Chemistry and structure of ganefromycin

Carter, Guy T.; Phillipson, Douglas W.; West, Robert R.; Borders, Donald B.

doi:10.1021/jo00076a016

Cited by 17 publications

(18 citation statements)

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“…[388][389][390][391][392][393][394][395][396][397][398][399][400][401] For 228 and some other congeners it was shown that the activity relies on an inhibition of elongation factor Tu (EF-Tu), [402][403][404][405][406] which plays a key role in protein biosynthesis by mediating the entry of aminoacyl-tRNAs into the ribosome. [407][408][409] For this reason, the name elfamycins was proposed for this compound family.…”

Section: Kirromycinmentioning

confidence: 99%

“…386,387 is a member of a larger family of structurally related compounds (229)(230)(231)(232)(233)(234)(235)(236)(237)(238)(239)(240)(241)(242)(243)(244)(245)(246)(247)(248), many of which exhibit narrow-spectrum activity against Gram-positive bacteria. [388][389][390][391][392][393][394][395][396][397][398][399][400][401] For 228 and some other congeners it was shown that the activity relies on an inhibition of elongation factor Tu (EF-Tu), [402][403][404][405][406] which plays a key role in protein biosynthesis by mediating the entry of aminoacyl-tRNAs into the ribosome. [407][408][409] For this reason, the name elfamycins was proposed for this compound family.…”

Section: Thailandamidesmentioning

confidence: 99%

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Biosynthesis of polyketides by trans-AT polyketide synthases

2010

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Section: Kirromycinmentioning

confidence: 99%

Section: Thailandamidesmentioning

confidence: 99%

Biosynthesis of polyketides by trans-AT polyketide synthases

2010

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“…The organic layer was washed with dilute HC1, H20, aqueous NaHCG3, and HzO, dried, filtered, and evaporated. The residue was crystallized from CH2Cl2-hexane to afford 1 (1.92 g, 81%) as white flakes, mp 170-172°; Arteag-9-en-7$,8$-diol-l-one [2] and arteag-9-en-7a.,8$-diol-l-one [31--A solution of rastevione mesylate [1] (500 mg) in MeOH (20 ml) was treated with a solution of KOH (500 mg) in H20 (0.7 ml).…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

Molecular Rearrangement of Rastevione Mesylate into Arteagane Derivatives

Román¹,

Zepeda²,

Morales³

et al. 1995

J. Nat. Prod.

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Molecular rearrangment of rastevione mesylate {!] in alkaline medium afforded two epimeric 2,6,6,11 -tetramethyltricyclo[5.4.0.04,8]undecane derivatives [2 and 3] by a 1,3-bond migration. Their stereostructures, which possess a new hydrocarbon skeleton named arteagane, were elucidated from nmr data in combination with X-ray diffraction analyses of 3 and its diacetate 7. The conformations of 2, 3, and several derivatives are reported.Molecular rearrangements of natural products offer the possibility of generating substances with novel skeletons (1-3) and increased understanding of their chemical behavior (4-6), which can be applied to synthetic approaches (7,8). In continuation of our research on molecular rearrangements of sesquiterpenes (9,10), we report herein the transformation of the longi^inene derivative rastevione mesylate [1] to the 2,6,6,11tetramethyltricyclo[5.4.0.0 ' Jundecane derivatives 2 and 3 by a 1,3-bond migration.

