Tubakialactones A-E, new polyketides from the endophytic fungus Tubakia sp ECN-111

被引:5
作者
Nakashima, Ken-ichi [1 ]
Tomida, Junko [2 ]
Hirai, Takao [1 ]
Morita, Yuji [2 ]
Kawamura, Yoshiaki [2 ]
Inoue, Makoto [1 ]
机构
[1] Aichi Gakuin Univ, Lab Med Resources, Sch Pharm, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan
[2] Aichi Gakuin Univ, Microbiol Lab, Sch Pharm, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan
关键词
Endophytic fungi; Isocoumarins; Phthalides; Polyketides; Natural Products;
D O I
10.1016/j.tetlet.2017.04.076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new isocoumarins and two new phthalides, tubakialactones A-E (1-5), together with three known polyketides including (R)-3,4-dihydro-4-hydroxyl-6,8-dimethoxy-4-methyl-3-methylene-1H-2-benzopyran-1-one (6), (-)-5,7-dimethoxy-3-methyl-1(3H)-isobenzofuranone (7), and isosclerone (8) were found in the endophytic fungus Tubakia sp. ECN-111 isolated from the leaves of Houttuynia cordata. The chemical structures of the new compounds were determined by spectroscopic analyses, including extensive 2D-NMR experiments. The absolute configuration of 3 and 7 was determined by optical rotation and circular dichroism. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2248 / 2251
页数:4
相关论文
共 13 条
[1]  
Cheplick GP, 2009, ECOLOGY EVOLUTION GR
[2]   Colomitides A and B: Novel Ketals with an Unusual 2,7-Dioxabicyclo [3.2.1]octane Ring System from the Aquatic Fungus YMF 1.01029 [J].
Dong, Jin-Yan ;
Wang, Li-Mei ;
Song, Hong-Chuang ;
Shen, Kai-Ze ;
Zhou, Yong-Ping ;
Wang, Le ;
Zhang, Ke-Qin .
CHEMISTRY & BIODIVERSITY, 2009, 6 (08) :1216-1223
[3]  
El-Ghoil NE, 1996, PLANT PATHOLOGY CIRC, P375
[4]   Bur oak blight, a new disease on Quercus macrocarpa caused by Tubakia iowensis sp nov. [J].
Harrington, Thomas C. ;
McNew, Doug ;
Yun, Hye Young .
MYCOLOGIA, 2012, 104 (01) :79-92
[5]   Poronitins A and B, 4-pyrone and 4-pyridone derivatives from the elephant dung fungus Poronia gigantea [J].
Isaka, Masahiko ;
Palasarn, Somporn ;
Chinthanom, Panida ;
Thongtan, Jiraporn ;
Sappan, Malipan ;
Somrithipol, Sayanh .
TETRAHEDRON LETTERS, 2012, 53 (36) :4848-4851
[6]   A NEW ISOCOUMARIN DERIVATIVE FROM AN ENDOPHYTIC FUNGUS THIELAVIA sp ISOLATED FROM CRASSULA OVATA [J].
Nakashima, Ken-ichi ;
Tomida, Junko ;
Hirai, Takao ;
Morita, Yuji ;
Kawamura, Yoshiaki ;
Inoue, Makoto .
HETEROCYCLES, 2017, 94 (01) :117-121
[7]   A NEW CHROMONE DERIVATIVE FROM AN ENDOPHYTIC FUNGUS XYLARIA sp ISOLATED FROM ARDISIA CRENATA [J].
Nakashima, Ken-ichi ;
Tomida, Junko ;
Tabata, Masanori ;
Hirai, Takao ;
Morita, Yuji ;
Kawamura, Yoshiaki ;
Inoue, Makoto .
HETEROCYCLES, 2017, 94 (02) :308-313
[8]   Identification of a naturally occurring retinoid X receptor agonist from Brazilian green propolis [J].
Nakashima, Ken-ichi ;
Murakami, Tohru ;
Tanabe, Hiroki ;
Inoue, Makoto .
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2014, 1840 (10) :3034-3041
[9]   Phthalide and Isocoumarin Derivatives Produced by an Acremonium sp Isolated from a Mangrove Rhizophora apiculata [J].
Rukachaisirikul, Vatcharin ;
Rodglin, Aekkachai ;
Sukpondma, Yaowapa ;
Phongpaichit, Souwalak ;
Buatong, Jirayu ;
Sakayaroj, Jariya .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (05) :853-858
[10]   S-Adenosyl-Methionine-Dependent Methyltransferases: Highly Versatile Enzymes in Biocatalysis, Biosynthesis and Other Biotechnological Applications [J].
Struck, Anna-Winona ;
Thompson, Mark L. ;
Wong, Lu Shin ;
Micklefield, Jason .
CHEMBIOCHEM, 2012, 13 (18) :2642-2655