Pyrenes and pyrendiones from Uvaria lucida

• Published in: Journal of natural medicines Vol. 66; no. 3; pp. 453 - 458
• Main Authors: Moriyasu, Masataka, Takeuchi, Sousuke, Ichimaru, Momoyo, Nakatani, Noriyshi, Nishiyama, Yumi, Kato, Atsushi, Mathenge, Simon G, Juma, Francis D, ChaloMutiso, Patrick B
• Format: Journal Article
• Language: English
• Published: Japan Springer-Verlag 01.07.2012; Springer Japan
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Apoptosis - drug effects; Biomedical and Life Sciences; Biomedicine; chloroform; Complementary & Alternative Medicine; cytotoxicity; HL-60 Cells; Humans; inhibitory concentration 50; leukemia; Medicinal Chemistry; Molecular Structure; Original Paper; Pharmacology/Toxicology; Pharmacy; Plant Sciences; Pyrenes - chemistry; Pyrenes - pharmacology; roots; spectroscopy; traditional medicine; Uvaria; Uvaria - chemistry; Pyrenes; Pyrenediones; Cytotoxicity against HL-60; Annonaceae
• ISSN: 1340-3443; 1861-0293
• DOI: 10.1007/s11418-011-0610-2

A chemical investigation of the chloroform extract of the roots of Uvaria ludida Benth. (Annonaceae), an important African traditional medicine, led to the isolation of six new compounds; three pyrenes, 2-hydroxy-1,8-dimethoxypyrene (1), 8-methoxy-1,2-methylenedioxypyrene (2), and 7-hydroxy-8-methoxy-1,2-methylenedioxypyrene (3), two pyrenediones, 2-hydroxy-1,8-pyrenedione (4) and 2-methoxy-1,8-pyrenedione (5), and a sesquiterpene, (−)-10-oxo-isodauc-3-en-15-oic acid (6), together with eight known compounds (7–14). The structural elucidation by spectroscopic studies of the compounds isolated is described. While pyrenes did not exhibit strong cytotoxicity against human promyelocytic leukemia HL-60 cells, pyrenediones showed strong cytotoxicity. The IC₅₀ of 4 was 70 ng mL⁻¹, which was close to that of etoposide (IC₅₀ = 60 ng mL⁻¹).