Tirucallane-Type Triterpenoids from the  Dysoxylum gaudichaudianum  Stem Bark: Phytochemical Study and Cytotoxicity Evaluation Against Human HeLa Cervical Cancer Cells

Faizah Maira; Al Arofatus Naini; Tri Mayanti; Sofa Fajriah; Kusumiyati Kusumiyati; Unang Supratman

doi:10.22146/ijc.103523

Tirucallane-Type Triterpenoids from the Dysoxylum gaudichaudianum Stem Bark: Phytochemical Study and Cytotoxicity Evaluation Against Human HeLa Cervical Cancer Cells

https://doi.org/10.22146/ijc.103523

Faizah Maira⁽¹⁾, Al Arofatus Naini⁽²⁾, Tri Mayanti⁽³⁾, Sofa Fajriah⁽⁴⁾, Kusumiyati Kusumiyati⁽⁵⁾, Unang Supratman^(6*)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(2) Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency (BRIN), Cibinong Science Center Complex – BRIN, Cibinong 16911, Bogor, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(4) Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency (BRIN), Cibinong Science Center Complex – BRIN, Cibinong 16911, Bogor, Indonesia
(5) Department of Agronomy, Faculty of Agriculture, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km, 21, Jatinangor, 45363, Sumedang, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Central Laboratory of Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(*) Corresponding Author

Abstract

A total of three tirucallane-type triterpenoids were successfully isolated from the n-hexane extract of the stem bark of Dysoxylum gaudichaudianum: 4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic (1), toonapubesin B (2), and 3β,22S-dihydroxy-tirucalla-7,24-dien-23-one (3). These compounds were isolated from D. gaudichaudianum for the first time. Structural characterization of the isolated compounds was accomplished through a series of spectroscopic analyses, including HR-TOF-MS, IR, and NMR. Based on previous reports, compound 1 was isolated from a member of the Meliaceae family for the first time. The cytotoxic properties of the isolated tirucallane-type triterpenoids were evaluated against cervical HeLa cancer cells. Among them, compounds 1 and 3 were inactive, with IC₅₀ values > 100 µM, while compound 2 exhibited the highest cytotoxicity, with an IC₅₀ value of 29.23 µM, with moderate activity. A structure–activity relationship also indicated the variation in cytotoxicity attributed to substituent effects within the molecular structures. The modification of the side chain in tirucallane-type triterpenoids was shown to be essential for their cytotoxic activity against human cervical cancer lines.

Keywords

Dysoxylum gaudichaudianum; Meliaceae; tirucallane-type triterpenoid, HeLa cervical cancer cells

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DOI: https://doi.org/10.22146/ijc.103523