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Labdane type diterpene derivatives and preparation method and application thereof

A derivative, the technology of Banhelia, is applied in the field of medicine to achieve the effect of inhibiting the activity of α-glucosidase

Active Publication Date: 2015-11-25
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the treatment of diabetes by the extract of Rhizoma Rhizoma Rhizoma and its chemical constituents

Method used

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  • Labdane type diterpene derivatives and preparation method and application thereof
  • Labdane type diterpene derivatives and preparation method and application thereof
  • Labdane type diterpene derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take 2 kg of Rhizoma Rhizoma Rhizoma, crush it and add 6L of ethanol with a volume fraction of 95% to carry out reflux extraction, reflux extraction 3 times, each time for 2 hours, filter and combine the extracts, recover the ethanol under reduced pressure and suspend the extract in In water, the suspension was extracted 5 times with ethyl acetate, the ethyl acetate layers were combined and the solvent was recovered under reduced pressure to obtain the ethyl acetate part; the obtained ethyl acetate part was subjected to silica gel column chromatography, and the volume ratio was 20: 1, 10:1, 8.5:1.5, 7:3 and 1:1 mixtures of petroleum ether and ethyl acetate were used for gradient elution, examined by thin-layer chromatography, and collected in sections to obtain 5 parts (Fr.1 ~Fr.5), wherein, Fr.2 and Fr.4 were firstly subjected to SephadexLH-20 column chromatography, eluted with a mixture of dichloromethane and methanol at a volume ratio of 1:1, and then subjected to sil...

Embodiment 2

[0029] Take 3 kg of the whole plant of Rhizoma Phragmatis, crush it, add 9 L of ethanol with a volume fraction of 95% for ultrasonic extraction, extract 3 times, each time for 30 minutes, filter and combine the extracts, recover the ethanol under reduced pressure, and suspend the extract in water; The suspension was extracted 5 times with ethyl acetate, the ethyl acetate layers were combined and the solvent was recovered under reduced pressure to obtain the ethyl acetate fraction; the obtained ethyl acetate fraction was subjected to silica gel column chromatography, and the volume ratio was 20:1, 10:1, 8:2, and 1:1 mixtures of petroleum ether and ethyl acetate were used for gradient elution and examined by thin-layer chromatography. Fractions containing diterpene were collected in sections to obtain 4 parts (Fr. 1~Fr.4); Among them, Fr.2 and Fr.3 were first subjected to SephadexLH-20 column chromatography, eluted with a mixture of dichloromethane and methanol at a volume ratio ...

Embodiment 3

[0052] Starch (polysaccharide) in food is digested by oral saliva and pancreatic amylase into oligosaccharides (or oligosaccharides) containing a few glucose molecules, and disaccharides and trisaccharides enter the small intestine and are decomposed into single glucose by α-glucosidase , Absorbed in the small intestine, resulting in elevated blood sugar. Therefore, inhibiting the activity of α-glucosidase can achieve the purpose of lowering postprandial blood sugar. The present invention reflects the hypoglycemic effect of compounds 1-6 by testing their inhibitory effect on α-glucosidase.

[0053] Prepare 0.1mol / LNa respectively 2 HPO 4 and KH 2 PO 4 , Mix the two solutions and adjust the pH value to 6.8 to obtain 0.1mol / L phosphate buffer solution. Prepare 0.26U / ml α-glucosidase with 0.1mol / L phosphate buffer solution with a pH value of 6.8. The substrate (4-nitrophenyl-α-D-glucopyranoside, PNPG) was prepared with 0.1 mol / L phosphate buffer at pH 6.8 to a concentration...

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Abstract

The invention provides a series of labdane type diterpene derivatives and a preparation method and application thereof. The derivatives are compounds containing structures as shown in general formula I, II or III or addition salts formed from compounds and pharmaceutically acceptable acids or alkalis. R1 is hydrogen, hydroxy or C1-C3 alkyloxy or acyloxy; R2 is C1-C3 saturated or unsaturated alkyl, C1-C3 oxygen-containing alkyl or C1-C3 acid and ester thereof or salt. The derivatives employ Labiatae Phlomis plant Phlomis umbrosa as a raw material, and solvent extraction, column chromatography separation and purification are carried out for preparation. According to the invention, based on separation for preparing the labdane type diterpene derivatives, the compounds have activity for inhibiting alpha-glucosidase is verified, so that lead compounds for developing oral medicaments for reducing blood glucose are provided, and the preparation method has important meanings for exploring new purposes of natural products and botanical drugs.

Description

technical field [0001] The invention relates to a heliotrope-type diterpene derivative, a preparation method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Phlomistuberose L. is a plant of the genus Phlomistuberose L. in the family Lamiaceae. Mongolian medicine name: Augulejin-Tuguriai [alias]: wild yam, Lugemuri. The traditional Chinese medicine is slightly bitter in taste and warm in nature. It is slightly poisonous. Promoting blood circulation to stimulate menstrual flow, detoxifying and treating sores. Mongolian medicine is sweet in taste, light in nature, rough and flat. Clearing away heat, stopping vomiting, eliminating "Qiha". Indications: traditional Chinese medicine for irregular menstruation, abdominal pain, carbuncle sores, syphilis. Mongolian medicine cures cold and fever, nasal itching and sneezing, phlegm and cough, hot and dry throat, chest fever, headache, arthralgia, bone "Qiha" disease, pulse "Qi...

Claims

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Application Information

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IPC IPC(8): C07D307/54C07D307/42C07D307/36C07H15/26C07H13/08C07H1/08A61P3/10
CPCC07D307/36C07D307/42C07D307/54C07H1/08C07H13/08C07H15/26
Inventor 王峥涛杨颖博祁萌杨莉陈凯先
Owner SHANGHAI UNIV OF T C M
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