Structure–activity relationship of lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ

• Published in: Bioorganic & medicinal chemistry letters 2010-08, Vol.20 (16), p.4927-4931
• Main Authors: Nhiem, Nguyen Xuan, Kiem, Phan Van, Minh, Chau Van, Tai, Bui Huu, Tung, Nguyen Huu, Ha, Do Thi, Soung, Kwang Su, Kim, Jun Ho, Ahn, Ji Young, Lee, Young-Mi, Kim, Young Ho
• Format: Article
• Language: English
• Subjects: Acankoreosides M–O; Acanthopanax koreanum; Araliaceae; Biological and medical sciences; Eleutherococcus - chemistry; General pharmacology; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; IFN-γ; IL-2; Interferon-gamma - metabolism; Interleukin-2 - metabolism; Lupane-triterpene glycoside; Lymphocytes - drug effects; Lymphocytes - immunology; Magnetic Resonance Spectroscopy; Medical sciences; Molecular Conformation; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Leaves - chemistry; Saponins - chemistry; Saponins - isolation & purification; Saponins - pharmacology; Spleen - cytology; Spleen - immunology; Structure-Activity Relationship; Triterpenes - chemistry
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2010.06.044

Phytochemical investigation resulted in isolation of three new lupane-triterpene glycosides acankoreosides M–O ( 1, 2 and 8) from the leaves of Acanthopanax koreanum (Araliaceae). Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells. Phytochemical investigation resulted in the isolation of three new lupane-triterpene glycosides acankoreosides M–O ( 1, 2 and 8) together with eight known lupane-triterpene glycosides ( 3– 7, 9– 11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.