CN104341376A - New sesquiterpene quinone compound from abelmoschus sagittifolius, as well as preparation method and applications thereof - Google Patents

New sesquiterpene quinone compound from abelmoschus sagittifolius, as well as preparation method and applications thereof Download PDF

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Publication number
CN104341376A
CN104341376A CN201410444309.XA CN201410444309A CN104341376A CN 104341376 A CN104341376 A CN 104341376A CN 201410444309 A CN201410444309 A CN 201410444309A CN 104341376 A CN104341376 A CN 104341376A
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new
compound
preparation
quinone compound
new compound
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CN104341376B (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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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention discloses a sesquiterpene quinone compound separated and purified from abelmoschus sagittifolius, as well as a preparation method and applications thereof, relating to the technical field of medicines. The new sesquiterpene quinone compound with antitumor activity is named as Acylhisbiscone B, with the molecular formula of C17H22O4 and the structural formula shown in the specification. According to the preparation method, the detection on the antitumor activity of the new compound is carried out by adopting an MTT method through combination of column chromatography and preparative liquid chromatography purification methods. In vitro experiment results show that the new sesquiterpene quinone compound has activity on significantly inhibiting the growth of Hela (human cervical carcinoma cells) and HepG-2 (human hepatoma carcinoma cells). The new sesquiterpene quinone compound can provide new chemical entity or lead compound for research of antitumor medicaments, and can also be used as food raw materials for preparation of health food.

