CN105732656B - A kind of tetraterpenes compound in meat sesame soft coral and application thereof - Google Patents
A kind of tetraterpenes compound in meat sesame soft coral and application thereof Download PDFInfo
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- CN105732656B CN105732656B CN201610195242.XA CN201610195242A CN105732656B CN 105732656 B CN105732656 B CN 105732656B CN 201610195242 A CN201610195242 A CN 201610195242A CN 105732656 B CN105732656 B CN 105732656B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
Abstract
The present invention relates to pharmaceutical technology field, the invention provides a kind of new tetraterpenes compound being isolated from meat sesame soft coral, shown in its chemical constitution such as formula (I)：
Description
Technical field
It is isolated a kind of new tetraterpene from marine animal meat sesame soft coral the present invention relates to pharmaceutical technology field
Class compound and its application in anti-tumor aspect.
Background technology
Meat sesame soft coral (Sarcophyton) belongs to Alcyonaria (Octocorallia), soft coral mesh
(Alcyonacea), Alcyoniidae (Alcyoniidae) animal.It, which is studied, can trace back to 1974, from S.glaucum
Isolated sarcophine indicate meat sesame soft coral belong to beginning that diterpene-kind compound in coral is studied (Ne ' eman I,
Fishelson L,Kashman Y.Sarcophine.New toxin from the soft coral Sarcophyton
glaucum(Alcyonaria).Toxicon,1974,12(6):593-598.〕.It is such in the time of nearly 40 years thereafter
Compound is because of its abundant Chemical Diversity and significant bioactivity progressively one of focus as Natural products research.It is related
Research has follow-up story in being summarized in Natural Product Reports marine natural products year, and India scholar is in 1997
Research overview before belonging to animal for meat sesame soft coral in year has carried out more detailed summary (Anjaneyulu A S R, Rao
G V.Chemical constituents of the soft coral species of Sarcophyton genus:a
review.Journal of Indian Chemitry Society,1997,74(4):272-278.), Lanzhou University of China is learned
Again to the Cesong alkyl type diterpine compound research in 1970 to the 1998 category corals in the monograph that person published in 2006
Give summary (Liang Xiao-tian, Fang Wei-shuo.Medical chemistry of bioactive
natural products.Hoboken:John Wiley&Sons Inc,2006:257-300.), the nearest big groups of Guo Yue are again
The chemical and biological activity of detailed overview nineteen eighty-two Cesong alkyl type diterpine dimeric compounds into meat sesame soft coral category in 2013
And nineteen ninety-five terpenoid chemical and biological activity (Li Yu-fen, Liang Lin- into meat sesame soft coral category in 2011
fu,Guo Yue-wei,et al.Progress in the study of biscembranoides from the soft
corals of the genus Sarcophyton.Chinese Journal of Organic Chemistry,2013,33:
1157-1166.；Liang Lin-Fu,Guo Yue-Wei.Terpenes from the soft corals of the
genus Sarcophyton:chemistry and biological activities.Chemistry&Biodiversity,
2013,10(12):2161-2196.), the seminar where the present inventor reviews 1988 to 2013 meat sesame soft coral category
(Yu Qing, Liu Baoshu, Zhang Wen wait diterpene-kind compound in meat sesames soft coral category to the chemical and biological activity of middle Cesong alkyl type diterpine
Chemistry and bioactivity The 2nd Army Medical Colleges journal .2014,35 (2):206-215.〕.In belonging to for meat sesame soft coral
Sarcophyton subviride kind animals, to an only document at present in 1992 to from this kind of soft coral of India
Report, and 9 steroid compounds are found that, wherein 4 are new steroidal, but activity (Raju B L, Subbaraju are not reported
G V,Reddy M C,et al.Polyhydroxysterols from the soft coral Sarcophyton
subviride of andaman and nicobar coasta[J].Journal of Natural Products,1992,
55(7):904-911.〕。
Meat sesame soft coral is as one of important member of coral family, and secondary metabolite therein mainly has terpene (outstanding
Its Cesong alkyl type diterpine), class Hu square-bottomed bamboo basket Bu Su classes, the prostanoid etc. of steroid and rareness, they the defence of coral, competition,
Important Ecological Functions may be played in terms of breeding, these compounds show in vitro in screening active ingredients it is antitumor,
The various biological activity such as anti-inflammatory, antibacterial, anti-oxidant, antiviral and protection bone, are worth with important medicinal study.
