TY - JOUR
T1 - Histone deacetylase inhibitor induced the production of three novel prenylated tryptophan analogs in the entomopathogenic fungus, Torrubiella luteorostrata
AU - Asai, Teigo
AU - Yamamoto, Takashi
AU - Oshima, Yoshiteru
N1 - Funding Information:
This work was supported in part by Grant-in-Aid for Scientific Research (No. 23710248 and 23590582) from the Ministry of Education, Science, Sports and Culture of Japan; A-STEP (FS-stage) (No. AS221Z01739G) from Japan Science and Technology Agency (JST); the Uehara Memorial Foundation; Japan Association for Chemical Innovation.
PY - 2011/12/28
Y1 - 2011/12/28
N2 - Suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, led to significant changes in the secondary metabolism of an entomopathogenic fungus, Torrubiella luteorostrata, and induced the production of three new prenylated tryptophan analogs, luteorides A-C (1-3). The structures are characterized by the presence of an (E)-oxime group, which is an unusual functional group in natural products, and a 3-methylbuta-1,3-dienyl unit as a common substituent. The method of culturing entomopathogenic fungi in the presence of HDAC inhibitors, such as SBHA, is convenient and attractive for obtaining novel secondary metabolites.
AB - Suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, led to significant changes in the secondary metabolism of an entomopathogenic fungus, Torrubiella luteorostrata, and induced the production of three new prenylated tryptophan analogs, luteorides A-C (1-3). The structures are characterized by the presence of an (E)-oxime group, which is an unusual functional group in natural products, and a 3-methylbuta-1,3-dienyl unit as a common substituent. The method of culturing entomopathogenic fungi in the presence of HDAC inhibitors, such as SBHA, is convenient and attractive for obtaining novel secondary metabolites.
KW - Entomopathogenic fungi
KW - Epigenetics
KW - Histone deacetylase inhibitor
KW - Secondary metabolites
KW - Tryptophan analogs
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U2 - 10.1016/j.tetlet.2011.10.020
DO - 10.1016/j.tetlet.2011.10.020
M3 - Article
AN - SCOPUS:82255191327
SN - 0040-4039
VL - 52
SP - 7042
EP - 7045
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 52
ER -