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Anti-tumor and anti-bacterial dodecacyclo lactone compounds and use thereof

A technology of ester compounds and twelve-membered rings, applied in the field of medicine

Active Publication Date: 2013-01-30
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the 12-membered ring lactone compound dendrochliods A~O isolated from Dendrodochium.sp. has antitumor and antibacterial activities and its application has not been reported yet

Method used

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  • Anti-tumor and anti-bacterial dodecacyclo lactone compounds and use thereof
  • Anti-tumor and anti-bacterial dodecacyclo lactone compounds and use thereof
  • Anti-tumor and anti-bacterial dodecacyclo lactone compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Twelve-membered ring lactone compounds 1 to 15 of the present invention ( dendrochliods A~O) Preparation

[0024] The present invention is from the symbiotic fungus of black milk sea cucumber in South China Sea Dendrodochium. 15 new twelve-membered ring lactone compounds dendrochliods A~O with antitumor and antibacterial activities isolated from sp., the above compounds have the following general chemical structure formula:

[0025]

[0026] The group collocation of described compound is as follows respectively:

[0027] .

[0028] Symbiotic fungi of sea cucumbers Dendrodochium. sp. (internal strain NO.10087) strain was isolated from the host black milk sea cucumber ( Holothuria nobilis Selenka). The strain was fermented in solid agar medium containing 5% biomalt extract (biomalt) for 28 days at room temperature, and then extracted several times with ethyl acetate. The extracts were combined, concentrated and evaporated to dryness under reduced p...

Embodiment 2

[0029] Example 2 Twelve-membered ring lactone compounds 1 to 15 of the present invention ( dendrochliods Identification of A~O)

[0030] 1. Dendrochliod A:C 12 h 20 o 5 , a colorless oil. 1 H and 13 See Table 1 for C NMR data.

[0031] 2. Dendrochliod B:C 12 h 18 o 5 , Pale yellow oil. 1 H and 13 See Table 2 for C NMR data.

[0032] 3. Dendrochliod C: C 12 h 18 o 5 , Pale yellow oil. 1 H and 13 See Table 3 for C NMR data.

[0033] 4. Dendrochliod D: C 12 h 18 o 5 , Pale yellow oil. 1 H and 13 See Table 4 for C NMR data.

[0034] 5. Dendrochliod E: C 13 h 20 o 5 , a colorless oil. 1 H and 13 See Table 5 for C NMR data.

[0035] 6. Dendrochliod F: C 13 h 20 o 5 , a colorless oil. 1 H and 13 See Table 6 for C NMR data.

[0036] 7. Dendrochliod G:C 12 h 20 o 6 , a colorless oil. 1 H and 13 See Table 7 for C NMR data.

[0037] 8. Dendrochliod H: C 12 h 18 o 4 , Pale yellow oil. 1 H and 13 See Table 8 for C NMR data.

[0038] 9. Dendr...

Embodiment 3

[0075] Example 3 Twelve-membered ring lactone compounds 1 to 15 of the present invention ( dendrochliods A~O) anti-tumor experiments

[0076] 1. Experimental method

[0077] The compound of the present invention was tested for inhibition of tumor cell proliferation by conventional MTT method.

[0078] 1. Cell lines used in the experiment: A549 (human lung cancer cells), Lovo (human colon cancer cells) and MG63 (human osteosarcoma cells). The cell lines used in the experiments were from the Institute of Cells, Chinese Academy of Sciences.

[0079] 2. Experimental reagents, consumables and instruments:

[0080] DMEM medium (Invitrigen); 1640 medium (Invitrigen); McCoy's 5a (Invitrigen); serum (Invitrigen); trypsin (Invitrigen); DMSO (sigma); MTT (sigma); Corning); pipette (Corning); 96-well plate (Corning); CO 2 Incubator (SANYO); microplate reader (Biotek76833)

[0081] 3. Experimental drugs:

[0082] Compounds 1-15 of the present invention (Dendrochliods A-O).

[00...

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Abstract

The invention relates to 15 anti-tumor and anti-bacterial dodecacyclo lactone compounds, namely dendrochliod A to dendrochliod O, which are separated from Dendrodochium.sp. The invention also provides the use of the 15 compounds. According to the result of in-vitro anti-tumor and in-vitro anti-bacterial activity tests, the compounds have obvious inhibition effect on many tumor cells such as human lung cancer cells, human colon cancer cells and human osteosarcoma cells and have potential activity for resisting fungi and bacteria such as candida mycoderma bacteria, filamentous fungi and Escherichia coli. The compounds can be used for pilot compounds for developing new anti-tumor or anti-bacterial medicines, and contribute to marine resource exploitation and utilization.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, is the symbiotic fungus of sea cucumber black breast from South China Sea Dendrodochium. Fifteen new twelve-membered ring lactone compounds dendrochliods A~O with antitumor and antibacterial activities isolated from sp. and their applications. Background technique [0002] So far, there are few reports on the research on the endophytic fungi of sea cucumbers at home and abroad. In the world, only the Institute of Pacific Biochemistry of the Far Eastern Branch of the Russian Academy of Sciences has successively obtained sea cucumber Eupentacta fraudatrix epiphytic fungi Acremonium striatisporum Nine secondary metabolites of diterpene saponins were isolated in the study, namely virescenosides M, N, O, P, Q, R, S, T and U. Pharmacological experiments showed that these compounds have good cytotoxic activity. However, there are relatively few domestic research reports on th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/00A61K31/365A61P35/00A61P31/04A61P31/10
CPCY02A50/30
Inventor 张文许东啸李玲易杨华汤华孙鹏刘宝姝
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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