CN109761948A - Miscellaneous terpenoid Dysiarenone in sponge source and the preparation method and application thereof - Google Patents
Miscellaneous terpenoid Dysiarenone in sponge source and the preparation method and application thereof Download PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The present invention relates to pharmaceutical technology fields, disclose a kind of miscellaneous terpenoid dysiarenone in sponge source, and chemical structural formula is as follows:The invention also discloses the methods for preparing dysiarenone.Expression and inflammatory mediator PGE of the compounds of this invention dysiarenone to COX-2 enzyme2Release show very strong inhibitory activity, can be used for preparing anti-inflammatory and anti-tumor drug.
Description
Technical field
The present invention relates to pharmaceutical technology fields, and in particular to the miscellaneous terpenoid dysiarenone in sponge source and its system
Preparation Method and application.
Background technique
Sponge is a kind of low multicellular animals, has more than 500,000,000 years Evolutionary Histories, the shape in the harsh competitive environment in ocean
At unique chemical defense mechanisms, active material can be efficiently produced, finds the activity of structure novel from sponge every year
Substance accounts for about the one third of marine natural products or more, in 7 marine drugs of the listing of U.S. FDA approval at present, there is 3 sources
From sponge, therefore, sponge has become the important sources of marine drug, is always the research hotspot of marine nature products chemistry man.
Stubborn sponge (Dysidea arenaria) is the ordinary guiding principle of Sponge (Demospongiae) net angle sponge
(Dictyoceratida) Spongiidae (Dysideidae) sponge is dug.Domestic and foreign scholars carried out the category sponge
The chemical component and bioactivity research of system.Miscellaneous terpene with 21 carbon is that the most important a kind of metabolism of stubborn Sponge sponge produces
Object, the type compound connects the 1,4-benzoquinone of 6 carbon by the sequiterpene of 15 carbon or quinhydrones is constituted, representativeization
Closing object has avarone and avarol.Its biosynthetic pathway mixed and changeable structure cause the extensive of domestic and foreign scholars
Concern, the miscellaneous terpene compound of many type are found from sponge.The variation of structure occurs mainly in sequiterpene, quinone/quinhydrones
And their connection type, such as boliaquinone[1]、avinosol[2]、adociaquinol[3]、frondosins[4]
And dysidavarones[5].The miscellaneous terpenoid of the type has extensive bioactivity, including antibacterial[6], it is antimycotic[7], it is anti-
Tumour[8], it is anti-oxidant[9], it is anti-inflammatory[10]And antiallergic activity[11].The extensive bioactivity of the type compound and changeable knot
Structure causes giving more sustained attention for chemist and biologist[12].(document: [1] De Guzman, F.S.；Copp,B.R.；
Mayne,C.L.；Concepcion,G.P.；Mangalindan,G.C.；Barrows,L.R.；Ireland,
