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

Suwannee Saisin; Kanda Panthong; Sakchai Hongthong; Chutima Kuhakarn; Sariyarach Thanasansurapong; Arthit Chairoungdua; Kanoknetr Suksen; Radeekorn Akkarawongsapat; Chanita Napaswad; Samran Prabpai; Narong Nuntasaen; Vichai Reutrakul

doi:10.1021/acs.jnatprod.2c00980

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

Suwannee Saisin, Kanda Panthong, Sakchai Hongthong, Chutima Kuhakarn, Sariyarach Thanasansurapong, Arthit Chairoungdua, Kanoknetr Suksen, Radeekorn Akkarawongsapat, Chanita Napaswad, Samran Prabpai, Narong Nuntasaen, Vichai Reutrakul

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

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 (EC₅₀) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).

Original language	English
Pages (from-to)	498-507
Number of pages	10
Journal	Journal of Natural Products
Volume	86
Issue number	3
DOIs	https://doi.org/10.1021/acs.jnatprod.2c00980
Publication status	Published - 24 Mar 2023
Externally published	Yes

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Saisin, S., Panthong, K., Hongthong, S., Kuhakarn, C., Thanasansurapong, S., Chairoungdua, A., Suksen, K., Akkarawongsapat, R., Napaswad, C., Prabpai, S., Nuntasaen, N., & Reutrakul, V. (2023). Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity. Journal of Natural Products, 86(3), 498-507. https://doi.org/10.1021/acs.jnatprod.2c00980

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title = "Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity",

abstract = "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 (EC50) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).",

author = "Suwannee Saisin and Kanda Panthong and Sakchai Hongthong and Chutima Kuhakarn and Sariyarach Thanasansurapong and Arthit Chairoungdua and Kanoknetr Suksen and Radeekorn Akkarawongsapat and Chanita Napaswad and Samran Prabpai and Narong Nuntasaen and Vichai Reutrakul",

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doi = "10.1021/acs.jnatprod.2c00980",

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Saisin, S, Panthong, K, Hongthong, S, Kuhakarn, C, Thanasansurapong, S, Chairoungdua, A, Suksen, K, Akkarawongsapat, R, Napaswad, C, Prabpai, S, Nuntasaen, N & Reutrakul, V 2023, 'Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity', Journal of Natural Products, vol. 86, no. 3, pp. 498-507. https://doi.org/10.1021/acs.jnatprod.2c00980

TY - JOUR

T1 - Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity

AU - Saisin, Suwannee

AU - Panthong, Kanda

AU - Hongthong, Sakchai

AU - Kuhakarn, Chutima

AU - Thanasansurapong, Sariyarach

AU - Chairoungdua, Arthit

AU - Suksen, Kanoknetr

AU - Akkarawongsapat, Radeekorn

AU - Napaswad, Chanita

AU - Prabpai, Samran

AU - Nuntasaen, Narong

AU - Reutrakul, Vichai

PY - 2023/3/24

Y1 - 2023/3/24

N2 - 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 (EC50) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).

AB - 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 (EC50) values ranging from 9.9 to 47 μM (selectivity index (SI) 2.4-4.5).

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JF - Journal of Natural Products

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ER -

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

Abstract

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