CN104341376B - A kind of new sequiterpene quinones and its preparation method and application in arrowleaf abelmoschus root - Google Patents

A kind of new sequiterpene quinones and its preparation method and application in arrowleaf abelmoschus root Download PDF

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CN104341376B
CN104341376B CN201410444309.XA CN201410444309A CN104341376B CN 104341376 B CN104341376 B CN 104341376B CN 201410444309 A CN201410444309 A CN 201410444309A CN 104341376 B CN104341376 B CN 104341376B
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sequiterpene
quinones
preparation
application
noval chemical
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CN104341376A (en
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陈德力
马国需
刘洋洋
王德立
魏建和
许旭东
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Institute of Medicinal Plant Development of CAMS and PUMC
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92Naphthofurans; Hydrogenated naphthofurans

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  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
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Abstract

A kind of sequiterpene quinones isolated and purified from arrowleaf abelmoschus root of the present invention and its preparation method and application, is related to pharmaceutical technology field.One class has the sequiterpene quinones noval chemical compound of antitumor activity, is named as Acyl hisbiscone B, and molecular formula is C17H22O4, structural formula is as follows.Its preparation method is combined by column chromatography and preparation liquid phase purification process, and has carried out antitumor activity detection using mtt assay to this noval chemical compound.Vitro Experimental Results show new sesquiterpenoids to Hela(Human cervical carcinoma cell)With HepG 2(Human liver cancer cell)There is the activity for significantly inhibiting growing multiplication, IC50Value is respectively 52.6μM、20.4μM.The present invention can provide new chemical entities or lead compound for developing antineoplastic, also can prepare health food as raw-food material.

