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黄花蒿悬浮培养细胞对两种新的二氢青蒿酸糖苷的立体及区域选择性生物合成。

Stereo and region-selective biosynthesis of two new dihydroartemisinic acid glycosides by suspension-cultured cells of Artemisia annua.

作者信息

Zhu Jianhua, Zeng Zihan, Song Liyan, Hu Yanshan, Wen Wei, Yu Rongming

机构信息

Biotechnological Institute of Chinese Materia Medica, Guangzhou 510632, China.

Department of Pharmacology Jinan University, Guangzhou 510632, China.

出版信息

Pharmacogn Mag. 2014 Jan;10(Suppl 1):S110-4. doi: 10.4103/0973-1296.127357.

DOI:10.4103/0973-1296.127357
PMID:24914289
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4047596/
Abstract

BACKGROUND

The system of plant-cultured cells is one of the optimal systems to investigate biosynthesis pathway and their bioactive intermediates.

OBJECTIVE

To study the biosynthesis of dihydroartemisinic acid (1) by suspension-cultured cells of Artemisia annua.

MATERIALS AND METHODS

Substrate (compound 1) was administered into the suspension-cultured cells of A. annua and co-cultured for 2 days. The methanol extract was separated on various column chromatography methods and the structures of two biosynthesis products were elucidated based on the analysis of (1)H NMR, (13)C NMR, 2D NMR, and ESI-MS. Time-course curve was also established. Furthermore, in vitro antitumor activities of compounds 1-3 against HepG2, K562, and A549 cell lines were evaluated by MTT assay.

RESULTS

Two new compounds were obtained, namely 3α-hydroxy-dihydroartemisinic acid-α-D-glucopyranosyl ester (2) and 15-hydroxy-cadin-4-en-12-oic acid-β-d-glucopyranosyl ester (3). The results demonstrated that the cultured cells of A. annua possessed the abilities to stereo-selective hydroxylate and region-selective glycosylate sesquiterpene compounds in a highly efficient manner. Inhibitory effects of compounds 1-3 on proliferation of HepG2, K562, and A549 cell lines in vitro were also investigated.

CONCLUSION

Two new dihydroartemisinic acid glycosides were obtained by stereo- and region-selective biosynthesis with cultured cells of A. annua.

摘要

背景

植物培养细胞体系是研究生物合成途径及其生物活性中间体的最佳体系之一。

目的

研究青蒿悬浮培养细胞中二氢青蒿酸（1）的生物合成。

材料与方法

将底物（化合物1）加入青蒿悬浮培养细胞中，共培养2天。甲醇提取物通过多种柱色谱方法进行分离，并基于1H NMR、13C NMR、二维NMR和电喷雾电离质谱分析阐明两种生物合成产物的结构。还建立了时间进程曲线。此外，通过MTT法评估化合物1-3对HepG2、K562和A549细胞系的体外抗肿瘤活性。

结果

获得了两种新化合物，即3α-羟基-二氢青蒿酸-α-D-吡喃葡萄糖酯（2）和15-羟基-杜松-4-烯-12-酸-β-D-吡喃葡萄糖酯（3）。结果表明，青蒿培养细胞具有以高效方式对倍半萜化合物进行立体选择性羟基化和区域选择性糖基化的能力。还研究了化合物1-3对HepG2、K562和A549细胞系体外增殖的抑制作用。

结论

通过青蒿培养细胞的立体和区域选择性生物合成获得了两种新的二氢青蒿酸糖苷。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53dd/4047596/8598f411d2cf/PM-10-110-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53dd/4047596/eb07d9a28356/PM-10-110-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53dd/4047596/8598f411d2cf/PM-10-110-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53dd/4047596/eb07d9a28356/PM-10-110-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/53dd/4047596/8598f411d2cf/PM-10-110-g002.jpg

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Three sesquiterpene compounds biosynthesised from artemisinic acid using suspension-cultured cells of Averrhoa carambola (Oxalidaceae).利用杨桃（酢浆草科）悬浮培养细胞从青蒿酸生物合成三种倍半萜化合物。
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