Bioactive Terphenyls Isolated from the Antarctic Lichen Stereocaulon alpinum

• Published in: Molecules
• Main Authors: Kim-Hoa Phi, Min-Ji Shin, Seulah Lee, Jae Eun So, Ji Hee Kim, Sung-Suk Suh, Man Hyung Koo, Seung Chul Shin, Jin-Hyoung Kim, Jun Hyuck Lee, Ui Joung Youn
• Format: Article in Journal/Newspaper
• Language: English
• Published: MDPI AG 2022
• Subjects: Stereocaulon alpinum; Antarctic lichen; terphenyl; cytotoxicity; anti-inflammation; Organic chemistry; QD241-441; Antarctic; The Antarctic; Antarc*
• Online Access: https://doi.org/10.3390/molecules27072363; https://doaj.org/article/7341f2538e644b0c95b1e1c75f940644

Three p -terphenyls ( 2 – 4 )—2-hydroxy-3,5-dimethoxy- p -terphenyl ( 2 ), 2-hydroxy-3,6-dimethoxy- p -terphenyl ( 3 ), and 2,3,5,6-tetramethoxy- p -terphenyl ( 4 )—were isolated for the first time as natural products along with seven known compounds ( 1 , 5 – 10 ) from the Antarctic lichen Stereocaulon alpinum. Structures of the new compounds were elucidated by comprehensive analyses of 1D and 2D NMR and HREIMS experiments. Compound 3 exhibited cytotoxicity against HCT116 cells with the IC 50 value of 3.76 ± 0.03 μM and also inhibited NO production in LPS-induced RAW264.7 macrophages with the IC 50 value of 22.82 ± 0.015 μM.