title: Myrtucommulones F-I, phloroglucinols with thyrotropin-releasing hormone receptor-2 binding affinity from the seeds of Corymbia scabrida.
abstract: High-throughput screening of a plant and marine invertebrate extract library to find natural products with rat thyrotropin-releasing hormone (TRH) receptor-2 binding affinity led to the isolation of four new, myrtucommulones F-I (3-6), and two known, myrtucommulones A (1) and D (2), active acylphloroglucinols from the seeds of the Queensland tree Corymbia scabrida. Their structures were assigned from interpretation of 2D NMR and high-resolution ESIMS data. The relative configuration of the stereogenic centers for all six compounds was deduced from ROESY correlations. This is the first time that myrtucommulone A (1) has been isolated as a single pure compound. The structure of myrtucommulone D (2) has been revised. Myrtucommulones A, D, and F-I showed rat TRH receptor-2 binding affinity with IC50 values of 39, 11, 16, 24, 31, and 16 microM, respectively.
authors.affiliation: Eskitis Institute, Griffith University, Brisbane, Queensland, Australia 4111.
authors.forename: Anthony R
authors.initials: AR
authors.lastname: Carroll
authors.forename: Jasmine
authors.initials: J
authors.lastname: Lamb
authors.forename: Roger
authors.initials: R
authors.lastname: Moni
authors.forename: Gordon P
authors.initials: GP
authors.lastname: Guymer
authors.forename: Paul I
authors.initials: PI
authors.lastname: Forster
authors.forename: Ronald J
authors.initials: RJ
authors.lastname: Quinn
mesh_terms: D000818:Animals; D015394:Molecular Structure; D027822:Myrtaceae / Q000737:chemistry*; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D011793:Queensland; D051381:Rats; D018025:Receptors, Thyrotropin-Releasing Hormone / Q000378:metabolism*; D012639:Seeds / Q000737:chemistry
chemical_list: D018025:Receptors, Thyrotropin-Releasing Hormone; C455139:myrtucommulone A; D010696:Phloroglucinol