Onoceranoid Triterpenes of Lansium domesticum Corr. cv. Kokossan and Their Cytotoxicity against MCF-7 Breast Cancer Cells

Authors

  • Tri Mayanti Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Salwa Alya Azahra Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Tasya Putri Syafriadi Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Nurlelasari Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Rani Maharani Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Euis Julaeha Department of Chemistry, Faculty of Mathematic and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Unang Supratman Central Laboratory, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Siska Elisahbet Sinaga Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 9978555, Japan
  • Savira Ekawardhani Department of Biomedical Sciences, Faculty of Medicine, Universitas Padjadjaran, Jatinangor 45363, Indonesia
  • Sofa Fajriah National Research and Innovation Agency, Jakarta 10340, Indonesia

DOI:

https://doi.org/10.48048/tis.2025.9000

Keywords:

Lansium domesticum Corr. cv. Kokossan, MCF-7 breast cancer cell, Onoceranoids

Abstract

The onoceranoid triterpenes isolated from the kokossan fruit peels were studied in vitro using MCF-7 breast cancer cells. Three onoceranoids, namely 8,14-secogammacera-8(26),14-dien-3,21-diol (1), 3β-hydroxyonocera-8(26),14-dien-21-one (2) and α,γ-onoceradienedione (3), were obtained from the ethyl acetate extract of kokossan fruit peels. Compounds 1 - 3 were obtained for the first time from this cultivar. Several spectroscopic methods, including IR, HR-TOFMS and 1,2 D-NMR, were used to determine the chemical structures of compounds (1 - 3), and the results were compared to spectrum data that had previously been published. Additionally, the activity of compounds 1 - 3 was assessed in vitro using MCF-7 cells. With an IC50 value of 17.11 µg/mL, compound 2 demonstrated the highest activity in the activity test findings, followed by compounds 3 and 1, with IC50 values of 19.66 and > 150 µg/mL, respectively. When compared to cisplatin as a positive control, compounds 2 and 3 showed considerable potency, while compound 1 showed no activity. Compounds 2 and 3 were the most promising candidates for the anticancer drug; nevertheless, more testing is necessary to ascertain their biological mechanism for future research.

HIGHLIGHTS

  • Lansium domesticum is a tropical fruit-bearing tree with significant economic and medicinal value. It has been traditionally used for various ailments, including fever, dysentery, and malaria, due to its rich phytochemical composition.
  • Kokossan is a cultivar of Lansium domesticum that has not been widely studied for its onoseronoid content, especially in the skin of the fruit. 8,14-sekogammacera-8(26),14-dien-3,21-diol (1), 3β-hydroxyonocera-8(26),14-dien-21-one (2), and α,γ-onoceradienedione (3). For the first time, these two compounds (1 and 2) were separated from this genus; earlier, this compound was the outcome of the reduction (synthesis) of compound 3.
  • 3β-hydroxyonocera-8(26),14-dien-21-one exhibited the highest IC50 value compared to α,γ-onoceradienedione and . 8,14-sekogammacera-8(26),14-dien-3,21-diol.
  • Compounds 2 and 3 demonstrated potential as anticancer agents, with activity comparable to the standard drug cisplatin. This provides insight that onoceranoids have the potential as chemopreventive agents to treat breast cancer.

GRAPHICAL ABSTRACT

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References

T Mayanti, SE Sinaga and U Supratman. Phytochemistry and biological activity of Lansium domesticum Corr. species: A review. Journal of Pharmacy and Pharmacology 2022; 74(11), 1568-1587.

T Mayanti, R Tjokronegoro, U Supratman, MR Mukhtar, K Awang and AHA Hadi. Antifeedant triterpenoids from the seeds and bark of Lansium domesticum cv Kokossan (Meliaceae). Molecules 2011; 16(4), 2785-2795.

QG Tan and XD Luo. Meliaceous limonoids: Chemistry and biological activities. Chemical Reviews 2011; 111(11), 7437-7522.

W Safriansyah, SE Sinaga, U Supratman and D Harneti. Phytochemistry and biological activities of Guarea genus (Meliaceae). Molecules 2022; 27(24), 8758.

Y Mulyani, SE Sinaga and U Supratman. Phytochemistry and biological activities of endophytic fungi from the Meliaceae family. Molecules 2023; 28(2), 778.

SE Sinaga, M Fajar, T Mayanti and U Supratman. Bioactivities screening and elucidation of terpenoid from the stembark extracts of Lansium domesticum Corr. cv. Kokosan (Meliaceae). Sustainability 2023; 15(3), 2140.

FM Fauzi, SR Meilanie, Zulfikar, K Farabi, T Herlina, J Al Anshori and T Mayanti. Kokosanolide d: A new tetranortriterpenoid from fruit peels of Lansium domesticum Corr. cv Kokossan. Molbank 2021; 2021(2), M1232.

Zulfikar, NK Putri, S Fajriah, M Yusuf, R Maharani, J Al Anshori, U Supratman and T Mayanti. 3-hydroxy-8,14-secogammacera-7,14-dien-21-one: A new onoceranoid triterpenes from Lansium domesticum Corr. cv Kokossan. Molbank 2020; 2020(4), M1157.

