ABSTRACT
Investigation of the chemical constituents of the fruits of Knema glauca (Myristicaceae) yielded a new acyclic diterpene acid, named glaucaic acid 4, together with four acylphenols, including 1-(2,6-dihydroxyphenyl) tetradecan-1-one 1, malabaricone A 6, dodecanoylphloroglucinol 7 and 1-(2,4,6-trihydroxyphenyl)-9-phenylnonan-1-one 8, two lignans sesamin 2 and asarinin 3, and a flavan, myristinin D 5. In addition, myristinin A 9 and (+/-)-7,4'-dihydroxy-3'-methoxyflavan 10 were isolated from its leaves and stems, respectively. When tested against small-cell lung cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines, compounds 1, 6-8 and 10 displayed weak to moderate cytotoxicity. The acylphenols 6-8 displayed antituberculosis activity against the microbe Mycobacterium tuberculosis with MIC values of 25, 50 and 100 microg/mL, respectively, and antiviral activity against herpes simplex virus type 1, with 7 as the most active compound (IC(50) = 3.05 microg/mL). Malabaricone A 6 was also active against the malarial parasite Plasmodium falciparum with an IC(50) value of 2.78 microg/mL.
Subject(s)
Antimalarials/isolation & purification , Antineoplastic Agents, Phytogenic/isolation & purification , Antitubercular Agents/isolation & purification , Antiviral Agents/isolation & purification , Diterpenes/isolation & purification , Hydrocarbons, Acyclic/isolation & purification , Myristicaceae/chemistry , Animals , Antimalarials/chemistry , Antimalarials/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antitubercular Agents/chemistry , Antitubercular Agents/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Diterpenes/chemistry , Diterpenes/pharmacology , Dose-Response Relationship, Drug , Fruit , Humans , Hydrocarbons, Acyclic/chemistry , Hydrocarbons, Acyclic/pharmacology , Inhibitory Concentration 50 , Microbial Sensitivity Tests , Molecular Structure , Mycobacterium tuberculosis/drug effects , Mycobacterium tuberculosis/growth & development , Plant Leaves , Plant Stems , Plasmodium falciparum/drug effects , Plasmodium falciparum/growth & development , Simplexvirus/drug effects , Simplexvirus/growth & developmentABSTRACT
A new arylnaphthalene lignan, named furfuracin, was isolated from the leaves of Knema furfuracea (Myristicaceae), whereas 7 known compounds including (+)-trans-1,2-dihydrodehydroguaiaretic acid, fragransin A(2), biochanin A, gingkolic acid, anarcardic acid, 2-hydroxy-6-(12-phenyldodecyl)-benzoic acid and 2-hydroxy-6-(12-phenyldodecen-8'Z-yl)-benzoic acid were obtained from its stems. The structure of the new lignan was established by analysis of spectroscopic data (UV, IR, MS and NMR).
