Germacrane type sesquiterpene lactone compound, and preparation method and application thereof

A technology of ester compounds and sesquiterpenes, which is applied in the field of gemane-type sesquiterpene lactones and their preparation, can solve the problems of single target, adverse reactions, and narrow treatment range, and achieve the purpose of inhibiting osteoclasts The effect of cell differentiation and good application prospects

Active Publication Date: 2021-01-01
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the defects or deficiencies of current clinical anti-osteoporosis drugs with single target, narrow therapeutic range and adverse reactions, and provide a gemane-type sesquiterpene lactone compound

Method used

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  • Germacrane type sesquiterpene lactone compound, and preparation method and application thereof
  • Germacrane type sesquiterpene lactone compound, and preparation method and application thereof
  • Germacrane type sesquiterpene lactone compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] XX-1 to XX-10 were prepared from C. adenoides.

[0041] The dry aerial part (5.0kg) of Glandularia spp., crushed into small pieces, was extracted with 95% ethanol aqueous solution at room temperature for 3 times, each time for 3 days; the extract was concentrated under reduced pressure to obtain the crude extract; The paste was suspended in water, extracted 5 times with ethyl acetate, concentrated under reduced pressure to obtain the ethyl acetate fraction, which was chromatographed on a 200-300 mesh silica gel column, and eluted with dichloromethane / methanol according to a gradient. The volume ratio of dichloromethane / methanol in gradient elution is 0→40min: 1:0→100:1, 40→80min: 100:1→50:1, 80→120min: 50:1→20:1, 120→160min: 20:1→10:1. After identification by thin-layer chromatography, it was divided and concentrated into 5 fractions (A~E). Fraction C (50 g) was subjected to reverse-phase column chromatography and eluted with methanol / water (30%-100%) to obtain compou...

Embodiment 2

[0060] Determination of anti-osteoporotic activity of compounds.

[0061] 1. Cell culture

[0062] Two types of cells were used in this experiment: primary mouse bone marrow macrophages (Bone Marrow Macrophage, BMM) and RAW264.7 mononuclear macrophages.

[0063] (1) Isolation and culture of BMM cells: 8-week-old female C57BL / 6 mice were sacrificed by cervical dislocation, soaked in 75% ethanol for 10 minutes, and then transferred to an ultra-clean workbench to dissect and separate the tibia and femur of both hind limbs. Remove excess muscle tissue and soak in α-MEM medium containing 1% double antibody for 5 minutes. The joints at both ends of the bone were cut open and placed in α-MEM complete medium containing 10% fetal bovine serum (FBS) and 1% double antibody. Blow out the bone marrow cells with a 1 mL syringe and filter the bone marrow cells with a cell strainer with a diameter of 40 μM. Transfer the cell suspension to a centrifuge tube, centrifuge at 1000rpm for 10min,...

Embodiment 3

[0088] According to the method of Example 1, the formulas (I), (II), (III) and (IV) were first prepared, and water for injection and Tween 80 were added as usual, finely filtered, potted and sterilized to make an injection.

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Abstract

The invention discloses a germacrane type sesquiterpene lactone compound, and a preparation method and application thereof. The germacrane type sesquiterpene lactone compound has structural formulas shown as formulas (I) to (IV). In the formulas (I) to (IV), R1 is H or OH; R2 is OH, OMeacr, or OEt; R3 is OAng, OH, or OMeacr; R4 is OTig or OAng; and R5 is CH2OH or CHO. The germacrane sesquiterpenelactone compound provided by the invention has an obvious differentiation inhibition effect on RANKL-induced osteoclasts, the IC50 of most of the compounds is 10.0 [mu]M or below, cytotoxicity is notshown under 10 [mu]M, and the germacrane sesquiterpene lactone can be applied to preparation of drugs for treating and/or preventing osteoporosis and has a good application prospect.

Description

technical field [0001] The invention relates to the technical field of compounds and medicines, in particular to a gemane-type sesquiterpene lactone compound and its preparation method and application. Background technique [0002] Osteoporosis (osteoporosis) is a systemic bone disease that reduces bone density and bone quality and destroys bone microstructure due to various reasons, resulting in increased bone fragility and prone to fractures. Osteoporosis is the most common. Due to the aggravation of population aging, osteoporosis has become a global public health problem, seriously affecting the quality of life of middle-aged and elderly people. [0003] The pathogenesis of osteoporosis is relatively complex, but ultimately leads to the breakdown of the dynamic balance maintained between bone formation under the action of osteoblasts and bone resorption mediated by osteoclasts, so that bone resorption is greater than bone formation, resulting in bone mass loss. Osteopor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93A61K31/365A61P19/10
CPCC07D307/93A61P19/10C07B2200/07Y02A50/30
Inventor 顾琼孙喆君张毓婷徐峻
Owner SUN YAT SEN UNIV
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