Sporiolides A and B, New Cytotoxic Twelve-Membered Macrolides from a Marine-Derived Fungus Cladosporium Species

Shigemori, Hideyuki; Kasai, Yuu; Komatsu, Keiichi; Tsuda, Masashi; Mikami, Yuzuru; Kobayashi, Jun’ichi

doi:10.3390/md204164

Cited by 66 publications

(65 citation statements)

References 8 publications

(12 reference statements)

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“…Initially, we tried to prepare 10 from 9, which was obtained by methylation of the known D D-glucal derivative 8, 5 through regioselective reductive cleavage of p-anisaldehyde acetal as illustrated in Scheme 1. Unfortunately, a poor selectivity was obtained using either DIBAL-H 5,6 or LiAlH 4 -AlCl 3 7 as reducing agents. When 9 was treated with NaCNBH 3 -TMSCl, 8 12 involving double bond migration was obtained unexpectedly in an excellent yield (90%), and its structure was confirmed unambiguously by 1 H NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…Esterification of 6 with (S)-6-hepten-2-ol (5) 13 saturated the double bond yielding sporiolide B, identical in every respect to the natural product. 3 The effects of sporiolide B against human MDA231, BEL-7402, and Hela cell growth were investigated with different methods. 3,18 Unfortunately, under these testing conditions, sporiolide B did not show significant inhibition on proliferation of either human MDA231, BEL-7402, or Hela cell lines at 0.25-1.0 lg/mL for 24, 48, and 72 h, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…separated from an Okinawan marine brown alga Actinotrichia fragilis, Kobayashi reported the isolation of a 12-membered ring macrolide sporiolide B (1) and proposed that structurally it corresponds to the 3-O-methyl ether of pandangolide 1 (2) 2 based on spectroscopic analyses (Chart 1). 3 Sporiolide B exhibits cytotoxicity against L1210 cells (IC 50 = 0.81 lg/mL) and antibacterial activity against Micrococcus luteus (MIC = 16.7 lg/mL). Attracted by its various biological activities, we already completed the first total synthesis of sporiolide B from D D-xylose in 3.5% overall yield.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of sporiolide B from d-glucal

Chen¹,

Du²

2007

Carbohydrate Research

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Abstract-A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of sporiolide B from d-glucal

Chen¹,

Du²

2007

Carbohydrate Research

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“…It should be noted that 85 represents the first 14-membered phenyl acetic acid macrolide with a 4-chromanone unit, and 86-91 were elucidated to be the antipodes of previously isolated curvularins by analysis of their specific optical rotation ([α] D ) values and electronic circular dichroism (ECD) spectra. Sporiolides A (17) and B (18) exhibited potent cytotoxicity against murine lymphoma cell line L1210 with IC 50 values of 0.13 and 0.81 μg/mL (0.37 and 3.14 μM), respectively, and the benzoyl group contributes more than the methyl group (Shigemori et al 2004). Macrolides 85, 86, and 88-90 showed cytotoxicity against various cancer cell lines, including bladder, glioblastoma, colon, stomach, head & neck, lung, breast, melanoma, ovary, pancreas, prostate, mesothelioma, kidney, and uterus ones, and 86 outstood with an mean IC 50 value of 1.25 μM (Greve et al 2008a).…”

Section: Structure and Bioactivity Polyketidesmentioning

confidence: 99%

Mycochemistry of marine algicolous fungi

Wang

2016

Fungal Diversity

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Marine algicolous fungi refer to the fungi inhabiting or associated with marine algae, which have attracted a great attention for natural product researchers due to their chemical diversity and biological activity during the past two decades. Up to the end of 2014, a total of 366 new natural products, including polyketides, terpenoids, polyketide-terpenoids, peptides, alkaloids, and shikimate derivatives, have been characterized from them. Among these metabolites, 240 compounds feature cytotoxic, antibacterial, antifungal, antimicroalgal, zooplankton-toxic, antiprotozoal, antioxidative, enzyme-modulatory, and/or some other activities. This review gives a comprehensive coverage of both chemical and biological aspects of the secondary metabolites from marine algicolous fungi.

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“…An example of this was the isolation of sporolids A and B obtained from a microscopic fungus of genus Cladosporium isolated from an alga (Shigemori et al, 2004). Both the compounds manifested a cytotoxic activity against murine lymphoma cell line L1210.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative effect of extract from endophytic fungusCurvularia trifoliiisolated from the “Veracruz Reef System” in Mexico

Couttolenc

Espinoza

Fernández

et al. 2016

Pharmaceutical Biology

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Context: It is well known that marine fungi are an excellent source of biologically active secondary metabolites, and by 2011, it was reported that over 400 bioactive metabolites were derived from marine fungi. Objective: This study establishes the basis for future research on antiproliferative compounds of marine endophytes inhabited in the Veracruz Reef System. Materials and methods: Isolation of the 34 fungal strains was carried out by microbiological method from samples of sponges, corals, and other biological material from the Veracruz Reef System. The fungal biomass and broth were separated and extracted with a mixture of solvents MeOH:CHCl 3 . Characterization and molecular identification of the fungal strains were performed through microbiological methods and the analysis of the ITS-rDNA regions. Antiproliferative activity was tested at a dose of 250 mg/mL on human solid tumor cell lines HBL-100, HeLa, SW1573, T-47D, and WiDr by the SRB assay after 48 h-exposure to the fungal extracts. Results: The extracts from five isolates showed an antiproliferative effect against one or more of the tested cell lines (percentage growth 5 50%). The mycelial extract from the isolate LAEE 03 manifested the highest activity against the five cell lines (% PG of 17 HBL-100, 19 HeLa, 23 SW1573, -6 T-47D, and 10 WiDr) and the strain was identified as Curvularia trifolii (Kauffman) Boedijn (Pleosporaceae). Discussion and conclusion: The results obtained indicate that the extract from a marine derived C. trifolii has the antiproliferative effect, thus suggesting that this organism is a good candidate for further analysis of its metabolites. ARTICLE HISTORY

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Sporiolides A and B, New Cytotoxic Twelve-Membered Macrolides from a Marine-Derived Fungus Cladosporium Species

Cited by 66 publications

References 8 publications

Synthesis of sporiolide B from d-glucal

Synthesis of sporiolide B from d-glucal

Mycochemistry of marine algicolous fungi

Antiproliferative effect of extract from endophytic fungusCurvularia trifoliiisolated from the “Veracruz Reef System” in Mexico

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