One stain-many compounds (OSMAC) method for production of phenolic compounds using Camarops sp., an endophytic fungus from Alibertia macrophylla (Rubiaceae)

Abstract

Camarops sp., AN ENDOPHYTIC FUNGUS FROM Alibertia macrophylla (RUBIACEAE). Seven phenolic derivatives including n-hexyl-3,4-dihydroxybenzoate (6) and n-octyl-3,4-dihydroxybenzoate (7) were produced using Camarops sp. via the one strain-many compounds (OSMAC) approach. Their structures were determined using 2D NMR and ESI-MS spectra and were compared with works reported in the literature. This paper deals with the first report of these compounds in Camarops sp.

Cultivable marine fungi from the Arctic Archipelago of Svalbard and their antibacterial activity

“…Bioactivity can be dependent on many factors such as culture medium, temperature, water activity, light, pH, salt content, culture time, and presence of small molecules (Sepcic et al 2011 ; Hewage et al 2014 ; Gubiani et al 2016 ). Our results illustrate medium-dependent changes of bioactivity.…”

Hyposterolactone A, a 3α‐Hydroxy Steroidal Lactone from the Deep‐Sea‐Derived FungusHypocreasp. ZEN14

“…By comparison of the spectroscopic data with those reported in literature, 25 known compounds were identified as stigmasta-7,22-diene-3β,5α,6α-triol (2), [22] 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (3), [27] 3β,5α,9α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (4), [28] and ergosterol peroxide (5), [29] alternariol 4-methyl ether (6), [30] alternariol (7), [30] 4-hydroxyalternariol (8), [31] porricacid D (9), [32] chrysophanol dimethyl ether (10), [33] α-cuparenol (11), [34] β-cuparenol (12), [34] p-hydroxybenzaldehyde (13), [35] 2-(4-hydroxyphenyl)-2oxoethanol( 14), [36] methyl 2-hydroxy-3-(4hydroxyphenyl)propanoate ( 15), [37] tyrosol ( 16), [38] jasmogin A (17), [39] cucurbic acid (18), [40] 2-hydroxybenzeneacetic acid ( 19), [41] N-(2-phenylethyl)octanamide (20), [42] (3S,6S)-3,6-dibenzylpiperazine-2,5-dione ( 21), [43] 1-(3-indolyl)-2R,3-dihydroxypropan-1-one ( 22), [44] p-hydroxyphenyllactic acid ( 23), [45] N-phenethyl-2-phenylacetamide ( 24), [46] felinone B (25), [47] and linoleic acid (26). [48] Since the crude extract of Hypocrea sp.…”

Natural Products from Endophytic Fungi Associated with Rubiaceae Species

“…-dihydroxybut-3-enyl)-5H-furan-2-one (21) and (2E,4R)-2,4dimethylnon-2-enoic acid (22); seven phenolic derivatives: p-hydroxyphenyllactic acid (23), phenyllactic acid (24), p-hydroxybenzoic acid (25), p-hydroxybenzaldehyde (26), n-butyl-3,4dihydroxybenzoate (27), n-hexyl-3,4-dihydroxybenzoate (28) and n-octyl-3,4-dihydroxybenzoate (29); and the known compound (2E,4S)-2,4-dimethyloct-2-enoic acid (30) ( Figure 5) [102]. The continuing search for endophytes associated on A. macrophylla led to five new eremophilane sesquiterpenes: xylarenones C-G (14)(15)(16)(17)(18) isolated from solid cultures of Camarops sp.…”

“…-dihydroxybut-3-enyl)-5H-furan-2-one (21) and (2E,4R)-2,4dimethylnon-2-enoic acid (22); seven phenolic derivatives: p-hydroxyphenyllactic acid (23), phenyllactic acid (24), p-hydroxybenzoic acid (25), p-hydroxybenzaldehyde (26), n-butyl-3,4dihydroxybenzoate (27), n-hexyl-3,4-dihydroxybenzoate (28) and n-octyl-3,4-dihydroxybenzoate (29); and the known compound (2E,4S)-2,4-dimethyloct-2-enoic acid (30) ( Figure 5) [102]. Extracts of solid cultures of Sporormiella minimoides (Sporormiaceae), isolated as an endophytic fungus from leaves Hintonia latiflora collected in Mexico, yielded five polyketides, 3,6-dimethoxy-8methyl-1H,6Hbenzo[de]isochromene-1,9-dione (31), 3-hydroxy-1,6,10-trimethoxy-8-methyl-1H,3Hbenzo[de]isochromen-9-one (32), 5-hydroxy-2,7-dimethoxy-8-methylnaphthoquinone (33), minimoidiones A (34) and B (35), along with four known compounds: corymbiferone (36), ziganein (37), brocaenol B (38) and preussochromone C (39) [103][104][105].…”

“…(Boliniaceae) [ 100 , 101 ]. This fungus was also able to produce two rearranged sesquiterpenes: 3,5,9-trihydroxy presilphiperfolane ( 19 ) and 4-deoxy-10-oxodihydrobotrydial ( 20 ); two branched polyketides: 4-((E)-pent-1-enyl)-3-((1’S,2’S)-1’,2’-dihydroxybut-3-enyl)-5H-furan-2-one ( 21 ) and (2E,4R)-2,4-dimethylnon-2-enoic acid ( 22 ); seven phenolic derivatives: p -hydroxyphenyllactic acid ( 23 ), phenyllactic acid ( 24 ), p -hydroxybenzoic acid ( 25 ), p -hydroxybenzaldehyde ( 26 ), n -butyl-3,4- dihydroxybenzoate ( 27 ), n -hexyl-3,4-dihydroxybenzoate ( 28 ) and n -octyl-3,4-dihydroxybenzoate ( 29 ); and the known compound (2E,4S)-2,4- dimethyloct-2-enoic acid ( 30 ) ( Figure 5 ) [ 102 ].…”