Marine-Derived Fungal Metabolites 32.3 Marine Organic Compounds 775
Part F | 32.3
lines, but had no effect on the viability of normal human
cell lines [32.121].
Acremonide (128, Fig. 32.9), one new phthalide
derivative and eight new isocoumarin derivatives, acremonones A–H (129–136) together with ten known
compounds were obtained from Acremonium sp. PSUMA70 isolated from a branch of the mangrove Rhizophora apiculata [32.122]. In the antifungal activity assay, some of the isolated compounds revealed
only moderate antifungal activity with MIC values of
32 g mL
1 when tested against Candida albicans and
C. neoformans, whereas against the latter the activity
was lower [32.122].
Two new hydroanthraquinone analogs, 4aepi-9˛-methoxydihydrodeoxybostrycin (137) and
10-deoxybostrycin (138), together with seven known
anthraquinone congeners were isolated from the
fungus Nigrospora sp. derived from an unidentified
sea anemone [32.123]. All isolated compounds were
evaluated in vitro for their antibacterial activity against
a panel of nine different bacterial strains. Among the
isolated compounds, 10-deoxybostrycin (138) and
3-acetyl-4-deoxybostrycin revealed the most promising
activities against Bacillus subtilis and B. cereus with
IC 50 values of 62:5 and 48:8 nM, respectively compared
to ciprofloxacin as a positive control with IC 50 values
of 31:2 and 1250 nM, respectively [32.123].
Chemical investigation of the cultural extract of
the marine-derived fungus Aspergillus sp. SCSIO F063
afforded seven new chlorinated anthraquinones (139–
145) related to averantin [32.124]. Interestingly, the
chlorinated anthraquinones were obtained upon using
sea salt-containing potato dextrose broth with the addition of sodium bromide to the broth. In the cytotoxicity (MTT) assay, 6-O-methyl-7-chloroaveratin (140)
displayed antiproliferative activity against three human tumor cell lines, SF-268, MCF-7, and NCI-H460,
with IC 50 values of 7:11, 6:64, and 7:42 M,
respectively [32.124].
Alterporriols K–M (146–148), three bianthraquinone derivatives, were reported for the first time
from extracts of the endophytic fungus Alternaria
sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea [32.125].
Compounds 146–148 were identified as the first alterporriols with a C-2-C-2 linkage. Alterporriols K and L
revealed moderate cytotoxic activities towards MDAMB-435 and MCF-7 cells with IC 50 values between
13:1 and 29:1 M [32.125].
Oxirapentyns B–D (149–151) and one known oxirapentyn A (152) were isolated from the lipophilic
extract of the marine-derived fungus Isaria felina
KMM4639 [32.126]. The absolute configuration of 149
was established to be 2R, 4S, 5S, 6S, 7R, 8S, 9S
based on both the modified Mosher’s method and Xray analysis together with NOESY data [32.126]. In
the cytotoxicity assay, oxirapentyn A (152) exhibited
moderate activities against T-47D, SK-Mel-5, and SKMel-28 cell lines with IC 50 values of 25, 19, and 17 M,
respectively [32.126].
Two new polyketides, arthropsadiol C (153) and
massarilactone H (154), together with six known
derivatives were isolated from the marine-derived fungus Phoma herbarum [32.127]. Some of the isolated compounds revealed moderate neuraminidase inhibitory activity with IC 50 values between 4:15, and
9:16 M [32.127].
Sorbiterrin A (155, Fig. 32.10), a novel sorbicillinoid featuring an hitherto unprecedented skeleton, was isolated from the marine sediment-derived
fungus Penicillium terrestre [32.128]. The structure including its absolute configuration was elucidated based on NMR, MS data, and time-dependent density functional theory (TDDFT) CD calculations. Sorbiterrin A showed a moderate acetylcholinesterase (AChE) inhibitory effect with IC 50 of
70 M [32.128].
Two novel chlorinated sorbicillinoids, namely
chloctanspirones A (156) and B (157), featuring an
unprecedented bicyclo[2.2.2]octane-2-spiro cyclohexane skeleton, together with two precursors terrestrols K
and L were isolated from a marine sediment-derived
fungus Penicillium terrestre [32.129]. In the in vitro
cytotoxicity assay, 156 revealed antiproliferative activity against both HL-60 and A-549 cells with IC 50
values of 9:2 and 39:7 M, respectively, while 157
showed only activity against HL-60 cells (IC 50 D
37:8 M) [32.129].
Five new polyketide derivatives including two benzopyrones (158 and 159), one isochroman (160), and
two anthraquinone-citrinin derivatives (161 and 162)
were isolated from the sea fan-derived fungus Penicillium citrinum PSU-F51 [32.130]. In the antimicrobial
activity assay, compound 161 revealed moderate activity against both S. aureus and MRSA with equal MIC
values of 30:8 M [32.130].
Seven new phenalenone derivatives (163–169) were
obtained from the fungus Coniothyrium cereale derived
from the green alga Enteromorpha sp. collected from
the Baltic Sea [32.131]. Conioscleroderolide (167)
showed antimicrobial activity toward S. aureus SG 511
with a MIC value of 24 M, which was suggested to
Part F | 32.3
lines, but had no effect on the viability of normal human
cell lines [32.121].
