Literature DB >> 24984794

Ascochlorin derivatives from the leafhopper pathogenic fungus Microcera sp. BCC 17074.

Masahiko Isaka1, Arunrat Yangchum1, Sumalee Supothina1, Pattiyaa Laksanacharoen1, J Jennifer Luangsa-Ard1, Nigel L Hywel-Jones1.   

Abstract

Two new ascochlorin derivatives, nectchlorins A (1) and B (2), together with eight known compounds (3-10), were isolated from cultures of the leafhopper pathogen Microcera sp. BCC 17074. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of 2 was determined by application of the modified Mosher's method. The absolute configuration of LL-Z 1272α epoxide (9), which is a plausible biosynthetic precursor of ascochlorins, was established by chemical correlations. Cytotoxic activities of these ascochlorin derivatives were evaluated.

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Year:  2014        PMID: 24984794     DOI: 10.1038/ja.2014.90

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  18 in total

1.  Chemistry and Biology of Cylindrols: Novel Inhibitors of Ras Farnesyl-Protein Transferase from Cylindrocarpon lucidum.

Authors:  Sheo B. Singh; Richard G. Ball; Gerald F. Bills; Carmen Cascales; Jackson B. Gibbs; Michael A. Goetz; Karst Hoogsteen; Rosalind G. Jenkins; Jerrold M. Liesch; Russell B. Lingham; Keith C. Silverman; Deborah L. Zink
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

2.  Bioactive substances from insect pathogenic fungi.

Authors:  Masahiko Isaka; Prasat Kittakoop; Kanyawim Kirtikara; Nigel L Hywel-Jones; Yodhathai Thebtaranonth
Journal:  Acc Chem Res       Date:  2005-10       Impact factor: 22.384

3.  Metabolites of Nectria coccinea.

Authors:  D C Aldridge; A Borrow; R G Foster; M S Large; H Spencer; W B Turner
Journal:  J Chem Soc Perkin 1       Date:  1972

4.  The ilicicolins, antibiotics from Cylindrocladium ilicicola.

Authors:  S Hayakawa; H Minato; K Katagiri
Journal:  J Antibiot (Tokyo)       Date:  1971-09       Impact factor: 2.649

5.  Ascochlorin inhibits matrix metalloproteinase-9 expression by suppressing activator protein-1-mediated gene expression through the ERK1/2 signaling pathway: inhibitory effects of ascochlorin on the invasion of renal carcinoma cells.

Authors:  Sahyun Hong; Kwan-Kyu Park; Junji Magae; Kunio Ando; Tae-Sung Lee; Taeg Kyu Kwon; Jong-Young Kwak; Cheorl-Ho Kim; Young-Chae Chang
Journal:  J Biol Chem       Date:  2005-04-29       Impact factor: 5.157

6.  Bioactive metabolites from the fungus Nectria galligena, the main apple canker agent in Chile.

Authors:  Margarita Gutiérrez; Cristina Theoduloz; Jaime Rodríguez; Mauricio Lolas; Guillermo Schmeda-Hirschmann
Journal:  J Agric Food Chem       Date:  2005-10-05       Impact factor: 5.279

7.  Antiviral and antitumor antibiotics. XIV. Effects of ascochlorin and other respiration inhibitors on multiplication of Newcastle disease virus in cultured cells.

Authors:  A Takatsuki; G Tamura; K Arima
Journal:  Appl Microbiol       Date:  1969-06

8.  Ascochlorin, a new antibiotic, found by the paper-disc agar-diffusion method. I. Isolation, biological and chemical properties of ascochlorin. (Studies on antiviral and antitumor antibiotics. I).

Authors:  G Tamura; S Suzuki; A Takatsuki; K Ando; K Arima
Journal:  J Antibiot (Tokyo)       Date:  1968-09       Impact factor: 2.649

9.  Ascochlorin activates p53 in a manner distinct from DNA damaging agents.

Authors:  Ji-Hak Jeong; Hiroo Nakajima; Junji Magae; Chiharu Furukawa; Keiko Taki; Kensuke Otsuka; Masanori Tomita; In-Seon Lee; Cheorl-Ho Kim; Hyeun-Wook Chang; Kwan-Sik Min; Kwang-Kyun Park; Kwan-Kyu Park; Young-Chae Chang
Journal:  Int J Cancer       Date:  2009-06-15       Impact factor: 7.396

10.  A novel ascochlorin glycoside from the insect pathogenic fungus Verticillium hemipterigenum BCC 2370.

Authors:  Prapairat Seephonkai; Masahiko Isaka; Prasat Kittakoop; Uraiwan Boonudomlap; Yodhathai Thebtaranonth
Journal:  J Antibiot (Tokyo)       Date:  2004-01       Impact factor: 2.649

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  1 in total

1.  Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum.

Authors:  Yasuko Araki; Takayoshi Awakawa; Motomichi Matsuzaki; Rihe Cho; Yudai Matsuda; Shotaro Hoshino; Yasutomo Shinohara; Masaichi Yamamoto; Yasutoshi Kido; Daniel Ken Inaoka; Kisaburo Nagamune; Kotaro Ito; Ikuro Abe; Kiyoshi Kita
Journal:  Proc Natl Acad Sci U S A       Date:  2019-04-05       Impact factor: 11.205

  1 in total

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