Dammarane-Type Triterpenoid from the Stem Bark of Aglaia elliptica (Meliaceae) and Its Cytotoxic Activities

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 19; p. 6757
• Main Authors: Farabi, Kindi, Harneti, Desi, Darwati, Mayanti, Tri, Nurlelasari, Maharani, Rani, Sari, Aprilia Permata, Herlina, Tati, Hidayat, Ace Tatang, Supratman, Unang, Fajriah, Sofa, Azmi, Mohamad Nurul, Shiono, Yoshihito
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 10.10.2022; MDPI
• Subjects: Aglaia; Aglaia elliptica; Antineoplastic Agents - pharmacology; B16-F10 cell line; Breast cancer; Breast Neoplasms; Cancer; Carbon; Chromatography; cytotoxic activity; Cytotoxicity; dammarane-type triterpenoid fatty acid ester; Dammaranes; Drug development; Esters; Fatty acids; Female; Humans; Ketones; Leukemia; MCF-7 cell line; Melanoma; Meliaceae; Molecular Structure; NMR; Nuclear magnetic resonance; Oleic Acid; Plant Bark; Reagents; Transesterification; Triterpenes - chemistry; Triterpenes - pharmacology; Two dimensional analysis; Indonesia; dammarane-type triterpenoid fatty acid ester; cytotoxic activity; MCF-7 cell line; Aglaia elliptica; B16-F10 cell line
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27196757

Two new dammarane-type triterpenoid fatty acid ester derivatives, 3β-oleate-20 -hydroxydammar-24-en ( ) and 3β-oleate-20 ,24 -epoxy-25-hydroxydammarane ( ) with a known dammarane-type triterpenoid compound, such as 20 -hydroxydammar-24-en-3-on ( ), were isolated from the stem bark of (C.DC.) Blume. The chemical structures were determined by spectroscopic methods, including FTIR, NMR (one and two-dimensional), and HRESITOF-MS analysis, as well as chemical derivatization and comparison with previous literature. Furthermore, the synthetic analog resulting from transesterification of and also obtained 3β,20 -dihydroxy-dammar-24-en ( ) and 20 ,24 -epoxy-3β,25-dihydroxydammarane ( ), respectively. The cytotoxic effect of all isolated and synthetic analog compounds was evaluated using PrestoBlue reagent against MCF-7 breast cancer cell and B16-F10 melanoma cell lines. The 20 -hydroxydammar-24-en-3-on ( ) showed the strongest activity against MCF-7 breast cancer and B16-F10 melanoma cell, indicating that the ketone group at C-3 in plays an essential role in the cytotoxicity of dammarane-type triterpenoid. On the other hand, compounds and had very weak cytotoxic activity against the two cell lines, indicating the presence of fatty acid, significantly decreasing cytotoxic activity. This showed the significance of the discovery to investigate the essential structural feature in dammarane-type triterpenoid, specifically for the future development of anticancer drugs.