Isolation, structure and synthesis of mahafacyclin B, a cyclic heptapeptide from the latex of Jatropha mahafalensis

Baraguey, Carine; Blond, Alain; Cavelier, Florine; Pousset, Jean-Louis; Bodo, Bernard; Auvin‐Guette, Catherine

doi:10.1039/b008538n

Cited by 51 publications

(70 citation statements)

References 18 publications

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“…These peptides exhibit a variety of essential biological activities. (Horsten, 1995;Baraguey et al, 2001;Mongkolvisut et al, 2006). Investigations of the structures of these cyclic peptides have indicated that their conformations are closely related to their biological activities (Cozzolino et al, 2005;Morita et al, 1997).…”

Section: Introductionmentioning

confidence: 96%

Jatrophidin I, a cyclic peptide from Brazilian Jatropha curcas L.: Isolation, characterization, conformational studies and biological activity

Altei¹,

Picchi²,

Abissi³

et al. 2014

Phytochemistry

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Section: Introductionmentioning

confidence: 96%

Jatrophidin I, a cyclic peptide from Brazilian Jatropha curcas L.: Isolation, characterization, conformational studies and biological activity

Altei¹,

Picchi²,

Abissi³

et al. 2014

Phytochemistry

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“…A total of 24 aromatic protons were observed in the 1 H NMR spectrum. Additionally, there were characteristic aromatic signals for tyrosine (Tyr) [13] at δ C 156.2, 130.4, 128.3, and 115.1, and 16 signals for phenylalanine (Phe) [14] with chemical shifts ranging from 126.4 to 138.2 in the 13 C NMR spectrum. Together, these findings suggested that compound 1 contained four Phe residues and one tyrosine residue.…”

Section: Resultsmentioning

confidence: 99%

Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

et al. 2018

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Two novel cyclic hexadepsipeptides, fusarihexin A (1: ) and fusarihexin B (2: ), and two known compounds, cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Val) (3: ) and cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Ile) (4: ), were isolated from the marine mangrove endophytic fungus sp. R5. Their chemical structures were elucidated on the basis of spectroscopic data and Marfey's analysis. In an bioassay, fusarihexin A (1: ) remarkably inhibited three plant pathogenic fungi: (Penz.) Sacc., which causes anthracnose in many fruits and vegetables, (Berk. and M. A. Curtis) Arx, which causes crown rot and anthracnose in bananas, and Schlecht. f. sp. lycopersici (Sacc.) W. C. Snyder et H. N. Hansen, which causes Fusarium wilt and fruit rot in tomatoes. Fusarihexin B (2: ) strongly inhibited and . The compounds were more potent than carbendazim, which is widely used as an agricultural and horticultural fungicide worldwide.

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“…However, the members of this family are also described as a source of bioactive orbitides [13]. Even though Euphorbiaceae comprises most of the orbitides described in the literature, they were isolated from the genera Jatropha [25][26][27][28][29][30][31][32][33][34] and Croton [35][36][37]. The 1990s were considered the gold period of investigations of orbitides, with the discovery of several new molecules, thus demonstrating that the search for their mechanisms of action, structures, and biosynthesis needs to be expanded [7].…”

Section: Biologically Active Orbitides From the Euphorbiaceae Familymentioning

confidence: 99%

“…Examination of Jatropha mahafalensis Jum. & H. Perrier, a tree endemic to Madagascar and also used to treat infected wounds in traditional medicine, led to the isolation of two cyclic heptapeptides named mahafacyclin A (20) [79] and mahafacyclin B (21) [33]. The amino acid sequence of mahafacyclin A (20) was determined to be cyclo(-Thr 1 -Ile 2 -Leu 3 -Gly 4 -Val 5 -Phe 6 -Gly 7 -), and according to the authors it was the first natural cyclic heptapeptide without proline to present the β-bulge characteristics [79].…”

Section: Peptides From the Jatropha Genusmentioning

confidence: 99%

Biologically Active Orbitides from the Euphorbiaceae Family

et al. 2017

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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.

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Isolation, structure and synthesis of mahafacyclin B, a cyclic heptapeptide from the latex of Jatropha mahafalensis

Cited by 51 publications

References 18 publications

Jatrophidin I, a cyclic peptide from Brazilian Jatropha curcas L.: Isolation, characterization, conformational studies and biological activity

Jatrophidin I, a cyclic peptide from Brazilian Jatropha curcas L.: Isolation, characterization, conformational studies and biological activity

Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

Biologically Active Orbitides from the Euphorbiaceae Family

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