Probing sponge-derived terpenoids for human 15-lipoxygenase inhibitors

被引：71

作者：

Carroll, J

Jonsson, EN

Ebel, R

Hartman, MS

Holman, TR ^{[1
]}

Crews, P

机构：

[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA

[2] Univ Calif Santa Cruz, Inst Marine Sci, Santa Cruz, CA 95064 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 21期

关键词：

D O I：

10.1021/jo015784t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A human 15-lipoxygenase (15-HLO) assay has been employed to discover new marine-sponge-derived bioactive compounds. Extracts from two different sponges, Jaspis splendens (order Choristida, family Jaspidae) and Suberea sp. (order Verongida, family Aplysinellidae), exhibited potent IC50 values of 0.4 and 0.1 mug/mL, respectively. Both are sources of terpenoids, and the former is a known source of (+)-jasplakinolide (7), which is inactive as a 15-HLO inhibitor. The terpenoids included (+)-(5S,6S)-subersin (1, IC50 > 100 muM), (-)-(5R,10R)-subersic acid (2, IC50 = 15 muM), jaspaquinol (3, IC50 = 0.3 muM), and (-)-jaspic acid (4, IC50 = 1.4 muM). Structure elucidations and lipoxygenase activity studies of these compounds are reported.

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页码：6847 / 6851

页数：5

相关论文

共 32 条

[21] Marine natural products as therapeutic agents [J].

Kerr, RG ;

Kerr, SS .

EXPERT OPINION ON THERAPEUTIC PATENTS, 1999, 9 (09) :1207-1222

[22] The diversity of the lipoxygenase family - Many sequence data but little information on biological significance [J].

Kuhn, H ;

Thiele, BJ .

FEBS LETTERS, 1999, 449 (01) :7-11

[23] THE PSEUDOPTEROSINS - A NEW CLASS OF ANTIINFLAMMATORY AND ANALGESIC DITERPENE PENTOSIDES FROM THE MARINE SEA WHIP PSEUDOPTEROGORGIA-ELISABETHAE (OCTOCORALLIA) [J].

LOOK, SA ;

FENICAL, W ;

MATSUMOTO, GK ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5140-5145

[24] Inhibitors of 15-lipoxygenase from orange peel [J].

Malterud, KE ;

Rydland, KM .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) :5576-5580

[25]

MEYER AMS, 1998, PHARM LETT, V62, P401

[26] Oleyl sulfate reveals allosteric inhibition of soybean lipoxygenase-1 and human 15-lipoxygenase [J].

Mogul, R ;

Johansen, E ;

Holman, TR .

BIOCHEMISTRY, 2000, 39 (16) :4801-4807

[27] Geographic variation in the tropical marine sponge Jaspis cf johnstoni: An unexpected source of new terpene-benzenoids [J].

Murray, LM ;

Johnson, A ;

Diaz, MC ;

Crews, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5638-5641

[28] CHEMICAL MECHANISM OF INACTIVATION OF BEE VENOM PHOSPHOLIPASE-A2 BY THE MARINE NATURAL-PRODUCTS MANOALIDE, LUFFARIELLOLIDE, AND SCALARADIAL [J].

POTTS, BCM ;

FAULKNER, DJ ;

DECARVALHO, MS ;

JACOBS, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5093-5100

[29] The first enantioselective synthesis of (-)-microcionin 2 [J].

Potvin, S ;

Canonne, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2821-2824

[30]

Sanders Miranda, 1999, Memoirs of the Queensland Museum, V44, P525

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