Marine-Derived Fungal Metabolites 32.3 Marine Organic Compounds 781
Part F | 32.4
ent human tumor cell lines, but only wentilactone (236)
exhibited a potent activity among the compounds tested
(IC 50 D 17 M) [32.145]. However, in the antimicrobial activity assay, compound 234 revealed a considerable antifungal activity against C. albicans with a MIC
value of 56 M [32.145].
Chemical investigation of the crude extract of the
fungus Aspergillus sp. obtained from the Mediterranean
sponge Tethya aurantium afforded five new meroterpenoids, austalides M–Q (239–243), together with nine
known compounds [32.146]. Absolute configurations
of 239 and 242 were established by TDDFT ECD
calculations, allowing the assignment of the absolute
configuration of analogs 240, 241, and 243 [32.146].
All isolated austalides were assessed for their cytotoxic
activity toward L5178Y cells using the MTT assay;
however, they exhibited only weak or no activity in this
assay [32.146].
Four new meroterpenes, guignardones F–I (244–
247), together with two known guignardones A (248)
and B (249), were obtained from the endophytic fungus A1 isolated from the mangrove plant Scyphiphora
hydrophyllacea [32.147]. Chemical structures and relative configurations of the isolated compounds were
determined based on spectroscopic data and singlecrystal X-ray crystallography [32.147]. In the antibacterial activity assay against MRSA, only guignardones I
(247) and B (249) exhibited inhibition zones of 9:0 and
8:0 mm at 65 M, respectively [32.147].
32.3.5 Marine Peptides and Proteins
Versicotides A (250) and B (251), cyclic pentapeptides containing an L-alanine residue, two anthranthilic
acid (2-aminobenzoic acid) residues, and two Nmethyl-L-alanine residues were isolated from the marine sediment-derived fungus Aspergillus versicolor
ZLN-60 [32.148]. The chemical structures of versicotides A and B were established on the basis of chemical and spectroscopic analyses. In the cytotoxicity
(MTT) assays, neither versicotide A (250) nor versicotide B (251) exhibited antitumor activity [32.148].
Cordyheptapeptides C–E (252–254), three new cycloheptapeptides, were purified from the culture extract
of the marine sediment-derived fungus Acremonium
persicinum SCSIO115 [32.149]. The absolute configurations of the amino acid residues were determined
by single-crystal X-ray diffraction, Marfey’s method,
and chiral-phase high performance liquid chromatography (HPLC) analysis. In the antiproliferative activity
assay, only cordyheptapeptides C (252) and E (254) revealed cytotoxic activities toward SF-268, MCF-7, and
NCI-H460 tumor cell lines with IC 50 values ranging between 2:512:1 M [32.149].
EGM-556 (255), a cyclodepsipeptide of hybrid
biosynthetic origin of both polyketide (PKS) and nonribosomal peptide (NRPS) syntheses, was prepared
through implementing the histone deacetylase (HDAC)
inhibitor suberoylanilide hydroxamic acid (SAHA) to
turn on its biosynthesis in the Floridian marine sediment-derived fungus Microascus sp. [32.150]. EGM556 (255) represents an interesting example for a fungal metabolite produced through induction of silent
biosynthetic genes activate by means of epigenetic
manipulation [32.150].
Two new tripeptides, namely pre-sclerotiotide F
(256) and sclerotiotide F (257), were isolated from
a marine sediment-derived fungus Aspergillus insulicola, along with five known compounds [32.151].
Both compounds 256 and 257 were inactive at
100 M for in vitro cytotoxicity (MTT) assay against
PC3 (prostate), MCF-7 (breast), and RAW (murine
macrophage) cancer cell lines [32.151]. Moreover, this
pair of tripeptides did not illustrate any inhibitory activity on NF-ÄB or iNOS pathways when tested in the
presence of LPS [32.151].
Pullularins E (258) and F (259), two new peptides,
were isolated from the endophytic fungus Bionectria
ochroleuca, derived from the mangrove plant Sonneratia caseolaris collected from the island of Hainan
(China) [32.152]. The chemical structures and absolute configurations of amino acids were determined by
HPLC analysis of acid hydrolysates using Marfey’s
method [32.152]. In the cytotoxicity assay, pullularins E
(258) and F (259) revealed moderate inhibitory activity
toward the L5178Y cell line with IC 50 values of 7:0 and
> 14:0 M [32.152].
Penilumamide (260), a novel lumazine peptide, was
obtained from the fungal strain Penicillium sp. CNL338, isolated from the red alga Laurencia sp. collected in the Bahamas Islands [32.153]. The chemical
structure of penilumamide revealed a lumazine system
with L-methionine sulfoxide and anthranilic acid ester [32.153]. Penilumamide (260) was assessed for its
cytotoxicity, antibacterial and antifungal activities, and
its influence on the Ca
2C levels in neuroendocrine cells
(PC12); however, it revealed no activity in any of the
aforementioned bioassays [32.153].
