Anti-complement Activity of Constituents from the Stem-Bark of Juglans mandshurica

• Published in: Biological & Pharmaceutical Bulletin Vol. 26; no. 7; pp. 1042 - 1044
• Main Authors: Min, Byung-Sun, Lee, Sun-Young, Kim, Jung-Hee, Lee, Joong-Ku, Kim, Tae-Jin, Kim, Dong-Hee, Kim, Young-Ho, Joung, Hyouk, Lee, Hyeong-Kyu, Nakamura, Norio, Miyashiro, Hirotsugu, Hattori, Masao
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 2003; Pharmaceutical Society of Japan; Maruzen; Japan Science and Technology Agency
• Subjects: 1,2,3,6-tetragalloylglucose; 1,2,6-trigalloylglucose; 3,5,7-trihydroxyflavone; Analytical, structural and metabolic biochemistry; Animals; anti-complement activity; Biological and medical sciences; Complement Inactivator Proteins - chemistry; Complement Inactivator Proteins - isolation & purification; Complement Inactivator Proteins - pharmacology; Complement System Proteins - metabolism; Dose-Response Relationship, Drug; Fundamental and applied biological sciences. Psychology; Humans; Juglans; Juglans mandshurica; Male; Medical sciences; Pharmacology. Drug treatments; Plant Bark; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Plant Stems; Sheep; Juglans; Bark; 3,5,7-trihydroxyflavone; Complement; Juglans mandshurica; Stem; anti-complement activity; 1,2,6-trigalloylglucose; Juglandaceae; 1,2,3,6-tctragalloylglucose; Dicotyledones; Angiospermae; Spermatophyta
• ISSN: 0918-6158; 1347-5215
• DOI: 10.1248/bpb.26.1042

Four known flavonoids and two galloyl glucoses isolated from the stem-bark of Juglans mandshurica (Juglandaceae), namely taxifolin (1), afzelin (2), quercitrin (3), myricitrin (4), 1,2,6-trigalloylglucose (5), and 1,2,3,6-tetragalloylglucose (6), were evaluated for their anti-complement activity against complement system. Afzelin (2) and quercitrin (3) showed inhibitory activity against complement system with 50% inhibitory concentrations (IC50) values of 258 and 440 μM. 1,2,6-Trigalloylglucose (5) and 1,2,3,6-tetragalloylglucose (6) exhibited anti-complement activity with IC50 values of 136 and 34 μM. In terms of the evaluation of the structure–activity relationship of 3,5,7-trihydroxyflavone, compounds 2, 3, and 4 were hydrolyzed with naringinase to give kaempferol (2a), quercetin (3a), and myricetin (4a) as their aglycones, and these were also tested for their anti-complement activity. Of the three aglycones, kaempferol (2a) exhibited weak anti-complement activity with an IC50 value of 730 μM, while quercetin (3a) and myricetin (4a) were inactive in this assay system. Among the compounds tested, 1,2,3,6-tetragalloylglucose (6) showed the most potent anticomplement activity (IC50, 34 μM).