Meyeroguilline E, a New Isoindolinone Alkaloid from the Poisonous Mushroom Chlorophyllum molybdites, and Identification of Compounds with Multidrug Resistance (MDR) Reversal Activities

Bum Soo Lee; Rhim Ryoo; Jin Song Park; Sang Un Choi; Se Yun Jeong; Yoon-Joo Ko; Jung Kyu Kim; Jin-Chul Kim; Ki Hyun Kim

doi:10.1021/acsomega.2c06155

Meyeroguilline E, a New Isoindolinone Alkaloid from the Poisonous Mushroom Chlorophyllum molybdites, and Identification of Compounds with Multidrug Resistance (MDR) Reversal Activities

ACS Omega. 2022 Oct 24;7(43):39456-39462. doi: 10.1021/acsomega.2c06155. eCollection 2022 Nov 1.

Authors

Bum Soo Lee¹, Rhim Ryoo², Jin Song Park³, Sang Un Choi³, Se Yun Jeong¹, Yoon-Joo Ko⁴, Jung Kyu Kim⁵, Jin-Chul Kim⁶, Ki Hyun Kim¹

Affiliations

¹ School of Pharmacy, Sungkyunkwan University, Suwon, Gyeonggi-do 16419, Republic of Korea.
² Special Forest Products Division, Forest Bioresources Department, National Institute of Forest Science, Suwon 16631, Republic of Korea.
³ Korea Research Institute of Chemical Technology, Deajeon 34114, Republic of Korea.
⁴ Laboratory of Nuclear Magnetic Resonance, National Center for Inter-University Research Facilities (NCIRF), Seoul National University, Gwanak-gu, Seoul 08826, Republic of Korea.
⁵ School of Chemical Engineering, Sungkyunkwan University, Suwon 16419, Republic of Korea.
⁶ KIST Gangneung Institute of Natural Products, Natural Product Research Center, Gangneung 25451, Republic of Korea.

Abstract

Three isoindolinone alkaloids (1-3), including one new isoindolinone-type alkaloid, meyeroguilline E (1), and six other known compounds (4-9) were isolated from the poisonous mushroom Chlorophyllum molybdites (Agaricaceae). The structure of the new compound was determined using extensive spectroscopic analyses via one-dimensional (1D) and two-dimensional (2D) NMR data interpretation and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). To the best of our knowledge, compound 1 is the first example of a natural isoindolinone with a butanoic acid moiety, and this study is the first to detect the other known compounds (2-9) in C. molybdites. The isolated compounds (1-9) were examined for their multidrug resistance (MDR) reversal activity against MES-SA, MES-SA/DX5, HCT15, and HCT15/CL02 human cancer cells. Based on the results, 20 μM of compounds 3 and 6 slightly potentiated paclitaxel (TAX)-induced cytotoxicity in MES-SA/DX5, HCT15, and HCT15/CL02 cells; however, the compounds had no effect on the cytotoxicity against MES-SA and nonMDR cells.