Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum.
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 microM, and expansol B (2) inhibited the proliferation of A549 and HL-60 cells with IC(50) values of 1.9 and 5.4 microM, respectively.
Lu
Zhenyu
Z
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
Zhu
Huajie
H
Fu
Peng
P
Wang
Yi
Y
Zhang
Zhihua
Z
Lin
Haipeng
H
Liu
Peipei
P
Zhuang
Yibin
Y
Hong
Kui
K
Zhu
Weiming
W
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D059808:Polyphenols; D043982:Rhizophoraceae / Q000382:microbiology*
D000972:Antineoplastic Agents, Phytogenic; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols