Furo[3,2-h]isochroman, furo[3,2-h]isoquinoline, isochroman, phenol, pyranone, and pyrone derivatives from the sea fan-derived fungus Penicillium sp. PSU-F40

Trisuwan, Kongkiat; Rukachaisirikul, Vatcharin; Sukpondma, Yaowapa; Phongpaichit, Souwalak; Preedanon, Sita; Sakayaroj, Jariya

doi:10.1016/j.tet.2010.04.073

Cited by 54 publications

(55 citation statements)

References 10 publications

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“…Several similar novel isoquinoline alkaloids have been reported from the genus of Penicillium, 17 Aspergillus, 18 Streptomyces 19,20 and Chaetomium. 21 Most isoquinoline alkaloids discovered from plants exhibit complicated structures, which were mainly synthesized from tyrosine, whereas most isoquinolines from lichens, fungi, and sponges show simple skeletons and are probably biosynthesized via mixed pathways.…”

Section: Resultsmentioning

confidence: 84%

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Yao¹,

Sebisubi²,

Voo³

et al. 2011

J. Braz. Chem. Soc.

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A investigação do extrato orgânico produzido na fermentação microbiológica de Penicillium sp. H9318 conduziu ao isolamento de um novo alcaloide isoquinolínico, o composto (5S)-3,4,5,7-tetrametil-5,8-di-hidróxi-6(5H)-isoquinolinona (1), juntamente com quatro outros conhecidos compostos derivados da citrinina (2-5). Uma atividade inibitória significativa no ensaio da inibição da formação dos halos (HFI), foi exibida pela citrinina (2), semelhante àquela observada pelo Streptomyces 85E, enquanto os compostos 1, 3, 4 e 5 não mostraram atividade inibitória com respeito ao ensaio HFI quando testados com 20 mg/disco. Em relação ao ensaio de citotoxicidade, a citrinina (2) demonstrou uma atividade inibitória mais fraca quando comparada as linhagens de células cancerosas MCF-7 (IC 50 71,93 µmol L -1 ), LNCaP (IC 50 77,92 µmol L -1 ), LU-1 (147,85 µmol L -1 ) e KB (IC 50 65,93 µmol L -1 ).Investigation of a microbial fermentation organic extract of Penicillium sp. H9318 led to the isolation of a new isoquinolinone alkaloid, (5S)-3,4,5,7-tetramethyl-5,8-dihydroxyl-6(5H)-isoquinolinone (1), along with four known citrinin derivatives (2-5). Citrinin (2) exhibited significant inhibitory activity against Streptomyces 85E in the hyphae formation inhibition (HFI) assay, while compounds 1, 3-5 were not active when tested at 20 mg/disk in the HFI assay. Citrinin (2) further demonstrated a weak inhibitory activity against MCF-7 (IC 50 71.93 µmol L -1 ), LNCaP (IC 50 77.92 µmol L -1 ), LU-1 (147.85 µmol L -1 ) and KB (IC 50 65.93 µmol L -1 ) cell lines, respectively, in the cytotoxicity assay.

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Section: Resultsmentioning

confidence: 84%

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Yao¹,

Sebisubi²,

Voo³

et al. 2011

J. Braz. Chem. Soc.

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“…They also reported that 42 induced depletion of intramolecular glutathione, which decreased cell viability. Structurally related natural products such as pergillin, 81) ustusolanes, 82) and penicisochroman A-C 83) have been reported. Among these was ustusorane C (43), a methyl acetal derivative of 42.…”

Section: Pseudodeflectusin and Ustusorane Cmentioning

confidence: 99%

Synthetic and Structure-Activity Relationship Studies on Bioactive Natural Products

Kuramochi

2013

Bioscience, Biotechnology, and Biochemistry

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“…The strategy employed an activated β-phenethyl alcohol derivative and did not require an acidic promoter. [18] Thus, heating anti-2-(3-hydroxyphenyl)cyclohexanol with cyclohexanone in a sealed tube for 15 h furnished 28 % of spiro [1,2,3,4,4a,10b-hexahydrobenzo [c]chromene-6,1Ј-cyclohexan]-9-ol. However, cyclization of less active substrates required HCl or TsOH assistance.…”

Section: Early Applications Of the Oxa-pictet-spengler Cyclizationmentioning

confidence: 99%

“…[43] It was observed that yields were affected by the presence of dehydrating agents such as 4 Å molecular sieves and MgSO 4 , and that when 2,4,6-tri-tert-butylpyridine (TTBP), a very hindered base, known to not interact with metal catalysts, [44] was added in order to neutralize traces of TfOH, no product was observed in the presence of various metal triflates.…”

Section: New Promoters Of the Oxa-pictet-spengler Cyclizationmentioning

confidence: 99%

“…[1] A statistical analysis of the number of indexed publications on the topic "isochroman" since 1910 counted about 900 articles, 300 of them published during the last decade and 35 in 2010 alone; Figure 1 displays a small selection of compounds embodying the isochroman motif. This includes excentricine (2a) and N-methylexcentricine (2b), alkaloids from the roots of Stephania excentrica carrying the tetracyclic stephaoxocane skeleton, [2] ilexchromane (3) obtained from the dried roots of Ilex pubescens Hook et Arn, [3] the penicisochromans D (4a) and E (4b) from Penicillium PSU-F40 [4] and the structurally unique Cytosporolides A-C (5a-c), recently isolated from Cytospora sp. [5] Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

2011

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The oxa‐Pictet–Spengler cyclization is the oxygen variation of the Pictet–Spengler reaction, in which an aromatic alcohol component (generally a β‐arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1‐substituted (or 1,1′‐disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa‐Pictet–Spengler are also analyzed.

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Furo[3,2-h]isochroman, furo[3,2-h]isoquinoline, isochroman, phenol, pyranone, and pyrone derivatives from the sea fan-derived fungus Penicillium sp. PSU-F40

Cited by 54 publications

References 10 publications

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Citrinin derivatives from the soil filamentous fungus Penicillium sp. H9318

Synthetic and Structure-Activity Relationship Studies on Bioactive Natural Products

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

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