C.M.Bolinaquinone:A Novel Cytotoxic Sesquiterpene Hydroxyquinone from a
Philippine Dysidea Sponge.J.Org.Chem.1998,63,8042–8044.；[2]Diaz-Marrero,A.R.；
Austin,P.；Soest,R.V.；Matainaho,T.；Roskelley,C.D.；Roberge,M.；Andersen,
R.J.Avinosol,A Meroterpenoid-Nucleoside Conjugate with Antiinvasion Activity
Isolated from the Marine Sponge Dysidea sp.Org.Lett.2006,8,3749–3752.；[3]
West,L.M.；Faulkner,D.J.Hexaprenoid Hydroquinones from the Sponge Haliclona
(aka Adocia)sp.J.Nat.Prod.2006,69,1001-1004.；[4]Patil,A.D.；Freyer,A.J.；
Killmer,L.；Offen,P.；Carte,B.；Jurewicz,A.J.；Johnson,R.K.Frondosins,Five New
Sesquiterpene Hydroquinone Derivatives with Novel Skeletons from the Sponge
Dysidea frondosa:Inhibitors of Interleukin-8 Receptors.Tetrahedron 1997,53,
5047-5060.；[5]Jiao,W.H.；Huang,X.J.；Yang,J.S.；Yang,F.；Piao,S.J.；Gao,H.；Li,J.；
Ye,W.C.；Yao,X.S.；Chen,W.S.；Lin,H.W.Dysidavarones A-D,New Sesquiterpene
Quinones from the Marine Sponge Dysidea avara.Org.Lett.2012,14,202-205.；[6]
(a)Urban,S.；Capon,R.J.5-epi-Isospongiaquinone,a New Sesquiterpene/Quinone
Antibiotic from an Australian Marine Sponge,Spongia hispida.J.Nat.Prod.1992,
55,1638–1642.(b)Schmalzbauer,B.；Herrmann,J.；Müller,R.；Menche,D.Total
Synthesis and Antibacterial Activity of Dysidavarone A.Org.Lett.2013,15,964-
967.；[7]Ciavatta,M.L.；Lopez Gresa,M.P.；Gavagnin,M.；Romero,V.；Melck,D.；Manzo,
E.；Guo,Y.W.；Van Soest,R.；Cimino,G.Studies on puupehenone-metabolites of a
Dysidea sp.:structure and biological activity.Tetrahedron 2007,63,1380–1384.；
[8](a)Daletos,G.；de Voogd,N.J.；Müller,W.E.G.；Wray,V.；Lin,W.；Feger,D.；
Kubbutat,M.；Aly,A.H.；Proksch,P.Cytotoxic and Protein Kinase Inhibiting
Nakijiquinones and Nakijiquinols from the Sponge Dactylospongia
metachromia.J.Nat.Prod.2014,77,218-226.(b)Hwang,I.H.；Oh,J.；Zhou,W.；Park,S.；
Kim,J.H.；Chittiboyina,A.G.；Ferreira,D.；Song,G.Y.；Oh,S.；Na,M.；Hamann,
M.T.Cytotoxic Activity of Rearranged Drimane Meroterpenoids against Colon
Cancer Cells via Down-Regulation ofβCatenin Expression.J.Nat.Prod.2015,78,
453-461.；[9]Utkina,N.K.；Denisenko,V.A.；Krasokhin,V.B.Sesquiterpenoid
Aminoquinones from the Marine Sponge Dysidea sp.J.Nat.Prod.2010,73,788–791.；
[10]McNamara,C.E.；Larsen,L.；Perry,N.B.；Harper,J.L.；Berridge,M.V.；Chia,E.W.；
Kelly,M.；Webb,V.L.Anti-inflammatory Sesquiterpene-quinones from the New
Zealand Sponge Dysidea cf.cristagalli.J.Nat.Prod.2005,68,1431–1433.；[11]Jiao,
W.H.；Cheng,B.H.；Shi,G.H.；Chen,G.D.；Gu,B.B.；Zhou,Y.J.；Hong,L.L.；Yang,F.；Liu,
Z.Q.；Qiu,S.Q.；Liu,Z.G.；Yang,P.C.；Lin,H.W.Dysivillosins A–D,Unusual
Antiallergic Meroterpenoids from the Marine Sponge Dysidea
villosa.Sci.Rep.2017,7,8947.；[12](a)Fukui,Y.；Narita,K.；Katoh,
T.Enantioselective Total Synthesis of Dysidavarone A,a Novel Sesquiterpenoid
Quinone from the Marine Sponge Dysidea avara.Chem.-Eur.J.2014,20,2436–2439.
(b)Moosmann,P.；Ueoka,R.；Grauso,L.；Mangoni,A.；Morinaka,B.I.；Gugger,M.；Piel,
J.Cyanobacterial ent-Sterol-Like Natural Products from a Deviated Ubiquinone
Pathway.Angew.Chem.Int.Ed.2017,56,4987–4990.)
But so far there are no has the expression inhibiting PEG for inhibiting COX-2 enzyme2The report of the miscellaneous terpene compound generated.
