Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils.
Six new phthalides, (S)-3-ethyl-7-hydroxy-6-methoxyphthalide (1), (S)-3-ethyl-7-hydroxy-5,6-dimethoxyphthalide (2), (S)-3-ethyl-5,6,7-trimethoxyphthalide (3), (R)-3-ethyl-7-hydroxy-6-methoxyphthalide (4), (Z)-3-ethylidene-7-hydroxy-6-methoxyphthalide (5), and (Z)-3-ethylidene-6,7-dimethoxyphthalide (6), have been isolated from the root of Pittosporum illicioides var. illicioides, together with seven known compounds. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1-4 exhibited inhibition (IC50<or=29.8 microM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 5 and 6 inhibited fMLP/CB-induced elastase release with IC50 values of 38.6+/-4.3 and 33.9+/-3.9 microM, respectively.
Chou
Tsung-Hsien
TH
Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan, Republic of China.
Chen
Ih-Sheng
IS
Hwang
Tsong-Long
TL
Wang
Tai-Chi
TC
Lee
Tzong-Huei
TH
Cheng
Lin-Yang
LY
Chang
Ya-Chih
YC
Cho
Jui-Ying
JY
Chen
Jih-Jung
JJ
D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003571:Cytochalasin B / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects* / Q000201:enzymology*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010196:Pancreatic Elastase / Q000187:drug effects / Q000378:metabolism; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D019685:Rosales / Q000737:chemistry*; D012402:Rotenone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013481:Superoxides / Q000378:metabolism*; D013624:Taiwan
D001572:Benzofurans; D012402:Rotenone; D013481:Superoxides; D003571:Cytochalasin B; D009240:N-Formylmethionine Leucyl-Phenylalanine; C480848:tephrosin; C082022:phthalide; D010196:Pancreatic Elastase; C107676:deguelin