Polyoxygenated cyclohexene derivatives isolated from Dasymaschalon sootepense and their biological activities

Sakchai Hongthong; Chutima Kuhakarn; Thaworn Jaipetch; Samran Prabpai; Palangpon Kongsaeree; Pawinee Piyachaturawat; Surawat Jariyawat; Kanoknetr Suksen; Jitra Limthongkul; Ampai Panthong; Narong Nuntasaen; Vichai Reutrakul

doi:10.1016/j.fitote.2015.09.001

Polyoxygenated cyclohexene derivatives isolated from Dasymaschalon sootepense and their biological activities

Fitoterapia. 2015 Oct:106:158-66. doi: 10.1016/j.fitote.2015.09.001. Epub 2015 Sep 5.

Affiliations

¹ Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, Thailand.
² Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, Thailand. Electronic address: chutima.kon@mahidol.ac.th.
³ Mahidol University, Center of Excellence for Innovation in Chemistry (PERCH-CIC), Kanchanaburi Campus, Saiyok, Kanchanaburi, Thailand.
⁴ Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, Thailand.
⁵ Department of Microbiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, Thailand.
⁶ Department of Pharmacology, Faculty of Medicine, Chiang Mai University, Chiang Mai, Thailand.
⁷ The Forest Herbarium National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Thailand.

PMID: 26347951
DOI: 10.1016/j.fitote.2015.09.001

Abstract

Six new naturally occurring polyoxygenated cyclohexene derivatives together with eight related known derivatives, two known alkaloids, and two known flavonoid derivatives were isolated from bioassay-guided fractionation of the ethyl acetate extract of the leaves and twigs of Dasymaschalon sootepense. The structure elucidation and determination of absolute configurations were established by various spectroscopic methods, X-ray diffraction techniques as well as comparison with the literature data. Several isolated compounds were evaluated for their cytotoxic, anti-HIV-1 RT and anti-inflammatory activities.

Keywords: Anti-HIV-1 RT; Anti-inflammatory; Chlorohydrins; Cyclohexene oxides; Cytotoxicity; Dasymaschalon sootepense.

Publication types

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

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification
Animals
Annonaceae / chemistry*
Anti-HIV Agents / chemistry*
Anti-HIV Agents / isolation & purification
Anti-Inflammatory Agents / chemistry*
Anti-Inflammatory Agents / isolation & purification
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Cell Line, Tumor
Cyclohexenes / chemistry*
Cyclohexenes / isolation & purification
HIV-1 / drug effects
Humans
Male
Mice
Molecular Structure
Plant Leaves / chemistry
Rats
Rats, Sprague-Dawley
Reverse Transcriptase Inhibitors / chemistry
Reverse Transcriptase Inhibitors / isolation & purification

Substances

Alkaloids
Anti-HIV Agents
Anti-Inflammatory Agents
Antineoplastic Agents, Phytogenic
Cyclohexenes
Reverse Transcriptase Inhibitors
cyclohexene