The punaglandins: 10-chloroprostanoids from the octocoral Telesto riisei

Telesto riisei, an octocoral from Hawaii, produces nineteen highly functionalized prostanoids, the punaglandins, which are characterized by various oxygenation at C-5, -6, -7, and -12, and a 10-chloro-9-cyclopentenone moiety. The absolute stereochemistry of the 10-chloroprostanoids is epimeric to that of the Pacific marine prostanoids without halogen. The punaglandins have shown anti-inflammatory and antitumor activity. A synthetic 10-thiomethyl derivative enhances in vivo mineralization in human osteoblasts.