S Purwani, J Nahar and T Mayanti. Molecular docking on kokosanolide A and C for anticancer activity against human breast cancer cell MCF-7. Jurnal Kimia Valensi 2021; 7(1), 52-57.

T Mayanti, Zulfikar, S Fawziah, AA Naini, R Maharani, K Farabi, Nurlelasari, M Yusuf, D Harneti, D Kurnia and U Supratman. New triterpenoids from Lansium domesticum Corr. cv kokossan and their cytotoxic activity. Molecules 2023; 28(5), 2144.

A Hardianto, SS Mardetia, W Destiarani, YP Budiman, D Kurnia and T Mayanti. Unveiling the anti-cancer potential of onoceranoid triterpenes from Lansium domesticum Corr. cv. kokosan: An in silico study against estrogen receptor alpha. International Journal of Molecular Sciences 2023; 24(19), 15033.

SE Sinaga, FF Abdullah, U Supratman, T Mayanti and R Maharani. Isolation and structure determination of stigmaterol from the stem bark of Lansium domesticum Corr. cv. Kokosan (Meliaceae). Chimica et Natura Acta 2022; 10(3), 106-111.

KL Ji, MY Dai, CF Xiao and YK Xu. Two new steroids with NO inhibitory effects from Lansium domesticum. Natural Product Research 2021; 35(7), 1147-1152.

HM Abdallah, GA Mohamed and SRM Ibrahim. Lansium domesticum - a fruit with multi-benefits: Traditional uses, phytochemicals, nutritional value, and bioactivities. Nutrients 2022; 14(7), 1531.

CY Ragasa, P Labrador and JA Rideout. Antimicrobial terpenoids from Lansium domesticum. Philippine Agricultural Scientist 2006; 89(1), 101-105.

K Fadhilah, S Wahyuono and P Astuti. Fractions and isolated compounds from Lansium domesticum fruit peel exhibited cytotoxic activity against T-47D and HepG2 cell lines. Biodiversitas Journal of Biological Diversity 2021; 22(9), 3743-3748.

T Matsumoto, T Kitagawa, T Ohta, T Yoshida, D Imahori, S Teo, HS bin Ahmad and T Watanabe. Structures of triterpenoids from the leaves of Lansium domesticum. Journal of Natural Medicines 2019; 73, 727-734.

T Potipiranun, W Worawalai and P Phuwapraisirisan. Lamesticumin G, a new α-glucosidase inhibitor from the fruit peels of Lansium parasiticum. Natural Product Research 2018; 32(16), 1881-1886.

Kanupriya, PC Kumar and A Sane. An assessment of fruiting and polyembryony in Langsat (Lansium domesticum Corr.) from Nilgiris, India. Journal of Horticultural Sciences 2019; 14(1), 79-82.

K Fadhilah, S Wahyuono and P Astuti. A sesquiterpene aldehyde isolated from ethyl acetate extract of Lansium domesticum fruit peel. Indonesian Journal of Pharmacy 2020; 32(3), 394-398.

SE Sinaga, T Mayanti, AA Naini, D Harneti, N Nurlelasari, R Maharani, K Farabi, U Supratman, S Fajriah and MN Azmi. Sesquiterpenoids from the stem bark of Lansium domesticum Corr. cv. Kokossan and their cytotoxic activity against MCF-7 breast cancer cell lines. Indonesian Journal of Chemistry 2022; 22(4), 1035-1042.

M Nishizawa, H Nishide, K Kuriyama and Y Hayashi. Regioselective reduction of α, γ-onoceradienedione: Synthesis of lansiolic acid. Chemical and Pharmaceutical Bulletin 1986; 34(10), 4443-4446.

W Safriansyah, SE Sinaga, N Rustaman, K Farabi, MN Azmi, R Maharani, N Nurlelasari, U Supratman, S Fajriah and D Harneti. The isolation of novel pregnane steroids from Aglaia pachyphylla Miq. and the cytotoxicity against breast cancer cell lines (MCF-7). RSC Advances 2024; 14, 25042-25047.

T Tanaka, M Ishibashi, H Fujimoto, E Okuyama, T Koyano, T Kowithayakorn, M Hayashi and K Komiyama. New onoceranoid triterpene constituents from Lansium domesticum. Journal of Natural Products 2002; 65(11), 1962-1964.

DF Veber, SR Johnson, HY Cheng, BR Smith, KW Ward and KD Kopple. Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry 2002; 45(12), 2615-2623.

A Manzari-Tavakoli, A Babajani, M M Tavakoli, F Safaeinejad and A Jafari. Integrating natural compounds and nanoparticle-based drug delivery systems: A novel strategy for enhanced efficacy and selectivity in cancer therapy. Cancer Medicine 2024; 13(5), e7010.

CA Lipinski. Lead-and drug-like compounds: The rule-of-five revolution. Drug Discovery Today: Technologies 2004; 1(4), 337-341.

NM Krstić, IZ Matić, ZD Juranić, IT Novaković and DM Sladić. Steroid dimers - in vitro cytotoxic and antimicrobial activities. The Journal of Steroid Biochemistry and Molecular Biology 2014; 143, 365-375.

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Published

2024-11-15

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