The content of the invention
It is an object of the invention to provide in a kind of subviride from meat sesame soft coral Sarcophyton isolated one
Plant new tetraterpenes compound bissubvilides A and B；The second object of the present invention is to provide with meat sesame soft coral
Sarcophyton subviride are raw material prepare compound bissubvilides A and B method；The 3rd mesh of the present invention
Be provide compound bissubvilides A and B prepare it is antitumor in application.
The present invention extracts from the meat sesame soft coral for being grown on the South China Sea Xisha Islands and is separated to a kind of tetraterpenes chemical combination
Thing, shown in its chemical constitution such as formula (I)：
Compound bissubvilide A and the bissubvilide B of present invention particular chemical such as formula (I A), formula
Shown in (I B), Chinese entitled meat sesame soft coral tetraterpene element A and B：
The preparation method and Structural Identification of the compounds of this invention are as follows：
(1) bissubvilide A (1) and bissubvilide B (2) preparation
A. extract：Meat sesame soft coral Sarcophyton subviride samples are shredded, carried through acetone and methanol ultrasound
Take, 90% methanol aqueous solution extract is concentrated into by ether-water, n-butanol-water and the extraction of the methanol aqueous solution of n-hexane -90%
It is dry, obtain total extract medicinal extract.
B. separate：Above-mentioned total extract medicinal extract is subjected to silica gel column chromatography, Sephandex LH-20 gel filtration chromatographies, C18
The flow point containing tetraterpenes compound, concentration are collected in reversed phase column chromatography and high performance liquid chromatography separation purifying, thin-layer chromatography detection
To dry, bissubvilides A (1) and bissubvilidesB (2) are obtained.
The preparation method of the compounds of this invention is specially：The meat sesame soft coral in the South China Sea Xisha Islands will be picked up from
After Sarcophytonsubviride choppings, extracted with acetone and methanol solvate, coarse extract obtained after the extract concentration of gained,
Coarse extract is dissolved in the aqueous solution, extracted after being suspended uniformly with ether, is suspended in after ether extraction liquid concentration in 90% methanol solution,
With n-hexane extraction, the methanol solution of gained 90% is concentrated to give bronzing medicinal extract；Medicinal extract dry method loading carries out silica gel column chromatography separation,
With methylene chloride/methanol mixed solution from 100:1 to 1:1 is eluent gradient elution, obtains 16 component Fr.A-P；Wherein
Fr.I carries out Sephadex LH-20 gel post separations, with methanol/chloroform 1:1 mobile phase elution, TLC point plates are merged into 7
Component Fr.I1~I7；Fr.I1 is separated with semi-preparative HPLC, obtains compound of the chemical structural formula as shown in (I).
Described medicinal extract dry method loading, reference can be made to document：Sun Wenji, Zhang Dengke, Dang Zhiwen, natural medicinal ingredients, which are extracted, to be divided
From with preparation, China Medical Science Press, 1999.
Described semi-preparative HPLC is separated, and condition is：78% methanol-water solution, flow velocity：1.5mL/min.
(2) bissubvilides A (1) and bissubvilidesB (2) Structural Identification
Parsing through a variety of advanced two dimensional NMR wave spectrums of various modern spectrum analysis, particularly integrated application, really
Bissubvilides A (1) and B (2) chemical constitution are determined.
Present invention also offers purposes of the above-claimed cpd in antineoplastic is prepared.
Described tumour, specially human osteosarcoma, lung cancer etc..
A kind of present invention new tetraterpenes compound isolated from marine animal meat sesame soft coral, is antineoplastic
Thing provides new lead compound, and the marine pharmaceutical organism resource to exploitation China is significant.
Embodiment
With reference to embodiment, the present invention is described in detail.
Meat sesame soft coral Sarcophyton subviride involved in the present invention, are gathered certainly by palace is pretty in June, 2012
Chinese Xisha Islands Yongxing Island surrounding waters, sample specimen is stored in The 2nd Army Medical College marine site drug research room (numbering GE-
15), protected through Chinese Academy of Sciences South Sea institute of oceanography assistant researcher Li Xiu and be accredited as Alcyonaria, soft coral mesh, soft coral
Section, meat sesame soft coral category, Sarcophyton subviride kinds.
