Abstract
The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus oryzae, collected from Red Sea marine sediments. The structure of asperorlactone (1) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from Aspergillus fungi and, more in general, from ascomycetes. Asperorlactone (1) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC50 values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model.
Highlights
The marine environment is an unsurpassed casket of chemodiversity and a prolific source of biologically active compounds with potential medicinal applications [1]
Sponges and tunicates are undoubtedly the most intensely studied marine organisms, but it is clear that marine microbes, isolated from sediments or from symbiotic plants or invertebrates, constitute a rich source for secondary metabolites
Tohfutsh,ethfiersEtCwDitshpethcteraexfopreRri-m1 eanntdalSE-1CwDesrepeocbttrauimnedal(lFoiwguedreu4s).aTchoenefixdteenn-t saivsseigsnimmielanrtitoyf tohfethabesfoirlusttewciothnfitghuereaxtipoenriomf eansptaelroErClaDctospneecatrsu5mR.allowed us a confident assignTmheenistoolfatthioenabosfoalsupteercoornlaficgtounraeti(o1n), oafsawspeellroarslaocftothnee raesla5tRe.d echinolactone D (2), is of great relevance because, to our knowledge, this is the first report of illudalane-type sesquiterpenes from an ascomycete (A. oryzae), since this class of metabolites has, until now, been found exclusively in basidiomycetes
Summary
The marine environment is an unsurpassed casket of chemodiversity and a prolific source of biologically active compounds with potential medicinal applications [1]. In the last 50 years, scientists all over the world have dedicated their efforts to uncover the potential of marine metabolites, succeeding in the isolation of thousands of natural products with peculiar architectures and interesting bioactivities [2]. In this context, terrestrial fungi are more explored, in comparison to their marine counterparts, a sucropnrtiesxint,ganltuhmoubgehr otefrsrtersutrcitaulrfaullnygui anriequmeocroemexppoluonredds, hinavceombepeanriissoonlattoedtheir marine counfrom fungi livingteinrpmaratrsi,naeshuarpbritiasitns g[6n]u. Tohfutsh,ethfiersEtCwDitshpethcteraexfopreRri-m1 eanntdalSE-1CwDesrepeocbttrauimnedal(lFoiwguedreu4s).aTchoenefixdteenn-t saivsseigsnimmielanrtitoyf tohfethabesfoirlusttewciothnfitghuereaxtipoenriomf eansptaelroErClaDctospneecatrsu5mR.allowed us a confident assignTmheenistoolfatthioenabosfoalsupteercoornlaficgtounraeti(o1n), oafsawspeellroarslaocftothnee raesla5tRe.d echinolactone D (2), is of great relevance because, to our knowledge, this is the first report of illudalane-type sesquiterpenes from an ascomycete (A. oryzae), since this class of metabolites has, until now, been found exclusively in basidiomycetes. The isolation of asperorlactone (1), as well as of the related echinolactone D (2), is of FFgiigrgueuaretre4r.e4El.exEvpaxernpimceereinbmteaelcnEauCtasDleEc,utCrovDeouocfurarksvpneorowrfllaaecsdtpogneeer,o(trrheldias)caitsnodnthecea(lcrfuierldsat)teardenEpdCoDcrtacloucfruvilelalsutfedodraRlEa-C1neD(b-ltacycupkr)evseessf-or R a(qnbudlaiStce-k1r)p(gaernneedens)S.f-r1om(graenenas).comycete (A. oryzae), since this class of metabolites has, until now, been found exclusively in basidiomycetes. Colorless oil; [ α]2D3−19.8 (c 0.6, MeOH); UV λmax (MeOH) nm (log ε): 230 (4.6); ECD λmax (MeOH) nm (∆ε): 238 (+ 9.6), 265 (−4.8); 1H NMR (700 MHz, CD3OD), and 13C NMR (175 MHz, CD3OD); see Table 1; ESIMS m/z 269.1150 [M + Na]+ (calc. for C15H18 O3 Na m/z 269.1154)
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