane gel column chromatography, acetone wash-out, be in charge of collection, thin-layer chromatography detects and obtains compound
2.
The present invention has also protected described sesquiterpenoids in the purposes of preparing in Cytostatic to tumor cell medicine, and in the purposes of preparing in antitumor drug.Described tumour cell is prostate cancer cell DU-145, C42B and LNCaP.
According to mass spectrum (ESI), high resolution mass spectrum (HRMS-EI), circular dichroism spectrum (CD), optically-active ([
a]), UV spectrum (UV), infrared spectra (IR) and NMR (Nuclear Magnetic Resonance) spectrum (
1h-NMR,
13c-NMR, HSQC, HMBC,
1h,
1h-COSY and NOESY) data compound is carried out to Structural Identification, can deterministic laminate structures.Utilize cell toxicant MTT(tetrazolium bromide) and method (referring to document Mosmann T. Rapid colorimetric assay for cellular growth and survival:application to proliferation and cytotoxicity assays[J]. J. Immunol Methods, 1983,65(1-2): 55-63.) anti-tumor activity of mensuration compound, finds the inhibition that it is stronger to having of prostate cancer cell DU-145, C42B and LNCaP.Result shows, described sesquiterpenoid has anti-tumor activity, can be applicable to prepare the active primer of antitumor drug or other biological.
Sesquiterpenoid novel structure of the present invention, has very strong anti-tumor activity.Utilize wild Pleurotus abalonus (
pleurotus cystidiosus) ZYB2013 fermentation makes, fermentation raw material source low price, preparation method is simple, easily realizes suitability for industrialized production.
Embodiment
The chemical structure of the compound 1,2 of indication in following embodiment:
The invention will be further described for following examples.
embodiment 1
Preparation solid PDA substratum (in every premium on currency, be sub-packed in 750 90 mm glass culture dishs containing 15 L, each 20 mL substratum that approximately fill, wild Pleurotus abalonus that after sterilizing, access has activated (
pleurotus cystidiosus) ZYB2013(is preserved in Chinese Typical Representative culture collection center on June 15th, 2014, deposit number is CCTCC M 2014256) mycelia piece, in 28 DEG C of constant incubators, cultivate 43 days.After cultivation, wild Pleurotus abalonus mycelium is shredded together with substratum, be placed in tap bottle, add organic solvent (ethyl acetate: methyl alcohol: acetic acid volume ratio=80:15:5) lixiviate 6 times, collect extracting solution, be evaporated to paste at 40 DEG C, paste extracts 6 times with pure water and ethyl acetate 1:1, ethyl acetate, with after anhydrous sodium sulfate dehydration, is evaporated to paste at 40 DEG C, and (4.4057 g) to obtain ethyl acetate extract medicinal extract.
By 4.4057 g ethyl acetate extracts in previous step, fully dissolve with appropriate methyl alcohol, carry out reverse phase silica gel (170 g) column chromatographies.Use methanol-water gradient: water, 30% methyl alcohol, 50% methyl alcohol, 70% methyl alcohol, methyl alcohol and water is wash-out 1.5 L, 1.5 L, 1.5 L, 1.4 L, 1 L and 1 L respectively, and flow velocity is about 20 mL/min, and every pipe is collected 200 mL, thin-layer chromatography is carried out in every test tube sampling, and (developping agent is chloroform: methyl alcohol=15:1, developer: 10% sulfuric acid ethanol; Lower same) analytical results, merge similar component, obtain Fr.A(195.5 mg), Fr.B(154.8 mg), Fr.C(495.7 mg), Fr.D(240.0 mg), Fr.E(1733.5 mg), Fr.F(693.0 mg) and Fr.G(318.8 mg) seven components.
