Jorunnamycins A-C, new stabilized renieramycin-type bistetrahydroisoquinolines isolated from the Thai nudibranch Jorunna funebris.
Jorunnamycins A-C (1a-c), three stabilized renieramycin-type bistetrahydroisoquinolines, were isolated from the mantles, the visceral organs, and the egg ribbons of the Thai nudibranch Jorunna funebris that was pretreated with potassium cyanide (KCN), along with five known compounds, renieramycins M (2m), N (2n), O (2o), and Q (2q) and mimosamycin (3). The structures of 1a-c were elucidated from spectroscopic data and by chemical conversion of renieramycin M (2m) into 1c via 1a. The chemical stability and the oxidative degradation generating simple isoquinoline alkaloids of a carbinolamine analog 1d, which was easily prepared by reacting 1c with silver nitrate in aqueous acetonitrile, are discussed. The results of cytotoxicity studies are also presented.
Charupant
Kornvika
K
Bioactive Marine Natural Products Chemistry Research Unit (BMNCU), Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand.
Suwanborirux
Khanit
K
Amnuoypol
Surattana
S
Saito
Emi
E
Kubo
Akinori
A
Saito
Naoki
N
D000818:Animals; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D007546:Isoquinolines