Description

A kind of new sesquiterpene quinones and its preparation method and application in arrowleaf abelmoschus root
Technical field
The present invention relates to field of natural medicinal chemistry, be specifically related to be separated from arrowleaf abelmoschus root obtain new sesquiterpene quinones and its production and use, particularly in preparation treatment and prophylaxis of tumours disease medicament or field of health care products.
Background technology
Arrowleaf abelmoschus root ( abelmoschus Sagittifolius(Kurz) Merr.) rather call safflower horse, also known as arrowleaf abelmoschus, Angiospermae (Angiospermae), Dicotyledoneae (Dioctyledoneae), Malvales (Malvales), Malvaceae (Malvaceae), Abelmoschus ( abelmoschus) annual or perennial suffruticose herbaceous plant, be mainly distributed in the ground such as Hainan, Guizhou, Guangxi, Guangdong of Vietnam, Burma, Thailand, Laos and China.Yin Qigen is similar to ginseng, therefore claims arrowleaf abelmoschus root, and can be used as medicine, its slightly warm in nature slightly sweet flavor, long-term taking has no side effect, and can produce refreshing effect to the mind, nourishing is kept fit, and also can treat neurasthenia, dizziness, stomachache, pain in the waist and lower extremities, diarrhoea etc.Outer as removing blood stasis to reduce swelling, osteopatia sprain and osteosynthesis medicine, North Vietnam makes only dysentery and tonic with root.
At present, have no the correlative study report of chemical composition and pharmacologically active thereof in arrowleaf abelmoschus root both at home and abroad, the present invention is by the chemical composition of research arrowleaf abelmoschus root, and anti-tumor activity detection is carried out to the new sesquiterpene quinones of wherein obtained one, be intended to obtain effective new compound or guide's material, and lay the foundation for the chemical composition of arrowleaf abelmoschus root and bioactivity research, provide scientific basis for better studying, developing, utilize arrowleaf abelmoschus root plant resources.
Summary of the invention
The present invention utilizes modern separation technology and Modern spectroscopy to learn a skill to carry out chemical constitution study to arrowleaf abelmoschus root, therefrom obtain 1 new sesquiterpene quinones, identify structure, rough determination anti-tumor activity, extends the medicinal of arrowleaf abelmoschus root and edibleness.
The object of this invention is to provide a kind of sesquiterpene quinones new compound with anti-tumor activity, its structural formula is as follows.
This new compound called after: Acyl hisbiscone B.
Two of object of the present invention is to provide the preparation method of described compound, and the method adopts following steps:
(1) arrowleaf abelmoschus root dry root powder is raw material, and acetone cold soaking extracts, and recycling design, obtains medicinal extract;
(2) get gained medicinal extract in (1), adopt silica gel (300-400 order) column chromatography, with sherwood oil: methylene dichloride, the gradient elution from 100:0 to 0:100, each Fraction collection 50ml, binding silica gel thin-layer chromatography and vitriol oil development process, merge and obtain A-H totally 8 positions;
(3) from B position, preparative liquid chromatography is adopted, in conjunction with SB-phenyl post, with 72% methanol solution isocratic elution, flow velocity 2ml/min, ultraviolet detection 210nm, retention time 22min place obtains this new compound;
(4) the present invention adopts MTT to send out sesquiterpene quinones new compound anti-tumor activity test, proves that this compound has good anti-tumor activity.This compound is to the IC of human cervical carcinoma cell (Hela) and human liver cancer cell (HepG-2) 50be respectively 52.6 μm, 20.4 μm.
The present invention also aims to be provided in prepare purposes in antitumor drug and be used as food raw material and preparing the purposes in protective foods.
Accompanying drawing explanation
Fig. 1 new compound 1h-NMR spectrogram
Fig. 2 new compound 13c-NMR spectrogram
Fig. 3 new compound 1h- 1h COSY spectrogram
The hsqc spectrum figure of Fig. 4 new compound
The HMBC spectrogram of Fig. 5 new compound
The NOESY spectrogram of Fig. 6 new compound
The structure iron of Fig. 7 new compound
specific implementation method
Listed embodiment contributes to those skilled in the art and understands the present invention better below, but does not limit the present invention in any way.
the preparation of embodiment 1 compound
Adopt arrowleaf abelmoschus root from Hainan Mt. Wu-zhi Shan, dry in the shade, section is pulverized, and amounts to 190g, uses acetone extraction 2h, leaves standstill, and gets acetone soln and concentrates, obtain medicinal extract 9g.Get 20g silica gel (100-200 order) dry method and mix sample, 40g silica gel (300-400 order) dry column-packing, with sherwood oil-acetone system elutions (1:0,9:1,4:1,2:1,0:1), every 250ml is a cut, concentrates in ampulla, obtains 26 cuts altogether.Merge acquisition 7 positions through thin-layer chromatography, be 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 position, carries out half preparative separation with liquid phase, and methanol-water (72:28) is moving phase, chromatographic column SB-Phenyl(5 μm, 9.4 × 250mm), flow velocity 2ml/min, UV-detector arranges 4 determined wavelength simultaneously, 210,230,254,270nm.Preparing CDL-4-5-1 is this new compound.
the qualification of embodiment 2 compound
New compound is clear crystal, m.p. 125 oc, [ α] 23.5 D+3 o( c1.15, CHCl 3), high resolution HR-ESI-MS provides m/zbe 290.1582 [M] +(calculated value 290.1579), determines that its molecular formula is C 17h 22o 4.Infrared spectra illustrates, containing carbonyl (1640 cm in molecule -1) and furan nucleus (1530,870 cm -1).According to 1h-NMR spectrogram can judge, 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 methynes at place.Meanwhile, exist δ h5.80 (1H, d, j=3.0 Hz, H-8), 7.89 (1H, s, H-11) have 2 Sauerstoffatom signals.According to 13c-NMR spectrogram can judge, containing 17 carbon signals in molecule, comprise 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) and 5 quaternary carbon signals ( δ c142.9,187.8,121.8,143.2,170.2).Comprehensive two-dimentional spectrogram ( 1h- 1h COSY, HSQC, HMBC, NOESY) data, show that molecular structure is sesquiterpene skeleton.In HMBC spectrogram, C-1 ' ( δ c170.2) with H-8 ( δ h5.80) and H-2 ' ( δ h1.98) relevant, illustrate that carbonyl is connected with C-8.In NOESY spectrogram, H-8 ( δ h5.80) and H-2 ' ( δ h1.98) and H-11 ( δ h7.89) relevant, illustrate that H-2 ' and H-8 is αposition.These compound data are close with known compound Hisbiscone B data, and unique difference is that the hydroxyl in Hisbiscone B on C-8 is acetylation, and becomes new compound, therefore called after Acyl hisbiscone B.
Table 1 Acyl hisbiscone B 1h-NMR and 13c-NMR (600,150MHz) (DMSO- d 6 )
the test of embodiment 3 anti-tumor activity
Choose Hela(human cervical carcinoma cell lines) and HepG-2(human hepatoma cell strain), select the DMEM nutrient solution containing 10% calf serum to cultivate, in 37 DEG C, the CO of 5% 2growth of Cells is cultured to certain density (1 × 10 in incubator 6).With the trysinization of 0.25%, blow and beat into single cell suspension, by cell suspension inoculation in 96 orifice plates (0.8 × 10 4/ hole), cultivate 24 h.Compound DMSO dissolves, and adds in 96 orifice plates, after cultivating 48 h, adds 100 μ l MTT/ holes (concentration is 5 mg/ml), cultivates 4 h for 37 DEG C.Removing supernatant, every hole adds 200 μ l DMSO and vibrates gently, and first a ceremonial jade-ladle, used in libation is dissolved completely, measures absorbancy (OD) value, calculate its cell mortality, with IC by microplate reader at 490nm wavelength place 50value represents the cytotoxic activity of compound.
Result shows the IC of this new compound to human cervical carcinoma cell (Hela) and human liver cancer cell (HepG-2) 50be respectively 52.6 μm, 20.4 μm.This sesquiterpene quinones new compound is described, there is good anti-tumor activity, therefore may be used for preparing antitumor drug.The present invention is that development antitumor drug provides new chemical entities or lead compound.

