O-ACETYL-N-(N′-BENZOYL-<scp>l</scp>-PHENYLALANYL)-<scp>l</scp>-PHENYLALANINOL. ISOLATION FROM EUPHORBIA FISCHERIANA STEUDEL

Uemura, Daisuke; Sugiura, Kimio; Hiratå, Yoshimasa

doi:10.1246/cl.1975.537

Cited by 11 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The genus Euphorbia also contains peptides. A molecule identified as a peptide derivative, aurentiamide acetate, compound 4, was isolated from the roots of Euphorbia fischeriana Steudel [84]. As mentioned previously, this compound was also found in the aerial parts of C. hieronymi Griseb [22].…”

Section: Peptides From Other Genera (Euphorbiaceae Family)mentioning

confidence: 60%

Biologically Active Orbitides from the Euphorbiaceae Family

et al. 2017

View full text Add to dashboard Cite

A comprehensive overview of natural orbitides isolated from Euphorbiaceae species and their most relevant biological activities are presented. Euphorbiaceae is a large and diverse family, which comprises about 300 genera, and is known as an important source of medicines and toxins. Several classes of secondary metabolites have been described for this taxon, however, orbitides have been broadly reported in and genera. Additionally, the latex is documented as the main source of orbitides in this family. Based on their structural and functional diversity, orbitides present a large variety of biological activities described as cytotoxicity, antimalarial, antibacterial, antifungal, enzymatic inhibition, and immunosuppressive, although the mechanism of action still needs to be further investigated. In recent years, the discovery of bioactive cyclic peptides from different sources has grown exponentially, making them promising molecules in the search for new drug leads. This review also highlights the attempts made by many researchers to organize the orbitides nomenclature and amino acid numbering, as well the important progress recently achieved in the biosynthetic study area.

show abstract

Section: Peptides From Other Genera (Euphorbiaceae Family)mentioning

confidence: 60%

Biologically Active Orbitides from the Euphorbiaceae Family

et al. 2017

View full text Add to dashboard Cite

show abstract

“…This is the first reported isolation of 3 and 7 from any Sigesbeckia species. Compound 3 has previously been isolated from Jurinea leptoloba [19] and Vernonia pectoralis [23], both belonging to the Asteraceae family, while compound 7 was found in Euphorbia fischeriana (Euphorbiaceae) [21]. Compound 1 was identified as a new natural product.…”

Section: Resultsmentioning

confidence: 99%

“…5S, Supporting Information). Therefore, compound 1 was identified as 17(13 → 14)-abeo-ent-3S*,13S*,16-trihydroxystrob-8(15)-ene.Compounds 2-9 were identified by NMR, MS, and comparison of the spectral data to those reported in the literature as 2-propenoic acid,2-methyl-2,3,3a,4,5,8,9,10,11,11a-decahydro-6,10-bis (hydroxymethyl)-3-methylene-2-oxocyclodeca[b]furan-4-yl ester (2)[17], urospermal A-8-O-methacrylate (3)[18,19], orientalide (4)[20], (3aR,4R,5S,6E,10E,11aS)-5-acetoxy-6-formyl-10-methyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl methacrylate (5)[18], darutoside(6) [18], aurantiamide acetate (7)[21], hythiemoside A (8)[22], and hythiemoside B (9)[22] (▶…”

mentioning

confidence: 99%

A New Diterpene and Anti-inflammatory Sesquiterpene Lactones from Sigesbeckia orientalis