Description

A kind of new sequiterpene quinones and its preparation method and application in arrowleaf abelmoschus root
Technical field
The present invention relates to field of natural medicinal chemistry, and in particular to isolated one new sequiterpene quinone from arrowleaf abelmoschus root Class compound and its production and use, is particularly preparing treatment and prevention tumor disease medicine or field of health care products.
Background technology
Arrowleaf abelmoschus root(Abelmoschus Sagittifolius(Kurz) Merr.)Another name safflower horse is peaceful, also known as arrow leaf Gumbo, Angiospermae(Angiospermae), Dicotyledoneae(Dioctyledoneae), Malvales(Malvales), Malvaceae(Malvaceae), Abelmoschus(Abelmoschus)Annual or perennial suffruticose herbaceous plant, main distribution In Hainan of Vietnam, Burma, Thailand, Laos and China, Guizhou, Guangxi, Guangdong and other places.Yin Qigen is similar to ginseng, therefore claims five Refer to wild ginseng, can be used as medicine, its slightly warm in nature slightly sweet flavor, long-term taking have no toxic side effect, and can refresh the mind, nourish salubrity, it is also possible to Treatment neurasthenia, dizziness, stomachache, pain in waist and lower extremities, diarrhoea etc..It is used as outward eliminating stasis to resolve swelling, osteopatia sprain and showy reiolaena root-bark, North Vietnam Make to stop dysentery and tonic with root.
At present, the correlative study report of chemical composition and its pharmacologically active in arrowleaf abelmoschus root is had no both at home and abroad, and the present invention is logical The chemical composition of research arrowleaf abelmoschus root is crossed, and antitumor activity is carried out to a kind of new sequiterpene quinones obtained in which Detection, it is intended to obtain effective noval chemical compound or guide's material, and the chemical composition and bioactivity research for arrowleaf abelmoschus root is established Fixed basis, provides scientific basis for preferably research, exploitation, using arrowleaf abelmoschus root plant resources.
Content of the invention
The present invention carries out chemical constitution study using modern separation technology and Modern spectroscopy technology to arrowleaf abelmoschus root, therefrom 1 new sequiterpene quinones is obtained, identify structure, Preliminary Determination antitumor activity extends arrowleaf abelmoschus root Medicinal and edibility.
It is an object of the invention to provide a kind of sequiterpene quinones noval chemical compound with antitumor activity, its structural formula is such as Under.
The noval chemical compound is named as:Acyl hisbiscone B.
The second object of the present invention is to provide the preparation method of the compound, and the method adopts following steps:
(1)Arrowleaf abelmoschus root dry root powder is raw material, and the extraction of acetone cold soaking, recycling design obtain medicinal extract;
(2)Take(1)Middle gained medicinal extract, using silica gel(300-400 mesh)Column chromatography, with petroleum ether:Dichloromethane, from 100:0 to 0:100 gradient elutions, each Fraction collection 50ml, binding silica gel thin-layer chromatography and concentrated sulfuric acid development process, merging are obtained Obtain A-H totally 8 positions;
(3)From B positions, using preparative liquid chromatography, in conjunction with SB- phenyl posts, with 72% methanol solution isocratic elution, flow Fast 2ml/min, ultraviolet detection 210nm obtain the noval chemical compound at retention time 22min;
(4)The present invention is sent out to sequiterpene quinones noval chemical compound anti-tumor activity test using MTT, it was demonstrated that the compound tool There is preferable antitumor activity.The compound is to human cervical carcinoma cell(Hela)And human liver cancer cell(HepG-2)IC50Point Wei 52.6μM、20.4μM.
The present invention also aims to provide the purposes in antineoplastic is prepared and be used as raw-food material preparing Purposes in health food.
Description of the drawings
Fig. 1 noval chemical compounds1H-NMR spectrum
Fig. 2 noval chemical compounds13C-NMR spectrograms
Fig. 3 noval chemical compounds1H-1H COSY spectrograms
The hsqc spectrum figure of Fig. 4 noval chemical compounds
The HMBC spectrograms of Fig. 5 noval chemical compounds
The NOESY spectrograms of Fig. 6 noval chemical compounds
The structure chart of Fig. 7 noval chemical compounds
Specific implementation method
Embodiment set forth below contributes to those skilled in the art and more fully understands the present invention, but limits never in any form The present invention.
The preparation of 1 compound of embodiment
Arrowleaf abelmoschus root is adopted from Hainan Mt. Wu-zhi Shan, is dried in the shade, section is crushed, altogether 190g, 2h is extracted with acetone, stand, take Acetone soln is concentrated, and obtains medicinal extract 9g.Take 20g silica gel(100-200 mesh)Dry method mixes sample, 40g silica gel(300-400 mesh)Dry method is filled Post, with petroleum ether-acetone system elutions(1:0,9:Isosorbide-5-Nitrae:1,2:1,0:1), it is a cut per 250ml, concentrates in ampulla, 26 cuts are obtained altogether.Merge through thin-layer chromatography and obtain 7 positions, respectively CDL-1-3, CDL-4-5, CDL-6-7, CDL- 8-10, CDL-11-17, CDL-18-20, CDL-21-26.Wherein CDL-4-5 positions, carry out half preparative separation with liquid phase, and methyl alcohol- Water(72:28)For mobile phase, chromatographic column SB-Phenyl(5 μm, 9.4 × 250mm), flow velocity 2ml/min, UV-detector is simultaneously Arrange 4 Detection wavelengths, 210,230,254,270nm.CDL-4-5-1 is prepared for the noval chemical compound.
The identification of 2 compound of embodiment
Noval chemical compound is clear crystal, m.p. 125oC, [α]23.5 D + 3o(c1.15, CHCl3), high-resolution HR- ESI-MS is givenm/zFor 290.1582 [M]+(Calculated value 290.1579), determine that its molecular formula is C17H22O4.Infrared spectrum is said Bright, contain carbonyl in molecule(1640 cm-1)And furan nucleus(1530, 870 cm-1).According to1H-NMR spectrum may determine that,δ HThere is 1 methyl at 1.98 (s, H-2 ') place,δ H1.20 (d,J=7.8 Hz, H-12), 0.96(d,J=7.2 Hz, H-14), 0.86(d,J=6.6 Hz, H-15) there are 3 methines at place.Meanwhile,δ H5.80 (1H, d,J= 3.0 Hz, H-8), 7.89 (1H, s, H-11) have 2 oxygen atom signals.According to13C-NMR spectrograms may determine that, contain in molecule 17 carbon signals, including 4 methyl signals(δ C15.7, 20.9, 15.9, 187.8), 2 methylene signals(δ C35.6, 29.2), 6 methine signals(δ C42.2, 29.9, 25.8, 63.0, 147.3, 40.4)With 5 quaternary carbon signals(δ C 142.9, 187.8, 121.8, 143.2, 170.2).Comprehensive two dimension spectrogram(1H-1H COSY, HSQC, HMBC, NOESY)Number According to, show molecular structure be sequiterpene skeleton.In HMBC spectrograms, C-1 ' (δ C170.2) with H-8 (δ HAnd H-2 ' 5.80) (δ H1.98) related, illustrate that carbonyl is connected with C-8.In NOESY spectrograms, H-8 (δ H5.80) and H-2 ' (δ H1.98) With H-11 (δ H7.89) related, illustrate that H-2 ' and H-8 areαPosition.The compound data and known compound Hisbiscone B datas are close, only difference is that the hydroxyl in Hisbiscone B on C-8 is acetylation, become new Compound, is therefore named as Acyl hisbiscone B.
1 Acyl hisbiscone B of table1H-NMR and13C-NMR (600, 150MHz) (DMSO-d 6 )
The test of 3 antitumor activity of embodiment
Choose Hela(Human cervical carcinoma cell lines)And HepG-2(Human hepatoma cell strain), select containing 10% calf serum DMEM nutrient solution cultures, in 37 DEG C, 5% CO2Cultivate in incubator to cell growth to certain density (1 × 106).With 0.25% Pancreatin digestion, blow and beat into single cell suspension, by cell suspension inoculation in 96 orifice plates(0.8×104/ hole), cultivate 24 h.Change Compound DMSO dissolves, and adds in 96 orifice plates, after 48 h of culture, adds 100 μ l MTT/ holes(Concentration is 5 mg/ml), 37 DEG C Cultivate 4 h.Supernatant is removed, is added per hole 200 μ l DMSO gently to vibrate, is completely dissolved first a ceremonial jade-ladle, used in libation, with ELIASA in 490nm ripples Strong point mensuration absorbance(OD)Value, calculates its cell mortality, with IC50Value represents the cytotoxic activity of compound.
As a result show the noval chemical compound to human cervical carcinoma cell(Hela)And human liver cancer cell(HepG-2)IC50Respectively For 52.6μM、20.4μM.The sequiterpene quinones noval chemical compound is described, with preferable antitumor activity, therefore be can be used for Prepare antineoplastic.The present invention provides new chemical entities or lead compound for developing antineoplastic.

