A new 9,11-secosterol from the soft coral Sinularia granosa.
Chemical investigations on the EtOAc-soluble fractions from the EtOH extract of Formosa soft coral afforded a new 9,11-secosteroid, 8αH-3β,11-dihydroxy-5α,6α-expoxy-24-methylene-9,11-secocholestan-9-one (1), along with one known steroid 3β,11-dihydroxy-5β,6β-expoxy-24-methylene-9,11-secocholestan-9-one (2) from Sinularia granosa. The structure of the new metabolite was elucidated on the basis of extensive spectroscopic analysis and by comparison of their NMR data with the known compounds, including 2. Both 1 and 2 were shown to significantly inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase protein, and 1 also was found to effectively reduce the level of cyclooxygenase-2 protein, in lipopolysaccharide-stimulated RAW264.7 macrophage cells at 10 μM. Furthermore, cytotoxic activity of 1 and 2 toward a limited panel of cancer cell lines was also discovered.
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, ROC.
Chiung-Yao
CY
Huang
Jui-Hsin
JH
Su
Chang-Yih
CY
Duh
Bo-Wei
BW
Chen
Zhi-Hong
ZH
Wen
Yao-Haur
YH
Kuo
Jyh-Horng
JH
Sheu
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D051546:Cyclooxygenase 2 / Q000737:chemistry / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D012632:Secosteroids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity
C575712:8H-3,11-dihydroxy-5,6-expoxy-24-methylene-9,11-secocholestan-9-one; D000970:Antineoplastic Agents; D012632:Secosteroids; D013256:Steroids; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2