Summary of the invention
The first object of the present invention is to disclose a kind of miscellaneous terpenoid dysiarenone in sponge source, chemistry knot
Structure formula is as follows:
The second object of the present invention is to disclose the preparation side of the miscellaneous terpenoid dysiarenone in the sponge source
Method comprising step:
(a) stubborn sponge is extracted with 75-95% (preferably 95%) ethyl alcohol cold soaking, then extracting solution is concentrated to get medicinal extract；
(b) medicinal extract is suspended with water, is then extracted with organic solvent, extract liquor successively passes through after being concentrated under reduced pressure:
Silica gel column chromatography separation is depressurized, using petroleum ether-ethyl acetate gradient elution, merges and contains sequiterpene quinones chemical combination
The fraction of object；
Sephadex LH-20 gel post separation is further enriched with using petroleum ether-methylene chloride-methanol system elutions
Sequiterpene quinones；
ODS pillar layer separation is pressed in reverse phase, using methanol-water system gradient elution, acquisition contains sesquiterpenoids
Fine fraction；
High performance liquid chromatography separation, using 95% acetonitrile water elution, obtains compound dysiarenone.
Preferably, stubborn sponge extraction is preceding first chilled and shreds in step (a).
Preferably, in step (b), the organic solvent of extraction be selected from methylene chloride, chloroform, dichloroethanes and
One of ethyl acetate is a variety of；It is preferred that methylene chloride.
Preferably, in step (b), petroleum ether-methylene chloride-methanol volume ratio of Sephadex LH-20 gel column use
For 4:1:5.
Preferably, the methanol-water system gradient for pressing ODS column to use in reverse phase is 50:50~100:0 in step (b).
Preferably, when high performance liquid chromatography separates, flow velocity 2.0mL/min, Detection wavelength 290nm.
The third object of the present invention is to disclose the application of the miscellaneous terpenoid dysiarenone in the sponge source,
Especially preparing the application in anti-inflammatory drug or anti-tumor drug.
Activity test in vitro proves, expression and inflammatory mediator PGE of the compounds of this invention dysiarenone to COX-2 enzyme2
Release show very strong inhibitory activity, COX-2 enzyme and PGE2Generation to inflammation, the angiogenesis to tumour and apoptosis are all
With close relationship, therefore it can be used for preparing anti-inflammatory and anti-tumor drug.
The anti-inflammatory drug, which refers to, is directly used in prevention, diagnosis, detection, protection, treatment and research body inflammatory reaction
And its one of product of directly related disease or a variety of, the inflammation include related to COX-2 enzyme or may be relevant
Inflammation refers to one of alterative inflammation, exudative inflammation, proliferative inflammation, gynaecological imflammation or specific inflammatory or a variety of.
The exudative inflammation is serous inflammation, fibrinous inflammation, suppurative inflammation, hemorrhagic inflammation, gangrenous inflammation or card
One of his property inflammation is a variety of.
The specific inflammatory is one of tuberculosis, syphilis, leprosy or poradenia or a variety of.
Gynaecology's property inflammation is one of pelvic inflammatory disease, vaginitis or cervicitis or a variety of.
The anti-tumor drug, which refers to, is directly used in prevention, diagnosis, detection, protection, treatment and research tumour and its straight
One of drug of related disease or a variety of is connect, is one in anti-lung-cancer medicament, medicament for resisting cervical cancer or drugs against colon cancer
Kind is a variety of；The tumour is one of lung cancer, cervical carcinoma or colon cancer or a variety of.
The anti-lung-cancer medicament, which refers to, is directly used in prevention, diagnosis, detection, protection, treatment and research lung cancer and its straight
One of drug of related disease or a variety of is connect, the lung cancer refers to one of non-small cell lung cancer and Small Cell Lung Cancer
Or it is a variety of, the non-small cell lung cancer is one of phosphorus cancer, gland cancer or maxicell lung cancer or a variety of.
The medicament for resisting cervical cancer refer to be directly used in prevention, diagnosis, detection, protection, treatment and research cervical carcinoma and
One of drug of its directly related disease is a variety of, and the cervical carcinoma is soaked in early days under atypical hyperplasia, carcinoma in situ, mirror
Moisten one of cancer or infiltrating carcinoma or a variety of.
