Isolation and biological activity of agrostophillinol from kaffir lime (Citrus hystrix) leaves

Songyot Anuchapreeda; Riki Anzawa; Natsima Viriyaadhammaa; Waranya Neimkhum; Wantida Chaiyana; Siriporn Okonogi; Toyonobu Usuki

doi:10.1016/j.bmcl.2020.127256

Isolation and biological activity of agrostophillinol from kaffir lime (Citrus hystrix) leaves

Bioorg Med Chem Lett. 2020 Jul 15;30(14):127256. doi: 10.1016/j.bmcl.2020.127256. Epub 2020 May 12.

Authors

Songyot Anuchapreeda¹, Riki Anzawa², Natsima Viriyaadhammaa³, Waranya Neimkhum⁴, Wantida Chaiyana⁵, Siriporn Okonogi⁶, Toyonobu Usuki⁷

Affiliations

¹ Department of Medical Technology, Faculty of Associated Medical Sciences, Chiang Mai University, Chiang Mai 50200, Thailand; Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo 102-8554, Japan; Cancer Research Unit of Associated Medical Sciences (AMS CRU), Faculty of Associated Medical Sciences, Chiang Mai University, Chiang Mai 50200, Thailand; Research Center of Pharmaceutical Nanotechnology, Chiang Mai University, Chiang Mai 50200, Thailand. Electronic address: sanuchapreeda@gmail.com.
² Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo 102-8554, Japan.
³ Department of Medical Technology, Faculty of Associated Medical Sciences, Chiang Mai University, Chiang Mai 50200, Thailand.
⁴ Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Huachiew Chalermprakiet University, Samutprakarn 10250, Thailand.
⁵ Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Chiang Mai 50200, Thailand; Research Center of Pharmaceutical Nanotechnology, Chiang Mai University, Chiang Mai 50200, Thailand.
⁶ Department of Pharmaceutical Sciences, Faculty of Pharmacy, Chiang Mai University, Chiang Mai 50200, Thailand; Research Center of Pharmaceutical Nanotechnology, Chiang Mai University, Chiang Mai 50200, Thailand. Electronic address: okng2000@gmail.com.
⁷ Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, Tokyo 102-8554, Japan. Electronic address: t-usuki@sophia.ac.jp.

PMID: 32527555
DOI: 10.1016/j.bmcl.2020.127256

Abstract

The leaves of the kaffir lime (Citrus hystrix) are commonly used in cuisine and folk medicine. The aim of this study was to isolate a bioactive compound in kaffir lime leaves and characterize its biological activity. The compound was isolated from a hexane fractional extract and identified as agrostophillinol. This is the first report of agrostophillinol isolated from kaffir lime leaves. In terms of cytotoxicity, agrostophillinol exhibited IC₅₀ values of 36.27 ± 7.30 and 53.44 ± 10.63 μg/mL against EoL-1 and HL60 cells, respectively. Agrostophillinol also exhibited potent anti-inflammatory activity, significantly inhibiting IL-6 secretion.

Keywords: Agrostophillinol; Anti-inflammatory; Anticancer; Antioxidant; Citrus hystrix; Kaffir lime.

Publication types

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

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Antioxidants / chemistry
Antioxidants / isolation & purification
Antioxidants / pharmacology*
Biphenyl Compounds / antagonists & inhibitors
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Citrus / chemistry*
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Interleukin-6 / antagonists & inhibitors*
Interleukin-6 / metabolism
Lanosterol / analogs & derivatives*
Lanosterol / chemistry
Lanosterol / isolation & purification
Lanosterol / pharmacology
Mice
Molecular Conformation
Picrates / antagonists & inhibitors
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Plant Leaves / chemistry
RAW 264.7 Cells
Structure-Activity Relationship

Substances

24-methylenelanosta-9(11)-en-3beta-ol
Anti-Inflammatory Agents
Antineoplastic Agents, Phytogenic
Antioxidants
Biphenyl Compounds
IL6 protein, human
Interleukin-6
Picrates
Plant Extracts
Lanosterol
1,1-diphenyl-2-picrylhydrazyl