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“…The trisaccharide unit is a-oleandose-b-cymarosea-oleandose and fits to the trisaccharide earlier described in phenelfamycins. 12,13 The linkage between the trisaccharide chain and the aglycone is established through HMBC couplings between C-1¢/33-H and C-33/ 1¢-H ( Figure 5). …”

Section: -H5mentioning

confidence: 99%

“…11 Finally, type 3 contains the phenelfamycins with a phenylacetyl substitution at position C-22 or C-23 and C-33 O-glycosylation with mono-(phenelfamycins A and B), di-(phenelfamycins C and D) or trisaccharide units (phenelfamycins E and F, also named as ganefromycins a and b). 12,13 All elfamycins show a very narrow antibacterial spectrum against human pathogens and most of them show excellent activities as growth-promoting agents in animals. 14 In this paper we report on the new phenelfamycins 1 and 2, the taxonomy of the producing strain, their fermentation, isolation, structure elucidation and biological activity.…”

Section: Introductionmentioning

confidence: 99%

Phenelfamycins G and H, new elfamycin-type antibiotics produced by Streptomyces albospinus Acta 3619

et al. 2011

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Phenelfamycins G and H are new members of the family of elfamycin antibiotics with the basic structure of phenelfamycins E and F, respectively, which are also well known as ganefromycins a and b. Phenelfamycins G and H differ from phenelfamycins E and F by an additional hydroxy group at position C-30, which is not described so far for any of the elfamycin-type antibiotics. The actinomycete strain that produced phenelfamycins G and H was identified to be Streptomyces albospinus based on its 16S rRNA gene sequence. Phenelfamycins G and H exhibit a narrow antibacterial spectrum with a pronounced inhibitory activity against Propionibacterium acnes. The Journal of Antibiotics (2011) 64, 257-266; doi:10.1038/ja2010.170; published online 2 February 2011 Keywords: elfamycin antibiotics; ganefromycin; phenelfamycin; Propionibacterium acnes; Streptomyces INTRODUCTIONEnvironmental samples were collected from untapped Malaysian ecological niches to isolate actinomycetes strains, which were investigated within our HPLC-diode array screening program for the production of secondary metabolites with the aim of detecting novel drugs for pharmaceutical applications. 1 Strain Acta 3619 was isolated from a soil collected from the rhizosphere of bamboo trees in the tropical rainforest of the University of Malaya Field Station at Gombak, Selangor, Malaysia. The strain was found to be of special interest, as it gave two significant peaks in the HPLC analysis of an extract of the culture filtrate having congruent UV-vis spectra that differed from all 937 reference compounds stored in our HPLC-UVvis database. 2 Structure elucidation of the two isolated compounds revealed a relationship with phenelfamycins E and F and therefore were named as phenelfamycins G (1) and H (2), respectively. Their structures are shown in Figure 1.Phenelfamycins belong to the elfamycin family of antibiotics, which inhibit protein synthesis of bacteria by an interaction with elongation factor Tu, demonstrated in prokaryotic cells. [3][4][5] Hence they derived their name from this interaction. Elfamycins can be subdivided into three types according to their structure. Type 1 includes kirromycin 6 (mocimycin), aurodox, 7,8 heneicomycin 9 and efrotomycin. 10 Type 2, elfamycin, is represented by kirrothricin with an open tetrahydrofuran ring in the aglycone. 11 Finally, type 3 contains the phenelfamycins with a phenylacetyl substitution at position C-22 or C-23 and C-33 O-glycosylation with mono-(phenelfamycins A and B), di-(phenelfamycins C and D) or trisaccharide units (phenelfamycins E and F, also named as ganefromycins a and b). 12,13 All elfamycins show a very narrow antibacterial spectrum against human pathogens and most of them show excellent activities as growth-promoting agents in animals. 14 In this paper we report on the new phenelfamycins 1 and 2, the taxonomy of the producing strain, their fermentation, isolation, structure elucidation and biological activity. RESULTS Taxonomy of the producing strainStrain Acta 3619 was isolated from the rhizosphere so...

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Chemistry and structure of ganefromycin

Cited by 17 publications

References 0 publications

Biosynthesis of polyketides by trans-AT polyketide synthases

Biosynthesis of polyketides by trans-AT polyketide synthases

Molecular Rearrangement of Rastevione Mesylate into Arteagane Derivatives

Phenelfamycins G and H, new elfamycin-type antibiotics produced by Streptomyces albospinus Acta 3619

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