title: (2S,3S)-sulfated pterosin C, a cytotoxic sesquiterpene from the Bangladeshi mangrove fern Acrostichum aureum.
abstract: Two new sesquiterpenes, (2R,3S)-sulfated pterosin C (1) and (2S,3S)-sulfated pterosin C (2), along with two known derivatives, (2S,3S)-pterosin C and (2R)-pterosin P, were isolated from a methanolic extract of the aerial parts of Acrostichum aureum. The structures of 1 and 2 were determined by the interpretation of their spectroscopic data. The isolated pterosins were evaluated for their cytotoxic activity against the AGS, HT-29, MDA-MB-231, and MCF-7 human cancer cell lines and the NIH3T3 normal mouse fibroblast cell line, using the MTT assay. Compound 2 showed IC50 values in the range 23.9-68.8 μM. The lowest IC50 value (23.9 μM) was recorded against AGS gastric adenocarcinoma cells. Compound 2 was found to exert an apoptotic effect on AGS cells within 24 h of treatment, which increased with time and was greater than the positive control, cycloheximide. The cytotoxicity of 2 seems to be due in part to the sulfate group on C-14 and the configuration at C-2.
authors: School of Pharmacy, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
authors: Shaikh J
authors: SJ
authors: Uddin
authors: Tracey L H
authors: TL
authors: Jason
authors: Karren D
authors: KD
authors: Beattie
authors: I Darren
authors: ID
authors: Grice
authors: Evelin
authors: E
authors: Tiralongo
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001459:Bangladesh; D004354:Drug Screening Assays, Antitumor; D029624:Ferns / Q000737:chemistry*; D006801:Humans; D007189:Indans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D051379:Mice; D041681:NIH 3T3 Cells; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D013463:Sulfuric Acid Esters / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: C562207:(2S,3S)-sulfated pterosin C; D000972:Antineoplastic Agents, Phytogenic; D007189:Indans; D012717:Sesquiterpenes; D013463:Sulfuric Acid Esters; C010772:pterosin