Publication:
Antiausterity agents from Uvaria dac and their preferential cytotoxic activity against human pancreatic cancer cell lines in a nutrient-deprived condition

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Issued Date

2012

Resource Type

Article

File Type

application/pdf

ISSN

1633864

DOI

10.1021/np300295h

Other identifier(s)

2-s2.0-84866465067

Rights Holder(s)

มหาวิทยาลัยศรีนครินทรวิโรฒ

Bibliographic Citation

Journal of Natural Products. Vol 75, No.6 (2012), p.1177-1183

Suggested Citation

Awale S., Ueda J.-Y., Athikomkulchai S., Abdelhamed S., Yokoyama S., Saiki I., Miyatake R. Antiausterity agents from Uvaria dac and their preferential cytotoxic activity against human pancreatic cancer cell lines in a nutrient-deprived condition. Journal of Natural Products. Vol 75, No.6 (2012), p.1177-1183. doi:10.1021/np300295h Retrieved from: https://hdl.handle.net/20.500.14740/7025

Title

Antiausterity agents from Uvaria dac and their preferential cytotoxic activity against human pancreatic cancer cell lines in a nutrient-deprived condition

Author(s)

Awale S.
 Ueda J.-Y.
 Athikomkulchai S.
 Abdelhamed S.
 Yokoyama S.
 Saiki I.
 Miyatake R.

Abstract

Human pancreatic cancer cell lines are known for their inherent tolerance to nutrition starvation, which enables them to survive under a hypovascular (austerity) tumor microenvironment. The search for agents that preferentially retard the survival of cancer cells under low nutrition conditions (antiausterity agent) is a novel approach to anticancer drug discovery. In this study, it was found that a dichloromethane extract of the stem of Uvaria dac preferentially inhibited PANC-1 human pancreatic cancer cells survival under nutrition-deprived conditions at a concentration of 10 μg/mL. Workup of this bioactive extract led to the discovery of (+)-grandifloracin (8) as a potent antiausterity agent as evaluated in a panel of four human pancreatic cancer cell lines, PANC-1 (PC50, 14.5 μM), PSN-1 (PC50, 32.6 μM), MIA PaCa-2 (PC50, 17.5 μM), and KLM-1 (32.7 μM). (+)-Grandifloracin (8) has been isolated from a natural source for the first time. Its absolute stereochemistry was established by single-crystal X-ray crystallography and circular dichroism spectroscopic analysis. In addition to this, seven other new highly oxygenated cyclohexene derivatives, named uvaridacanes A (1) and B (2), uvaridacols A-D (3, 4, 6, 7), and uvaridapoxide A (5), were also isolated and structurally characterized. © 2012 American Chemical Society and American Society of Pharmacognosy.

Subject(s)

Cyclohexene derivative
 Dichloromethane
 Grandifloracin
 Unclassified drug
 Uvaridacane A
 Uvaridacane B
 Uvaridacol A
 Uvaridacol B
 Uvaridacol C
 Uvaridacol D
 Uvaridapoxide A
 Antineoplastic agent
 Bridged compound
 Cyclohexene derivative
 Grandifloracin
 Uvaridacane A
 Uvaridacane B
 Annonaceae
 Article
 Cancer cell culture
 Cell strain KLM 1
 Cell strain MIA PaCa 2
 Cell strain PANC 1
 Cell strain PSN 1
 Circular dichroism
 Cytotoxicity
 Drug isolation
 Drug structure
 Human
 Human cell
 Nutritional deficiency
 Pancreas cancer
 Stereochemistry
 Tumor microenvironment
 Uvaria dac
 X ray crystallography
 Chemistry
 Drug screening
 Isolation and purification
 Nuclear magnetic resonance
 Pancreas tumor
 Thailand
 Uvaria
 Agouti paca
 Uvaria
 Antineoplastic Agents, Phytogenic
 Bridged Compounds
 Crystallography, X-Ray
 Cyclohexenes
 Drug Screening Assays, Antitumor
 Humans
 Nuclear Magnetic Resonance, Biomolecular
 Pancreatic Neoplasms
 Thailand
 Uvaria

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URI

https://hdl.handle.net/20.500.14740/7025

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Scopus: Year 1983-2021

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