Meroterpenoids from a Tropical Dysidea sp. Sponge

Abstract

Six new meroterpenoids (1-6), along with arenarol (7), a known rearranged drimane sesquiterpene hydroquinone, were isolated from a Dysidea sp. sponge collected from the Federated States of Micronesia. On the basis of the results of combined spectroscopic analysis, compound 1 was determined to be the cyclic ether derivative of 7, whereas 2 and 3 were assigned as the corresponding sesquiterpene quinones containing taurine-derived substituents. Compounds 4-6 possess a novel tetracyclic skeleton formed by a direct linkage between the quinone and sesquiterpene moieties. The configurations of these new compounds were assigned on the basis of combined NOESY and ECD analysis. These compounds exhibited cytotoxic and antimicrobial activities and weak inhibition against Na(+)/K(+)-ATPase.

Regiodivergent Remote Arylation of Cycloalkanols to Dysideanone′s Fused Carbotetracycles and Its Bridged Isomers

“…However, in dysideanones, an oxidized arene moiety was connected to both A and B rings of the decalin system, forming a structurally distinct tetracyclic 6‐6‐6‐6 framework . On the other hand, the isomeric natural products, dysiherbols, which are built on 6‐6‐5‐6 fused carbacycles, contain three contiguous all‐carbon quaternary stereocenters. Installing the carbon‐aryl bond at C8 in the A‐ring, which is away from the heteroatom functionality, demands substantial synthetic challenges for the construction of dysideanone frameworks.…”

Marine Pharmacology in 2014–2015: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, Antiviral, and Anthelmintic Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…PSU-SP2/4 [42]; natural brominated furanones (25,26), isolated from the marine alga Delisea pulchra [43]; a novel meroterpenoid aureol B (27), isolated from the Micronesian Dysidea sp. sponge [44]; a novel meroterpenoid dysidinoid A (28), isolated from the South China sea sponge Dysidea sp. [45]; a terpenoid fuscoside E peracetate (29) and a lipid batyl alcohol (30), isolated from the Colombian soft coral Eunicea sp.…”

Gold(I)‐Catalyzed Synthesis of Indenes and Cyclopentadienes: Access to (±)‐Laurokamurene B and the Skeletons of the Cycloaurenones and Dysiherbols

“…[11] Similarly,cyclopentadienes are important substrates,m ainly as reactive diene components in the Diels-Alder reaction and as ligands in organometallic chemistry. [12] To illustrate the application of the new gold(I)-catalyzed (3+ +2) cycloaddition reactions in the context of natural product synthesis,wehave developed aroute for the construction of the tetracyclic carbon skeleton common to the cycloaurenones (8a-c) [13] and the dysiherbols (9a-c), [14] and at otal synthesis of (AE)-laurokamurene B( 10) [15] ( Figure 1). …”