The component Fr.C(495.7 mg that previous step is obtained) carry out reverse phase silica gel (30 g) column chromatographies, respectively taking 35% methanol-water and 45% methanol-water as eluent, be in charge of collection, thin-layer chromatography is carried out in every test tube sampling, merges similar component and obtains Fr.C1(222.9 mg) and Fr.C2(134.1 mg).Fr.C1 is through Sephadex LH-20 dextrane gel (120 g) column chromatographies, acetone wash-out obtains Fr.C1.1(88.6 mg), then through reversed-phase silica gel column chromatography, (30 g), 300 mL 40% methanol-eluted fractions obtain Fr.C1.1.1(56.5mg), Fr.C1.1.1 is through purification on normal-phase silica gel (2 g) column chromatographies, 150 mL chloroforms: methyl alcohol (200:1) wash-out obtains compound
1(6.1 mg).By Fr.C2 through Sephadex LH-20 dextrane gel (120 g) column chromatography, acetone wash-out obtains Fr.C2.1(16.6 mg) and Fr.C2.2(49.0 mg).(1 g) the column chromatography of purification on normal-phase silica gel for Fr.C2.1,150 mL chloroforms: methyl alcohol (200:1) wash-out obtains Fr.C2.1.1(7.3 mg), then through Sephadex LH-20 dextrane gel (30 g) column chromatographies, acetone wash-out, be in charge of collection, thin-layer chromatography detects and obtains compound
2(3.0 mg).
By the compound of previous step gained
1,
2, carry out mass spectrum (ESI), high resolution mass spectrum (HRMS-EI), circular dichroism spectrum (CD), optically-active ([
a]), UV spectrum (UV), infrared spectra (IR) and NMR (Nuclear Magnetic Resonance) spectrum (
1h-NMR,
13c-NMR, HSQC, HMBC,
1h,
1h-COSY and NOESY) measure, and deterministic laminate structures.
Compound
1, white is amorphous, is soluble in methyl alcohol, [
a]
+ 51.7 (
c=0.23, MeOH); UV-vis (MeOH),
λ/ nm:216; HRMS-EI,
m/z: 266.1521 (theoretical values 266.1518); IR (KBr) n
max: 3441,1749,1623 cm
-1; In conjunction with
1h and
13c NMR spectrum data (table 1) determine that molecular formula is C
15h
22o
4.In infrared spectra, compound
1at 3441,1749 and 1623 cm
-1have more by force and absorb, point out respectively at compound
1contain hydroxyl, carbonyl and two key group.Analyze
1h and
13c NMR and DEPT spectrum, show compound
1contain 3 methyl, 3 methylene radical (one of them is the methylene radical on end alkene), 5 methynes (wherein 3 oxygen even, 1 be alkene methyne), 4 quaternary carbons (wherein 1 company's oxygen, 2 is olefinic carbon, 1 is carbonyl).In HMBC spectrum, two methyl proton H
3-12 and H
3-13 with C-11 and C-10 and the obvious hydrocarbon distant relation of existence each other, then according to the hydrocarbon distant relation of H-10 and C-9, C-12 and C-13 and C-9(δ
cchemical displacement value 199.8s), shows compound
1contain the isoprene fragment with carbonyl being formed by C-9, C-10, C-11, C-12 and C-13.Observable following hydrocarbon distant relation in composing according to HMBC: the methylene radical H of end alkene
2-15 with C-6 and C-8, H-1 and C-2, C-7 and C-8, H-6 and C-7, H-8 and C-7, and
1h-
1the H-6 existing in H COSY spectrum is relevant to the stronger hydrogen hydrogen of H-1, can set up the furan structure fragment of the end alkene replacement being made up of C-1, C-6, C-7, C-8 and C-15.
1h-
1in H COSY spectrum, H-1 and H-2 and H-6, and H
2-5 have stronger reference point with H-4 and H-6, then according to H
3-14 with C-2, C-3 and the stronger hydrocarbon distant relation of HMBC of C-4, can set up formed by C-1, C-2, C-3, C-4, C-5, C-6 and C-15 by hydroxyl and methyl substituted cyclohexane structure fragment, and can be by H
2-4 further confirm with C-2, C-5, C-6 and the stronger hydrocarbon distant relation of HMBC of C-14.In HMBC spectrum, be also found H-8 and C-9, and H
2-5 relevant to C-7 and C-15, accordingly can be by three fragments composition compounds
1basic structure.H-1 and H-6 in NOESY spectrum, H-6 and H-5a, it is obvious relevant that H-5a and H-6 have, show H-1, H-6, H-5a same towards, meanwhile, H-2 and H
3it is relevant that-14, H-2 and H-8 have obvious NOESY, shows H-2, H
3-14, H-8 is towards the opposite, therefore compound
1relative configuration set up, through retrieval compound
1for bisabolane type sesquiterpene, called after pleuroton A.
