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2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae).
Fitoterapia. 2017 Jul; 120:103-107.F

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±4.08μM, 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±0.42μM 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±0.86μM and was nearly equally cytotoxic to the Vero cell line.

Authors+Show Affiliations

Department of Chemistry, Faculty of Science, Chiang Mai University, Sutep, Muang, Chiang Mai 50200, Thailand; The Graduate School, Chiang Mai University, Sutep, Muang, Chiang Mai 50200, Thailand.Department of Chemistry, Faculty of Science, Chiang Mai University, Sutep, Muang, Chiang Mai 50200, Thailand.School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.Medical Molecular Biology Research Unit, National Center for Genetic Engineering and Biotechnology, National Science and Technology Development Agency, Thailand Science Park, Pathumthani 12120, Thailand.Medical Molecular Biology Research Unit, National Center for Genetic Engineering and Biotechnology, National Science and Technology Development Agency, Thailand Science Park, Pathumthani 12120, Thailand.Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.Department of Chemistry, Faculty of Science, Chiang Mai University, Sutep, Muang, Chiang Mai 50200, Thailand. Electronic address: thunwadee.r@cmu.ac.th.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28596029

Citation

Auranwiwat, Chiramet, et al. "2-Phenylnaphthalenes and a Polyoxygenated Cyclohexene From the Stem and Root Extracts of Uvaria Cherrevensis (Annonaceae)." Fitoterapia, vol. 120, 2017, pp. 103-107.
Auranwiwat C, Wongsomboon P, Thaima T, et al. 2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae). Fitoterapia. 2017;120:103-107.
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. https://doi.org/10.1016/j.fitote.2017.06.002
Auranwiwat C, et al. 2-Phenylnaphthalenes and a Polyoxygenated Cyclohexene From the Stem and Root Extracts of Uvaria Cherrevensis (Annonaceae). Fitoterapia. 2017;120:103-107. PubMed PMID: 28596029.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae). AU - Auranwiwat,Chiramet, AU - Wongsomboon,Puttandon, AU - Thaima,Thanaphat, AU - Rattanajak,Roonglawan, AU - Kamchonwongpaisan,Sumalee, AU - Willis,Anthony C, AU - Lie,Wilford, AU - Pyne,Stephen G, AU - Limtharakul Née Ritthiwigrom,Thunwadee, Y1 - 2017/06/09/ PY - 2017/03/23/received PY - 2017/05/30/revised PY - 2017/06/04/accepted PY - 2017/6/10/pubmed PY - 2017/8/2/medline PY - 2017/6/10/entrez KW - Annonaceae KW - Antiplasmodial activity KW - Cytotoxic activity KW - Phenylnaphthalene KW - Polyoxygenated cyclohexene KW - Uvaria cherrevensis SP - 103 EP - 107 JF - Fitoterapia JO - Fitoterapia VL - 120 N2 - 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±4.08μM, 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±0.42μM 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±0.86μM and was nearly equally cytotoxic to the Vero cell line. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/28596029/2_Phenylnaphthalenes_and_a_polyoxygenated_cyclohexene_from_the_stem_and_root_extracts_of_Uvaria_cherrevensis__Annonaceae__ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0367-326X(17)30442-2 DB - PRIME DP - Unbound Medicine ER -