Journal
JOURNAL OF NATURAL PRODUCTS
Volume 73, Issue 5, Pages 911-914Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np100059m
Keywords
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Funding
- National Basic Research Program of China [2010CB833800]
- National Natural Science Foundation of China [30670219, 30770235]
- Project of Chinese National Programs for High Technology Research and Development [2007AA09Z447]
- Program for Social Profit of China Ministry of Science and Technology [2004D1B3J072]
- Key Laboratory of Marine Drugs of Ministry of Education [KLMD-OUC-200607]
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Two new polyphenols containing both phenolic bisabolane sesquiterpenoid and diphenyl ether units, expansols A (1) and B (2), and two new phenolic bisabolane sesquiterpenoids, (S)-(+)-11-dehydrosydonic acid (3) and (7S,11S)-(+)12-acetoxysydonic acid (4), along with two known compounds, (S)-(+)-sydonic acid (5) and diorcinol (6), were isolated from the metabolites of the marine-derived fungus Penicillium expansum 091006 endogenous with the mangrove plant Excoecaria agallocha. On the basis of spectroscopic analysis, chemical transformation, and theoretical calculation, the structures of 1-4 were elucidated as (S)-(+)-2[3-hydroxy-4-(2- methoxy-6-methylheptan-2-yl)benzyl]-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol, S-(+)-2-[3-hydroxy-4-(2-hydroxy-6-methylheptan-2-yl)benzyl]-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol, (S)-(+)-3-hydroxy-4-(2-hydroxy-6-methylhept-6-en-2-yl)benzoic acid, and 4-[(2S,6S)-7-acetoxy-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid, respectively. Expansol A (1) exhibited moderate cytotoxicity against the HL-60 cell line with an IC(50) value of 15.7 mu M, and expansol B (2) inhibited the proliferation of A549 and HL-60 cells with IC(50) values of 1.9 and 5.4 mu M, respectively.
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