New Anti-Inflammatory 9,11-Secosterols with a Rare Tricyclo[5,2,1,1]decane Ring from a Formosan Gorgonian Pinnigorgia sp.

Abstract

Pinnigorgiols D (1) and E (2), two new 9,11-secosterols with a rearranged carbon skeleton, were isolated from a Taiwan gorgonian Pinnigorgia sp. The structures of these two compounds were elucidated on the basis of spectroscopic methods and were proven to possess a tricyclo[5,2,1,1]decane ring. The new secosterols 1 and 2 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.

New Marine Sterols from a Gorgonian Pinnigorgia sp.

“…The sterol analogues isolated from Pinnigorgia sp. were found to display interesting anti-inflammatory activities [ 1 , 2 , 3 , 5 , 6 ]. Based on these findings, the anti-inflammatory testing of sterols 1 and 2 were assayed and 1 showed inhibitory effects on the generation of superoxide anions and the release of elastase, respectively, by human neutrophils ( Table 3 ).…”

“…Gorgonian corals belonging to the genus Pinnigorgia have proven to be a rich source of sterols with unusual structural features [ 1 , 2 , 3 , 4 , 5 , 6 ]. In continuation of our effort to discover new natural products of this organism, its ethyl acetate extract exhibited anti-inflammatory activities by inhibiting the expression of superoxide anions and elastase by human neutrophils with IC 50 values of 1.89 and 1.57 μg/mL, respectively.…”

Marine Pharmacology in 2016–2017: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…SCSIOW2 [191]; a known alkaloid echinulin (170) iso-lated from an Antarctic Ross Sea "unidentified" marine organism-derived Aspergillus sp. SF-5976 [192]; a novel halogenated 5α-iodozoanthenamine (171) isolated from the colorful Taiwanese zoanthid Zoanthus kuroshio [193]; two novel steroids klyflaccisteroid J and K (172, 173) isolated from the Taiwanese soft coral Klyxum flaccidum [194,195]; a known lobane diterpenoid (174) isolated from a Taiwanese soft coral Lobophytum varium [196]; two new bioactive steroids petasitosterones B and C (175, 176) isolated from the Taiwanese soft coral Umbellulifera petasites [197]; two new sterols (177,178) [198], and novel 9,11-secosterols pinnigorgiol A (179) [199], pinnigorgiol E (180) [200], pinnisterol A (181) [201] and pinnisterol H (182) [202] isolated from the Taiwanese gorgonian coral Pinnigorgia sp. ; a new pyrrole oligoglycoside plancipyrroside B (183) isolated from an extract of the Vietnamese starfish Acanthaster planci [203]; a novel steroidal glycoside protolinckioside A (184) isolated from an Arabian sea starfish Protoreaster lincki [204]; a known terpenoid sarcophytonolide O (185) isolated from the Chinese soft coral Lobophytum crassum [205]; two novel norcembranoids sinulerectols A and B (186, 187) isolated from South China Sea soft coral Sinularia erecta [206]; a known terpenoid sinubrasolide A (188) and the steroid sinubrasone D (189) isolated from the Taiwanese "cultivation pool" soft coral Sinularia brassica [207,208]; and the novel diterpenes uprolides N, O and P (190)(191)(192) isolated from the Panamanian octocoral Eunicea succinea [209].…”

The Bioactive Extract of Pinnigorgia sp. Induces Apoptosis of Hepatic Stellate Cells via ROS-ERK/JNK-Caspase-3 Signaling

“…Recently, various natural compounds from a gorgonian coral Pinnigorgia sp. have been shown to exhibit anti-inflammatory potential in human neutrophils [ 11 , 12 , 13 , 14 , 15 ]. In addition, the coralline extract from Pinnigorgia sp.…”