Acremonide (128, Fig. 32.9), one new phthalide
derivative and eight new isocoumarin derivatives, acremonones A–H (129–136) together with ten known
compounds were obtained from Acremonium sp. PSUMA70 isolated from a branch of the mangrove Rhizophora apiculata [32.122]. In the antifungal activity assay, some of the isolated compounds revealed
only moderate antifungal activity with MIC values of
32 g mL
1 when tested against Candida albicans and
C. neoformans, whereas against the latter the activity
was lower [32.122].
Two new hydroanthraquinone analogs, 4aepi-9˛-methoxydihydrodeoxybostrycin (137) and
10-deoxybostrycin (138), together with seven known
anthraquinone congeners were isolated from the
fungus Nigrospora sp. derived from an unidentified
sea anemone [32.123]. All isolated compounds were
evaluated in vitro for their antibacterial activity against
a panel of nine different bacterial strains. Among the
isolated compounds, 10-deoxybostrycin (138) and
3-acetyl-4-deoxybostrycin revealed the most promising
activities against Bacillus subtilis and B. cereus with
IC 50 values of 62:5 and 48:8 nM, respectively compared
to ciprofloxacin as a positive control with IC 50 values
of 31:2 and 1250 nM, respectively [32.123].
Chemical investigation of the cultural extract of
the marine-derived fungus Aspergillus sp. SCSIO F063
afforded seven new chlorinated anthraquinones (139–
145) related to averantin [32.124]. Interestingly, the
chlorinated anthraquinones were obtained upon using
sea salt-containing potato dextrose broth with the addition of sodium bromide to the broth. In the cytotoxicity (MTT) assay, 6-O-methyl-7-chloroaveratin (140)
displayed antiproliferative activity against three human tumor cell lines, SF-268, MCF-7, and NCI-H460,
with IC 50 values of 7:11, 6:64, and 7:42 M,
respectively [32.124].
Alterporriols K–M (146–148), three bianthraquinone derivatives, were reported for the first time
from extracts of the endophytic fungus Alternaria
sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea [32.125].
Compounds 146–148 were identified as the first alterporriols with a C-2-C-2 linkage. Alterporriols K and L
revealed moderate cytotoxic activities towards MDAMB-435 and MCF-7 cells with IC 50 values between
13:1 and 29:1 M [32.125].
Oxirapentyns B–D (149–151) and one known oxirapentyn A (152) were isolated from the lipophilic
extract of the marine-derived fungus Isaria felina
KMM4639 [32.126]. The absolute configuration of 149
was established to be 2R, 4S, 5S, 6S, 7R, 8S, 9S
based on both the modified Mosher’s method and Xray analysis together with NOESY data [32.126]. In
the cytotoxicity assay, oxirapentyn A (152) exhibited
moderate activities against T-47D, SK-Mel-5, and SKMel-28 cell lines with IC 50 values of 25, 19, and 17 M,
respectively [32.126].
Two new polyketides, arthropsadiol C (153) and
massarilactone H (154), together with six known
derivatives were isolated from the marine-derived fungus Phoma herbarum [32.127]. Some of the isolated compounds revealed moderate neuraminidase inhibitory activity with IC 50 values between 4:15, and
9:16 M [32.127].
Sorbiterrin A (155, Fig. 32.10), a novel sorbicillinoid featuring an hitherto unprecedented skeleton, was isolated from the marine sediment-derived
fungus Penicillium terrestre [32.128]. The structure including its absolute configuration was elucidated based on NMR, MS data, and time-dependent density functional theory (TDDFT) CD calculations. Sorbiterrin A showed a moderate acetylcholinesterase (AChE) inhibitory effect with IC 50 of
70 M [32.128].
Two novel chlorinated sorbicillinoids, namely
chloctanspirones A (156) and B (157), featuring an
unprecedented bicyclo[2.2.2]octane-2-spiro cyclohexane skeleton, together with two precursors terrestrols K
and L were isolated from a marine sediment-derived
fungus Penicillium terrestre [32.129]. In the in vitro
cytotoxicity assay, 156 revealed antiproliferative activity against both HL-60 and A-549 cells with IC 50
values of 9:2 and 39:7 M, respectively, while 157
showed only activity against HL-60 cells (IC 50 D
37:8 M) [32.129].
Five new polyketide derivatives including two benzopyrones (158 and 159), one isochroman (160), and
two anthraquinone-citrinin derivatives (161 and 162)
were isolated from the sea fan-derived fungus Penicillium citrinum PSU-F51 [32.130]. In the antimicrobial
activity assay, compound 161 revealed moderate activity against both S. aureus and MRSA with equal MIC
values of 30:8 M [32.130].
Seven new phenalenone derivatives (163–169) were
obtained from the fungus Coniothyrium cereale derived
from the green alga Enteromorpha sp. collected from
the Baltic Sea [32.131]. Conioscleroderolide (167)
showed antimicrobial activity toward S. aureus SG 511
with a MIC value of 24 M, which was suggested to