C21 steroid Asclepiasterol, preparation method and application thereof in preparation of tumor multidrug resistance reversal agent

A multi-drug resistance, tumor technology, applied in the field of natural medicinal chemistry, to achieve the effect of low cytotoxicity, low toxicity, and increase the degree of accumulation

Inactive Publication Date: 2016-06-15
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Invention patent (201410824396.1) discloses an extract of milkweed milk rich in cardiac glycosides, its preparation method and its application in anti-tumor dr

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  • C21 steroid Asclepiasterol, preparation method and application thereof in preparation of tumor multidrug resistance reversal agent
  • C21 steroid Asclepiasterol, preparation method and application thereof in preparation of tumor multidrug resistance reversal agent
  • C21 steroid Asclepiasterol, preparation method and application thereof in preparation of tumor multidrug resistance reversal agent

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[0035] Example 1

[0036] Extract 1 kg of milkweed whole herb twice with 3 times the amount of 50% alcohol, combine the extracts, and concentrate under reduced pressure to obtain the total extract (95 g). Dilute the total extract with water to obtain a diluent; add cyclohexane to the diluent for extraction, and collect the extracted cyclohexane layer; then add ethyl acetate to the remaining aqueous layer for extraction, and collect ethyl acetate The aqueous layer was discarded, and the ethyl acetate layer was concentrated under reduced pressure at 30°C to obtain the ethyl acetate fraction (16 g) of the milkweed extract. The ethyl acetate part was chromatographed with silica gel (200 mesh, 160g) column, and the volume ratio of 100:0, 100:1, 50:1, 20:1, 10:1 CHCl 3 -MeOH eluted two column volumes each. The 10:1 eluted fraction was recrystallized with methanol to obtain C21 steroid Asclepiasterol (52mg).

Example Embodiment

[0037] Example 2

[0038] Extract 1 kg of whole milkweed herb with 5 times the amount of 100% alcohol for 4 times, combine the extracts, and concentrate under reduced pressure to obtain the total extract (95 g). Dilute the total extract with water to obtain a diluent; add cyclohexane to the diluent for extraction, and collect the extracted cyclohexane layer; then add ethyl acetate to the remaining aqueous layer for extraction, and collect ethyl acetate The aqueous layer was discarded, and the ethyl acetate layer was concentrated under reduced pressure at 50° C. to obtain the ethyl acetate fraction (16 g) of the milkweed extract. The ethyl acetate part was chromatographed with silica gel (300 mesh, 160g) column, and the volume ratio of 100:0, 100:1, 50:1, 20:1, 10:1 CHCl 3 -MeOH eluted two column volumes each. The 10:1 eluted fraction was recrystallized with methanol to obtain C21 steroid Asclepiasterol (63mg).

Example Embodiment

[0039] Example 3

[0040] Extract 1 kg of milkweed whole plant with 4 times the amount of 70% alcohol for 3 times, combine the extracts, and concentrate under reduced pressure to obtain the total extract (100.5 g). Dilute the total extract with water to obtain a diluent; add cyclohexane to the diluent for extraction, and collect the extracted cyclohexane layer; then add ethyl acetate to the remaining aqueous layer for extraction, and collect ethyl acetate The aqueous layer was discarded, and the ethyl acetate layer was concentrated under reduced pressure at 40°C to obtain the ethyl acetate fraction (16 g) of the milkweed extract. The ethyl acetate part was chromatographed with silica gel (250 mesh, 160g) column, and the volume ratio of 100:0, 100:1, 50:1, 20:1, 10:1 CHCl 3 -MeOH eluted two column volumes each. The 10:1 eluted fraction was recrystallized with methanol to obtain C21 steroid Asclepiasterol (58mg).

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Abstract

Belonging to the field of natural pharmaceutical chemistry, the invention discloses a C21 steroid Asclepiasterol, a preparation method and application thereof in preparation of a tumor multidrug resistance reversal agent. The structural formula of C21 steroid Asclepiasterol is shown as the specification. The Asclepiasterol involved in the invention has low cytotoxicity, but can significantly increase the accumulation degree of antitumor drugs in drug resistant cells, can enhance the effect of antitumor drugs in inducing drug resistant cell apoptosis, and can be applied in combination with antitumor drugs to significantly inhibit the formation rate of drug resistant tumor cell colonies and obviously decline the expression level of P-gp in two drug resistant cell lines without lowering drug resistant gene expression, thus suggesting that Asclepiasterol probably affects P-gp expression at the level of transcription and translation and has a unique mechanism of action. Therefore, compared with the existing tumor multidrug resistance reversal agents, the C21 steroid Asclepiasterol provided by the invention has high reversal activity and low toxicity, and is in accordance with the high efficiency and low toxicity characteristics of antitumor drugs.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a C21 steroid Asclepiasterol, a preparation method thereof and its application in preparing a tumor multidrug resistance reversal agent. Background technique [0002] Tumor multidrug resistance (MDR) refers to the cross-resistance of tumor cells to other anti-tumor drugs with completely different structures and mechanisms of action while developing resistance to one anti-tumor drug. Tumor drug resistance is the main reason for the failure of current clinical chemotherapy. According to the American Cancer Society estimates, more than 90% of cancer patients died of varying degrees of drug resistance. The mechanism of multidrug resistance is very complex and has not been fully elucidated so far. It is currently believed that its main molecular biological mechanisms include decreased drug uptake and increased efflux by cells, enhanced cellular detoxification sy...

Claims

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Application Information

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IPC IPC(8): C07J17/00A61K31/704A61P35/00
CPCC07J17/005
Inventor 江仁望蔡绍辉李文学袁玮琪张容容
Owner JINAN UNIVERSITY
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