title: Lycophlegmariols A-D: cytotoxic serratene triterpenoids from the club moss Lycopodium phlegmaria L.
abstract: Lycopodium serratene triterpenoids, along with an abietane-type diterpene were isolated from the methanol extract of club moss Lycopodium phlegmaria L. The structures of these hitherto unknown lycopodium terpenoids were elucidated on the basis of spectroscopic analysis. Pentacyclic triterpenoids, 21β-hydroxy-serrat-14-en-3α-ol (1) and 21β-hydroxy-serrat-14-en-3α-yl acetate (2) were isolated together with four serratene triterpeneoids established as 21β,29-dihydroxyserrat-14-en-3α-yl dihydrocaffeate (lycophlegmariol A, 5), 21β,24,29-trihydroxyserrat-14-en-3β-yl dihydrocaffeate (lycophlegmariol B, 6), 21α,24-dihydroxyserrat-14-en-3β-yl 4-hydroxycinnamate (lycophlegmariol C, 7), and 14β,21α,29-trihydroxyserratan-3β-yl dihydrocaffeate (lycophlegmariol D, 8) as well as a known lycophlegmarin (9). An abietane-type diterpene, 8,11,13-abietatriene-3β,12-dihydroxy-7-one (margocilin, 10), was isolated for the first time from a Lycopodium plant. Lycophlegmariol B (6), D (8) and compound 1 showed inhibitory effects against MOLT-3 acute lymphoblastic leukemia (T-lymphoblast) with IC(50) of 14.7, 3.0 and 2.9 μM, respectively.
authors.affiliation: Laboratory of Natural Product, Chulabhorn Research Institute, Laksi, Bangkok 10210, Thailand.
authors.forename: Sawangjitt
authors.initials: S
authors.lastname: Wittayalai
authors.forename: Supaporn
authors.initials: S
authors.lastname: Sathalalai
authors.forename: Sakornrat
authors.initials: S
authors.lastname: Thorroad
authors.forename: Prateep
authors.initials: P
authors.lastname: Worawittayanon
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
authors.forename: Nopporn
authors.initials: N
authors.lastname: Thasana
mesh_terms: D045784:Abietanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000107:Acetylation; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival; D004354:Drug Screening Assays, Antitumor; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D032502:Lycopodium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C572814:21beta-hydroxy-serrat-14-en-3alpha-ol; D045784:Abietanes; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D014315:Triterpenes; C508405:lycophlegmarin; D000432:Methanol