Three New Adjacent Bis-tetrahydrofuran Acetogenins with Four Hydroxyl Groups from Asimina triloba

• Published in: Journal of natural products (Washington, D.C.) Vol. 59; no. 11; pp. 1029 - 1034
• Main Authors: He, Kan, Shi, Guoen, Zhao, Geng-Xian, Zeng, Lu, Ye, Qing, Schwedler, Jon T, Wood, Karl V, McLaughlin, Jerry L
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.1996; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 10-hydroxyasimicin; 10-hydroxytrilobacin; AGENTES ANTINEOPLASTICOS; Animals; annonacin; annonacin a; ANTINEOPLASTIC AGENTS; Artemia; ASIMINA TRILOBA; BARK; BIOASSAYS; Biological and medical sciences; bullatetrocin; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHEMISTRY; Chemistry, Medicinal; CHIMIE; cis/trans-gigantetrocin a-ones; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CORTEZA; CREVETTE; DOSAGE BIOLOGIQUE; DRUG PLANTS; Drug Screening Assays, Antitumor; ECORCE; ENSAYO BIOLOGICO; ESPECTROMETRIA; ESTRUCTURA QUIMICA; FURANE; FURANOS; FURANS; Furans - isolation & purification; Furans - pharmacology; GAMBAS Y CAMARONES; General pharmacology; GENERO HUMANO; GENRE HUMAIN; gigantetrocin a; Humans; INDIANA; LARVAE; LARVAS; LARVE; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; MANKIND; Mass Spectrometry; Medical sciences; MEDICAMENT CYTOSTATIQUE; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Epidermis - chemistry; Plant Sciences; PLANTAS MEDICINALES; PLANTE MEDICINALE; Plants, Medicinal - chemistry; PRAWNS AND SHRIMPS; QUIMICA; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; Spectrometry, Mass, Fast Atom Bombardment; STEMS; STEREOCHEMISTRY; STRUCTURE CHIMIQUE; Structure-Activity Relationship; TALLO; TIGE; Tumor Cells, Cultured; SEEDS; BULLATA; BARK; CONFIGURATION; ANNONACEOUS ACETOGENINS; ESTABLISHMENT; CARCINOMA; CELL-LINE; Antineoplastic agent; Solid tumor; Toxicity; Bark; Cytotoxicity; Oxygen heterocycle; Medicinal plant; Crustacea; Dicotyledones; Angiospermae; Established cell line; Annonaceae; Secondary alcohol; Branchiopoda; Tumor cell; Human; Artemia salina; Aliphatic compound; Pharmacognosy; Lactone; In vitro; Biological activity; Arthropoda; Animal; Absolute configuration; Plant origin; Isolation; Spermatophyta; Invertebrata; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9605145

Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure−activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1−3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.