Claims (5)

1. a kind of sequiterpene quinones, it is characterised in that structural formula is as follows:
2. a kind of extraction preparation method of sequiterpene quinones as claimed in claim 1, it is characterised in that the method Step is as follows:
(1) total medicinal extract is prepared:With arrowleaf abelmoschus root dry root as raw material, after raw material is crushed, volume ratio by weight adds 15 times of volumes Acetone soln, extracts 3 times, and extract is evaporated to without acetone, is dried, is obtained total medicinal extract;
(2) isolate and purify:Gained medicinal extract in (1) is taken, using silica gel 300-400 mesh column chromatographies, with petroleum ether:Dichloromethane, from 100:0 to 0:100 gradient elutions, each Fraction collection 50ml, binding silica gel thin-layer chromatography and concentrated sulfuric acid development process, merge and obtain A-H totally 8 positions;(2) from B positions, using preparative liquid chromatography, in conjunction with SB- phenyl posts, wash so that 72% methanol solution is isocratic De-, flow velocity 2ml/min, ultraviolet detection 210nm obtain the noval chemical compound at retention time 22min.
3. application of a kind of sequiterpene quinones in medicament for resisting cervical cancer is prepared as claimed in claim 1.
4. application of a kind of sequiterpene quinones in medicines resistant to liver cancer is prepared as claimed in claim 1.
5. a kind of sequiterpene quinones is preparing answering in health food as raw-food material as claimed in claim 1 With.
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