Triterpenoids from the Stem Bark of  Aglaia cucullata  (Meliaceae) and Their Cytotoxic Activity against A549 Lung Cancer Cell Line

Desi Harneti; Iqbal Wahyu Mustaqim; Darwati Darwati; Al Arofatus Naini; Purnama Purnama; Erina Hilmayanti; Tri Mayanti; Nurlelasari Nurlelasari; Shabarni Gaffar; Rani Maharani; Kindi Farabi; Unang Supratman; Sofa Fajriah; Mohamad Nurul Azmi; Yoshihito Shiono

doi:10.22146/ijc.78748

Triterpenoids from the Stem Bark of Aglaia cucullata (Meliaceae) and Their Cytotoxic Activity against A549 Lung Cancer Cell Line

https://doi.org/10.22146/ijc.78748

Desi Harneti^(1*), Iqbal Wahyu Mustaqim⁽²⁾, Darwati Darwati⁽³⁾, Al Arofatus Naini⁽⁴⁾, Purnama Purnama⁽⁵⁾, Erina Hilmayanti⁽⁶⁾, Tri Mayanti⁽⁷⁾, Nurlelasari Nurlelasari⁽⁸⁾, Shabarni Gaffar⁽⁹⁾, Rani Maharani⁽¹⁰⁾, Kindi Farabi⁽¹¹⁾, Unang Supratman⁽¹²⁾, Sofa Fajriah⁽¹³⁾, Mohamad Nurul Azmi⁽¹⁴⁾, Yoshihito Shiono⁽¹⁵⁾

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(7) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(8) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(9) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(10) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(11) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(12) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia; Central Laboratory, Universitas Padjadjaran, Jl. Raya Bandung-Sumedang Km. 21, Jatinangor, Sumedang 45363, Indonesia
(13) Research Center for Pharmaceutical Ingredients and Traditional Medicine, National Research and Innovation Agency (BRIN), Komplek Cibinong Science Center – BRIN, Jl. Raya Bogor Km. 46, Cibinong 16911, Indonesia
(14) School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Malaysia
(15) Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan
(*) Corresponding Author

Abstract

The Aglaia species, which contains triterpenoids, is the most numerous in the Meliaceae family. The A. cucullata species, of which there are only a few known examples, has received scant research attention. This investigation aims to identify triterpenoids in an n-hexane preparation of A. cucullata stem bark and evaluate their effects against the A549 lung cancer cell line. Five dammarane-type triterpenoids were isolated from the A. cucullata trunk bark, which is (1) (20S)-20-hydroxydammar-24-en-3-one, (2) cabraleone, (3) cabralealactone, (4) eichlerianic acid, and (5) (+)-fouquierol. Their chemical structures were determined using infrared, high-resolution mass spectrometry, and nuclear magnetic resonance, as well as through data comparison of the reported compounds. Compound 1 was priorly separated from the Aglaia genus, compounds 2–4 were first isolated from the A. cucullata species, and compound 5 has been reportedly isolated from the Meliaceae family and the Aglaia genus. All substances were tested for their lethal potential against the A549 lung cancer cell type. A seco structure in the A ring of dammarane-type triterpenoid might play an important part in the lethal activity of component 4, which showed the greatest activity with an IC₅₀ value of 32.17 µM against the A549 lung cancer cell line.

Keywords

Aglaia cucullate; cytotoxic activity; lung cancer cell (A549); Meliaceae triterpenoids

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DOI: https://doi.org/10.22146/ijc.78748