Part F | 32.4
ent human tumor cell lines, but only wentilactone (236)
exhibited a potent activity among the compounds tested
(IC 50 D 17 M) [32.145]. However, in the antimicrobial activity assay, compound 234 revealed a considerable antifungal activity against C. albicans with a MIC
value of 56 M [32.145].
Chemical investigation of the crude extract of the
fungus Aspergillus sp. obtained from the Mediterranean
sponge Tethya aurantium afforded five new meroterpenoids, austalides M–Q (239–243), together with nine
known compounds [32.146]. Absolute configurations
of 239 and 242 were established by TDDFT ECD
calculations, allowing the assignment of the absolute
configuration of analogs 240, 241, and 243 [32.146].
All isolated austalides were assessed for their cytotoxic
activity toward L5178Y cells using the MTT assay;
however, they exhibited only weak or no activity in this
assay [32.146].
Four new meroterpenes, guignardones F–I (244–
247), together with two known guignardones A (248)
and B (249), were obtained from the endophytic fungus A1 isolated from the mangrove plant Scyphiphora
hydrophyllacea [32.147]. Chemical structures and relative configurations of the isolated compounds were
determined based on spectroscopic data and singlecrystal X-ray crystallography [32.147]. In the antibacterial activity assay against MRSA, only guignardones I
(247) and B (249) exhibited inhibition zones of 9:0 and
8:0 mm at 65 M, respectively [32.147].
32.3.5 Marine Peptides and Proteins
Versicotides A (250) and B (251), cyclic pentapeptides containing an L-alanine residue, two anthranthilic
acid (2-aminobenzoic acid) residues, and two Nmethyl-L-alanine residues were isolated from the marine sediment-derived fungus Aspergillus versicolor
ZLN-60 [32.148]. The chemical structures of versicotides A and B were established on the basis of chemical and spectroscopic analyses. In the cytotoxicity
(MTT) assays, neither versicotide A (250) nor versicotide B (251) exhibited antitumor activity [32.148].
Cordyheptapeptides C–E (252–254), three new cycloheptapeptides, were purified from the culture extract
of the marine sediment-derived fungus Acremonium
persicinum SCSIO115 [32.149]. The absolute configurations of the amino acid residues were determined
by single-crystal X-ray diffraction, Marfey’s method,
and chiral-phase high performance liquid chromatography (HPLC) analysis. In the antiproliferative activity
assay, only cordyheptapeptides C (252) and E (254) revealed cytotoxic activities toward SF-268, MCF-7, and
NCI-H460 tumor cell lines with IC 50 values ranging between 2:512:1 M [32.149].
EGM-556 (255), a cyclodepsipeptide of hybrid
biosynthetic origin of both polyketide (PKS) and nonribosomal peptide (NRPS) syntheses, was prepared
through implementing the histone deacetylase (HDAC)
inhibitor suberoylanilide hydroxamic acid (SAHA) to
turn on its biosynthesis in the Floridian marine sediment-derived fungus Microascus sp. [32.150]. EGM556 (255) represents an interesting example for a fungal metabolite produced through induction of silent
biosynthetic genes activate by means of epigenetic
manipulation [32.150].
Two new tripeptides, namely pre-sclerotiotide F
(256) and sclerotiotide F (257), were isolated from
a marine sediment-derived fungus Aspergillus insulicola, along with five known compounds [32.151].
Both compounds 256 and 257 were inactive at
100 M for in vitro cytotoxicity (MTT) assay against
PC3 (prostate), MCF-7 (breast), and RAW (murine
macrophage) cancer cell lines [32.151]. Moreover, this
pair of tripeptides did not illustrate any inhibitory activity on NF-ÄB or iNOS pathways when tested in the
presence of LPS [32.151].
Pullularins E (258) and F (259), two new peptides,
were isolated from the endophytic fungus Bionectria
ochroleuca, derived from the mangrove plant Sonneratia caseolaris collected from the island of Hainan
(China) [32.152]. The chemical structures and absolute configurations of amino acids were determined by
HPLC analysis of acid hydrolysates using Marfey’s
method [32.152]. In the cytotoxicity assay, pullularins E
(258) and F (259) revealed moderate inhibitory activity
toward the L5178Y cell line with IC 50 values of 7:0 and
> 14:0 M [32.152].
Penilumamide (260), a novel lumazine peptide, was
obtained from the fungal strain Penicillium sp. CNL338, isolated from the red alga Laurencia sp. collected in the Bahamas Islands [32.153]. The chemical
structure of penilumamide revealed a lumazine system
with L-methionine sulfoxide and anthranilic acid ester [32.153]. Penilumamide (260) was assessed for its
cytotoxicity, antibacterial and antifungal activities, and
its influence on the Ca
2C levels in neuroendocrine cells
(PC12); however, it revealed no activity in any of the
aforementioned bioassays [32.153].