Anti-inflammatory cyclopeptides from exocarps of sugar-apples.
Two new cyclic peptides, fanlizhicyclopeptide A, cyclo(Pro(1)-Pro(2)-Tyr(3)-Leu(4)-Pro(5)-Gly(6)-Val(7)) (1), and fanlizhicyclopeptide B, cyclo(Pro(1)-Ile(2)-Tyr(3)-Ala(4)-Gly(5)) (2), were isolated along with six known kaurane diterpenoids and a known clovane sesquiterpene from the exocarps of sugar-apples, the fruit of Annona squamosa. Their structures were elucidated by ESI MS/MS experiments, 1D and 2D NMR data and chemical degradation. In the anti-inflammatory assay, both 1 and 2 showed in vitro inhibitory effects on the production of pro-inflammatory cytokines, TNF-α and IL-6, in LPS-stimulated RAW 264.7 macrophages.
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
Ping
P
Wu
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
Min
M
Wu
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
Liangxiong
L
Xu
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
Haihui
H
Xie
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China. Electronic address: wxy@scbg.ac.cn.
Xiaoyi
X
Wei
D000818:Animals; D031041:Annona / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D015850:Interleukin-6 / Q000276:immunology; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D010449:Peptide Mapping; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D014409:Tumor Necrosis Factor-alpha / Q000276:immunology
D000893:Anti-Inflammatory Agents; D015850:Interleukin-6; D010456:Peptides, Cyclic; D010936:Plant Extracts; D014409:Tumor Necrosis Factor-alpha
Annona squamosa; Anti-inflammatory activity; Cyclopeptides; Fanlizhicyclopeptides; Sugar-apple