Dehydroconicasterol and Aurantoic Acid, a Chlorinated Polyene Derivative, from the Indonesian Sponge Theonella swinhoei

Abstract

The chlorinated polyene aurantoic acid (1) and the 4-methylene sterol dehydroconicasterol (2) were isolated from the Indonesian sponge Theonella swinhoei, and their structures were elucidated by interpretation of spectroscopic data. Aurantoic acid is a unique member in the class of naturally occurring conjugated polyene derivatives, while dehydroconicasterol is the likely biogenetic precursor of the major Theonella 4-methylene sterols.

Chromatography with silver nitrate: part 2

“…37 A further example requiring SNIS was that of dehydroconicasterol (31), which was isolated from the Indonesian sponge Theonella swinhoei as reported by Taglialatela-Scafati. 38,39 Figure 9…”

“…Overall a mixed stationary phase consisting of a phenyl-cation exchange, charged with silver ions, facilitated useful separation of the capsaicinoids, a method that was later refined by the same group. 41 In related work, not only in chemical structure but also in chromatographic technique, Liang Andersson 43 prepared silver (I)-mercaptopropano silica gel and evaluated its performance against crude oil and found that it allows an efficient group separation of polycyclic sulfur containing aromatic compounds (36)(37)(38)(39)(40)(41)(42). Size played an important role and separation fell into three bands (top, middle and below), with the most abundant having a single substituent containing a variety of unidentified eight carbon (C 8 ) atom isomers ( Figure 11).…”

Beyond Bile Acids: Targeting Farnesoid X Receptor (FXR) with Natural and Synthetic Ligands

“…A number of 4-methylen-polyhydroxilated sterols isolated from Theonella swinhoei, a marine sponge collected at Solomon Islands, showed to be ligand of both FXR and Pregnane X Receptor (PXR) [57][58][59][60][61][62][63][64][65][66][67]. Among these, Theonellasterol G (19) showed antagonist activity on FXR transactivation in presence of CDCA (2) increasing the expression of OST , SULT2A1, and MDR1, as well as PXR activity (Fig.…”

Natural Products from the Lithistida: A Review of the Literature since 2000

“…During an LC-MS screening study by the Crews group to predict which phenotypes of Theonella swinhoei contain swinholide A or motuporin, they isolated another series of compounds called the isomotuporins A–D ( 30 – 33 ) (Figure 7) [30,31,32,33,34,35]. The loss of the methoxy group in the 3-amino-9-methoxy-10-phenyl-2,6,8-trimethyldeca-4,6-dienoic acid (ADDA) residue in isomotuporin D ( 33 ) is the first report of that variation from a natural source.…”

“…They were also inactive in an anti-HIV assay when tested at concentrations of 20, 15, and 12.8 µM, respectively. Aurantoic acid ( 116 ) is a chlorinated polyene moiety that is evident in the structures of the 113 – 115 (Figure 31) [30]. 116 was isolated from T. swinhoei collected at a depth of 20–50 m in Bunaken Marine Park, North Sulawesi, Indonesia along with dehydroconicasterol ( 120 , discussed later).…”