Highly oxygenated antiausterity agents from the leaves of Uvaria dac

Suresh Awale; Ahmed M Tawila; Dya Fita Dibwe; Jun-Ya Ueda; Sijia Sun; Sirivan Athikomkulchai; Chandrashaker Balachandran; Ikuo Saiki; Kinzo Matsumoto; Hiroyasu Esumi

doi:10.1016/j.bmcl.2017.03.021

Highly oxygenated antiausterity agents from the leaves of Uvaria dac

Bioorg Med Chem Lett. 2017 May 1;27(9):1967-1971. doi: 10.1016/j.bmcl.2017.03.021. Epub 2017 Mar 11.

Authors

Affiliations

¹ Division of Natural Drug Discovery, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan. Electronic address: suresh@inm.u-toyama.ac.jp.
² Division of Natural Drug Discovery, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan; Pharmacognosy Department, National Research Centre, 33-El-Bohouth St., Dokki, Giza, Egypt.
³ Division of Natural Drug Discovery, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
⁴ Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure, Hiroshima 737-0112, Japan.
⁵ Faculty of Pharmacy, Srinakharinwirot University, Nakhon Nayok 26120, Thailand.
⁶ Division of Pathogenic Biochemistry, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
⁷ Division of Medicinal Pharmacology, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
⁸ Research Institute for Biomedical Sciences, Tokyo University of Science, 2669 Yamazaki, Noda, Chiba 278-8510, Japan.

PMID: 28342587
DOI: 10.1016/j.bmcl.2017.03.021

Abstract

From the chloroform extract of the leaves of Uvaria dac, four new highly-oxygenated cyclohexene derivatives named uvaridacols I-L (1-4) were isolated together with nine previously reported compounds (5-13). Their structures were determined based on the extensive NMR spectroscopic data and circular dichroism spectroscopic analysis. Among the new compounds, uvaridacol L (4) displayed strong preferential cytotoxicity in the nutrient deprived medium against five different tested pancreatic cancer cell lines, PANC-1 (PC₅₀, 20.1μM), PSN-1 (PC₅₀, 9.7μM), MIA PaCa-2 (PC₅₀, 29.1μM), Capan-1 (73.0μM) and KLM-1 (25.9μM).

Keywords: Antiausterity agents; PANC-1; Pancreatic cancer; Preferential cytotoxicity; Uvaria dac.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Line, Tumor
Cyclohexenes / chemistry*
Cyclohexenes / isolation & purification
Cyclohexenes / pharmacology*
Drug Screening Assays, Antitumor
Humans
Oxygen / chemistry*
Pancreas / drug effects
Pancreatic Neoplasms / drug therapy
Plant Leaves / chemistry
Uvaria / chemistry*

Substances

Antineoplastic Agents, Phytogenic
Cyclohexenes
cyclohexene
Oxygen