An Antibacterial 9,11-Secosterol from a Marine Sponge Ircinia sp.

Aplysiasecosterols B and C: two new 9,11-secosteroids with a cis -fused 1,4-quinone structure from the sea hare Aplysia kurodai

“…Recently, two 9,11-secosteroids that are structurally-related to aplysiasecosterols B and C were isolated from the Korean marine sponge Ircinia sp., which have a trans-fused 3β,5α-dihydroxy-1,4-quinone moiety. 7,3 As noted by Yang et al, 13 C NMR data for the trans-fused compound (δC3 66.6 and δC5 80.5) were close to those of a 3β,5α-dihydroxy-6-one steroid derivative (δC3 66.8 and δC5 80.3). 11 Similarly, 13 C NMR data for aplysiasecosterols B (2) and C (3) (δC3 65.1 and δC5 81.0) coincided with those for a 3β,5β-dihydroxy-6-one steroid derivative (δC3 65.5 and δC5 81.9), rather than a 5α isomer.…”

“…S1). [6][7][8][9] To establish the relative stereochemistry of the cyclohexane ring part for aplysiasecosterols B (2) and C (3), MTPA esters were then prepared (Scheme 1). While 3,11,24-tris-(S) and (R)-MTPA esters 4 were tentatively obtained from 2 in analytically pure form, the C-3 ester moiety was selectively hydrolyzed at -30 °C for less than one week to give 11,24-bis-(S) and (R)-MTPA esters 5.…”

A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.

“…We previously isolated a secosterol (2) that was structurally related to compound 1 (Yang et al 2014). As the previously identified steroid (2) exhibited antibacterial activities, compound 1 was also investigated for its antibacterial activity against seven pathogens (Table 2).…”

“…During the chemical and pharmacological investigation on the extract of Korean marine invertebrates, anti-bacterial activity was observed from an extract of Ircinia sp., of which a 9,11-secosterol was identified as an anti-bacterial component (Yang et al 2014). An intensive chemical investigation of the residual extract led us to the purification of a new 9,11-secosterol.…”

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

“…[53]; "unprecedented" 9,11 secosterols with "the 2-ene-1,4-dione moiety" (43,44) from the Korean marine sponge Ircinia sp. [54,55]; two polybrominated diphenyl ethers (45,46) from the Papuan New Guinea marine sponge Lendenfeldia dendyi and the soft coral Sinularia dura [56]; a novel polyketide lindgomycin (47) from the Baltic sea and Arctic Lindgomycetaceae family marine fungal strains KF970 and LF327 [57]; a novel cycloheptadepsipeptide marfomycin D (48), isolated from a South China marine Streptomyces drozdowiczii SCSIO 10141 [58]; an glycohexadepsipeptide-polyketide mollemycin A (49) from an Australian marine-derived Streptomyces sp. strain CMB-M0244 [59]; a novel laurene-type sesquiterpene neolaurene (50) from a Bornean marine alga Laurencia nangii [60]; a new polyketide and ambuic acid analogue penicyclone A (51), isolated form an extract from a deep-sea derived fungus Penicillium sp.…”