title: An anti-mycobacterial bisfunctionalized sphingolipid and new bromopyrrole alkaloid from the Indonesian marine sponge Agelas sp.
abstract: In the course of our studies on anti-mycobacterial substances from marine organisms, the known dimeric sphingolipid, leucettamol A (1), was isolated as an active component, together with the new bromopyrrole alkaloid, 5-bromophakelline (2), and twelve known congeners from the Indonesian marine sponge Agelas sp. The structure of 2 was elucidated based on its spectroscopic data. Compound 1 and its bis TFA salt showed inhibition zones of 12 and 7 mm against Mycobacterium smegmatis at 50 μg/disk, respectively, while the N,N'-diacetyl derivative (1a) was not active at 50 μg/disk. Therefore, free amino groups are important for anti-mycobacterial activity. This is the first study to show the anti-mycobacterial activity of a bisfunctionalized sphingolipid. Compound 13 exhibited weak PTP1B inhibitory activity (29% inhibition at 35 μM).
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan.|Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia.
authors.forename: Delfly B
authors.initials: DB
authors.lastname: Abdjul
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan. yamazaki@tohoku-mpu.ac.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamazaki
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan.
authors.forename: Syu-Ichi
authors.initials: SI
authors.lastname: Kanno
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan.
authors.forename: Ayako
authors.initials: A
authors.lastname: Tomizawa
authors.affiliation: Faculty of Mathematic and Natural Sciences, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia.
authors.forename: Henki
authors.initials: H
authors.lastname: Rotinsulu
authors.affiliation: Faculty of Mathematic and Natural Sciences, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia.
authors.forename: Defny S
authors.initials: DS
authors.lastname: Wewengkang
authors.affiliation: Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia.
authors.forename: Deiske A
authors.initials: DA
authors.lastname: Sumilat
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan.
authors.forename: Kazuyo
authors.initials: K
authors.lastname: Ukai
authors.affiliation: Faculty of Nursing, University of Pembangunan Indonesia, Bahu, Manado, 95115, Indonesia.
authors.forename: Magie M
authors.initials: MM
authors.lastname: Kapojos
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan.
authors.forename: Michio
authors.initials: M
authors.lastname: Namikoshi
mesh_terms: D047230:Agelas / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007214:Indonesia; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects* / Q000254:growth & development; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013107:Sphingolipids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000625113:5-bromophakelline; D000470:Alkaloids; D000900:Anti-Bacterial Agents; D001688:Biological Products; D004791:Enzyme Inhibitors; D011758:Pyrroles; D013107:Sphingolipids; C540199:leucettamol A; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1
keywords: Bromopyrrole alkaloid; Leucettamol A; Marine sponge Agelas sp.; Mycobacterium smegmatis; Protein tyrosine phosphatase 1B