Extending the Record of Meroditerpenes from Cacospongia Marine Sponges

Abstract

A new meroditerpene, (+)-isojaspic acid (1), along with two known meroditerpenes, cacospongin D (2) and jaspaquinol (3), have been isolated from a marine sponge Cacospongia. Comprehensive taxonomic identification distinguished this Cacospongia apart from morphologically similar Psammocinia. The absolute stereochemistry of 1 was elucidated on the basis of extensive 1D and 2D NMR techniques and analysis of the optical rotation versus (+)-zonarol (8), (+)-isozonarol (9), (-)-dactylosponol (10), and (+)-hyatellaquinone (11). Furthermore, bioactivity evaluation showed that the meroditerpenes isolated significantly inhibited Staphylococcus epidermidis.

Extraction and Characterization of Bioactive Compounds with Health Benefits from Marine Resources: Macro and Micro Algae, Cyanobacteria, and Invertebrates

“…The PLE extraction has been carried out using three independent runs of three solvents, hexane, dichloromethane, and methanol, obtaining the highest percentage yield of the total organic extract in the fi rst extraction. Meroditerpenes, such as isojaspic acid, cacospongin, and jaspquinol, with antimicrobial properties against Staphylococcus epidermidis have been isolated from Cacospongia marine sponge (Rubio et al 2007 ) whereas sesquiterpenes, such as aignopsanoic acid A and methyl aignopsanoate A, which are moderately active against the parasite responsible for sleeping sickness, along with isoaignopsanoic acid have been obtained from Cacospongia mudofi jiensis (Johnson et al 2009 ) . In a recent work, the utility of methanol partitioning and PLE to extract 12 bioactive natural products (including isojaspic acid and aignopsanpic acid A) from fi ve marine sponges has been investigated.…”

Marine Sponges: Potential Sources of New Antimicrobial Drugs

“…The meroditerpenes, isojaspic acid, cacospongin D and jaspaquinol have been isolated from a sponge of the genus Cacospongia. The bioactivity evaluation showed that the meroditerpenes isolated significantly inhibited Staphylococcus epidermidis [90].…”

Structures and Cytotoxic Evaluation of New and Known Acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge

“…were collected from America Samoa and immediately preserved and stored according to our standard laboratory procedures. 14 A portion of the specimen (11.1 g) was worked up using a recently validated accelerated solvent extraction (ASE) protocol. 15 Four crude solvent extract fractions were obtained and included a water wash (extract code XFW: 2.3 g), followed by organic solvent fractions of: hexanes (extract code XFH: 0.025 g), dichloromethane (extract code XFD: 0.3 g) and methanol (extract code XFM: 1.5 g) (Scheme S1; S denotes Supporting Information).…”