The drugs against colon cancer refer to be directly used in prevention, diagnosis, detection, protection, treatment and research colon cancer and
One of drug of its directly related disease is a variety of, and the colon cancer refers to proportion of cancer of left side of colon, Right-sided Colon Cancer or straight
One of intestinal cancer is a variety of.
The beneficial effects of the present invention are: preparation method of the present invention is simple, the compound being prepared by this method
Expression and inflammatory mediator PGE of the dysiarenone to COX-2 enzyme2Release inhibitory activity it is significant.The present invention is research and development
New anti-inflammatory, anti-tumor drug provides new lead compound, provides science to develop and use China's Ocean Medicinal resource
Foundation.
Detailed description of the invention
The actual measurement ECD curve and two kinds of configurations that Fig. 1 is the compounds of this invention dysiarenone calculate ECD curve；
Fig. 2 a shows the inhibitory activity that dysiarenone expresses lipopolysaccharide-induced COX-1, COX-2 and β-actin；
Fig. 2 b shows that dysiarenone discharges PGE to lipopolysaccharide-induced 264.7 mouse macrophage of RAW2Inhibition it is living
Property；
Fig. 3 shows that dysiarenone, avarol and dexamethasone are thin to lipopolysaccharide-induced 264.7 mouse macrophage of RAW
Born of the same parents discharge PGE2Inhibitory activity.
Specific embodiment
Below in conjunction with specific embodiment, the invention will be further described.It should be understood that following embodiment is merely to illustrate this
Invention is not for limiting the scope of the invention.
The preparation of 1 compound dysiarenone of embodiment
The stubborn sponge (weight in wet base 520g) that freezes and shred in advance is taken, respectively with 95% ethyl alcohol (1L) cold soaking extraction 8 times, every time
One week, total medicinal extract was concentrated under reduced pressure to obtain in combined extract, extracting solution, total medicinal extract was suspended into water, then with isometric dichloromethane
Alkane carries out extraction 5 times, and combining extraction liquid is concentrated under reduced pressure, obtains dichloromethane extract (2.7g).
Above-mentioned dichloromethane extract (2.7g) is separated with decompression silica gel column chromatography, using petroleum ether-ethyl acetate ladder
Degree elution is analyzed according to thin-layer chromatography TLC as a result, obtaining the fraction containing sequiterpene quinones, then use Sephadex
LH-20 gel column is further enriched with the fraction, using petroleum ether-methylene chloride-methanol (4:1:5) system, obtain into
One step is enriched with the fraction of sequiterpene quinones, then carries out pressing ODS pillar layer separation in reverse phase again to the fraction, using first
Alcohol-water system gradient elution (10:90,30:70,50:50,70:30,80:20,90:10 and 100:0), for containing for acquisition
The fine fraction of sesquiterpenoids, then separated with high performance liquid chromatography (95% acetonitrile water, flow velocity 2.0mL/min,
Detection wavelength 280nm), obtain compound dysiarenone (C42H56O4)。
The physicochemical property and nuclear magnetic resonance data of Dysiarenone is as follows:
Faint yellow solid；(c 0.11,MeCN)；UV(MeOH)λmax(logε)199.4(4.67)nm；IR
(KBr)νmax 3367,2957,2925,2856,1682,1665,1604,1459,1340cm-1；HRESIMS m/z
623.4105[M-H]-(calcd for C42H55O4,623.4100)。1H(600MHz,in CDCl3) and13C NMR(150MHz,
in CDCl3) it is shown in Table 1；
Nuclear magnetic resonance modal data (the CDCl of 1 compound dysiarenone of table3)
Fig. 1 shows the actual measurement ECD curve of compound dysiarenone (1) and the calculating ECD of two kinds of configurations (1a and 1b)
Curve, determine the compound (Part A:C-1-C-21) absolute configuration be 1S, 5S, 8S, 9R, 10S, 16S, 17S, 21S,
The absolute configuration of Part B (C-1 '-C-21 ') is 5 ' S, 8 ' S, 9 ' R, 10 ' S.Structural formula is as follows,
Embodiment 2 inhibits lipopolysaccharides (LPS) induction 264.7 mouse macrophage of RAW to discharge PGE in vitro2Experiment
Respectively with the compounds of this invention dysiarenone, avarol and dexamethasone (Dexamethasone, it is artificial synthesized
Anti-inflammatory agent) inhibited lipopolysaccharide-induced 264.7 mouse macrophage of RAW to discharge PGE in vitro as sample2Experiment, simultaneously
Carry out blank group (control) parallel laboratory test for being not added with sample.Sample is dissolved with DMSO, cryo-conservation, and DMSO is in final body
Concentration in system controls within the scope of not influencing to detect active.Each sample concentration is respectively provided with 3 multiple holes in testing.
