title: Dactyloditerpenol acetate, a new prenylbisabolane-type diterpene from Aplysia dactylomela with significant in vitro anti-neuroinflammatory activity.
abstract: A new regular diterpene possessing an unusual 1,6-anti-3-methylcyclohex-2-en-1-ol ring system, dactyloditerpenol acetate (1), has been extracted from the tropical sea hare Aplysia dactylomela and its stereostructure elucidated by spectroscopic methods. The absolute configuration of 1 was determined as 1S, 6S, 7R, 10S, and 11R by application of Kishi's method for the assignment of absolute configuration of alcohols. The new diterpene potently inhibited in vitro thromboxane B2 (TXB2) (IC50 0.4μM) and superoxide anion (O2(-)) (IC50 1μM) generation from Escherichia coli lipopolysaccharide (LPS)-activated rat neonatal microglia, with concomitant low short-term toxicity.
authors.affiliation: Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, PR 00931-3346, United States.
authors.forename: Carlos
authors.initials: C
authors.lastname: Jiménez-Romero
authors.affiliation: Department of Pharmacology, Chicago College of Osteopathic Medicine, Midwestern University, 555, 31st Street, Downers Grove, IL 60515, United States.
authors.forename: Alejandro M S
authors.initials: AM
authors.lastname: Mayer
authors.affiliation: Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, PR 00931-3346, United States. Electronic address: abimael.rodriguez1@upr.edu.
authors.forename: Abimael D
authors.initials: AD
authors.lastname: Rodríguez
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001048:Aplysia / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000737:chemistry / Q000378:metabolism; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D017628:Microglia / Q000187:drug effects / Q000378:metabolism; D008958:Models, Molecular; D008968:Molecular Conformation; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013929:Thromboxane B2 / Q000037:antagonists & inhibitors* / Q000096:biosynthesis
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D004224:Diterpenes; D008070:Lipopolysaccharides; C588120:dactyloditerpenol acetate; D013481:Superoxides; D013929:Thromboxane B2
keywords: Aplysia dactylomela; Diterpene; Prenylbisabolane; Tuberculosis; anti-Neuroinflammatory activity