Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India.
College of Pharmacy, The Ohio State University, Ohio, Columbus, OH-43210, USA.
Chem Biodivers. 2024 Jun;21(6):e202301874. doi: 10.1002/cbdv.202301874. Epub 2024 May 23.
Lichens are a symbiotic association of algae and fungus, belonging to the family Parmeliaceae. Some lichen species are edible and used as an active ingredient for preparation of exotic spices as well as folklore medicine to cure different kinds of ailments. A specimen of lichen was collected from Munner in the Kerala State of South India for chemical profiling. Chemical analyses of the diethyl ether extract of the defatted lichen led to the isolation of six phenols 1-6 with variation of relative abundance. Amongst them, the relative abundance of compound 3 was the greatest (1 % of crude extract) and it was identified as atranorin. The structures of known compounds were confirmed by comparison of their H-NMR, C NMR, and mass data with published values available in the literature. In vitro bioassay for anti-proliferative activity of these compounds has been conducted against various human cancer cell lines in comparison with paclitaxel as control using SRB assay. Interestingly, a new compound 5 was found along with previously reported compounds from this lichen. This new compound was designated as fluoroatranorin 5 which was reported for the first time herein. The structural characterization of a new depside was determined by spectral methods such as H-NMR, C NMR, F NMR, IR, LC-HRESI-MS, and LC-MS/MS study. Its structure was confirmed by single crystal X-ray diffraction study. This new compound was designated as fluoroatranorin 5 which was reported first time herein. Anti-proliferative activity of all these compounds was evaluated against six different cancer cell lines. The inhibitory activity, IC value of compounds 1-3 and 5 exhibited at 99.64, 102.04, 109.20, 53.0 and 2.4 μM on cancer cell lines HT-29 (colon), Hela (cervical), HT-29, HPAC (pancreas) and A2780 (ovarian cancer cell line) respectively in comparison with paclitaxel as control. The new compound 5 exhibited significant activity with IC value 2.4 μM on A2780 ovarian cancer cell line.
地衣是藻类和真菌共生的一种生物，属于松萝科。一些地衣物种可食用，并被用作制备异国香料的活性成分，也是民间医学治疗各种疾病的药物。从印度南部喀拉拉邦的 Munner 采集了地衣标本进行化学分析。对脱脂地衣的乙醚提取物进行化学分析，导致分离出六种酚类化合物 1-6，其相对丰度有所不同。其中，化合物 3 的相对丰度最大（占粗提取物的 1%），并被鉴定为无羁萜。通过与文献中可用的 H-NMR、C NMR 和质谱数据比较，确定了已知化合物的结构。通过 SRB 测定法，对这些化合物在体外对各种人类癌细胞系的抗增殖活性进行了测定，并与紫杉醇作为对照进行了比较。有趣的是，在这种地衣中发现了一种新化合物 5，以及以前报道过的化合物。这种新化合物被指定为氟无羁萜 5，这是本文首次报道。通过光谱方法，如 H-NMR、C NMR、F NMR、IR、LC-HRESI-MS 和 LC-MS/MS 研究，确定了新的缩酚酸的结构特征。通过单晶 X 射线衍射研究确定了其结构。这种新化合物被指定为氟无羁萜 5，这是本文首次报道。对所有这些化合物进行了抗增殖活性评估，共测试了六种不同的癌细胞系。与紫杉醇作为对照相比，化合物 1-3 和 5 的抑制活性，IC 值在 99.64、102.04、109.20、53.0 和 2.4μM 时，分别在 HT-29（结肠）、Hela（宫颈）、HT-29、HPAC（胰腺）和 A2780（卵巢癌细胞系）上表现出抗癌活性。新化合物 5 在 A2780 卵巢癌细胞系中表现出显著的活性，IC 值为 2.4μM。
