Sesquiterpenes from the Hainan Sponge Dysidea septosa.
Five new sesquiterpenes, named lingshuiolides A (1) and B (2), lingshuiperoxide (6), isodysetherin (10), and spirolingshuiolide (12), along with several known related analogues (7- 9, 11, and 13- 15), were isolated from the Hainan marine sponge Dysidea septosa. The structures of new compounds 1, 2, 6, 10, and 12 were determined by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds. The absolute configuration of lingshuiolide B (2) was established by using the modified Mosher's method. Spirolingshuiolide (12) represents the first example of a sesquiterpene with a rearranged drimane skeleton. Compounds 7- 9 and 15 exhibited significant inhibitory activity against human protein tyrosine phosphatase 1B (hPTP1B), an enzyme involved in the regulation of insulin signaling. In particular, 15 showed the most potent effect, with an IC 50 value of 1.9 microg/mL.
Huang
Xiao-Chun
XC
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
Li
Jia
J
Li
Zhen-Yu
ZY
Shi
Lei
L
Guo
Yue-Wei
YW
D000818:Animals; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization
D004791:Enzyme Inhibitors; D012717:Sesquiterpenes; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1