Specific experiment step:
264.7 mouse macrophage of Raw purchased from Shanghai school of life and health sciences is in (including 10% (v/v) of RPMI 1640
The streptomysin of FBS, 100U/mL penicillin, 100 μ g/mL) in culture；Cultivation temperature is 37 DEG C, leads to 5% (v/v) CO2.Cell
From 25cm2Culture dish take out, by cell on 96 orifice plates bed board (5 × 105).Cell compound pair is detected with CCK-8 method first
The toxicity of macrophage.By mouse macrophage (5 × 105Cells/well, 100 μ L/well) it is layered on 96 orifice plates, add 2-32
The sample culturing of μM concentration range.After culture for 24 hours, the CCK-8 culture solution of 10 μ L is added in cell culture medium, 37 DEG C of incubations
4h.Absorbance is tested in 450nm.The cell of blank group is set as 100%, is existed by detection discovery compound dysiarenone
2-8 μM of concentration range does not show cytotoxicity.
PGE is discharged in order to evaluate compound dysiarenone to lipopolysaccharide-induced mouse macrophage RAW 264.72
Inhibitory activity go the supernatant of cell for inflammatory factor PGE using the ELISA method of standard2Discharge active detection.
PGE2Release using anti-Rat TNF- antibody test after purification.The concentration of cell measures under 450nm wavelength,
It is corrected under 540nm wavelength condition.
As a result as follows:
Fig. 2 a shows compound dysiarenone to COX-2 in lipopolysaccharide-induced 264.7 mouse macrophage of RAW
Selective inhibitory activity is expressed, and there is good dose-effect relationship, but to normal cell release COX-1 but without aobvious
Writing influences, and compound dysiarenone does not show cytotoxicity in 2-8 μM of concentration range.
Fig. 2 b shows that compound dysiarenone discharges PGE to lipopolysaccharide-induced 264.7 mouse macrophage of RAW2
With very strong inhibitory activity, there is significant difference, P < 0.01 at 4 μM, P < 0.001 at 8 μM.
Fig. 3 show dysiarenone, avarol and Dexamethasone of various concentration to PGE2Inhibiting rate and half
The effective inhibition concentration IC of number50Value.From the figure 3, it may be seen that compound dysiarenone is huge to lipopolysaccharide-induced 264.7 mouse of RAW
Phagocyte discharges inflammatory mediator PGE2With very strong inhibitory activity, IC50Value is 6.4 μM, and about the 10 of avarol times, be positive
25 times of medicine Dexamethasone, therefore can be used for preparing anti-inflammatory drug and anti-tumor drug.The present invention is to develop newly anti-inflammatory
Drug and anti-tumor drug provide new lead compound.
The preferred embodiment of the present invention has been described in detail above, but the invention be not limited to it is described
Embodiment, those skilled in the art can also make various equivalent on the premise of not violating the inventive spirit of the present invention
Variation or replacement, these equivalent variation or replacement are all included in the scope defined by the claims of the present application.
