Terpenoid and steroid constituents of the Indian ocean soft coral Sinularia maxima

Diterpenoids from the Soft Coral <i>Sinularia maxima</i> and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells

“…15) Compound 1 was obtained as a colorless oil. Its molecular formula, C 22 H 28 O 8 (nine degrees of unsaturation), was determined by a pseudo-molecular ion peak at m/z 443.16819 [M+ Na] + using Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS).…”

Clionasterol: A Potent Inhibitor of Complement Component C1

“…Acetylation of clionasterol (1a, 30 mg) with Ac 2 O/Py followed by a usual work-up gave white crystals of clionasterol monoacetate (1b, 26 mg). The structures of 1a and 2 were elucidated by 1 H-and 13 C-NMR spectrometry and by comparison with the literature [2], [5], [7]. The optical rotation values were as follow: clionasterol (1a) [a] D 20 : ±13.508…”

“…This is the first report of anticomplementary activity of marine sterols. The structures of 1a and 2 were established by comparison of their MS, 1 H-, 13 C-NMR and rotation data with those of the authentic sample [4], as well as with those previously reported [3], [5].The effects of 1a, 1b, 2 and 3 on the CP and AP of human complement activation are summarized in Table 1. All the sterols studied Abstract Clionasterol (1a), clionasterol monoacetate (1b) and 5a,8a-epidioxy-24a-ethylcholest-6-en-3-ol (2), isolated from the marine sponge Xestospongia exigua, and b-sitosterol (3) were tested for their influence on the classical (CP) and alternative (AP) pathways of activation of the human complement system in vitro.…”

“…This is the first report of anticomplementary activity of marine sterols. The structures of 1a and 2 were established by comparison of their MS, 1 H-, 13 C-NMR and rotation data with those of the authentic sample [4], as well as with those previously reported [3], [5].…”

Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts

“…There are 10 known polycyclic furanobutenolide-derived cembranoids, including macrocycles BSK ( 6 ) 16 and verrillin ( 13 ), 31 polycycles intricarene ( 7 ), 17 rameswaralide ( 8 ), 18,19 havellockate ( 14 ), 32 and the closely related plumarellide ( 15 ), 1,23,33 plumarellate ( 16 ), 1,23,33 mandapamate ( 17 ), 34 isomandapamate ( 18 ), 35 bishomoisomandapamate ( 19 ), 36 and confertdiate ( 20 , Figure 4). 37 Decorated by a variety of oxygenation states and patterns, these diterpenes display a variety of complex, highly compact, stereochemically dense architectures.…”