ChemInform Abstract: BE‐40644, a New Human Thioredoxin System Inhibitor Isolated from Actinoplanes sp. A40644.

Torigoe, Koichiro; Wakasugi, Naomi; Sakaizumi, Nami; Ikejima, Takashi; Suzuki, Hajime; Kojiri, Katsuhisa; Suda, Hiroyuki

doi:10.1002/chin.199635247

Cited by 7 publications

(7 citation statements)

References 1 publication

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“…Among them, tauranin [10,13] and BE-40644 [14,15] displayed potent in vitro cytotoxic activity against cancer cells. In vitro cytotoxic effects of penicilliumin A was tested against three cancer cell lines—A375, B16 and Hela—using 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) assay.…”

Section: Resultsmentioning

confidence: 99%

A New Cytotoxic Sesquiterpene Quinone Produced by Penicillium sp. F00120 Isolated from a Deep Sea Sediment Sample

et al. 2012

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A new fungal strain, displaying strong toxic activity against brine shrimp larvae, was isolated from a deep sea sediment sample collected at a depth of 1300 m. The strain, designated as F00120, was identified as a member of the genus Penicillium on the basis of morphology and ITS sequence analysis. One new sesquiterpene quinone, named penicilliumin A (1), along with two known compounds ergosterol (2) and ergosterol peroxide (3), were isolated and purified from the cultures of F00120 by silica gel column, Sephadex LH-20 column, and preparative thin layer chromatography. Their structures were elucidated by detailed nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analysis as well as comparison with literature data. The new compound penicilliumin A inhibited in vitro proliferation of mouse melanoma (B16), human melanoma (A375), and human cervical carcinoma (Hela) cell lines moderately.

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Section: Resultsmentioning

confidence: 99%

A New Cytotoxic Sesquiterpene Quinone Produced by Penicillium sp. F00120 Isolated from a Deep Sea Sediment Sample

et al. 2012

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“…This specifically concerns the product called BE-40644, isolated from the actinobacterium Actinoplanes sp. A40644 and shown to have an inhibitory effect on the human thioredoxin system [82]. It is synthesized from sedoheptulose 7-phosphate by first converting it to 2-epi-5-epi-valiolone by the enzyme EEVS encoded by one of the genes of the BE-40644 synthesis gene cluster [66,83].…”

Section: Resultsmentioning

confidence: 99%

The plastid genome of some eustigmatophyte algae harbours a bacteria-derived six-gene cluster for biosynthesis of a novel secondary metabolite

et al. 2016

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Acquisition of genes by plastid genomes (plastomes) via horizontal gene transfer (HGT) seems to be a rare phenomenon. Here, we report an interesting case of HGT revealed by sequencing the plastomes of the eustigmatophyte algae Monodopsis sp. MarTras21 and Vischeria sp. CAUP Q 202. These plastomes proved to harbour a unique cluster of six genes, most probably acquired from a bacterium of the phylum Bacteroidetes, with homologues in various bacteria, typically organized in a conserved uncharacterized putative operon. Sequence analyses of the six proteins encoded by the operon yielded the following annotation for them: (i) a novel family without discernible homologues; (ii) a new family within the superfamily of metallo-dependent hydrolases; (iii) a novel subgroup of the UbiA superfamily of prenyl transferases; (iv) a new clade within the sugar phosphate cyclase superfamily; (v) a new family within the xylose isomerase-like superfamily; and (vi) a hydrolase for a phosphate moiety-containing substrate. We suggest that the operon encodes enzymes of a pathway synthesizing an isoprenoid–cyclitol-derived compound, possibly an antimicrobial or other protective substance. To the best of our knowledge, this is the first report of an expansion of the metabolic capacity of a plastid mediated by HGT into the plastid genome.

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“…5) It has been reported to inhibit the thioredoxin (TRX) system and to exhibit cytotoxicity against several human tumor cell lines. [5][6][7] In addition, strong repression of human immunodeficiency virus (HIV) virus replication was also reported for this compound. 7) In spite of its interesting biological activities, the absolute configurations of (Ϫ)-2 have not been determined, while racemic synthesis of an epimer (rac-3) at C(6a) of 2 was reported.…”

mentioning

confidence: 85%

“…[5][6][7] In addition, strong repression of human immunodeficiency virus (HIV) virus replication was also reported for this compound. 7) In spite of its interesting biological activities, the absolute configurations of (Ϫ)-2 have not been determined, while racemic synthesis of an epimer (rac-3) at C(6a) of 2 was reported. 8) At the same time, (Ϫ)-2 has recently become an attractive subject for biochemists due to its unusual biosynthetic pathway.…”

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confidence: 85%

First Syntheses of (-)-Tauranin and Antibiotic (-)-BE-40644 Based on Lipase-Catalyzed Optical Resolution of Albicanol

Ishii

Fujii

Akita

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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First syntheses of sesquiterpene quinones (؊ ؊)-tauranin and (؊ ؊)-BE-40644 which exhibited strong cytotoxicity against several cancer cell lines, were achieved from (8aS)-albicanol obtained by enzymatic optical resolution. By comparison of the sign of specific rotation between synthetic (12bS)-BE-40644 and natural (؊ ؊)-BE-40644, the absolute configurations of natural (؊ ؊)-BE-40644 were determined to be 4aS, 6aS, 12aR, 12bS.

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ChemInform Abstract: BE‐40644, a New Human Thioredoxin System Inhibitor Isolated from Actinoplanes sp. A40644.

Cited by 7 publications

References 1 publication

A New Cytotoxic Sesquiterpene Quinone Produced by Penicillium sp. F00120 Isolated from a Deep Sea Sediment Sample

A New Cytotoxic Sesquiterpene Quinone Produced by Penicillium sp. F00120 Isolated from a Deep Sea Sediment Sample

The plastid genome of some eustigmatophyte algae harbours a bacteria-derived six-gene cluster for biosynthesis of a novel secondary metabolite

First Syntheses of (-)-Tauranin and Antibiotic (-)-BE-40644 Based on Lipase-Catalyzed Optical Resolution of Albicanol

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