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来自针叶的半日花烷型二萜及其抗活性。

Labdane-type Diterpenes from Needles and Their Anti- Activity.

作者信息

Jeong Se Yun, Na Myung Woo, Park Eon Chung, Kim Jin-Chul, Kang Dong-Min, Hamishehkar Hamed, Ahn Mi-Jeong, Kim Jung Kyu, Kim Ki Hyun

机构信息

School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.

KIST Gangneung Institute of Natural Products, Natural Product Informatics Research Center, Gangneung 25451, Republic of Korea.

出版信息

ACS Omega. 2022 Aug 15;7(33):29502-29507. doi: 10.1021/acsomega.2c04147. eCollection 2022 Aug 23.

Abstract

is a medicinal tree used in traditional herbal medicine for the treatment of bronchial asthma and various skin diseases. As part of our ongoing search for bioactive phytochemicals with novel structures in natural products, we performed a phytochemical analysis of the methanol (MeOH) extract from needles collected in Iran. Phytochemical investigation of the MeOH extract, aided by liquid chromatography-mass spectrometry-based analysis, resulted in the isolation and identification of three labdane-type diterpenes (), including a new and relatively unique norlabdane-type diterpene with a peroxide moiety, eldaricoxide A (). The chemical structures of the isolated labdane-type diterpenes were elucidated by analyzing the spectroscopic data from 1D and 2D NMR and high-resolution electrospray ionization-mass spectrometry. The absolute configuration of eldaricoxide A () was established by employing a computational method, including electronic circular dichroism calculation and specific optical rotation. An anti- test was conducted, where compound exhibited the most potent antibacterial activity against strain 51, inducing 72.7% inhibition (MIC value of 92 μM), whereas eldaricoxide A () exhibited moderate antibacterial activity against strain 51, inducing 54.5% inhibition (MIC value of 95 μM). These findings demonstrated that the identified bioactive labdane-type diterpenes and can be applied in the development of novel antibiotics against for the treatment of gastric and duodenal ulcers.

摘要

是一种用于传统草药治疗支气管哮喘和各种皮肤病的药用树。作为我们持续在天然产物中寻找具有新颖结构的生物活性植物化学物质的一部分,我们对从伊朗收集的针叶的甲醇(MeOH)提取物进行了植物化学分析。在基于液相色谱 - 质谱分析的辅助下,对MeOH提取物进行植物化学研究,结果分离并鉴定出三种半日花烷型二萜(),包括一种具有过氧化物部分的新的且相对独特的降半日花烷型二萜,艾达瑞氧化物A()。通过分析一维和二维核磁共振以及高分辨率电喷雾电离质谱的光谱数据阐明了分离出的半日花烷型二萜的化学结构。通过采用包括电子圆二色性计算和比旋光度在内的计算方法确定了艾达瑞氧化物A()的绝对构型。进行了抗菌测试,其中化合物对菌株51表现出最强的抗菌活性,诱导72.7%的抑制率(MIC值为92μM),而艾达瑞氧化物A()对菌株51表现出中等抗菌活性,诱导54.5%的抑制率(MIC值为95μM)。这些发现表明,所鉴定的生物活性半日花烷型二萜和可应用于开发针对治疗胃和十二指肠溃疡的新型抗生素。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ed2/9404486/39e31db1d1b8/ao2c04147_0002.jpg

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