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没药中的萜类化合物及其对 HeLa 细胞的细胞毒性活性。

Terpenoids from Myrrh and Their Cytotoxic Activity against HeLa Cells.

机构信息

Lehrstuhl Pharmazeutische Biologie, Universitätsstraße 31, D-93053 Regensburg, Germany.

Repha GmbH Biologische Arzneimittel, Alt-Godshorn 87, D-30855 Langenhagen, Germany.

出版信息

Molecules. 2023 Feb 8;28(4):1637. doi: 10.3390/molecules28041637.

DOI:10.3390/molecules28041637
PMID:36838624
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9964945/
Abstract

The oleo-gum resin of (Nees) Engl. has a long history of medicinal use, although many of its constituents are still unknown. In the present investigation, 34 secondary metabolites were isolated from myrrh resin using different chromatographic techniques (silica flash chromatography, CPC, and preparative HPLC) and their structures were elucidated with NMR spectroscopy, HRESIMS, CD spectroscopy, and ECD calculations. Among the isolated substances are seven sesquiterpenes (-), one disesquiterpene (), and two triterpenes (, ), which were hitherto unknown, and numerous substances are described here for the first time for or the genus . Furthermore, the effects of selected terpenes on cervix cancer cells (HeLa) were studied in an MTT-based in vitro assay. Three triterpenes were observed to be the most toxic with moderate IC values of 60.3 (), 74.5 (), and 78.9 µM (). Due to the different activity of the structurally similar triterpenoids, the impact of different structural elements on the cytotoxic effect could be discussed and linked to the presence of a 1,2,3-trihydroxy substructure in the A ring. The influence on TNF-α dependent expression of the intercellular adhesion molecule 1 (ICAM-1) in human microvascular endothelial cells (HMEC-1) was also tested for -, -, , , , and in vitro, but revealed less than 20% ICAM-1 reduction and, therefore, no significant anti-inflammatory activity.

摘要

没药（Nees）的油胶树脂具有悠久的药用历史，尽管其许多成分仍不清楚。在本研究中，使用不同的色谱技术（硅胶快速色谱、CPC 和制备 HPLC）从没药树脂中分离出 34 种次生代谢产物，并通过 NMR 光谱、HRESIMS、CD 光谱和 ECD 计算阐明了它们的结构。分离出的物质中有 7 种倍半萜（-）、1 种二倍半萜（）和 2 种三萜（、），这些物质以前在没药中或该属中均未被发现，这里还首次描述了许多物质。此外，还在基于 MTT 的体外测定中研究了选定萜类化合物对宫颈癌细胞（HeLa）的影响。观察到三种三萜类化合物的毒性最强，IC 值为 60.3（）、74.5（）和 78.9µM（）。由于结构相似的三萜类化合物具有不同的活性，可以讨论不同结构元素对细胞毒性的影响，并将其与 A 环中存在 1,2,3-三羟基结构联系起来。还测试了 -、-、、、和在体外对 TNF-α 依赖性人微血管内皮细胞（HMEC-1）中细胞间黏附分子 1（ICAM-1）表达的影响，但仅观察到不到 20%的 ICAM-1 减少，因此没有明显的抗炎活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/a9d2d768058b/molecules-28-01637-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/8656dd0f3950/molecules-28-01637-g001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/755a5430a8a1/molecules-28-01637-g005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/3b3f5fce6dcb/molecules-28-01637-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/60658530e739/molecules-28-01637-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/6f175cc1cb94/molecules-28-01637-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/50859e83c777/molecules-28-01637-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/3f9fb39af633/molecules-28-01637-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/957178a72d8c/molecules-28-01637-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/7abb6cf714a5/molecules-28-01637-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/a9d2d768058b/molecules-28-01637-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/8656dd0f3950/molecules-28-01637-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/0f860595403b/molecules-28-01637-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/1ac35f38512c/molecules-28-01637-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/aa2cb8a394bf/molecules-28-01637-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/755a5430a8a1/molecules-28-01637-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/445bf411203a/molecules-28-01637-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/3b3f5fce6dcb/molecules-28-01637-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/60658530e739/molecules-28-01637-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/6f175cc1cb94/molecules-28-01637-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/50859e83c777/molecules-28-01637-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/3f9fb39af633/molecules-28-01637-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/957178a72d8c/molecules-28-01637-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/7abb6cf714a5/molecules-28-01637-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9a82/9964945/a9d2d768058b/molecules-28-01637-g014.jpg

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