2009
DOI: 10.5012/bkcs.2009.30.10.2345
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Bioactive Cyclopentenone Derivatives from Marine Isolates of Fungi

Abstract: As part of an effort to discover bioactive natural products from marine sources, we investigated the bioactive secondary metabolites from two marine isolates of the fungi, Trichoderma viride and Rhizopus stolonifer. Three cyclopentenones, myrothenones A (1) and B (2) and trichodenone A (3), were isolated from T. viride and two cyclopentenones, 2-bromomyrothenone B (4) and botrytinone (5), were isolated from R. stolonifer. The molecular structures and absolute stereochemistries of the cyclopentenones were deter… Show more

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Cited by 17 publications
(2 citation statements)
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“…Chiral hydroxylated cyclopentenone derivatives are indispensable in the total synthesis of nucleosides and anticancer drugs, the antibiotic pentomycin and derivatives, , and several natural products with various biological and medicinal properties. ,,, The stereochemistry of the hydroxyl group attached to the stereogenic carbon is of paramount concern in these structures because the biological activity is often critically dependent upon its orientation. The direct asymmetric oxidation of the parent carbonyl compounds allows an efficient route to enantiomerically enriched hydroxyketones.…”
Section: Asymmetric Functionalization Of Existing Cyclopentenone Unitsmentioning
confidence: 99%
“…Chiral hydroxylated cyclopentenone derivatives are indispensable in the total synthesis of nucleosides and anticancer drugs, the antibiotic pentomycin and derivatives, , and several natural products with various biological and medicinal properties. ,,, The stereochemistry of the hydroxyl group attached to the stereogenic carbon is of paramount concern in these structures because the biological activity is often critically dependent upon its orientation. The direct asymmetric oxidation of the parent carbonyl compounds allows an efficient route to enantiomerically enriched hydroxyketones.…”
Section: Asymmetric Functionalization Of Existing Cyclopentenone Unitsmentioning
confidence: 99%
“…In contrast, although a pharmacological activity was described, and an IC 50 for inhibition of an enzyme or receptor determined, detailed molecular mechanism of action studies were unavailable at the time of publication for the following 47 marine compounds included in Table 3: alotaketals A and B ( 183 , 184 ) [166]; aquastatin A ( 185 ) [167]; australin E ( 186 ) [168]; lyngbyastatins 9 & 10 ( 187 , 188 ) [169]; brunsvicamides A, B and C ( 189 – 191 ) [170]; carteriosulfonic acids A, B and C ( 192 – 194 ) [171]; Carteriospongia foliascens sesterterpenoids ( 195 , 196 ) [172]; clavatadines D and E ( 197 , 198 ) [173]; fibrosterol sulfates A and B ( 199 , 200 ) [174]; gracilin L ( 201 ) [175]; grassystatins A, B and C ( 141 – 143 ) [133]; 2-hydroxycircumdatin C ( 202 ) [176]; jaspaquinol ( 203 ) [177]; largamides A, B and C ( 204 – 206 ) [178]; largamide D oxazolidine ( 207 ) [179]; Laurencia similis brominated metabolites ( 208 , 209 ) [180]; molassamide ( 210 ) [181]; myrothenone A ( 211 ) [182]; 42-hydroxy-palytoxin ( 212 ) [183]; plectosphaeroic acids A, B and C ( 213 – 215 ) [184]; puupehenone ( 216 ) [177]; Sinularia numerosa oxylipin ( 217 ) [185]; sipholenone E ( 218 ) [186]; spartinoxide ( 219 ) [187]; 23- nor -spiculoic acid B ( 220 ) [188]; tanikolide dimer ( 221 ) [189]; tamulamides A and B ( 222 , 223 ) [190]; terretonins E and F ( 224 , 225 ) [191]; and tetrangulol methyl ether ( 226 ) [192]. …”
Section: Marine Compounds With Miscellaneous Mechanisms Of Actionmentioning
confidence: 99%