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Novel labdane-type diterpenoid compound, preparation method and application thereof, pharmaceutical composition and application of pharmaceutical composition

A kind of compound, the technology of haloane, which is applied in the field of helianthane type diterpenoids and its preparation

Inactive Publication Date: 2017-02-15
CHINA ACAD OF SCI NORTHWEST HIGHLAND BIOLOGY INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, there have been few domestic and foreign research reports on the chemical constituents of Auranthus nudica, and the main constituents isolated from it are flavonoids, terpenes, volatile oils and phenols, etc.

Method used

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  • Novel labdane-type diterpenoid compound, preparation method and application thereof, pharmaceutical composition and application of pharmaceutical composition
  • Novel labdane-type diterpenoid compound, preparation method and application thereof, pharmaceutical composition and application of pharmaceutical composition
  • Novel labdane-type diterpenoid compound, preparation method and application thereof, pharmaceutical composition and application of pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Isolation, Preparation and Structure Confirmation of a New Helicanoid Diterpene Compound

[0023] Sources of reagents: ethanol, petroleum ether, ethyl acetate, n-butanol, and dichloromethane were of analytical grade, purchased from Shanghai Lingfeng Chemical Reagent Co., Ltd. Methanol, of analytical grade, were purchased from Jiangsu Hanbang Chemical Reagent Co., Ltd.

[0024] Preparation method: (a) Grind the dry aerial part (10kg) of Aurora nudiflora, extract with 75% ethanol under hot reflux (25L×3 times), combine the extracts, concentrate until no alcohol smell (3L), and successively use petroleum Ether (3L×3 times), ethyl acetate (3L×3 times) and water-saturated n-butanol (3L×3 times) were extracted to obtain petroleum ether extract, ethyl acetate extract (431g) and n-butanol Extract; (b) in step (a), the ethyl acetate extract is removed with D101 macroporous resin, first eluted with 10% ethanol for 8 column volumes, then with 80% ethanol for 10 column v...

Embodiment 2

[0026] Embodiment 2: A kind of pharmacological effect test of new helianthene type diterpene compound

[0027] 1. Materials and Instruments

[0028] Human pancreatic cancer MiaPaCa-2 cells were kindly donated by the Cancer Research Institute of the Cancer Hospital Affiliated to Tianjin Medical University. The compound is self-made, and the HPLC normalized purity is greater than 98%. FBS and trypsin-EDTA digestion solution were purchased from Hyclone Company in the United States. PBS powder was purchased from Tianjin Runtai Technology Development Co., Ltd. DMEM low-sugar medium was purchased from Gibco, USA. MTT was purchased from Sigam, USA. DMSO was purchased from Beijing Chemical Plant. Penicillin Sodium for Injection was purchased from Harbin Pharmaceutical Group General Pharmaceutical Factory. Streptomycin sulfate for injection was purchased from Dalian Merro Pharmaceutical Factory.

[0029] Ultra-clean bench, cell incubator (Thermo Company, USA), 4°C refrigerator, ...

Embodiment 3

[0053] Preparation of tablets: firstly prepare the compound according to the method in Example 1, and utilize organic acids such as tartaric acid, or citric acid or formic acid or oxalic acid, etc., inorganic acids such as hydrochloric acid or sulfuric acid or phosphoric acid to make salts; Add excipients at a weight ratio of 1:7, granulate and compress into tablets.

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PUM

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Abstract

The invention discloses a novel labdane-type diterpenoid compound. The compound is reported for the first time and is a labdane-type diterpenoid compound with a novel structure. The compound can be prepared from the dry above-ground part of callicarpa nudiflora through extraction, separation and purification. In vitro tests show that the compound has a remarkable proliferation inhibition effect on human pancreatic carcinoma MiaPaCa-2 cells under an anaerobic culture condition, the inhibition effect is more remarkable with increase of the concentration of the compound and the prolonging of acting time, that is, time-dosage dependency exists within a certain concentration range, and the compound can be further developed into a drug for treating pancreatic carcinoma.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a new helianthene-type diterpenoid compound isolated from the dried aerial parts of Auranthus nudica and its preparation method and medical application. Background technique [0002] Callicarpa nudiflora Hook.et Arn. is a plant of the genus Verbenaceae. It grows in hillsides, roadsides, valleys, streams or shrubs from plains to 1200m above sea level. The annual average temperature is 15-25℃, It grows well in an environment with high humidity. It is mainly distributed in Guangdong, Guangxi, Hainan and other places in China. In Hainan, it is produced in Ding'an, Danzhou, Chengmai, Baisha, Changjiang, Dongfang, Sanya, Lingshui, Baoting, Qiongzhong and other places. Among them, Wuzhishan in Hainan is the top grade; abroad, it is mainly distributed in India, Indochina Peninsula, Malay Peninsula and Singapore. [0003] The medicinal part of naked flower purple pearl is t...

Claims

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Application Information

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IPC IPC(8): C07D303/16C07D301/32A61K31/336A61P35/00
CPCC07D301/32C07D303/16
Inventor 陈涛李玉林
Owner CHINA ACAD OF SCI NORTHWEST HIGHLAND BIOLOGY INST
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