Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity.

Autor: Saisin S; Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Panthong K; Division of Physical Sciences and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand., Hongthong S; Division of Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand., Kuhakarn C; Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Thanasansurapong S; Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Chairoungdua A; Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Suksen K; Department of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Akkarawongsapat R; Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Napaswad C; Department of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Prabpai S; Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand., Nuntasaen N; The Forest Herbarium National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Bangkok 10900, Thailand., Reutrakul V; Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
Jazyk: angličtina
Zdroj: Journal of natural products [J Nat Prod] 2023 Mar 24; Vol. 86 (3), pp. 498-507. Date of Electronic Publication: 2023 Feb 14.
DOI: 10.1021/acs.jnatprod.2c00980
Abstrakt: Seven previously undescribed compounds, including five pyranonaphthoquinones (ventilanones L-P) and two naphthoquinones (ventilanones Q and R), along with 15 known compounds were isolated from the stem bark of Ventilago harmandiana (Rhamnaceae). The structures were established by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone L was established from single crystal X-ray crystallographic analysis using Cu Kα radiation and from its electronic circular dichroism data. Anti-HIV-1 activity using a syncytium inhibition assay and the cytotoxic activities of some isolated compounds were evaluated. Compounds 12 , 13 , 15 , and 16 showed activity against syncytium formation with half maximal effective concentration (EC 50 ) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).
Databáze: MEDLINE