New cyclic peptides from the seeds of Annona squamosa L. and their anti-inflammatory activities.
Two new cyclic peptides, cyclosquamosin H ( 1) and I ( 2), together with six known cyclic peptides, squamin A ( 3), squamin B ( 4), cyclosquamosin A ( 6), cyclosquamosin D ( 7), cyclosquamosin E ( 8), and cherimolacyclopeptide B ( 9), were isolated from the seeds of Annona squamosa. All structures were confirmed by 2D nuclear magnetic resonance, chemical evidence, and electrospray ionization-mass spectromotry/mass spectrometry (ESI-MS/MS). Compound 9 was isolated from this plant for the first time. In the anti-inflammatory assay, compound 7 showed an inhibitory effect on the production of pro-inflammatory cytokines within lipopolysaccharide and Pam3Cys-stimulated J774A.1 macrophages.
Yang
Yu-Liang
YL
Graduate Institute of Natural Products, School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Hua
Kuo-Feng
KF
Chuang
Pei-Hsuan
PH
Wu
Shih-Hsiung
SH
Wu
Kuen-Yuh
KY
Chang
Fang-Rong
FR
Wu
Yang-Chang
YC
D000818:Animals; D031041:Annona / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D002460:Cell Line; D016207:Cytokines / Q000096:biosynthesis; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012639:Seeds / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
D000893:Anti-Inflammatory Agents; D016207:Cytokines; D010456:Peptides, Cyclic; C527767:cyclosquamosin D