Abstract
Two novel urushiols, 1 and 2, and two known urushiols, 3 and 4, were isolated from the leaves of Rhus verniciflua and were examined for their human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) inhibitory activity. The novel urushiols were found to be 1,2-dihydroxyphenyl-3-[7′(E),9′(Z),11′(Z)-pentadecatrienyl]-14′-ol (1) and 1,2-dihydroxyphenyl-3-[8′(Z),10′(E),12′(E)-pentadecatrienyl]-14′-ol (2) by spectroscopic analyses. The absolute configuration at C-14′ in 1 and 2 was determined to be a racemic mixture of (R) and (S) isomers by ozonolysis. Compound 2 (IC50: 12.6 µM) showed the highest HIV-1 RT inhibitory activity among the four urushiols, being 2.5-fold more potent than the positive control, adriamycin (IC50: 31.9 µM). Although the known urushiols were isolated from the sap and leaves of R. verniciflua, 1 was exclusively present in the leaves, and higher amounts of 2 were found in the leaves than in the sap. Present findings indicate that the leaves of R. verniciflua represent a new biological resource from which novel and known urushiols may be prepared, and the possible use of novel urushiols as bioactive products.
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Acknowledgments
We are extremely grateful to Representative Chairman Masahito Hoashi, Kibun Foods, Inc., for supporting the present work. We are indebted to Professor Emeritus Haruki Yamada, Kitasato University for his perceptive suggestions. We are grateful to Professor Nobuhiro Hirai, Kyoto University for analysis of the NMR spectra and advice on determination of absolute configuration. We also express our sincere thanks to Professor Shinichiro Kajiyama, Kinki University (formerly Osaka University), and Associate Professor Wataru Hakamata, Nihon University, for recording the NMR spectra.
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Kadokura, K., Suruga, K., Tomita, T. et al. Novel urushiols with human immunodeficiency virus type 1 reverse transcriptase inhibitory activity from the leaves of Rhus verniciflua . J Nat Med 69, 148–153 (2015). https://doi.org/10.1007/s11418-014-0871-7
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DOI: https://doi.org/10.1007/s11418-014-0871-7