2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae)

Authors

Chiramet Auranwiwat, Chiang Mai University
Puttandon Wongsomboon, Chiang Mai University
Thanaphat Thaima, University of WollongongFollow
Roonglawan Rattanajak, National Science and Technology Development Agency, Thailand
Sumalee Kamchonwongpaisan, National Science and Technology Development Agency, Thailand
Anthony C. Willis, Australian National University
Wilford Lie, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Thunwadee Ritthiwigrom, Chiang Mai University

RIS ID

114610

Publication Details

Auranwiwat, C., Wongsomboon, P., Thaima, T., Rattanajak, R., Kamchonwongpaisan, S., Willis, A. C., Lie, W., Pyne, S. G. & Limtharakul (née Ritthiwigrom, T. (2017). 2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae). Fitoterapia, 120 103-107.

Abstract

Three new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A-C (1-3), and a new polyoxygenated cyclohexene derivative, (−)-uvaribonol F (4) together with six known compounds, 5-10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysis. The structures of 3 and 4 were further confirmed by single crystal X-ray diffraction methods. Compound 2 exhibited modest antiplasmodial activity against the P. falciparum stains TM4/ 8.2 and K1CB1 with IC₅₀ values of 18.8 ± 3.63 and 23.4 ± 4.08 μM, respectively, and weak cytotoxicity to a Vero cell line. Furthermore, compound 4 displayed cytotoxic activity against a KB cell line with an IC₅₀ value of 22.1 ± 0.42 μM but was non-cytotoxic to the Vero cell line. Compound 5 revealed stronger cytotoxicity towards the KB cell line, with an IC₅₀ value of 5.05 ± 0.86 μM and was nearly equally cytotoxic to the Vero cell line