New isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp.
Two new renieramycin-type bistetrahydroisoquinolinequinone alkaloids, fennebricins A (1) and B (5), and one new isoquinolinequinone alkaloid, N-formyl-1,2-dihydrorenierol (7), were isolated from the skin of the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp., together with eight known metabolites, including three bistetrahydroisoquinolinequinones (2-4) and five isoquinolinequinones (8-12). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison with data for related known compounds. All the metabolites except for 7 occurred simultaneously in the two animals, supporting recent ecological studies that the nudibranch J. funebris preys on the sponge of the genus Xestospongia.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China.
Wen-Fei
WF
He
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China.
Yan
Y
Li
School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, PR China.
Mei-Tang
MT
Feng
Istituto di Chimica Biomolecolare (ICB), CNR, Via Campi Flegrei 34, 80078 Pozzuoli, Naples, Italy.
Margherita
M
Gavagnin
Istituto di Chimica Biomolecolare (ICB), CNR, Via Campi Flegrei 34, 80078 Pozzuoli, Naples, Italy.
Ernesto
E
Mollo
School of Pharmacy, Nanchang University, 461 Bayi Road, Nanchang 330006, PR China. Electronic address: maoshuichun@ncu.edu.cn.
Shui-Chun
SC
Mao
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China. Electronic address: ywguo@mail.shcnc.ac.cn.
Yue-Wei
YW
Guo
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D049851:Gastropoda / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry / Q000302:isolation & purification; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification*; D044005:Tetrahydroisoquinolines / Q000737:chemistry / Q000302:isolation & purification*; D047131:Xestospongia / Q000737:chemistry*
D000470:Alkaloids; D007546:Isoquinolines; C000596887:N-formyl-1,2-dihydrorenierol; D015363:Quinolones; D011809:Quinones; D044005:Tetrahydroisoquinolines; C000596885:fennebricin A; C000596886:fennebricin B
Isoquinolinequinones; Jorunna funebris; Renieramycin-type alkaloids; Xestospongia sp.