Depsidones, aromatase inhibitors and radical scavenging agents from the marine-derived fungus Aspergillus unguis CRI282-03.
Three new depsidones ( 1, 3, and  4), a new diaryl ether ( 5), and a new natural pyrone ( 9) (synthetically known), together with three known depsidones, nidulin ( 6), nornidulin ( 7), and 2-chlorounguinol ( 8), were isolated from the marine-derived fungus  ASPERGILLUS UNGUIS CRI282-03. Aspergillusidone C ( 4) showed the most potent aromatase inhibitory activity with the IC (50) value of 0.74 µM, while depsidones  1, 3, 6- 8 inhibited aromatase with IC (50) values of 1.2-11.2 µM. It was found that the structural feature of depsidones, not their corresponding diaryl ether derivatives (e.g.  5), was important for aromatase inhibitory activity. Aspergillusidones A ( 1) and B ( 3) showed radical scavenging activity in the XXO assay with IC (50) values of 16.0 and < 15.6 µM, respectively. Compounds  1 and  3- 7 were mostly inactive or showed only weak cytotoxic activity against HuCCA-1, HepG2, A549, and MOLT-3 cancer cell lines.
Chulabhorn Research Institute, Laksi, Bangkok, Thailand.
Sanya
S
Sureram
Suthep
S
Wiyakrutta
Nattaya
N
Ngamrojanavanich
Chulabhorn
C
Mahidol
Somsak
S
Ruchirawat
Prasat
P
Kittakoop
D000818:Animals; D047072:Aromatase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001230:Aspergillus / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification; D001483:Base Sequence; D045744:Cell Line, Tumor; D002470:Cell Survival; D004271:DNA, Fungal / Q000737:chemistry / Q000235:genetics; D004275:DNA, Ribosomal / Q000737:chemistry / Q000235:genetics; D053630:Depsides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010082:Oxepins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D011161:Porifera / Q000382:microbiology; D017422:Sequence Analysis, DNA
D047072:Aromatase Inhibitors; D004271:DNA, Fungal; D004275:DNA, Ribosomal; D053630:Depsides; D016166:Free Radical Scavengers; D007783:Lactones; D010082:Oxepins; C576208:aspergillusidone A; C576209:aspergillusidone B; C576210:aspergillusidone C; C000875:depsidone