Resorcinosides A and B, Glycosylated Alkylresorcinols from a Marine-Derived Strain of the Fungus Penicillium janthinellum

  • J Nat Prod. 2019 Nov 22;82(11):3186-3190. doi: 10.1021/acs.jnatprod.9b00776.
Byeoung-Kyu Choi  1  2 ,  Thi Hoai Trinh Phan  3  4 ,  Sunghoon Hwang  5 ,  Dong-Chan Oh  5 ,  Jong Soon Kang  6 ,  Hwa-Sun Lee  2 ,  Thi Duy Ngoc Ngo  3 ,  Thi Thanh Van Tran  3  4 ,  Hee Jae Shin  1  2
Affiliations
  • 1. Department of Marine Biotechnology , University of Science and Technology (UST) , 217 Gajungro Yuseong-gu , Daejeon 34113 , Republic of Korea.
  • 2. Marine Natural Products Chemistry Laboratory , Korea Institute of Ocean Science and Technology (KIOST) , 385 Haeyang-ro , Yeoungdo-gu, Busan 49111 , Republic of Korea.
  • 3. Nha Trang Institute of Technology Research and Application , Vietnam Academy of Science and Technology , 02 Hung Vuong , Nha Trang 650000 , Vietnam.
  • 4. Graduate University of Science and Technology, Vietnam Academy of Science and Technology , 18 Hoang Quoc Viet , Cau Giay , Ha Noi 100000 , Vietnam.
  • 5. Natural Products Research Institute, College of Pharmacy , Seoul National University , Seoul 08826 , Republic of Korea.
  • 6. Laboratory Animal Resource Center , Korea Research Institute of Bioscience and Biotechnology , 30 Yeongudanjiro , Cheongju 28116 , Republic of Korea.
PMID: 31668073 DOI: 10.1021/acs.jnatprod.9b00776
Abstract

Two new glycosylated alkylresorcinols, resorcinosides A (1) and B (2), were isolated from a strain of the fungus Penicillium janthinellum derived from a marine sediment sample collected from Cu Lao Cham Island, Vietnam. The structures of 1 and 2 were established by interpretation of 1D and 2D NMR and high-resolution ESIMS data, and their absolute configurations were confirmed by the coupling constant of the anomeric proton, acid hydrolysis, subsequent HPLC analysis, Mosher's method, and quantum-mechanics-based computational analysis of NMR chemical shifts. The structure elucidation indicated that 1 and 2 are new alkylresorcinols with d-glucose, and 2 has an α-pyrone moiety attached to the aromatic ring. Compound 1 exhibited cytotoxic activity against the NUGC-3 Cancer cell line with a GI50 value of 9.3 μM.