Embodiment 1：It is prepared by bissubvilides A (1) and bissubvilides B (2) separation
The meat sesame soft coral Sarcophyton subviride samples (weight in wet base 4.1kg) of the Chinese Xisha Islands collection of selection,
Shredded, then crushed with machine, acetone ultrasonic extraction 7 times, again with methanol ultrasonic extraction 3 times, each 5L, 30 minutes, to carrying
Take liquid substantially colorless.Merge acetone and methanol extract liquid, be concentrated under reduced pressure to obtain coarse extract, coarse extract is mixed with 1L distilled water ultrasound
It is outstanding, 5 times (1L/ times) is extracted with ether, merges ether extraction liquid, is concentrated under reduced pressure, obtains brown ether layer medicinal extract 110g.Ether layer soaks
Cream is suspended with 0.5L 90% methanol-water solution ultrasound, with n-hexane extraction 5 times (0.5L/ times), merges n-hexane layer extraction
Liquid, be concentrated under reduced pressure to obtain brown medicinal extract 100g, and 90% methanol-water solution of concentration obtains bronzing medicinal extract 10g.
By the 10g of 90% methanol-water solution, sample is mixed in 20g silica gel (300-400 mesh), through 300g normal-phase silica gel column chromatographies
(column internal diameter about 5.8cm, pillar height about 27.5cm, 200-300 mesh silica gel), with methylene chloride/methanol gradient elution (100:1-1:
1), monitored, and developed the color by 10% sulfuric acid vanillic aldehyde according to HSGF254 lamellaes, collected, received altogether by stream part polarity size respectively
Collection merges to obtain 16 stream part Fr.A~Fr.P.By Fr.I (116.0mg) by Sephandex LH-20 gel column chromatographies chromatography
(column internal diameter about 2cm, pillar height about 143cm), mobile phase is methanol:Chloroform=1:1, collected by automatic receptor, lamellae monitoring,
It is divided into 7 flow point Fr.I1~I7, wherein Fr.I1 is isolated and purified (78% methanol-water solution, stream with semi-preparative HPLC
Speed：1.5mL/min), obtain compound 1 (3.5mg, tR=45.1min) and compound 2 (1.8mg, tR=61.2min).
Embodiment 2：Bissubvilides A (1) and bissubvilides B (2) Structural Identification
The present invention is isolated 2 from Chinese Xisha Islands of South China Sea meat sesame soft coral Sarcophyton subviride
Noval chemical compound is planted, bissubvilides A (1) and bissubvilides B (2) is named as.
Table 1 is the nuclear magnetic data of above two compound, and specific physicochemical data is as follows：
Bissubvilide A(1):White amorphous powder；Optical activityElectronic Circle
Two chromatogram ECD (MeOH, c 3.0 × 10-4)λmax(Δ ε)=202 (+10.48), 233 (- 2.91) nm；UV absorption data UV
(MeOH)λmax(logε)203(4.35),230(3.93)nm；Infrared absorption data IR (film) νmax=3417,2957,2931,
1682,1651,1621,1446,1347cm-1；1H and 13C NMR datas are shown in Table 1；High resolution mass spectrum HRESIMS [M+H]+m/z
651.4263(calcd for C40H59O7,651.4255).
Bissubvilide B(2):White amorphous powder；Optical activityElectronic Circle
Two chromatogram ECD (MeOH, c 2.0 × 10-4)λmax(Δ ε)=203 (+9.70), 240 (- 1.29) nm；UV absorption data UV
(MeOH)λmax(logε)205(4.59),238(4.35)nm；Infrared absorption data IR (film) νmax=3427,2929,2857,
1713,1674,1451,1374,1238cm-1；1H and 13C NMR datas are shown in Table 1；High resolution mass spectrum；HRESIMS[M+H]+m/
z 649.4109(calcd for C40H57O7,649.4099).
Table 1.bissubvilides A's (1) and B (2)13C NMR with1H NMR datas
aIn CDCl3,500MHz for 1H and 125MHz for 13C.
Embodiment 3：Tetraterpenes compound bissubvilides A and the bissubvilides B's of the present invention is antitumor
Experiment
First, experimental method
Cytostatic to tumor cell experiment is carried out to the compounds of this invention using conventional mtt assay.(mtt assay is referring to such as Lv
Qiu Jun is edited《Developmental pharmacology research method》, Chemical Industry Press, 2007：242-243).
1. experiment cell line：MG63 (human osteosarcoma cell) and A549 (human lung carcinoma cell).Experiment is originated with cell line
In cell institute of the Chinese Academy of Sciences.
