Anti-cancer and immunostimulatory activity of chromones and other constituents from Cassia petersiana.
Phytochemical investigation of Cassia petersiana Bolle leaves afforded four new compounds, including two chromone derivatives, 7-acetonyl-5-hydroxy-2-methylchromone (petersinone 1, 1) and 7-(propan-2'-ol-l'-yl)-5-hydroxy-2-methylchromone (petersinone 2, 2), two benzoic acid derivatives, 5-methyl-3-(propan-2'-on-1'-yl) benzoic acid (petersinone 3, 3) and 5-(methoxymethyl)-3-(propan-2'-ol-1'-yl) benzoic acid (petersinone 4, 4), and glyceryl-1-tetracosanoate (6), in addition to the known compound sistosterol-3-beta-D-glycoside (5). The structures of these compounds were determined by comprehensive NMR studies, including DEPT, COSY, HMQC, HMBC, MS and IR. Compounds 1, 2, 5 and 6 were tested for antioxidant, anti-cancer and immunostimulatory properties. The biological investigations indicated that compound 6, among others, possessed the highest anti-cancer activity against hepatocellular carcinoma, immunoproliferative activity via induction of T-lymphocytes and macrophage proliferation, anti-inflammatory activity as indicated by NO inhibition, and antioxidant activity against DPPH radicals. Moreover, compound 5 was the most effective cytotoxic compound against breast carcinoma and stimulated a consistent immunoproliferative effect on lymphocytes and macrophages combined with strong NO inhibitory activity, while compound 1 was promising as immunoproliferative agent and may act as anti-inflammatory agent as a consequence of its NO inhibitory activity.
Gamal-Eldeen
Amira M
AM
Cancer Biology Laboratory, Nobel Project, Department of Biochemistry, National Research Centre, Dokki 12622, Cairo, Egypt. aeldeen7@yahoo.com
Djemgou
Pierre C
PC
Tchuendem
Marguérite
M
Ngadjui
Bonaventure T
BT
Tane
Pierre
P
Toshifumi
Hirata
H
D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D002163:Cameroon; D002366:Cassia / Q000737:chemistry*; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D006834:Hydrazines / Q000737:chemistry; D007700:Kinetics; D008262:Macrophage Activation / Q000187:drug effects*; D008264:Macrophages; D051379:Mice; D009573:Nitrites / Q000032:analysis; D010851:Picrates; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry*
D000276:Adjuvants, Immunologic; D000970:Antineoplastic Agents; D001713:Biphenyl Compounds; D002867:Chromones; D006834:Hydrazines; D009573:Nitrites; D010851:Picrates; D010936:Plant Extracts; C004931:1,1-diphenyl-2-picrylhydrazyl