Relative and Absolute Stereochemistry of Quinadoline B, an Inhibitor of Lipid Droplet Synthesis in Macrophages

被引：46

作者：

Koyama, Nobuhiro ^{[1
]}

Inoue, Yusuke ^{[2
]}

Sekine, Masae ^{[1
]}

Hayakawa, Yoichi ^{[2
]}

Homma, Hiroshi ^{[1
]}

Omura, Satoshi ^{[3
]}

Tomoda, Hiroshi ^{[1
]}

机构：

[1] Kitasato Univ, Sch Pharm, Minato Ku, Tokyo 1088641, Japan

[2] Tokyo Univ Sci, Fac Pharmaceut Sci, Chiba 2788501, Japan

[3] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

关键词：

D O I：

10.1021/ol802089p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New fungal metabolites, designated quinadolines A (1) and 8 (2), were isolated from culture broth of Aspergillus sp. FKI-1746, and their structures were elucidated by NMR spectroscopy. The complete relative and absolute stereochemistry of 2 was determined by X-ray crystallography and amino acid analysis using a chiral column. Quinadolines moderately inhibited lipid droplet synthesis in mouse macrophages.

引用

页码：5273 / 5276

页数：4

共 14 条

[1] SPIROQUINAZOLINE, A NOVEL SUBSTANCE-P INHIBITOR WITH A NEW CARBON SKELETON, ISOLATED FROM ASPERGILLUS FLAVIPES [J].

BARROW, CJ ;

SUN, HH .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (04) :471-476

[2] Quinazoline alkaloids in nature [J].

D'yakonov A.L. ;

Telezhenetskaya M.V. .

Chemistry of Natural Compounds, 1997, 33 (3) :221-267

[3]

Fujimoto H, 1996, CHEM PHARM BULL, V44, P1843, DOI 10.1248/cpb.44.1843

[4] Regional distribution and postnatal changes of D-amino acids in rat brain [J].

Hamase, K ;

Homma, H ;

Takigawa, Y ;

Fukushima, T ;

Santa, T ;

Imai, K .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 1997, 1334 (2-3) :214-222

[5]

HELDGE BB, 2002, CHEMBIOCHEM, V3, P619

[6] FLUORIMETRIC DETERMINATION OF SECONDARY AMINO-ACIDS BY 7-FLUORO-4-NITROBENZO-2-OXA-1,3-DIAZOLE [J].

IMAI, K ;

WATANABE, Y .

ANALYTICA CHIMICA ACTA, 1981, 130 (02) :377-383

[7] Spylidone, a novel inhibitor of lipid droplet accumulation in mouse macrophages produced by Phoma sp FKI-1840 [J].

Koyama, N ;

Nagahiro, T ;

Yamaguchi, Y ;

Ohshiro, T ;

Masuma, R ;

Tomoda, H ;

Omura, S .

JOURNAL OF ANTIBIOTICS, 2005, 58 (05) :338-345

[8] Inhibition of lipid droplet accumulation in mouse macrophages by stemphone derivatives [J].

Koyama, Nobuhiro ;

Kobayashi, Kakeru ;

Yamazaki, Hiroyuki ;

Tomoda, Hiroshi .

JOURNAL OF ANTIBIOTICS, 2008, 61 (08) :509-514

[9] Fungal isobisvertinol, a new inhibitor of lipid droplet accumulation in mouse macrophages [J].

Koyama, Nobuhiro ;

Ohshiro, Taichi ;

Tomoda, Hiroshi ;

Omura, Satoshi .

ORGANIC LETTERS, 2007, 9 (03) :425-428

[10] Antiatherogenic activity of fungal beauveriolides, inhibitors of lipid droplet accumulation in macrophages [J].

Namatame, I ;

Tomoda, H ;

Ishibashi, S ;

Omura, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (03) :737-742

← 1 2 →