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Split-ring labdane diterpenoid compound as well as separation method and application thereof

A separation method and compound technology, applied in the field of phytochemistry, can solve the problems of good effect and few monomeric compounds with anti-tumor effect, and achieve remarkable results

Active Publication Date: 2020-09-01
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art discloses that the ethyl acetate extract of Aurantia nudica has a certain anti-metastasis effect on breast cancer, but the effect is good
Moreover, few monomeric compounds with anti-tumor effects have been found so far.

Method used

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  • Split-ring labdane diterpenoid compound as well as separation method and application thereof
  • Split-ring labdane diterpenoid compound as well as separation method and application thereof
  • Split-ring labdane diterpenoid compound as well as separation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The preparation of embodiment 1 split ring cyperane type diterpenoids

[0054] Include the following steps:

[0055] (1) Grind the dried leaves of Aurantia nudica, take 1500g of Aurantia nudica powder, and extract 3 times by heating 50-60°C with 2L ethanol solution (volume fraction 75%) for each kilogram of Aurantia nudica powder, each extraction 3h, combined extracts, concentrated under reduced pressure to obtain crude extract (about 300g);

[0056] (2) After every 100 grams of crude extract was diluted with 300 mL of distilled water to make a suspension, it was extracted 4 times with dichloromethane and ethyl acetate successively, and the combined organic phase was concentrated under reduced pressure to obtain a medicinal extract; The volume consumption of solvent is 1.2 times of water volume.

[0057] (3) Get the medicinal extract (80g) that step (2) extracts with ethyl acetate, first through silica gel column chromatography, adopt sherwood oil-ethyl acetate mixed ...

Embodiment 2

[0060] The preparation of embodiment 2 split ring helianthin type diterpenoids

[0061] Include the following steps:

[0062] (1) Grinding the dried leaves of Aurantia nudiflora, taking 1600g of Aurantia nudiflora powder, heating 50~60°C with 2L of ethanol solution (volume fraction 95%) to extract 4 times per kilogram of Aurantia nudiflora powder, each extraction 2h, the combined extracts were concentrated under reduced pressure to obtain a crude extract (about 330 g);

[0063] (2) After every 100 grams of crude extract is diluted with 400 mL of water to make a suspension, it is extracted 5 times with dichloromethane and ethyl acetate successively, and the combined organic phase is concentrated under reduced pressure to obtain a medicinal extract; The volume dosage is 1.3 times of the water volume.

[0064] (3) Take the medicinal extract (about 95g) obtained by extraction with ethyl acetate in step (2), and perform gradient elution using petroleum ether-ethyl acetate mixed s...

Embodiment 3

[0067] Example 3 Structural identification of split-ring helianthin-type diterpenoids

[0068] Using Spectrum ( 1 H NMR, 13 C NMR, HSQC, HMBC, NOESY) and modern structure identification techniques such as MS, determine the chemical structure of the compound A1-A3 obtained in embodiment 1 and embodiment 2.

[0069] The structural identification data are as follows:

[0070] Compound A1: It is a colorless crystal, easily soluble in methanol. Its molecular formula is determined as C 18 h 26 o 3 ;according to 1 H, 13 C and two-dimensional nuclear magnetic resonance data to determine its structure, the skeleton type is a split-ring helicanoid diterpene, which is named callnudoid D, and its 1 H and 13 See Table 1 for C NMR data attribution. [400MHz( 1 H), 100MHz ( 13 C), solvent: CDCl 3 ].

[0071] Compound A2: It is a colorless crystal, easily soluble in methanol. High resolution mass spectrometry HRESI(-)MS(m / z 303.1572[M+Na] + , theoretical value 303.1571) determi...

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Abstract

The invention belongs to the technical field of phytochemistry, and discloses a split-ring labdane diterpenoid compound as well as a separation method and application thereof. The new labdane diterpenoid compound A1-A3 with 3, 4-ring splitting and carbon reduction characteristics is extracted from callicarpa nudiflora, and the compound A1 has a C13-C17 cyclization new carbon skeleton characteristic. The compound disclosed by the invention has certain antitumor activity, has an obvious inhibiting effect on human liver cancer, gastric cancer or ovarian cancer cells, and can be applied to preparation of antitumor drugs. The method is simple, feasible and low in cost.

Description

technical field [0001] The invention belongs to the technical field of phytochemistry, and in particular relates to a split-helmane type diterpenoid compound and its separation method and application. Background technique [0002] Callicarpa nudiflora Hook.et Arn. is a deciduous shrub of the genus Callicarpa in the family Verbenacase, also known as rice soup leaves and white flower tea. Mainly produced in Hainan, Yunnan, Guangdong, Guangxi and other places. Nude flower purple pearl is one of the commonly used medicinal materials in the Li nationality area of ​​Hainan Province. Its dried stems, branches and leaves can be used as medicine. It is bitter, astringent, and cool in taste. It returns to the stomach, liver, and lung meridians. Hematemesis, traumatic bleeding, sore throat, pyretic sores and other symptoms. It is clinically used for various postoperative hemorrhagic diseases such as dermatology, gynecology, facial features, and surgery. It has been included in the n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/46C07C57/26C07C69/73C07C51/47C07C51/48C07C67/56C07C67/58A61P35/00
CPCC07C59/46C07C57/26C07C69/73C07C51/47C07C51/48C07C67/56C07C67/58A61P35/00C07C2601/14C07C2602/28
Inventor 余章昕陈光英李小宝宋小平
Owner HAINAN NORMAL UNIV