Effect of the 4′-substituted phenylalanine moiety of sansalvamide A peptide on antitumor activity

Liu, Shouxin; Yang, Yihua; Zhao, Cui; Huang, Jing; Han, Chao; Han, Jiahuai

doi:10.1039/c3md00294b

Cited by 5 publications

(3 citation statements)

References 19 publications

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“…The ethyl acetate extracts of all treatments presented typical metabolic profiles in HPLC analysis (Figure 2): the known compounds (− )-citreoisocoumarin ( 6), ( − )-citreoisocoumarinol (7), lateropyrone (8), enniatin B (9), enniatin B1 (10), enniatin A1 (11), enniatin A (12) and fusaristatin A (13) were readily identified by LC-MS analysis and by comparison with authentic standards that had either previously been isolated from the same fungal strain, 33 or in the case of phenyl acetic acid ( 14) by comparison with a commercially available standard. The amounts of 6-13 per flask irrespective of the presence or absence of juice were comparable to those of previous experiments (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…5 Enniatins are currently being investigated as potential anticancer agents, 6,7 and so are semisynthetic derivatives of the cyclic depsipeptide sansalvamide A, another Fusarium metabolite with strong in vitro cytotoxicity against pancreatic, colon and breast cancer cell lines. [8][9][10][11] In addition, Fusarium strains have transiently produced several antineoplastic agents formerly known from plants such as paclitaxel, camptothecin and L-asparaginase, 12-14 as well as podophyllotoxin, 15 the latter being the lead compound that led to the clinically used semisynthetic drugs etoposide and teniposide.…”

Section: Introductionmentioning

confidence: 99%

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OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum

et al. 2017

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Using the OSMAC (One Strain MAny Compounds) approach, the fungal endophyte Fusarium tricinctum was cultivated on fruit and vegetable juice-supplemented solid rice media. This led to an up to 80-fold increase in the accumulation of the new natural product fusarielin J (1), as well as to the induction of two new natural products fusarielin K (2) and fusarielin L (3) and the known derivatives fusarielins A (4) and B (5). Compounds 2-5 were not detected when the fungus was grown on rice media lacking either fruit or vegetable juice. The highest increase in the accumulation of compound 1 was observed in the presence of apple and carrot juice, whereas the stimulating effect was weaker for banana juice. Compound 1 exhibited cytotoxicity against the human ovarian cancer cell line A2780, with an IC value of 12.5 μM.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum

et al. 2017

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“…In the recent past, mainly the groups of Silverman and McAlpine prepared more than 100 sansalvamide A analogues, both on solid-phase and in solution. Some of those showed excellent chemotherapeutic activities [33,34,35,36,37,38,39].…”

Section: Cyclopentadepsipeptidesmentioning

confidence: 99%

Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug Research

Sivanathan

Scherkenbeck

2014

Molecules

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Abstract:Faced with the need to find new drugs for all kinds of diseases, science sees that Nature offers numerous classes of compounds showing an impressively high biological potential. Among those are the cyclodepsipeptides, hybrid structures composed of amino and hydroxy acids. In the past decades numerous cyclodepsipeptides have been isolated and their potential as drugs has been studied extensively. For several cyclodepsipeptides total syntheses both in solution and on solid-phase have been established, allowing the production of combinatorial libraries. In addition, the biosynthesis of specific cyclodepsipeptides has been elucidated and used for the chemoenzymatic preparation of nonnatural analogues. This review summarizes the recent literature on cyclic tetra-to decadepsipeptides, composed exclusively of α-amino-and α-hydroxy acids.

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Structural Diversity using Hyp “Customizable Units”: Proof‐of‐Concept Synthesis of Sansalvamide‐Related Antitumoral Peptides

et al. 2021

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The potential of “customizable units” to generate structural diversity for biological screenings is highlighted in this proof‐of‐concept synthesis of new peptides related to the potent antitumoral Sansalvamide A. Using L‐4‐hydroxyproline (Hyp) as a customizable unit in a linear parent peptide, an improved procedure for selective peptide modification was developed. A divergent Hyp scission‐reductive amination process was carried out, affording five linear peptides with cationic residues, and notably, an N‐alkyl moiety that affected the conformation of the peptide. After two steps (saponification and macrocyclization), sixteen differently N1‐substituted linear and cyclic peptides were obtained. For the first time, the activity of the linear and cyclic compounds was compared. Not only some linear analogs but also cyclic compounds with scarcely studied cationic residues were active against MCF7 breast cancer line. Thus, the structural diversity generated from customizable units can be valuable in drug discovery.

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Effect of the 4′-substituted phenylalanine moiety of sansalvamide A peptide on antitumor activity

Cited by 5 publications

References 19 publications

OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum

OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum

Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug Research

Structural Diversity using Hyp “Customizable Units”: Proof‐of‐Concept Synthesis of Sansalvamide‐Related Antitumoral Peptides

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