2. experiment reagent, consumptive material and instrument：
DMEM nutrient solutions (Invitrigen)；1640 culture medium (Invitrigen)；McCoy's 5a(Invitrigen)；
Serum (Invitrigen)；Pancreatin (Invitrigen)；DMSO(sigma)；MTT(sigma)；CCK8 (Japanese colleague)；Culture
Ware (Corning)；Pipette (Corning)；96 orifice plates (Corning)；CO2Incubator (SANYO)；ELIASA
(Biotek76833)
3. experimental drug：
The compounds of this invention bissubvilides A (1) and bissubvilides B (2)
Positive control drug：Adriamycin (Adriamycin).
4. cell culture
MG63 cell culture：Human osteosarcoma cell (MG63), with the McCoy's 5a nutrient solutions containing 10% hyclone
In, 37 DEG C of 5%CO2Under the conditions of cultivate, treat that cell reaches 106During left and right, 1000rpm 5min centrifugation passages adjust cell density
To 105Individual/ml, is inoculated in 96 orifice plates with every μ l of hole 100, in being tested after 18~24h.
A549 cell culture：Human lung adenocarcinoma cell (A549) is with the DMEM nutrient solutions containing 10% hyclone, 37 DEG C
5%CO2Under the conditions of cultivate, after behind cell confluent cultures ware bottom 70%~80%, digested with 0.25% pancreatin, adjustment carefully
Born of the same parents' density is to 105Individual/ml, is inoculated in 96 orifice plates with every μ l of hole 100, in being tested after 18~24h.
5. cell viability test experience
A549 and MG63 cell viability test experiences：In 24h before experiment with 104The cell concentration in individual/hole is inoculated with 96 orifice plates.
1 μ l are administered respectively per hole, final concentration respectively reaches 30 μ g/ml, sets up three repeating groups and DMSO negative control groups and adriamycin
(30 μ g/ml) positive controls.After administration, 37 DEG C of 5%CO2Under the conditions of be incubated 24h.10 μ l 5mg/ml MTT (thiophenes are added per hole
Azoles is blue), 37 DEG C of 5%CO2Under the conditions of be incubated 4h.Suck the cell culture fluid in culture plate.150 μ l DMSO solutions are added per hole,
15min is shaken in shaking table at 37 DEG C.The OD values under 570nm are detected with ELIASA.
2nd, experimental result
Compound bissubvilides A (1) and bissubvilides B (2) cell in vitro poison is determined by mtt assay
Activity, the inhibition rate of tumor cell of each compound is shown in Table 2.
Table 2 compound bissubvilides A and B (1-2) Cytostatic to tumor cell experiment (μM)
| Compound | MG63 | A549 |
| bissubvilide A(1) | 43.9 | 33.5 |
| bissubvilide B(2) | 32.7 | 28.1 |
| Adriamycin | 2.2 | 2.9 |
From table 2, compound bissubvilides A and B (1-2) are to MG63 (human osteosarcoma cell) and A549 (people
Lung carcinoma cell) there is different degrees of inhibitory action.
Above-described embodiment is not limited for the present invention preferably embodiment, but embodiments of the present invention by above-described embodiment
System.The deformation made under other any spirit and principle for not departing from the present invention, is considered as protection scope of the present invention.
Claims (6)
1. a kind of tetraterpenes compound, shown in its chemical constitution such as formula (I)：
2. a kind of preparation method of tetraterpenes compound as claimed in claim 1, described method includes：
After meat sesame soft coral Sarcophyton subviride are shredded, extracted with acetone and methanol solvate, the extract of gained
Coarse extract is obtained after concentration, coarse extract is dissolved in the aqueous solution, is extracted after being suspended uniformly with ether, is suspended after ether extraction liquid concentration
In 90% methanol solution, with n-hexane extraction, the methanol solution of gained 90% is concentrated to give bronzing medicinal extract；
Medicinal extract dry method loading carries out silica gel column chromatography separation, with methylene chloride/methanol mixed solution from 100:1 to 1:1 is flowing
Phase gradient is eluted, and obtains 16 component Fr.A-P；Wherein Fr.I carries out Sephadex LH-20 gel post separations, with methanol/chlorine
Imitative 1:1 mobile phase elution, TLC point plates are merged into 7 component Fr.I1~I7；Fr.I1 is separated with semi-preparative HPLC, is obtained
Compound of the chemical constitution as shown in formula (I).
3. the preparation method of a kind of tetraterpenes compound according to claim 2, it is characterised in that described is semi-preparative
HPLC is separated, and condition is：78% methanol-water solution, flow velocity：1.5mL/min.
