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All Journal VALENSI Indonesian Journal of Chemistry
Maira, Faizah
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Chemical Engineering, Chemistry & Bioengineering Chemistry

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Tirucallane-Type Triterpenoids from the Dysoxylum gaudichaudianum Stem Bark: Phytochemical Study and Cytotoxicity Evaluation Against Human HeLa Cervical Cancer Cells Maira, Faizah; Naini, Al Arofatus; Mayanti, Tri; Fajriah, Sofa; Kusumiyati, Kusumiyati; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 4 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.103523

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.
Eudesman-Type Sesquiterpenoids from Stem Bark Dysoxylum gaudichaudianum and Cytotoxic Evaluation Against Human HeLa Cervical Cancer Maira, Faizah; Naini, Al Arofatus; Mayanti, Tri; Farabi, Kindi; Fajriah, Sofa; Retnowati, Rurini; Supratman, Unang
Jurnal Kimia Valensi Jurnal Kimia VALENSI, Volume 11, No. 2, November 2025
Publisher : Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v11i2.46788

Abstract

Two eudesmane-type sesquiterpenoids were isolated from the stem bark of Dysoxylum gaudichaudianum: 6α-hydroxy-eudesm-4(15)-en-1-one (1) and eudesm-4(15),7-dien-1β-ol (2). This study represents the first report of these compounds not only from D. gaudichaudianum but also from the genus Dysoxylum. The cytotoxic potential of two sesquiterpenoids was assessed against human cervical carcinoma (HeLa) cells employing the Resazurin-based PrestoBlue assay. Using cisplatin as a positive control, compound 1 exhibited moderate cytotoxicity with an IC₅₀ of 28.04 µM, whereas compound 2 showed comparatively weaker activity, with an IC₅₀ of 58.37 µM. Their structures were elucidated through comprehensive spectroscopic analyses, including HR-ESI-MS, ¹H NMR, and ¹³C NMR. Structure–activity relationship analysis indicates that hydroxylation at C-6 enhances cytotoxic activity, whereas the C-6/C-7 olefinic moiety reduces potency, likely due to increased molecular rigidity, highlighting key structural features for activity modulation in the eudesmane scaffold.
Co-Authors Farabi, Kindi Kusumiyati Naini, Al Arofatus Rurini Retnowati Sofa Fajriah Tri Mayanti Unang Supratman