1,5-Diphenylpent-3-en-1-ynes and methyl naphthalene carboxylates from Lawsonia inermis and their anti-inflammatory activity.
Lawsonia inermis (Lythraceae) known as henna is one of the most popular and ancient plants used in cosmetics and hair dying. It is cultivated for its leaves but other parts such as seeds, flowers, stem bark and roots are also used in traditional medicine for millennia. Henna tattoo paste also proved to be beneficial for wound healing and in several skin diseases suggesting potent anti-inflammatory activity. To evaluate henna anti-inflammatory activity, 31 compounds, including three 1,5-diphenylpent-3-en-1-yne derivatives, lawsochylin A-C and three methyl naphthalene carboxylates, lawsonaphthoate A-C, were isolated from the stems and leaves of henna utilizing a bioassay-guided fractionation. The structures of the compounds were elucidated by spectroscopic data. Two compounds, lawsochylin A and lawsonaphthoate A showed potent anti-inflammatory activity by inhibition of superoxide anion generation (IC(50)=1.80 and 1.90 μg/ml) and elastase release (IC(50)=1.58 and 3.17 μg/ml) of human neutrophils in response to fMLP or cytochalasin B. Moreover, the known compounds, luteolin, apigenin, 4S-4-hydroxy-α-tetralone, and 2-butoxysuccinic acid, also showed potent inhibition of superoxide anion generation (IC(50)=0.75-1.78 μg/ml) and elastase release (IC(50)=1.62-3.61 μg/ml).
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Jing-Ru
JR
Liou
Mohamed
M
El-Shazly
Ying-Chi
YC
Du
Chao-Neng
CN
Tseng
Tsong-Long
TL
Hwang
Yueh-Lin
YL
Chuang
Yu-Ming
YM
Hsu
Pei-Wen
PW
Hsieh
Chin-Chun
CC
Wu
Shu-Li
SL
Chen
Ming-Feng
MF
Hou
Fang-Rong
FR
Chang
Yang-Chang
YC
Wu
D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000737:chemistry* / Q000145:classification / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D031564:Lawsonia Plant / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000145:classification / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects*; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry
D000893:Anti-Inflammatory Agents; D002264:Carboxylic Acids; D009281:Naphthalenes; C031721:naphthalene