title: Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry.
abstract: Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca(2+) signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective β-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca(2+) signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating.
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Nozomi
authors.initials: N
authors.lastname: Tsutsui
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Genki
authors.initials: G
authors.lastname: Gotoh
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Nao
authors.initials: N
authors.lastname: Morita
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Naohisa
authors.initials: N
authors.lastname: Nomura
authors.affiliation: Laboratory of Molecular Pharmacogenomics, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Ayako
authors.initials: A
authors.lastname: Kita
authors.affiliation: Laboratory of Molecular Pharmacogenomics, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan. Electronic address: sugiurar@phar.kindai.ac.jp.
authors.forename: Reiko
authors.initials: R
authors.lastname: Sugiura
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan. Electronic address: muraoka@phar.kindai.ac.jp.
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
mesh_terms: D020013:Calcium Signaling / Q000187:drug effects*; D060326:Chemistry Techniques, Synthetic; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008358:Mannose / Q000737:chemistry; D049990:Membrane Transport Modulators / Q000737:chemistry / Q000494:pharmacology; D012568:Schizosaccharomyces / Q000187:drug effects / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry
chemical_list: D006017:Glycolipids; D049990:Membrane Transport Modulators; D013402:Sugar Alcohols; C579014:acremomannolipin A; D008358:Mannose
keywords: Acremomannolipin A; Acremonium strictum; Calcium signal modulator; Glycolipid; SAR study