Structure and absolute stereochemistry of syphonoside, a unique macrocyclic glycoterpenoid from marine organisms.
The glycoterpenoid syphonoside (1) is the main secondary metabolite of both the marine mollusk Syphonota geographica and the sea-grass Halophila stipulacea, two Indo-Pacific species migrated to the Mediterranean Sea through the Suez Canal. The structure and the absolute stereochemistry of 1, which displays unique structural features, has been accomplished by using a combination of spectroscopic techniques, degradation reactions, and conformational analysis methods. Compound 1 was able to inhibit high density induced apoptosis in a number of human and murine carcinoma cell lines.
Gavagnin
Margherita
M
Istituto di Chimica Biomolecolare, CNR, Via Campi Flegrei 34, 80078 Pozzuoli (Naples), Italy. mgavagnin@icmib.na.cnr.it
Carbone
Marianna
M
Amodeo
Pietro
P
Mollo
Ernesto
E
Vitale
Rosa Maria
RM
Roussis
Vassilios
V
Cimino
Guido
G
D000818:Animals; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D047028:Macrocyclic Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D006109:Poaceae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
D047028:Macrocyclic Compounds; D013729:Terpenes; C522937:syphonoside