Maeruines A−E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation
Issued Date
2025-01-01
Resource Type
ISSN
00319422
Scopus ID
2-s2.0-85204773669
Pubmed ID
39326485
Journal Title
Phytochemistry
Volume
229
Rights Holder(s)
SCOPUS
Bibliographic Citation
Phytochemistry Vol.229 (2025)
Suggested Citation
Nukulkit S., Nalinratana N., Aree T., Suriya U., Suttisri R., Nuengchamnong N., Chang H.S., Chansriniyom C. Maeruines A−E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation. Phytochemistry Vol.229 (2025). doi:10.1016/j.phytochem.2024.114291 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/102966
Title
Maeruines A−E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation
Corresponding Author(s)
Other Contributor(s)
Abstract
Five previously undescribed indole alkaloids, maeruines A−E (1−5), bearing imino-2H-thieno[2,3-b]indol-3(8H)-one skeleton, were obtained from the stems of Maerua siamensis. Their chemical structures were elucidated using spectroscopic techniques [NMR, MS, IR, and UV], and single-crystal X-ray diffraction. Maeruine D (4) displayed selective cyclooxygenase-2 (COX-2) inhibitory activity in vitro with an IC50 of 29.72 ± 6.36 μM. Molecular dynamics simulations revealed that maeruine D could form a stable complex with human COX-2, predominantly driven by hydrophobic interactions. In addition, five amino-acid residues including Val349, Leu352, Leu384, Val523, and Ala527 were identified as hot-spot ones, which may lead to high binding affinity and selectivity. Furthermore, it exhibited cytotoxicity against HT-29 colorectal cancer cells with an IC50 of 29.32 ± 4.76 μM, and, at 0.1−10 μM, significantly inhibited their proliferation, induced by the proinflammatory cytokine interleukin-1β (IL-1β), in a dose-dependent manner.