4. a kind of preparation method of tetraterpenes compound according to claim 2, it is characterised in that described preparation method
For：
After the meat sesame soft coral Sarcophyton subviride that the Chinese Xisha Islands is gathered are crushed, acetone ultrasonic extraction 2-8
Secondary, again with methanol ultrasonic extraction 2-4 times is every time substantially colorless to extract solution, merges acetone extract and methanol extract liquid, subtracts
Pressure is concentrated to give coarse extract；Coarse extract is suspended with distilled water ultrasound, extracted 2-6 times with ether, merges ether extraction liquid, is depressurized dense
Contracting, obtains brown ether layer medicinal extract；Ether layer medicinal extract is suspended with 90% methanol-water solution ultrasound, with n-hexane extraction 2-6 time, conjunction
And n-hexane layer extract, be concentrated under reduced pressure to obtain brown medicinal extract, and 90% methanol-water solution of concentration obtains bronzing medicinal extract；
By bronzing medicinal extract in silica gel mixed sample, through normal-phase silica gel column chromatography, with methylene chloride/methanol mixed solution from 100:1 arrives
1:1 is eluent gradient elution, is monitored according to HSGF254 lamellaes, and is developed the color by 10% sulfuric acid vanillic aldehyde, respectively by stream part
Polarity size is collected, and collects merge to obtain 16 stream part Fr.A~Fr.P altogether；Fr.I is passed through into Sephandex LH-20 gel column colors
Spectrum chromatography, mobile phase is methanol:Chloroform=1:1, collected by automatic receptor, lamellae monitoring, be divided into 7 flow point Fr.I1~
I7, wherein Fr.I1 are isolated and purified with semi-preparative HPLC, and condition is 78% methanol-water solution, flow velocity：1.5mL/min,
Obtain compound of the chemical constitution as shown in formula (I).
5. purposes of a kind of tetraterpenes compound in antineoplastic is prepared as claimed in claim 1.
6. a kind of purposes of the tetraterpenes compound according to claim 5 in antineoplastic is prepared, it is characterised in that
Described tumour is human osteosarcoma or lung cancer.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448128A2 (en) * | 1986-12-09 | 1991-09-25 | Mitsubishi Kasei Corporation | Cembrane-type diterpene compounds for use in the production of compositions containing histamine release inhibitors |
| CN1861605A (en) * | 2005-05-13 | 2006-11-15 | 中国科学院上海药物研究所 | Fleshy glossy ganoderma lactone A, preparation process and use thereof |
| CN101328184A (en) * | 2007-06-22 | 2008-12-24 | 中国科学院上海药物研究所 | Dimeric cembrane tetraterpene compounds ruga soft coral sarcophyton lactone deoxyschizandrin and Schisandrin B, preparing methods and uses thereof |
| CN102229588A (en) * | 2011-03-25 | 2011-11-02 | 中国人民解放军第二军医大学 | Briarane type diterpenoid compounds with anti-tumor and antibacterial activities and application thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58150596A (en) * | 1982-03-03 | 1983-09-07 | Mitsubishi Chem Ind Ltd | Deoxysarcophine |
| JPH0794388B2 (en) * | 1987-03-17 | 1995-10-11 | 三菱化学株式会社 | Remedy for psoriasis |
| JPH09175913A (en) * | 1995-12-27 | 1997-07-08 | Kaiyo Biotechnol Kenkyusho:Kk | Antifouling agent |
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2016
- 2016-03-31 CN CN201610195242.XA patent/CN105732656B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448128A2 (en) * | 1986-12-09 | 1991-09-25 | Mitsubishi Kasei Corporation | Cembrane-type diterpene compounds for use in the production of compositions containing histamine release inhibitors |
| CN1861605A (en) * | 2005-05-13 | 2006-11-15 | 中国科学院上海药物研究所 | Fleshy glossy ganoderma lactone A, preparation process and use thereof |
| CN101328184A (en) * | 2007-06-22 | 2008-12-24 | 中国科学院上海药物研究所 | Dimeric cembrane tetraterpene compounds ruga soft coral sarcophyton lactone deoxyschizandrin and Schisandrin B, preparing methods and uses thereof |
| CN102229588A (en) * | 2011-03-25 | 2011-11-02 | 中国人民解放军第二军医大学 | Briarane type diterpenoid compounds with anti-tumor and antibacterial activities and application thereof |
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