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  3. Phytochemical study of Fissistigma fulgens (Hook.f. & Thomson) Merr. leaves: Previously undescribed dihydrochalcone derivatives and their biological activities

Phytochemical study of Fissistigma fulgens (Hook.f. & Thomson) Merr. leaves: Previously undescribed dihydrochalcone derivatives and their biological activities

  • Phytochemistry. 2026 Mar:243:114735. doi: 10.1016/j.phytochem.2025.114735.
Passakorn Teerapongpisan 1,  Wuttichai Jaidee 2,  Theanchai Wiwasuku 3,  Sarot Cheenpracha 4,  Natcha Injan 4,  Somkiat Nokbin 5,  Kittirat Saharat 6,  Atthapan Morchang 7,  Phateep Hankittichai 7,  Rawiwan Charoensup 8,  Raymond J Andersen 9,  Surat Laphookhieo 10
Affiliations

Affiliations

  • 1 Futuristic Science Research Center, School of Science, Walailak University, Nakhon Si Thammarat, 80160, Thailand; Research Center for Theoretical Simulation and Applied Research in Bioscience and Sensing, Walailak University, Nakhon Si Thammarat, 80160, Thailand.
  • 2 Medicinal Plant Innovation Center of Mae Fah, Luang University, Chiang Rai, 57100, Thailand.
  • 3 School of Science, Walailak University, Nakhon Si Thammarat, 80161, Thailand; Functional Materials and Nanotechnology Center of Excellence, Walailak University, Nakhon Si Thammarat, 80161, Thailand.
  • 4 Division of Chemistry, School of Science, University of Phayao, Phayao, 56000, Thailand.
  • 5 Laboratory for Computational and Applied Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok, 10900, Thailand; Center for Advanced Studies in Nanotechnology for Chemical, Food and Agricultural Industries, Kasetsart University Institute for Advanced Studies, Kasetsart University, Bangkok, 10900, Thailand.
  • 6 School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
  • 7 School of Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Cancer and Immunology Research Unit (CIRU), Mae Fah Luang University, Chiang Rai, 57100, Thailand.
  • 8 Medicinal Plant Innovation Center of Mae Fah, Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
  • 9 Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
  • 10 Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai, 57100, Thailand. Electronic address: [email protected].
PMID: 41344390 DOI: 10.1016/j.phytochem.2025.114735
Abstract

The first phytochemical investigation of the leaves of Fissistigma fulgens (Hook.f. & Thomson) Merr. led to the isolation and identification of five previously undescribed dihydrochalcone derivatives, including two dimeric Dihydrochalcones, fissisfulgenones A and B (1 and 2), and three monomeric Dihydrochalcones, fissisfulgenones C-E (3-5), along with three known compounds. Their structures were elucidated by spectroscopic analysis. The dimeric structure of fissisfulgenone A (1) was confirmed by single-crystal X-ray diffraction analysis using Cu-Kα radiation. The pure enantiomers of the scalemic mixtures of 1-3 were successfully resolved using chiral-phase HPLC, and their absolute configurations were determined by comparing experimental and calculated ECD spectra. Fissisfulgenones A (1), C (3), and D (4) were evaluated for biological activities, including cytotoxicity against human breast adenocarcinoma (MDA-MB231), human lung carcinoma (A549), human hepatocellular carcinoma (Huh7), and human colorectal adenocarcinoma (SW480 and HT29), Antiviral activity against Dengue Virus (DENV), and nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 macrophages. Among them, fissisfulgenone C (3) exhibited the highest cytotoxicity against SW480 and HT29 cells with IC50 values of 40.6 and 68.0 μM, respectively, whereas fissisfulgenone D (4) showed cytotoxicity against MDA-MB231, A549, and Huh7 cell lines with IC50 values of 48.7, 38.3, and 21.2 μM, respectively. Notably, fissisfulgenone A (1) significantly reduced virus production in DENV-infected Huh7 cells at a sub-toxic dose of 50.0 μM. Regarding anti-inflammatory activity, fissisfulgenone C (3) exhibited strong nitric oxide inhibition, markedly reducing LPS-induced levels with an IC50 value of 5.27 μM and preserving normal macrophage morphology. Fissisfulgenone A (1) also showed similar effects at lower, non-toxic concentrations.

Keywords

Annonaceae; Anti-DENV; Cytotoxicity; Dihydrochalcones; Fissistigma fulgens; Nitric oxide production inhibitory activity.

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