Table 1 compound
1nMR data (MeOD, 500M)
(note: alphabetical q, t, d, s represents respectively the primary, the second month in a season, uncle, quaternary carbon, is determined by DEPT figure; DH:H chemical shift; DC:C chemical shift; J: coupling constant; Multiplicity: the multiple peak that splits, Hereinafter the same).
Compound
2, white is amorphous, is soluble in methyl alcohol, [
a]
+ 79.6 (
c=0.32, MeOH); UV-vis (MeOH),
λ/ nm:247; ESI,
m/z: 281.2 [M-H]
-; HRMS-EI,
m/z: 282.1461 (theoretical values 282.1467); IR (KBr) n
max: 3443,1758,1684,1622 cm
-1; In conjunction with
1h and
13c NMR spectrum data (table 2) determine that molecular formula is C
15h
22o
5.Analyze
1h and
13c NMR and DEPT spectrum, show compound
2contain 3 methyl, 3 methylene radical (one of them is the methylene radical on end alkene), 4 methynes (wherein 2 oxygen even, 1 be alkene methyne), 5 quaternary carbons (wherein 2 company's oxygen, 2 is olefinic carbon, 1 is carbonyl).By the comparison of NMR data, show compound
2with compound
1similar, only compound
1in C-8 position be to connect the methyne of oxygen, and compound
2in C-8 position be dioxygen replace quaternary carbon.Compound
2the hydrocarbon distant relation (H that observes in also being tested by HMBC of structure
3-12 and H
3-13 with C-11 and C-10 and each other, H-10 and C-12, C-13 and C-9, H-1 and C-2, C-7 and C-8, H-4 and C-5, C-14, C-6, C-3 and C-2, H-5 and C-4, C-6, C-3 and C-7, H
3-14 with C-2, C-3 and C-4, H
2-15 with C-6, C-7 and C-8), and
1h-
1the stronger hydrogen hydrogen relevant (H-1 and H-6 and H-2, H-5 and H-4 and H-6) existing in H COSY spectrum adds their confirmation.H-1 and H-6 in NOESY spectrum, H-6 and H-5a, it is obvious relevant that H-5a and H-6 have, show H-1, H-6, H-5a same towards, meanwhile, H-2 and H
3it is relevant that-14, H-2 and H-4b have obvious NOESY, shows H-2, H
3-14, H-4b is towards the opposite, accordingly compound
2relative configuration also set up.Compound
2also be bisabolane type sesquiterpene, called after pleuroton B.
Table 2 compound
2nMR data (MeOD, 500M)
Embodiment 2
Inhibition with mtt assay mensuration compound to prostate cancer cell DU-145, C42B and LNCaP.Cultured prostate cancer cell DU-145, C42B and LNCaP are made to single cell suspension, and counting and be diluted to cell concn with cell plate is 6 × 10
4individual/mL.Inoculating cell in 96 orifice plates, every hole 80 μ L.Separately establish 2 holes acellular, only have 80 μ L nutrient solutions [Dulbecco ' s modified Eagle ' s media(DMEM, Gibco, USA)+10% calf serum] the blank hole for instrument zeroing.Put 37 DEG C, 5%CO
2incubator in cultivate 24 h, the sample that then adds 20 μ L to dilute with nutrient solution.Meanwhile, add 20 μ L cis-platinums toward positive control hole, respectively add 20 μ L nutrient solutions toward negative control hole and blank hole.Continue to cultivate 72h, every hole adds 10 μ L 5 mg/mL MTT.37 DEG C of reaction 3 h, every hole adds 100 μ L 10%SDS-0.01mol/L HCl dissolvings and spends the night.Microplate reader colorimetric estimation (measuring wavelength 570 nm, reference wavelength 655 nm).Inhibiting rate method of calculation to tumour cell are (negative control group OD value-experimental group OD value)/(the blank group of negative control group OD Zhi – OD value) × 100%.Adopt SPSS computed in software IC
50value.Experiment shows, compound
1to the IC of prostate cancer cell DU-145, C42B and LNCaP
50value is respectively 0.174,0.104 and 0.091 mM, compound
2to the IC of prostate cancer cell DU-145, C42B and LNCaP
50value is respectively 0.028,0.052 and 0.051 mM, and compound 1-2 has shown the activity of stronger inhibition prostate cancer cell.Visible, sesquiterpenoid of the present invention can be used as antitumor drug or the active primer of other biological.
