title: Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: role of the length of alditol side chain.
abstract: Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca(2+) signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective β-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca(2+) signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity.
authors.affiliation: Laboratory of Pharmaceutical Organic Chemistry, Faculty 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, Faculty 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, Faculty 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, Faculty of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Yoshitomo
authors.initials: Y
authors.lastname: Okayama
authors.affiliation: Laboratory of Molecular Pharmacogenomics, Faculty 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, Faculty 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, Faculty 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: D000164:Acremonium / Q000737:chemistry; D019703:Calcineurin / Q000172:deficiency / Q000235:genetics*; D002118:Calcium / Q000378:metabolism*; D002120:Calcium Channel Agonists / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D020013:Calcium Signaling; D005656:Fungal Proteins / Q000235:genetics* / Q000378:metabolism; D015870:Gene Expression; D006017:Glycolipids / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D017136:Ion Transport; D012568:Schizosaccharomyces / Q000187:drug effects / Q000235:genetics / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry
chemical_list: D002120:Calcium Channel Agonists; D005656:Fungal Proteins; D006017:Glycolipids; D013402:Sugar Alcohols; C579014:acremomannolipin A; D019703:Calcineurin; D002118:Calcium
keywords: Acremomannolipin A; Acremonium strictum; Calcium signal modulator; Glycolipid; SAR study