et al. 2020

View full text Add to dashboard Cite

Sigesbeckia orientalis, more commonly referred to as Herba Sigesbeckiae or Xi Xian Cao in traditional Chinese medicine and hy thiêm in traditional Vietnamese medicine, is used in China and Vietnam to treat inflammatory diseases such as arthritis, rheumatism, and joint pain. In initial investigations, the dichloromethane extract from the aerial parts of S. orientalis showed distinct inhibitory effects on the release of interleukin-8 in human neutrophils. Therefore, the purpose of the present study was the phytochemical investigation of the bioactive dichloromethane extract and the in vitro analysis of the effects of the isolated compounds on interleukin-8, interleukin-1β, tumor necrosis factor-α, and monocyte chemoattractant protein 1 release, and surface expression of adhesion molecules (CD11a, CD11b, and CD62L) in lipopolysaccharide-stimulated human neutrophils to identify the active principle(s). The separation of the bioactive dichloromethane extract using various chromatographic techniques led to the isolation of nine compounds. Their chemical structures were elucidated from nuclear magnetic resonance and mass spectrometry data. One diterpene, 17(13 → 14)-abeo-ent-3S*,13S*,16-trihydroxystrob-8(15)-ene, was identified as a new natural product. Three germacranolide sesquiterpene lactones inhibited interleukin-8 production with IC50 values between 1.6 and 6.3 µM, respectively, and tumor necrosis factor-α production with IC50 values between 0.9 and 3.3 µM, respectively. Furthermore, they significantly inhibited interleukin-1β and monocyte chemoattractant protein 1 production and diminished the effects of lipopolysaccharide on the surface expression of the adhesion molecules CD11a, CD11b, and CD62L. These findings support the traditional use of S. orientalis in the treatment of inflammatory diseases.

show abstract

“…C-Terminal l -Pheol is commonly found in peptaibiotics [17] [18] but has also been infrequently reported as a constituent of other plant and fungal secondary metabolites such as N -benzoyl- l -phenylalaninol from Catharanthus pusillus [95] and Diospyros quaesita [96], O -acetyl- N -( N ′-benzoyl- l -phenylalanyl)- l -phenylalaninol from Euphorbia fischeriana and E. kansui [97], and N -benzoyl- O -[ N ′-benzoyl- l -phenylalanyl]- l -phenylalaninol from Penicillium arenicola (syn. P. canadense) [98].…”

Section: Discussionmentioning

confidence: 99%

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

Röhrich

Iversen

Jaklitsch

et al. 2013

Chemistry & Biodiversity

View full text Add to dashboard Cite

To investigate the significance of antibiotics for the producing organism(s) in the natural habitat, we screened a specimen of the fungicolous fungus Trichoderma phellinicola (syn. Hypocrea phellinicola) growing on its natural host Phellinus ferruginosus. Results revealed that a particular group of non-ribosomal antibiotic polypeptides, peptaibiotics, which contain the non-proteinogenic marker amino acid, α-aminoisobutyric acid, was biosynthesized in the natural habitat by the fungicolous producer and, consequently, released into the host. By means of liquid chromatography coupled to electrospray high-resolution time-of-flight mass spectrometry, we detected ten 20-residue peptaibols in the specimen. Sequences of peptaibiotics found in vivo were independently confirmed by analyzing the peptaibiome of an agar plate culture of T. phellinicola CBS 119283 (ex-type) grown under laboratory conditions. Notably, this strain could be identified as a potent producer of 39 new 17-, 18-, and 19-residue peptaibiotics, which display the same building scheme as the 20-residue peptaibols found in the specimen. Two of the 19-residue peptaibols are tentatively assigned to carry tyrosinol, a novel C-terminal residue, as deduced from high-resolution tandem mass-spectrometry data. For the new peptaibiotics produced by T. phellinicola, the name ‘hypophellin(s)’, based on the teleomorph name, is introduced.

show abstract

O-ACETYL-N-(N′-BENZOYL-l-PHENYLALANYL)-l-PHENYLALANINOL. ISOLATION FROM EUPHORBIA FISCHERIANA STEUDEL

Abstract: O-Acetyl-N-(N′-benzoyl-l-phenylalanyl)-l-phenylalaninol was isolated from Euphorbia fischeriana Steudel. The structure has been established by nmr spectral analysis and the synthesis of this compound.

Cited by 11 publications

References 0 publications

Biologically Active Orbitides from the Euphorbiaceae Family

Biologically Active Orbitides from the Euphorbiaceae Family

A New Diterpene and Anti-inflammatory Sesquiterpene Lactones from Sigesbeckia orientalis

Screening the Biosphere: The Fungicolous Fungus Trichoderma phellinicola, a Prolific Source of Hypophellins, New 17‐, 18‐, 19‐, and 20‐Residue Peptaibiotics

Contact Info

Product

Resources

About