Claims (5)
1. a sesquiterpenoids, has as shown in the formula a kind of structural formula in 1-2:
。
2. a preparation method for sesquiterpenoids as claimed in claim 1, is characterized in that: by the wild Pleurotus abalonus of fermentation culture (
pleurotus cystidiosus) ZYB2013, obtain fermented product, then from fermented product, separation and purification goes out this compound, described wild Pleurotus abalonus (
pleurotus cystidiosus) ZYB2013, being preserved in Chinese Typical Representative culture collection center on June 15th, 2014, deposit number is CCTCC M 2014256.
3. sesquiterpenoids claimed in claim 1 is in the purposes of preparing in Cytostatic to tumor cell medicine.
4. sesquiterpenoids claimed in claim 1 is in the purposes of preparing in antitumor drug.
5. the application of sesquiterpenoids according to claim 3, is characterized in that: described tumour cell is prostate cancer cell DU-145, C42B and LNCaP.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130932A (en) * | 2015-07-14 | 2015-12-09 | 中国科学院微生物研究所 | Compounds and uses of compounds in preparation of PTP1B inhibitors and drugs for treatment and/or prevention of diabetes type II |
| CN105801445A (en) * | 2016-04-13 | 2016-07-27 | 福建师范大学 | Nonprotein amino acid with antibacterial activity and preparation method of nonprotein amino acid |
| CN105949154A (en) * | 2016-05-16 | 2016-09-21 | 苏州毕诺佳医药技术有限公司 | Benzofuran type sesquiterpenoid compound as well as preparation method and medical application thereof |
| CN115850049A (en) * | 2022-12-26 | 2023-03-28 | 中国海洋大学 | Separation method and application of terpenoid with anti-tumor activity |
-
2014
- 2014-07-08 CN CN201410320456.6A patent/CN104059040B/en not_active Expired - Fee Related
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130932A (en) * | 2015-07-14 | 2015-12-09 | 中国科学院微生物研究所 | Compounds and uses of compounds in preparation of PTP1B inhibitors and drugs for treatment and/or prevention of diabetes type II |
| CN105130932B (en) * | 2015-07-14 | 2017-06-16 | 中国科学院微生物研究所 | Compound and its purposes in the medicine for preparing PTP1B inhibitor and treatment and/or prevention type II diabetes |
| CN105801445A (en) * | 2016-04-13 | 2016-07-27 | 福建师范大学 | Nonprotein amino acid with antibacterial activity and preparation method of nonprotein amino acid |
| CN105949154A (en) * | 2016-05-16 | 2016-09-21 | 苏州毕诺佳医药技术有限公司 | Benzofuran type sesquiterpenoid compound as well as preparation method and medical application thereof |
| CN105949154B (en) * | 2016-05-16 | 2018-07-06 | 苏州毕诺佳医药技术有限公司 | A kind of benzofuran type sesquiterpenoids and preparation method thereof and medical usage |
| CN115850049A (en) * | 2022-12-26 | 2023-03-28 | 中国海洋大学 | Separation method and application of terpenoid with anti-tumor activity |
| CN115850049B (en) * | 2022-12-26 | 2024-02-13 | 中国海洋大学 | Separation method of terpenoid with anti-tumor activity and application thereof |
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