Sesquiterpenoids and sesquiterpenoid dimers from the stem bark of Dysoxylum parasiticum (osbeck) kosterm

Al Arofatus Naini; Tri Mayanti; Desi Harneti; Darwati; Nurlelasari; Rani Maharani; Kindi Farabi; Tati Herlina; Unang Supratman; Sofa Fajriah; Hadi Kuncoro; Mohamad Nurul Azmi; Yoshihito Shiono; Siriporn Jungsuttiwong; Suda Chakthong

doi:10.1016/j.phytochem.2022.113477

Sesquiterpenoids and sesquiterpenoid dimers from the stem bark of Dysoxylum parasiticum (osbeck) kosterm

Phytochemistry. 2023 Jan:205:113477. doi: 10.1016/j.phytochem.2022.113477. Epub 2022 Oct 22.

Authors

Affiliations

¹ Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia; Central Laboratory, Universitas Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia.
² Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia; Study Centre of Natural Product Chemistry and Synthesis, Faculty of Mathematics and Natural, Sciences, Universitas Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia.
³ Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia.
⁴ Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas, Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia; Central Laboratory, Universitas Padjadjaran, Jatinangor, 45363, Sumedang, West Java, Indonesia. Electronic address: unang.supratman@unpad.ac.id.
⁵ Research Center for Chemistry, National Research and Innovation Agency (BRIN), Kawasan PUSPIPTEK Serpong Tangerang, Selatan, 15314, Indonesia.
⁶ Faculty of Pharmacy, Universitas Mulawarman, Samarinda, 75123, East Kalimantan, Indonesia.
⁷ School of Chemical Sciences, Universiti Sains Malaysia, 11800, Minden, Penang, Malaysia.
⁸ Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata, 997-8555, Japan.
⁹ Department of Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190, Thailand.
¹⁰ Division of Physical Science, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, 90110, Thailand.

PMID: 36283447
DOI: 10.1016/j.phytochem.2022.113477

Abstract

Two undescribed sesquiterpenoids, namely dysoticans A and B, and three undescribed sesquiterpenoid dimers, namely dysoticans C-E, together with six analogs, were isolated from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae), growing in West Java, Indonesia. Their structures were elucidated based on extensive spectroscopic analysis and theoretical simulations of ECD spectra and ¹³C NMR shifts. Dysoticans A and B possessed undescribed cadinanes with minor modifications, while C and D featured unprecedented pseudo-sesquiterpenoid dimers through O-ether linkages of cadinanes and guaianes, respectively. Dysotican E was also characterized as the true-sesquiterpenoid dimer featuring eudesmane-germacrene hybrid framework from the Meliaceae family. Furthermore, A-C and E showed moderate activities against the human breast cancer MCF-7 and cervical cancer HeLa cell lines with IC₅₀ values ranging from 22.15 to 45.14 μM. D selectively exhibited significant cytotoxicity against the HeLa cell line with an IC₅₀ value of 13.00 ± 0.13 μM.

Keywords: Cytotoxic activity; Dysoticans A-E; Dysoxylum parasiticum (Osbeck) kosterm.; Meliaceae; Sesquiterpenoids.

MeSH terms

HeLa Cells*
Humans
Indonesia