5-(2-Methylphenyl)-4-pentenoic Acid from a Terrestrial Streptomycete

Venugopal, M.; Maskey, Rajendra P.; Monecke, Peter; Grün-Wollny, Iris; Laatsch, Hartmut

doi:10.1515/znb-2002-0312

Cited by 14 publications

(20 citation statements)

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“…Purification of the less polar SF A led to spatozoate (6). Further purification of SF C on Sephadex LH-20 gave 5-(2-methylphenyl)-4-pentenoic acid) (7) 13 and monensin B, 14,15 whereas the middle polar SF D afforded 5-oxo-5-o-tolylpentanoic acid (8a), along with glucopiericidin A (1), 6 piericidin A (2) 5,16 and phenylacetic acid. Separation of the most polar SF E by PTLC, followed by chromatography on Sephadex LH-20, gave glucopiericidin C (3), 2¢-deoxy-uridin and 2¢-deoxy-thymidin.…”

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confidence: 99%

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Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate

Shaaban

Helmke

Kelter³

et al. 2010

J Antibiot

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More than 35 naturally occurring piericidins 1,2 and closely related antibiotics 3,4 have been reported. They are derived from prenylated polyoxypyridines and exhibit interesting biological activities. Among them, glucopiericidin A (1), B and some others display antimicrobial properties and in vitro inhibitory activity against antibody formation. 5 For glucopiericidiols A1 and A2, additional cytocidal activities against HeLa S3 cells in vitro have been reported, 6 and others demonstrate insecticidal activity. 7 The biological activities of the glucopiericidins are strongly influenced by the structure and position of the sugar unit: glucopiericidins A (1) and B show higher antimicrobial activities than piericidin A (2) or other glycosides such as 3¢-rhamnopiericidin A1 (SN-198-C), 8 3¢-deoxytalopiericidin A1 (DTPA) 9 and 7-demethyl-3¢-rhamnopiericidin A1. 10 In contrast, acute toxicities of the latter three substances in mice were lower than those of piericidin A (2). 5 In our search for new secondary metabolites from marine bacteria, we isolated a new cytotoxic piericidin derivative, glucopiericidin C (3), and for the first time as natural product, 5-oxo-5-o-tolyl-pentanoic acid (8a) together with further 10 known metabolites. The algal metabolite spatozoate (6) was isolated here for the first time from bacteria.The crude extract obtained by fermentation of the marine-derived Streptomyces isolate B8112 was moderately active against Grampositive and Gram-negative bacteria and Candida albicans, but strongly active against the fungus Mucor miehei (Tü284). Additionally, a pronounced in vitro antitumor activity with a mean IC 70 of o10 mg ml À1 was found in a six cell line panel. 11 TLC of the extract exhibited numerous UV absorbing bands: two of them (3, 6) turned blue with anisaldehyde/sulfuric acid and later to dark green in the case of 3, whereas 8a changed to purple on standing.For preparative isolation, the strain was cultivated on M 2 + medium as a shake culture at 28 1C for 7 days, and extracted as reported previously. 12 Chromatography on Sephadex LH-20 (Lipophilic Sephadex, Amersham Bioscience, purchased from Sigma-Aldrich Chemie, Steinheim, Germany) led to the isolation of indole-3-carboxylic acid and uracil; flash silica gel column chromatography of fraction I delivered five subfractions (SFs) ABE. Purification of the less polar SF A led to spatozoate (6). Further purification of SF C on Sephadex LH-20 gave 5-(2-methylphenyl)-4-pentenoic acid) (7) 13 and monensin B, 14,15 whereas the middle polar SF D afforded 5-oxo-5-o-tolylpentanoic acid (8a), along with glucopiericidin A (1), 6 piericidin A (2) 5,16 and phenylacetic acid. Separation of the most polar SF E by PTLC, followed by chromatography on Sephadex LH-20, gave glucopiericidin C (3), 2¢-deoxy-uridin and 2¢-deoxy-thymidin. The known compounds were identified by means of their NMR and mass data using AntiBase, 2 and by comparison with authentic spectra.The physicochemical properties of compound 3 are summarized in Table 1. The UV data and the proton N...