Claims (9)
1. a kind of miscellaneous terpenoid dysiarenone in sponge source, chemical structural formula are as follows:
2. the preparation method of the miscellaneous terpenoid dysiarenone in sponge source as described in claim 1, which is characterized in that
Itself comprising steps of
(a) stubborn sponge is extracted with 75~95% ethyl alcohol cold soakings, then extracting solution is concentrated to get medicinal extract；
(b) medicinal extract is suspended with water, is then extracted with organic solvent, extract liquor successively passes through after being concentrated under reduced pressure:
Silica gel column chromatography separation is depressurized, using petroleum ether-ethyl acetate gradient elution, merging contains sequiterpene quinones
Fraction；
Sephadex LH-20 gel post separation is further enriched with sesquialter using petroleum ether-methylene chloride-methanol system elutions
Terpene quinones；
ODS pillar layer separation is pressed in reverse phase, using methanol-water system gradient elution, obtains the essence containing sesquiterpenoids
Subfraction；
High performance liquid chromatography separation, using 95% acetonitrile water elution, obtains compound dysiarenone.
3. method according to claim 2, which is characterized in that in step (a), stubborn sponge extraction is preceding first chilled and shreds.
4. method according to claim 2, which is characterized in that in step (b), the organic solvent of extraction is selected from dichloro
One of methane, chloroform, dichloroethanes and ethyl acetate are a variety of.
5. method according to claim 2, which is characterized in that in step (b), the stone of Sephadex LH-20 gel column use
Oily ether-methylene chloride-methanol volume ratio is 4:1:5.
6. method according to claim 2, which is characterized in that in step (b), the methanol-water system of ODS column use is pressed in reverse phase
System gradient is 50:50~100:0.
7. method according to claim 2, which is characterized in that when high performance liquid chromatography separates, flow velocity 2.0mL/min, inspection
Survey wavelength 290nm.
8. the miscellaneous terpenoid dysiarenone in sponge source as described in claim 1 is preparing anti-inflammatory drug or antitumor
Application in drug.
9. application as claimed in claim 8, which is characterized in that its using dysiarenone inhibit COX-2 enzyme expression and/
Or inflammatory mediator PGE2Release.
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| CN112159376A (en) * | 2020-09-24 | 2021-01-01 | 中国人民解放军海军特色医学中心 | Sesterterpene compound and application thereof in preparing anti-inflammatory drugs |
| CN112521398A (en) * | 2020-07-30 | 2021-03-19 | 上海交通大学医学院附属仁济医院 | Sponge epiphyte-derived open-loop rearrangement steroid compound and preparation method and application thereof |
| CN112707805A (en) * | 2019-10-24 | 2021-04-27 | 上海交通大学医学院附属仁济医院 | Sponge source heteraianones and preparation method and application thereof |
| CN113045552A (en) * | 2019-12-26 | 2021-06-29 | 上海交通大学医学院附属仁济医院 | Photinine derived from sponge epiphytic fungi as well as preparation method and application thereof |
| CN115197188A (en) * | 2021-04-12 | 2022-10-18 | 南开大学 | Sesquiterpene hydroquinone compounds with pentacyclic skeleton and preparation method thereof |
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| CN113045552A (en) * | 2019-12-26 | 2021-06-29 | 上海交通大学医学院附属仁济医院 | Photinine derived from sponge epiphytic fungi as well as preparation method and application thereof |
| CN112521398A (en) * | 2020-07-30 | 2021-03-19 | 上海交通大学医学院附属仁济医院 | Sponge epiphyte-derived open-loop rearrangement steroid compound and preparation method and application thereof |
| CN112521398B (en) * | 2020-07-30 | 2022-03-15 | 上海交通大学医学院附属仁济医院 | Sponge epiphyte-derived open-loop rearrangement steroid compound and preparation method and application thereof |
| CN112159376A (en) * | 2020-09-24 | 2021-01-01 | 中国人民解放军海军特色医学中心 | Sesterterpene compound and application thereof in preparing anti-inflammatory drugs |
| CN112159376B (en) * | 2020-09-24 | 2022-04-05 | 中国人民解放军海军特色医学中心 | Sesterterpene compound and application thereof in preparing anti-inflammatory drugs |
| CN115197188A (en) * | 2021-04-12 | 2022-10-18 | 南开大学 | Sesquiterpene hydroquinone compounds with pentacyclic skeleton and preparation method thereof |
| CN115197188B (en) * | 2021-04-12 | 2023-12-26 | 南开大学 | Sesquiterpene hydroquinone compound with pentacyclic skeleton and preparation method thereof |
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