Open AccessSinularamides A–G, Terpenoid-Derived Spermidine and Spermine Conjugates with Casitas B-Lineage Lymphoma Proto-Oncogene B (Cbl-b) Inhibitory Activities from a Sinularia sp. Soft Coral
Author(s) -
Wei Jiang,
Dongdong Wang,
Brice A P Wilson,
Donna Voeller,
Heidi R. Bokesch,
Emily A. Smith,
Stanley Lipkowitz,
Barry R. O’Keefe,
Kirk R. Gustafson
Publication year - 2021
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/acs.jnatprod.1c00367
Subject(s) - terpenoid , chemistry , spermine , spermidine , stereochemistry , biochemistry , natural product , biology , enzyme
An extract of a Sinularia sp. soft coral showed inhibitory activity against the E3-ubiquitin ligase casitas B-lineage lymphoma proto-oncogene B (Cbl-b). Subsequent bioassay-guided separation of the extract provided a series of terpenoid-derived spermidine and spermine amides that were named sinularamides A-G ( 1 - 7 ). Compounds 1 - 7 represent new natural products; however, sinularamide A ( 1 ) was previously reported as a synthetic end product. The structures of sinularamides A-G ( 1 - 7 ) were elucidated by analysis of spectroscopic and spectrometric data from NMR, IR, and HRESIMS experiments and by comparison with literature data. All of the isolated compounds showed Cbl-b inhibitory activities with IC 50 values that ranged from approximately 6.5 to 33 μM.