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Synthesis and Antitumor Activity of Phytosterol Derivatives and Synthesis of γ-Mangostin Derivatives

Author: ShiGuangZong
Tutor: LuYu
School: Nanchang University
Course: Organic Chemistry
Keywords: phytosterol stigmasterol Synthesis Anti-tumor activity γ-mangostin
CLC: TQ464
Type: Master's thesis
Year: 2011
Downloads: 18
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Abstract


The graduation thesis consists of two chapters. In the first chapter described the synthesis of derivatives of phytosterol and anti-tumor activities tested by MTT method. The second chapter described the design and synthesis of a series of derivatives of y-mangostin.Phytosterol belongs to a molecular class of steroid nuclear, which don’t have side effect to human body and with high physiological activity of a kind of natural active substances. Scientists praise that phytosterol is life’s key.Phytosterol has numerous biological activities, such as anticancer, antioxidant, cholesterol reducing, anti-prostate disease, skin care, hairdressing and so on. The derivatives of phytosterol have similar pharmacological activity of phytosterol. Some of these compounds are superior to phytosterol in the activity and selectivity, and stability is often better than phytosterol. Therefore, the derivatives of phytosterol have become a research hotspot in recent years.In this paper, the natural extract of phytosterol as the raw material,9 derivatives of phytosterol compounds are synthesized. The structures are confirmed by 1H NMR, MS,IR. Biological activities of synthetic compounds are investigated and the relationship between the chemical structure and anti-tumor activity on the basis is discussed. The main content are as follows:AT-1, AT-2, AT-3, AT-4, AT-5 are obtained by modifing the hydroxyl group of phytosterol. AT-6, AT-7, AT-8, AT-9 are obtained by modifing the hydroxyl group of stigmasterol. The structure is confirmed by 1H NMR, MS,IR.Anti-tumor activities of derivatives of phytosterol are tested by MTT method, and the structure-activity relationship is discussed. The compound AT-8 has the best anti-tumor activity than others of derivatives of resveratrol against the MCF-7 cell line. The compound AT-9 has the best anti-tumor activity against the MCF-7,A549,HepG2 cell line.This experiment also has proved that the hydroxyl groups in sterol can enhance anti-tumor activity. It has been found that derivatives of sterol with Cl substitute have good anti-tumor activity against the MCF-7,A549,HepG2 cell line and derivatives of sterol with benzene substitute are better than derivatives of sterol with straight-chain substitute in cell-growth inhibiton activitiy.In the second chapter,γ-mangostin as the raw material,2 kinds of derivatives ofγ-mangostin are synthesized.γ--mangostin has four hydroxyl groups which have a strong capacity for electronic, soγ-mangostin has a strong antioxidant activity. On this basis, BT-1, BT-2 are obtained by modifing the four hydroxyl groups ofγ-mangostin. The structure is confirmed by 1H NMR, MS.

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