Antipyretic, analgesic, anti-inflammatory and antioxidant activities of two major chromenes from Melicope lunu-ankenda.
OBJECTIVE
Melicope lunu-ankenda (Gaertn.) T.G. Hartley is used in Indian traditional medicine for fever, improving complexion and as a tonic. Previous studies have isolated fungicidal, antifeedant, anti-inflammatory and immunomodulatory compounds from Melicope lunu-ankenda. This study is aimed at the isolation and biological activity screening of potential molecules from the volatile oils and extracts of Melicope lunu-ankenda in the light of traditional applications.


METHODS
Volatile oil of Melicope lunu-ankenda leaves was isolated by hydrodistillation, characterized by GC-FID, GC-MS, LRI determination, Co-GC and database searches. Major chromene-type compounds in Melicope lunu-ankenda leaf oil, evodione and leptonol, were isolated by preparative TLC and characterized by UV-Vis, IR, 1H-, 13C-, 13C-DEPT NMR and EIMS. They were also isolated from the petroleum ether and acetone extracts of the leaves of Melicope lunu-ankenda by column chromatography in petroleum ether-ethyl acetate. Their contents in leaf oil, leaf and inflorescence extracts were estimated by HPTLC. Antipyretic (Baker's yeast-induced fever test), analgesic (acetic acid-induced writhing, tail immersion assays), anti-inflammatory (carrageenan-induced paw edema) and in vitro antioxidant (DPPH radical, superoxide radical scavenging) activities of evodione and leptonol were tested.


CONCLUSIONS
Gas chromatographic analyses found 50.7% monoterpene hydrocarbons, 0.4% oxygenated monoterpenes, 3.2% sesquiterpene hydrocarbons, 0.7% oxygenated sesquiterpenes and 43.7% chromene-type compounds in Melicope lunu-ankenda leaf oil, with evodione (20.2%) and leptonol (22.5%) as its two major constituents. HPTLC estimations in the petroleum ether, acetone extracts (leaf, inflorescence) and leaf oil found evodione 1.0% (dr. wt., leaf), 1.1% (inflorescence), 0.04% (fr. wt. leaves, leaf oil), and leptonol 0.3% (leaf), 0.3% (inflorescence) and 0.04% (leaf oil). Leptonol (200 mg/kg) showed good antipyretic activity. DPPH radical scavenging assay found moderate activity for leptonol (68.7%, 500 microM), whereas evodione showed near-zero activity. A very similar trend was found in superoxide radical scavenging activity of leptonol (64.5%) and evodione (10.3%), both at 100 microg/ml. Evodione and leptonol showed moderate analgesic activities in acetic acid-induced writhing and tail immersion assays. Moderate anti-inflammatory activity was found for both evodione (59.4%) and leptonol (49.0%) at 100 mg/kg.


BACKGROUND
Biological activities of evodione and leptonol isolated from Melicope lunu-ankenda justify its traditional uses as a remedy for fever, inflammation and as a tonic.
Johnson
Anil J
AJ
Phytochemistry & Phytopharmacology Division, Tropical Botanic Garden & Research Institute, Pacha-Palode, Thiruvananthapuram, Kerala, India.
Kumar R
Arun
A
Rasheed
Sherin A
SA
Chandrika
Sreeja P
SP
Chandrasekhar
Arun
A
Baby
Sabulal
S
Subramoniam
Appian
A
D019342:Acetic Acid; D000700:Analgesics / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018712:Analgesics, Non-Narcotic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002351:Carrageenan; D002623:Chemistry Techniques, Analytical; D004195:Disease Models, Animal; D004305:Dose-Response Relationship, Drug; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005334:Fever / Q000382:microbiology / Q000517:prevention & control; D006358:Hot Temperature; D007249:Inflammation / Q000139:chemically induced / Q000517:prevention & control; D051379:Mice; D015394:Molecular Structure; D009822:Oils, Volatile; D010146:Pain / Q000209:etiology / Q000517:prevention & control; D017288:Pain Threshold / Q000187:drug effects; D018515:Plant Leaves; D010938:Plant Oils; D051381:Rats; D027821:Rutaceae; D012441:Saccharomyces cerevisiae; D013481:Superoxides / Q000737:chemistry
D000700:Analgesics; D018712:Analgesics, Non-Narcotic; D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D001578:Benzopyrans; D009822:Oils, Volatile; D010938:Plant Oils; D013481:Superoxides; D002351:Carrageenan; D019342:Acetic Acid