title: Insights into the Biosynthetic Origin of 3-(3-Furyl)alanine in Stachylidium sp. 293 K04 Tetrapeptides.
abstract: The marine-sponge-derived fungus Stachylidium sp. 293 K04 produces the N-methylated peptides endolide A (1) and endolide B (2), showing affinity for the vasopressin receptor 1A and serotonin receptor 5HT2B, respectively. Both peptides feature the rare amino acid 3-(3-furyl)alanine. Isotope labeling experiments, employing several13C-enriched precursors, revealed that this unprecedented heterocyclic amino acid moiety in endolide A (1) is synthesized from a cyclic intermediate of the shikimate pathway, but not from phenylalanine. Two new tetrapeptide analogues, endolides C and D (3 and 4), were characterized, as well as the previously described hirsutide (5).
authors: Institute for Pharmaceutical Biology, University of Bonn , Nussallee 6, D-53115 Bonn, Germany.|Department of Pharmacognosy and Tissue Culture, National Organization for Drug Control and Research , Cairo, Egypt.
authors: Fayrouz
authors: F
authors: El Maddah
authors: Institute for Pharmaceutical Biology, University of Bonn , Nussallee 6, D-53115 Bonn, Germany.
authors: Stefan
authors: S
authors: Kehraus
authors: Institute for Pharmaceutical Biology, University of Bonn , Nussallee 6, D-53115 Bonn, Germany.
authors: Mamona
authors: M
authors: Nazir
authors: Institute for Pharmaceutical Biology, University of Bonn , Nussallee 6, D-53115 Bonn, Germany.|UCIBIO-REQUIMTE, Departamento de Ciências da Vida, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa , Caparica 2829-516, Portugal.
authors: Celso
authors: C
authors: Almeida
authors: Institute for Pharmaceutical Biology, University of Bonn , Nussallee 6, D-53115 Bonn, Germany.
authors: Gabriele M
authors: GM
authors: König
mesh_terms: D000409:Alanine; D000818:Animals; D001203:Ascomycota / Q000737:chemistry*; D001315:Australia; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D010649:Phenylalanine / Q000737:chemistry; D011161:Porifera / Q000382:microbiology
chemical_list: D010456:Peptides, Cyclic; C000608371:endolide A; C000608389:endolide B; C504294:hirsutide; D010649:Phenylalanine; D000409:Alanine