A Sterol and Spiroditerpenoids from a Penicillium sp. Isolated from a Deep Sea Sediment Sample

Abstract

A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I–K (2–4), and the known breviones (5–8), were isolated from the crude extract of a Penicillium sp. obtained from a deep sea sediment sample that was collected at a depth of 5115 m. The structures of 1–4 were elucidated primarily by NMR experiments, and 1 was further confirmed by X-ray crystallography. The absolute configurations of 2 and 3 were deduced by comparison of their CD spectra with those of the model compounds. Compounds 2 and 5 showed significant cytotoxicity against MCF-7 cells, which is comparable to the positive control cisplatin.

Deep-Sea Fungi Could Be the New Arsenal for Bioactive Molecules

“…Breviones (96-99), isolated from the deepest sediment-derived fungus Penicillium sp. (5115 m depth), displayed diverse activities, such as cytotoxicity against HeLa, MCF-7, and A549 cells with IC50 values of 7.44 to 32.5 µ M, respectively, and growth inhibition of HIV-1 with EC50 value of 14.7 µ M against C8166 cells [22,38]. Compounds 100-110 showed antibiotic and inhibition activities against silkworm, while 20-nor-isopimarane diterpenoids, including aspewentins (114-118), asperethers (121-125), asperoloids (119-120), and compounds 130 and 131, showed cytotoxic activities [33,[39][40][41][42][43][44][45].…”

“…(132-151; Figure 7). Penipacids A-F (134-139), polyoxygenated sterol (132), dicitrinone B (133) and butanolide A (140), which were isolated from deep-sea sediments-derived Penicillium spp., showed cytotoxic activities against RKO, MCF-7, PTP1B and A375 cancer cell lines with IC 50 values of 8.4-28.4 µM [38,42,48,49]. Similarly, four isocoumarins, penicillisocoumarin A-D (147-150), and an isocoumarins aspergillumarin B (151) were also isolated from Penicillium which showed weak antibacterial activities [33].…”

Recent advances in deep-sea natural products

“…The compounds (136)(137) exhibited cytotoxicity against HeLa cells with IC 50 values between 80 and 500 nM. 176 Four new meroterpenes, alisiaquinones A-C (142-144) and alisiaquinol (145), were isolated from a New Caledonian deepwater sponge, Xestospongia sp., collected by trawling on a deep-sea mount between depths of 250 and 400 m in the South of New Caledonia, Norfolk Rise. 175 Earlier syntheses had established the geometry of the central double bond and the absolute conguration of the chiral centres in (+)and (À)-duryne.…”

Structure–activity relationship studies of the phytotoxic properties of the diterpenic moiety of breviones

“…2). 11,12 The first compounds reported from P. brevicompactum were breviones A to E (8 to 12), followed by breviones F to H (13 to 15) 13 and breviones I to K (16 to 18), 14 which were isolated from a Penicillium spp. strand extracted from samples of deep seafloor sediments collected at 5115 m depth in the eastern Pacific Ocean (Fig.…”

“…Besides their unique structure, breviones are also characterised by their phytotoxicity [breviones E (12) and C (10)], 11 cytotoxity [breviones F to H (13 to 15)] and anti-HIV-1 13 activity [breviones A (8) and I (16)]. 14 In view of the great potential of these compounds, the authors have undertaken the synthesis of brevione and abeo-brevione analogues, starting in the first phase with their western half. 19 The present paper sets out the results of a structure-activity relationship (SAR) study with 25 compounds having a decalin (19 to 22), saturated phenanthrene-like (23 to 34) and expanded phenanthrene-like (35 to 43) backbone (Fig.…”