Absolute Configuration of Sesquiterpenes from Crossopetalum tonduzii and Their Inhibitory Effects on Epstein−Barr Virus Early Antigen Activation in Raji Cells

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 8; pp. 1047 - 1050
• Main Authors: Jiménez, Ignacio A, Bazzocchi, Isabel L, Núñez, Marvin J, Mukainaka, Teruo, Tokuda, Harukuni, Nishino, Hoyoku, Konoshima, Takao, Ravelo, Angel G
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Acetylation; Anticarcinogenic Agents - chemistry; Anticarcinogenic Agents - isolation & purification; Anticarcinogenic Agents - pharmacology; Antigens, Viral - drug effects; Biological and medical sciences; Celastraceae - chemistry; Chemistry, Medicinal; General pharmacology; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Panama; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Plants, Medicinal - chemistry; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Stereoisomerism; Asia; America; Latin America; Panama; LEISHMANIA-TROPICA LINE; CELASTRACEAE; Gammaherpesvirinae; Terpenoid; Pharmacognosy; Herpesviridae; Celastraceae; Plant leaf; Epstein Barr virus; Anticarcinogen; Biological activity; Medicinal plant; Virus; Folk medicine; Dicotyledones; Sesquiterpenes; Angiospermae; Absolute configuration; Plant origin; Isolation; Spermatophyta; Polyol; Acylate; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0301240

Two new sesquiterpenoids (1 and 2) with a dihydro-β-agarofuran skeleton were isolated from Crossopetalum tonduzii. Their structures were elucidated on the basis of spectral analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC, and HMBC). Their absolute configurations were determined by CD studies on 3, the benzoylated derivative of 1. Chemical correlations have allowed the absolute configurations of 4 and 5, two previously known dihydro-β-agarofuran analogues, to be reported for the first time. Compounds 1, 2, and 5 showed strong antitumor-promoting effects on Epstein−Barr virus early antigen (EBV-EA) activation.