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“…In the 13 C NMR spectrum of 8a, two carbonyls at d 203.4 and d 179.6 indicated the presence of a conjugated ketone and a carboxylic acid, respectively. Owing to the shift of H-6¢, it was deduced that the ketone must be attached directly to the benzene ring.…”

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confidence: 99%

Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate

Shaaban

Helmke

Kelter³

et al. 2010

J Antibiot

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“…Based on the revealed spectroscopic data and searching in AntiBase [61] , 5-(otolyl)-4-pentenoic acid (187a) was deduced, which was further confirmed by comparison with the literature [295] and finally confirmed using 2D experiments (HMBC and COSY correlations) ( Figure 104). …”

Section: Spatozoatementioning

confidence: 64%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…This result indicated that the presence of a longer chain of the carboxylic group in 2 had not been involved in the antimicrobial activity. Biological activities of the E-isomer of AB204-A (1), (E)-5-(2-methylphenyl)-4-pentenoic acid was previously reported to be an inactive compound against bacteria and fungi but the tested concentration and the strain of tested microorganisms have not been indicated [33]. However, the difference of an antimicrobial activity between (E)-5-(2-methylphenyl)-4-pentenoic acid and new compounds, AB204-A (1) and AB204-B (2), revealed that the existence of Z-olefin in 1 and 2 had been involved in their antifungal activity.…”

Section: Discussionmentioning

confidence: 99%

“…The geometry of two substitutes of the aromatic ring was confirmed by NOE correlations, as is shown in Figure 2. From some Streptomyces strains, E-isomer of 1, (E)-5-(2-methylphenyl)-4-pentenoic acid was identified [33][34][35]; however, there was no report on the Z-isomer (1) obtained from natural sources. Therefore, it was concluded that 1 was a novel natural product.…”

Section: Biological Activity-guided Purification Of Active Componentsmentioning

confidence: 99%

New Antimicrobial Phenyl Alkenoic Acids Isolated from an Oil Palm Rhizosphere-Associated Actinomycete, Streptomyces palmae CMU-AB204T

et al. 2020

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Basal stem rot (BSR), or Ganoderma rot disease, is the most serious disease associated with the oil palm plant of Southeast Asian countries. A basidiomycetous fungus, Ganoderma boninense, is the causative microbe of this disease. To control BSR in oil palm plantations, biological control agents are gaining attention as a major alternative to chemical fungicides. In the course of searching for effective actinomycetes as potential biological control agents for BSR, Streptomyces palmae CMU-AB204T was isolated from oil palm rhizosphere soil collected on the campus of Chiang Mai University. The culture broth of this strain showed significant antimicrobial activities against several bacteria and phytopathogenic fungi including G. boninense. Antifungal and antibacterial compounds were isolated by antimicrobial activity-guided purification using chromatographic methods. Their structures were elucidated by spectroscopic techniques, including Nuclear Magnetic Resonance (NMR), Mass Spectrometry (MS), Ultraviolet (UV), and Infrared (IR) analyses. The current study isolated new phenyl alkenoic acids 1–6 and three known compounds, anguinomycin A (7), leptomycin A (8), and actinopyrone A (9) as antimicrobial agents. Compounds 1 and 2 displayed broad antifungal activity, though they did not show antibacterial activity. Compounds 3 and 4 revealed a strong antibacterial activity against both Gram-positive and Gram-negative bacteria including the phytopathogenic strain Xanthomonas campestris pv. oryzae. Compounds 7–9 displayed antifungal activity against Ganoderma. Thus, the antifungal compounds obtained in this study may play a role in protecting oil palm plants from Ganoderma infection with the strain S. palmae CMU-AB204T.

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5-(2-Methylphenyl)-4-pentenoic Acid from a Terrestrial Streptomycete

Abstract: From a terrestrial Streptomycete, GW 10/2517, the new 5-(2-methylphenyl)-4-pentenoic acid (1a) was isolated. The structure of 1a was proven by a detailed spectroscopic analysis and by synthesis.

Cited by 14 publications

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Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate

Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

New Antimicrobial Phenyl Alkenoic Acids Isolated from an Oil Palm Rhizosphere-Associated Actinomycete, Streptomyces palmae CMU-AB204T

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