Two new diketopiperazine alkaloids, named protuboxepin C (1) and protuboxepin D (2), which contain D-Phe residue and oxepin ring, were isolated from EtOAc extract of sponge-derived fungus Aspergillus sp SCSIO XWS02F40. Their structures were elucidated by 1D, 2D NMR and HRESIMS dates, and their absolute configurations were confirmed by single crystal X-ray diffraction experiments and CD analyses. The in vitro cytotoxicity of these two new compounds was further evaluated using A549 and Hela cell lines.
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http://dx.doi.org/10.1080/14786419.2017.1423303 | DOI Listing |
Phytochemistry
October 2023
State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, School of Biotechnology, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China; Marine Biomedical Science and Technology Innovation Platform of Lin-gang Special Area, No.4, Lane 218, Haiji Sixth Road, Shanghai, 201306, China. Electronic address:
Four previously undescribed diketopiperazine-type alkaloids including one oxepin-containing diketopiperazine-type alkaloid, oxepinamide L (1), three 4-quinazolinone alkaloids, puniceloids E-G (10-12), together with 12 known analogues, protuboxepin D (2), oxepinamides D-G, J-K and I (3-9), puniceloids B-D (13-15) and protubonine B (16), were isolated from the culture of the marine-derived fungus Aspergillus puniceus FAHY0085. The structures of the previously undescribed compounds were comprehensively elucidated by detailed interpretation of their NMR and HRESIMS data. Their absolute configurations were unambiguously determined by ROESY experiments, Marfey's method, calculated ECD experiments and single-crystal X-ray diffraction analysis.
View Article and Find Full Text PDFPhytochemistry
January 2023
Yunnan Key Laboratory of Tobacco Chemistry, China Tobacco Yunnan Industrial Co., Ltd, Kunming, 650231, China; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming, 650031, China. Electronic address:
Nicotiana tabacum (tobacco) has attracted interest as one of the most economically important industrial crops widely cultivated in China, whose dried leaves are popularly consumed medicinally and recreationally by human societies. In this study, five undescribed alkaloids derivatives, isoaspergillines A-E, together with eight known alkaloids, notoamide D, (1R,4S)-4-benzyl-1-isopropyl-2,4-dihydro-1H-pyrazino-[2,1-b]quinazoline-3,6-dione, protuboxepin K, notoamide C, notoamide M, deoxybrevianamide E, cyclo (D-Pro-L-Trp), and versicolamide B, were obtained from the culture of the Nicotiana tabacum-derived fungus Aspergillus versicolor. Their structures were mainly elucidated through comprehensive analyses of spectroscopic data.
View Article and Find Full Text PDFJ Antibiot (Tokyo)
August 2020
Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
A new diketopiperazine-like compound, designated protuboxepin K (1), was isolated together with the known structurally related protuboxepin A (2) from culture broth of the marine-derived fungal strain Aspergillus sp. BFM-0085 isolated from a sediment sample of Tokyo Bay. The structure of protuboxepin K was elucidated by spectroscopic data, including 1D and 2D NMR.
View Article and Find Full Text PDFNat Prod Res
November 2018
b CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology , South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou , China.
Two new diketopiperazine alkaloids, named protuboxepin C (1) and protuboxepin D (2), which contain D-Phe residue and oxepin ring, were isolated from EtOAc extract of sponge-derived fungus Aspergillus sp SCSIO XWS02F40. Their structures were elucidated by 1D, 2D NMR and HRESIMS dates, and their absolute configurations were confirmed by single crystal X-ray diffraction experiments and CD analyses. The in vitro cytotoxicity of these two new compounds was further evaluated using A549 and Hela cell lines.
View Article and Find Full Text PDFNat Prod Res
October 2014
a BIO-MAR , Merowingerplatz 1a, D-40225 Düsseldorf , Germany.
Chemical investigation of the mycelial extract of a mixed culture of two marine alga-derived fungal strains of the genus Aspergillus has yielded one new cyclotripeptide, psychrophilin E (1), the recently reported oxepin-containing alkaloids, protuboxepin A (2) and oxepinamide E (3), together with three other polyketide derivatives (4-6). The chemical structure and relative and absolute configurations of psychrophilin E (1) were unambiguously established based on HRMS, 1D, 2D NMR and chiral-phase HPLC analysis of its hydrolysate. All the isolated compounds were assessed for their anti-proliferative activity against four different human cancer cell lines and some of them revealed selective activities.
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