Cytotoxic and natural killer cell stimulatory constituents of Phyllanthus songboiensis

Yulin Ren; Chunhua Yuan; Youcai Deng; Ragu Kanagasabai; Tran Ngoc Ninh; Vuong Tan Tu; Hee-Byung Chai; Djaja D Soejarto; James R Fuchs; Jack C Yalowich; Jianhua Yu; A Douglas Kinghorn

doi:10.1016/j.phytochem.2014.12.014

Cytotoxic and natural killer cell stimulatory constituents of Phyllanthus songboiensis

Phytochemistry. 2015 Mar:111:132-40. doi: 10.1016/j.phytochem.2014.12.014. Epub 2015 Jan 14.

Authors

Affiliations

¹ Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
² Campus Chemical Instrument Center, The Ohio State University, Columbus, OH 43210, USA.
³ Comprehensive Cancer Center, The Ohio State University, Columbus, OH 43210, USA.
⁴ Division of Pharmacology, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.
⁵ Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam.
⁶ Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA; Science and Education, Field Museum of Natural History, Chicago, IL 60605, USA.
⁷ Comprehensive Cancer Center, The Ohio State University, Columbus, OH 43210, USA; Division of Hematology, Department of Internal Medicine, College of Medicine, The Ohio State University, Columbus, OH 43210, USA.
⁸ Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA. Electronic address: kinghorn.4@osu.edu.

Abstract

A dichapetalin-type triterpenoid and a dibenzylbutyrolactone-type lignan, together with five known lignans, a known aromatic diterpenoid, and a known acylated phytosterol, were isolated from the aerial parts of Phyllanthus songboiensis, collected in Vietnam. Their structures were determined by interpretation of the spectroscopic data, and the inhibitory activity toward HT-29 human colon cancer cells of all isolates was evaluated by a cytotoxicity assay. The known arylnaphthalene lignan, (+)-acutissimalignan A, was highly cytotoxic toward HT-29 cells, with an IC50 value of 19 nM, but this compound was inactive as a DNA topoisomerase IIα (topo IIα) poison. The known phytosterol, (-)-β-sitosterol-3-O-β-D-(6-O-palmitoyl)glucopyranoside, was found to stimulate natural killer (NK) cells at a concentration of 10μM in the presence of interleukin 12 (IL-12).

Keywords: Cytotoxicity; DNA topoisomerase IIα; Lignan; Natural killer cell; Phyllanthaceae; Phyllanthus songboiensis; Phytosterol.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Antigens, Neoplasm / metabolism*
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology*
DNA Topoisomerases, Type II / metabolism*
DNA-Binding Proteins / metabolism*
Drug Screening Assays, Antitumor
HT29 Cells
Humans
Interleukin-12 / metabolism
Killer Cells, Natural / drug effects
Lignans / chemistry
Lignans / isolation & purification*
Lignans / pharmacology*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Phyllanthus / chemistry*
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology*
Vietnam

Substances

Antigens, Neoplasm
Antineoplastic Agents, Phytogenic
DNA-Binding Proteins
Lignans
Triterpenes
Interleukin-12
DNA Topoisomerases, Type II

Abstract

Publication types

MeSH terms

Substances

Grants and funding