Immunomodulatory Effects of New Phenanthrene Derivatives from Dendrobium crumenatum

• Published in: Journal of natural products (Washington, D.C.) Vol. 86; no. 5; pp. 1294 - 1306
• Main Authors: Kongkatitham, Virunh, Dehlinger, Adeline, Wang, Meng, Poldorn, Preeyaporn, Weidinger, Carl, Letizia, Marilena, Chaotham, Chatchai, Otto, Carolin, Ruprecht, Klemens, Paul, Friedemann, Rungrotmongkol, Thanyada, Likhitwitayawuid, Kittisak, Böttcher, Chotima, Sritularak, Boonchoo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.05.2023; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Dendrobium - chemistry; Fluorenes - chemistry; Fluorenes - pharmacology; Humans; Leukocytes, Mononuclear; Life Sciences & Biomedicine; Monocytes; Pharmacology & Pharmacy; Phenanthrenes - chemistry; Phenanthrenes - pharmacology; Plant Sciences; Science & Technology; T-Lymphocytes; Tetradecanoylphorbol Acetate - pharmacology; CD4(+); ORCHID; EXPRESSION; CD8(+) T-CELLS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.3c00107

Three new phenanthrene derivatives (1, 2, 4), one new fluorenone (3), and four known compounds (5–8) were isolated from the ethyl acetate extract of Dendrobium crumenatum Sw. stems using column chromatography. The chemical structures were elucidated by analysis of spectroscopic data. The absolute configuration of 4 was determined by electronic circular dichroism calculation. We also evaluated the immunomodulatory effects of compounds isolated from D. crumenatum in human peripheral blood mononuclear cells from healthy individuals and those from patients with multiple sclerosis in vitro. Dendrocrumenol B (2) and dendrocrumenol D (4) showed strong immunomodulatory effects on both CD3+ T cells and CD14+ monocytes. Compounds 2 and 4 could reduce IL-2 and TNF production in T cells and monocytes that were treated with phorbol-12-myristate-13-acetate and ionomycin (PMA/Iono). Deep immune profiling using high-dimensional single-cell mass cytometry could confirm immunomodulatory effects of 4, quantified by the reduction of activated T cell population under PMA/Iono stimulation, in comparison to the stimulated T cells without treatment.