TY - JOUR
T1 - Hatsusamides A and B
T2 - Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
AU - Matsuo, Hirotaka
AU - Hokari, Rei
AU - Ishiyama, Aki
AU - Iwatsuki, Masato
AU - Higo, Mayuka
AU - Nonaka, Kenichi
AU - Nagano, Yuriko
AU - Takahashi, Yōko
AU - Ōmura, Satoshi
AU - Nakashima, Takuji
N1 - Funding Information:
Funding: This study was supported by funds from the Institute for Fermentation, Osaka (IFO), Japan, a JSPS KAKENHI for Young Scientists (B) (grant nos. JP17K15250 and JP15K18601), and a Kitasato University Research Grant for Young Researchers awarded to Hirotaka, M.
Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2020/10
Y1 - 2020/10
N2 - Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicillium steckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by physicochemical (PC) screening. The structures of 1 and 2 were determined as a tanzawaic acid B-trichodermamide C hybrid structure and a new analog of aspergillazines, respectively. The absolute configuration of 1 was determined by comparing the values of tanzawaic acid B and trichodermamide C in the literatures, such as1 H-nuclear magnetic resonance (1 H-NMR) data and optical rotation, after hydrolysis of 1. Compounds 1–4 were evaluated for cytotoxicity and anti-malarial activities. Compounds 1 and 3 exhibited weak anti-malarial activity at half-maximal inhibitory concentration (IC50 ) values of 27.2 and 78.5 µM against the K1 strain, and 27.9 and 79.2 µM against the FCR3 strain of Plasmodium falciparum, respectively. Furthermore, 1 exhibited cytotoxicity against HeLa S3, A549, Panc1, HT29 and H1299 cells, with IC50 values of 15.0, 13.7, 12.9, 6.8, and 18.7 µM, respectively.
AB - Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicillium steckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by physicochemical (PC) screening. The structures of 1 and 2 were determined as a tanzawaic acid B-trichodermamide C hybrid structure and a new analog of aspergillazines, respectively. The absolute configuration of 1 was determined by comparing the values of tanzawaic acid B and trichodermamide C in the literatures, such as1 H-nuclear magnetic resonance (1 H-NMR) data and optical rotation, after hydrolysis of 1. Compounds 1–4 were evaluated for cytotoxicity and anti-malarial activities. Compounds 1 and 3 exhibited weak anti-malarial activity at half-maximal inhibitory concentration (IC50 ) values of 27.2 and 78.5 µM against the K1 strain, and 27.9 and 79.2 µM against the FCR3 strain of Plasmodium falciparum, respectively. Furthermore, 1 exhibited cytotoxicity against HeLa S3, A549, Panc1, HT29 and H1299 cells, with IC50 values of 15.0, 13.7, 12.9, 6.8, and 18.7 µM, respectively.
KW - anti-malarial activity
KW - anti-tumor activity
KW - deep-sea-derived fungus
KW - hatsusamides A and B
KW - tanzawaic acid B
KW - trichodermamide C
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U2 - 10.3390/MD18100513
DO - 10.3390/MD18100513
M3 - Article
C2 - 33053770
AN - SCOPUS:85092885873
SN - 1660-3397
VL - 18
JO - Marine Drugs
JF - Marine Drugs
IS - 10
M1 - 513
ER -