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

A Wuzhishan ginseng and compound technology, applied in the field of new sesquiterpene quinone compounds and their preparation, to achieve good anti-tumor activity

Active Publication Date: 2015-02-11
INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI HAINAN BRANCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there are no relevant research reports on the chemical components and pharmacological activities of Wuzhi ginseng at home and abroad. The present invention studies the chemical components of Wuzhi ginseng and detects the anti-tumor activity of a new sesquiterpene quinone compound obtained therein. , aiming at obtaining effective new compounds or leading substances, laying the foundation for the research on the chemical composition and biological activity of Wuzhishan ginseng, and providing a scientific basis for better research, development and utilization of Wuzhishan ginseng plant resources

Method used

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of embodiment 1 compound

[0024] Collect Wuzhishan ginseng from Wuzhi Mountain in Hainan, dry it in the shade, slice and crush it, totaling 190g, extract it with acetone for 2 hours, let it stand still, take the acetone solution to concentrate, and obtain 9g extract. Take 20g of silica gel (100-200 mesh) for dry mixing, 40g of silica gel (300-400 mesh) for dry packing, and elute with petroleum ether-acetone system (1:0, 9:1, 4:1, 2: 1, 0:1), each 250ml is a fraction, concentrated in an ampoule, and a total of 26 fractions are obtained. After thin-layer chromatography, 7 parts were obtained, namely CDL-1-3, CDL-4-5, CDL-6-7, CDL-8-10, CDL-11-17, CDL-18-20, CDL -21-26. Among them, the CDL-4-5 part is semi-preparatively separated in liquid phase, methanol-water (72:28) is used as mobile phase, chromatographic column SB-Phenyl (5μm, 9.4×250mm), flow rate 2ml / min, and ultraviolet detector at the same time Set 4 detection wavelengths, 210, 230, 254, 270n...

Embodiment 2

[0025] Identification of Example 2 Compounds

[0026] The new compound is a colorless crystal, m.p. 125 o C, [ α ]23.5 D + 3 o ( c 1.15, CHCl 3 ), high-resolution HR-ESI-MS gives m / z 290.1582 [M] + (calculated value 290.1579), determine its molecular formula as C 17 h 22 o 4 . The infrared spectrum shows that the molecule contains a carbonyl group (1640 cm -1 ) and furan ring (1530, 870 cm -1 ). according to 1 The H-NMR spectrum can be judged, in δ H There is a methyl group at 1.98(s, H-2’), at δ H 1.20 (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) with 3 methine groups. At the same time, in δ H 5.80 (1H, d, J = 3.0 Hz, H-8), 7.89 (1H, s, H-11) with 2 oxygen atom signals. according to 13 It can be judged from the C-NMR spectrum that the molecule contains 17 carbon signals, including 4 methyl signals ( δ C 15.7, 20.9, 15.9, 187.8), 2 methylene signals ( δ C 35.6, 29.2), 6 methine signals ( δ C 42.2, 29...

Embodiment 3

[0030] Example 3 Test of antitumor activity

[0031] Hela (human cervical cancer cell line) and HepG-2 (human liver cancer cell line) were selected and cultured in DMEM medium containing 10% calf serum at 37°C and 5% CO 2 Cultured in an incubator until the cells grew to a certain density (1×10 6 ). Digest with 0.25% trypsin, pipette into a single cell suspension, and inoculate the cell suspension in a 96-well plate (0.8×10 4 / well), cultured for 24 h. The compound was dissolved in DMSO and added to a 96-well plate. After 48 h of incubation, 100 μl of MTT / well (concentration of 5 mg / ml) was added and incubated at 37°C for 4 h. Remove the supernatant, add 200 μl DMSO to each well and shake gently to completely dissolve the formazan, measure the absorbance (OD) value at a wavelength of 490 nm with a microplate reader, and calculate the cell death rate as IC 50 Values ​​represent the cytotoxic activity of the compounds.

[0032] The results showed that the new compound had IC...

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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

technical field [0001] The invention relates to the field of natural medicinal chemistry, in particular to a new sesquiterpene quinone compound isolated from Wuzhi ginseng and its preparation method and application, especially in the field of preparation of medicines or health products for treating and preventing tumor diseases. Background technique [0002] Five Fingers Ginseng ( Abelmoschus Sagittifolius (Kurz) Merr.) alias safflower Manin, also known as arrow leaf okra, Angiospermae, Dioctyledoneae, Malvales, Malvaceae, Okra ( Abelmoschus ) Annual or perennial subshrub herbaceous plants, mainly distributed in Vietnam, Myanmar, Thailand, Laos, and Hainan, Guizhou, Guangxi, Guangdong and other places in China. Because its root resembles ginseng, it is called Wuzhishan ginseng. It can be used as medicine. It is slightly warm in nature and sweet in taste. It has no toxic and side effects after long-term use. wait. It is used externally for dispelling blood stasis and red...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92A61P35/00A23L1/29A23L33/00
CPCC07D307/92
Inventor 陈德力马国需刘洋洋王德立魏建和许旭东
Owner INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI HAINAN BRANCH
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