Cyclo-(l-tryptophyl-l-phenylalanyl), a plant growth regulator produced by the fungus Penicillium sp.

Citrinolactones A, B and C, and Sclerotinin C, Plant Growth Regulators fromPenicillium citrinum

“…[1][2][3][4][5] Isocoumarins are a group of fungal metabolites that include such plant growth regulators as 4-hydroxykigelin and 6-demethylkigelin from Aspergillus terreus.…”

Cyclo-(TRP-PHE) diketopiperazines from the endophytic fungus Aspergillus versicolor isolated from Piper aduncum

“…In fact, this result, in effect, suggests that compound 2 bears the same absolute configuration as the compound isolated from Penicillium sp. 8 The molecular formula C 40 H 36 N 6 O 4 of compound 3 was established by 13 It is worth pointing out the remarkable similarities that were found between the 1 H NMR spectra of 3 and 2, with the decrease observed in the extension of the tryptophan aromatic amino acid through the reduction of Δ 2-3 present in the indole system besides the connection of C-2 (δ C 79. The 13 C NMR showed one primary diaminic and one quaternary carbon linker between two monomers of the dimer attributed to C-2 and C-3, respectively.…”

“…The structures of the compounds were elucidated using 1-D, 2-D NMR (Table 1 and 2), MS techniques were also carried out and comparison was made with the literature data. [7][8][9][10][11][12] The compounds were identified as three peptide derivatives: cyclo-(tryptophyl-phenylalanyl) (2), diketopiperazine dimer WIN 64821 (3), 3-hydroxy-15H-tryptophenaline (4) and 2-hydroxy-6-N-isopentenyl-adenine (5), 4-methoxyphtalide (1) and 3-hydroxy-4-(1-hydroxy-1,5-dimethyl-hexyl) benzoic acid (6) (Figure 1). The molecular formula C 9 H 8 O 3 of compound 1 was established by 13 C NMR and HREIMS analysis, which showed the protonated molecular ion peak [M+H] + at m/z 165.0597 (Calcd.…”

Biological active metabolite cyclo (l-Trp-l-Phe) produced by South China Sea sponge Holoxea sp. associated fungus Aspergillus versicolor strain TS08

“…Finally, the structure of the isolated compound was determined to be cyclo (L-Trp-L-Phe) by comparison with the reported data (Fig. 5) [10]. The growth curve of A. versicolor strain TS08 and its production dynamics for cyclo (L-Trp-L-Phe) are summarized in Fig.…”

“…DKPs play an important role in regulatory mechanism of quorum sensing as signal molecules and have become a research hot point in ecological chemistry [8,9]. As one of the DKPs, cyclo (L-Trp-L-Phe) has the biological activities of plant growth regulation and moderate cytotoxicity [10,11], In addition, cyclo (L-Trp-L-Phe) is most likely the biosynthetic precursor to complex diketopiperazine WIN 64821, a nonpeptide neurokinin antagonist [12]. Thus, cyclo (L-Trp-L-Phe) has the application potential in pharmaceutical and agricultural biotechnologies.…”