Claims (5)

1. have a new sesquiterpene quinones for anti-tumor activity, chemistry Acyl hisbiscone B by name, molecular formula is C 17h 22o 4, it is characterized in that from arrowleaf abelmoschus root separation and purification obtains, structural formula is as follows.
2. an extraction preparation method for compound according to claim 1, is characterized in that the step of the method is as follows:
(1) prepare total medicinal extract: with arrowleaf abelmoschus root dry root for raw material, after raw material pulverizing, volume ratio adds the acetone soln of 15 times of volumes by weight, lixiviate 3 times, and extracting solution is evaporated to not containing acetone, dry, obtains total medicinal extract;
(2) separation and purification: get gained medicinal extract in (1), adopts silica gel (300-400 order) column chromatography, with sherwood oil: methylene dichloride, the gradient elution from 100:0 to 0:100, each Fraction collection 50ml, binding silica gel thin-layer chromatography and vitriol oil development process, merge and obtain A-H totally 8 positions; (2) from B position, adopt preparative liquid chromatography, in conjunction with SB-phenyl post, with 72% methanol solution isocratic elution, flow velocity 2ml/min, ultraviolet detection 210nm, retention time 22min place obtains this new compound.
3. sesquiterpene quinones new compound according to claim 1 proves to have good anti-tumor activity through antitumor pharmacodynamics test, and this compound is to the IC of human cervical carcinoma cell (Hela) and human liver cancer cell (HepG-2) 50be respectively 52.6 μm, 20.4 μm.
4. sesquiterpene quinones new compound according to claim 1 is preparing the purposes in antitumor drug.
5. sesquiterpene quinones new compound according to claim 1 is preparing the purposes in protective foods as food raw material.
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Publication number Priority date Publication date Assignee Title
CN105541562A (en) * 2016-02-05 2016-05-04 林厚文 Sesquiterpene quinone compound Dysiherbols A, and preparation method and application thereof
CN107496475A (en) * 2017-09-06 2017-12-22 中国医学科学院药用植物研究所海南分所 A kind of preparation method and application of arrowleaf abelmoschus root extract
CN108164484A (en) * 2017-12-22 2018-06-15 中国医学科学院药用植物研究所云南分所 A kind of 4 inhibitor of non-phagocytic cell oxidizing ferment and its application
CN110522776A (en) * 2019-09-26 2019-12-03 中国医学科学院药用植物研究所 It is a kind of Huang the rose of Sharon in anti-tumor effective component preparation method and application

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105541562A (en) * 2016-02-05 2016-05-04 林厚文 Sesquiterpene quinone compound Dysiherbols A, and preparation method and application thereof
CN105541562B (en) * 2016-02-05 2021-10-29 林厚文 Sesquiterpene quinone compound Dysiherbols A and preparation method and application thereof
CN107496475A (en) * 2017-09-06 2017-12-22 中国医学科学院药用植物研究所海南分所 A kind of preparation method and application of arrowleaf abelmoschus root extract
CN108164484A (en) * 2017-12-22 2018-06-15 中国医学科学院药用植物研究所云南分所 A kind of 4 inhibitor of non-phagocytic cell oxidizing ferment and its application
CN108164484B (en) * 2017-12-22 2021-08-06 中国医学科学院药用植物研究所云南分所 Non-phagocyte oxidase 4 inhibitor and application thereof
CN110522776A (en) * 2019-09-26 2019-12-03 中国医学科学院药用植物研究所 It is a kind of Huang the rose of Sharon in anti-tumor effective component preparation method and application
CN110522776B (en) * 2019-09-26 2022-06-07 中国医学科学院药用植物研究所海南分所 Preparation method and application of anti-tumor effective part in hibiscus syriacus

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