New 3-[2'(R)-Hydroxybutyl]-7-Hydroxyphthalide from Marine Isolate of the Fungus Penicillium claviforme

被引：9

作者：

Afiyatullov, Sh. Sh. ^{[1
]}

Leshchenko, E. V. ^{[2
]}

Sobolevskaya, M. P. ^{[1
]}

Gerasimenko, A. V. ^{[3
]}

Khudyakova, Yu. V. ^{[1
]}

Kirichuk, N. N. ^{[1
]}

Mikhailov, V. V. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Far East Branch, GB Elyakov Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia

[2] Far East Fed Univ, Vladivostok 690950, Russia

[3] Russian Acad Sci, Far East Branch, Inst Chem, Vladivostok 690022, Russia

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2015年 / 51卷 / 01期

基金：

俄罗斯科学基金会;

关键词：

strain Penicillium claviforme; Zostera marina; 3-[2 '(R)-hydroxybutyl]-7-hydroxyphthalide; XSA; ALKALOIDS;

D O I：

10.1007/s10600-015-1214-y

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The new phthalide derivative 3-[2'(R)-hydroxybutyl]-7-hydroxyphthalide (2) and the five known compounds (-)-3-butyl-7-hydroxyphthalide (1), isopatulin (3), m-hydroxybenzyl alcohol (4), cyclopenin (5), and cyclopeptine (6) were isolated from the marine isolate of the fungus Penicillium claviforme associated with the seagrass Zostera marina. The structures of the compounds were established using NMR spectroscopy and mass spectrometry. The absolute configuration of the C-2' asymmetric center was determined using a modified Mosher method.

引用

页码：111 / 115

页数：5

共 12 条

[1]

Blunt JW, 2013, NAT PROD REP, V30, P237, DOI [10.1039/d0np00089b, 10.1039/c2np20112g]

[2]

Bruker, 2010, APEX2

[3] CYCLOPEPTIN AND DEHYDROCYCLOPEPTIN - INTERMEDIATES OF BIOSYNTHESIS OF ALKALOIDS OF CYCLOPENIN VIRIDICATIN GROUP IN PENICILLIUM-CYCLOPIUM WESTLING [J].

FRAMM, J ;

NOVER, L ;

ELAZZOUNI, A ;

RICHTER, H ;

WINTER, K ;

WERNER, S ;

LUCKNER, M .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1973, 37 (01) :78-85

[4] Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum [J].

Kusano, M ;

Koshino, H ;

Uzawa, J ;

Fujioka, S ;

Kawano, T ;

Kimura, Y .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (12) :2559-2568

[5] The modified Mosher's method and the sulfoximine method [J].

Kusumi, Takenori ;

Ooi, Takashi ;

Ohkubo, Yumi ;

Yabuuchi, Tetsuya .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (07) :965-980

[6] Antibacterial Polyketides from the Jellyfish-Derived Fungus Paecilomyces variotii [J].

Liu, Juan ;

Li, Famei ;

La Kim, Eun ;

Li, Jian Lin ;

Hong, Jongki ;

Bae, Kyung Sook ;

Chung, Hae Young ;

Kim, Hyung Sik ;

Jung, Jee H. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (08) :1826-1829

[7]

Makino M, 1998, HETEROCYCLES, V48, P1931

[8] A new isopatulin derivative pintulin produced by Penicillium vulpinum F-4148 taxonomy, isolation, physico-chemical properties, structure and biological properties [J].

Mikami, A ;

Okazaki, T ;

Sakai, N ;

Ichihara, T ;

Hanada, K ;

Mizoue, K .

JOURNAL OF ANTIBIOTICS, 1996, 49 (10) :985-989

[9] Synthesis and absolute configuration of (-)-3-butyl-7-hydroxyphthalide, a cytotoxic metabolite of Penicillium vulpinum [J].

Ohzeki, T ;

Mori, K .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2003, 67 (10) :2240-2244

[10] Secondary metabolites of fungi from marine habitats [J].

Rateb, Mostafa E. ;

Ebel, Rainer .

NATURAL PRODUCT REPORTS, 2011, 28 (02) :290-344

← 1 2 →