Triproamide and Pemukainalides, Cyclic Depsipeptides from the Marine Cyanobacterium Symploca hydnoides

• Main Authors: Ma Yadanar Phyo (8037719), Jun Xian Goh (8037728), Lik Tong Tan (2248375)
• Format: Other Non-Article Part of Journal/Newspaper
• Language: unknown
• Published: 2022
• Subjects: Biochemistry; Ecology; Cancer; Environmental Sciences not elsewhere classified; Biological Sciences not elsewhere classified; Chemical Sciences not elsewhere classified; two new analogues; symploca hydnoides </; phase hplc analyses; mass spectrometric data; 1 (< b; new cyclic depsipeptide; b (< b; known molecule kulokainalide; 50 </ sub; triproamide (< b; (< b; cyclic depsipeptides; relative configurations; rare 4; polar vlc; planar structures; marine cyanobacterium; marfey ’; j -</; extracts prepared; extensive nmr; elucidated based; dolastatin 16; determined utilizing; derived fraction; based configuration; amino acid; 6 μm; DML
• Online Access: https://doi.org/10.1021/acs.jnatprod.1c00996.s001

A new cyclic depsipeptide, triproamide ( 1 ), containing the rare 4-phenylvaline (dolaphenvaline, Dpv) and a β-amino acid, dolamethylleucine (Dml), originally found in dolastatin 16, was isolated from the polar VLC-derived fraction of the extracts prepared from the marine cyanobacterium Symploca hydnoides . Triproamide ( 1 ) was isolated along with the known molecule kulokainalide-1 ( 2 ), as well as its two new analogues, pemukainalides A ( 3 ) and B ( 4 ). Their planar structures were elucidated based on extensive NMR and mass spectrometric data. The absolute and relative configurations of the compounds were determined utilizing a combination of Marfey’s method, J- based configuration, and chiral-phase HPLC analyses. Kulokainalide-1 ( 2 ) and pemukainalide A ( 3 ) exhibited cytotoxicity against the MOLT-4 leukemia cell line with IC 50 values of 5.9 and 5.6 μM, respectively.