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Open AccessArticle

Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus Penicillium chrysogenum LD-201810

by Lin-Lin Jiang 1,2,3,†, Jin-Xiu Tang 1,†, Yong-Heng Bo 2, You-Zhi Li 2, Tao Feng 2, Hong-Wei Zhu 1,2,3, Xin Yu 1,2,3, Xing-Xiao Zhang 1,3,*, Jian-Long Zhang 1,2,3,* and Weiyi Wang 4,*
1
School of Life Sciences, Ludong University, Yantai 264025, China
2
Shandong Provincial Key Laboratory of Quality Safty Monitoring and Risk Assessment for Animal Products, Ji’nan 250022, China
3
Yantai Key Laboratory of Animal Pathogenetic Microbiology and Immunology, Yantai 264025, China
4
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Mar. Drugs 2020, 18(5), 276; https://doi.org/10.3390/md18050276
Received: 6 May 2020 / Revised: 20 May 2020 / Accepted: 20 May 2020 / Published: 22 May 2020
(This article belongs to the Special Issue Marine Natural Products as Anticancer Agents)
A new pentaketide derivative, penilactonol A (1), and two new hydroxyphenylacetic acid derivatives, (2’R)-stachyline B (2) and (2’R)-westerdijkin A (3), together with five known metabolites, bisabolane-type sesquiterpenoids 46 and meroterpenoids 7 and 8, were isolated from the solid culture of a marine alga-associated fungus Penicillium chrysogenum LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in 1 were determined by the (Mo2(OAc)4)-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in 2 was established using single-crystal X-ray diffraction analysis. Compounds 2 and 3 adapt the 2’R-configuration as compared to known hydroxyphenylacetic acid-derived and O-prenylated natural products. The cytotoxicity of 18 against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound 3 exhibited cytotoxicity to the HepG2 cell line with an IC50 value of 22.0 μM. Furthermore, 5 showed considerable activities against A549 and THP-1 cell lines with IC50 values of 21.2 and 18.2 μM, respectively. View Full-Text
Keywords: alga; marine-derived fungus; Penicillium chrysogenum; polyketide; hydroxyphenylacetic acid; cytotoxicity alga; marine-derived fungus; Penicillium chrysogenum; polyketide; hydroxyphenylacetic acid; cytotoxicity
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MDPI and ACS Style

Jiang, L.-L.; Tang, J.-X.; Bo, Y.-H.; Li, Y.-Z.; Feng, T.; Zhu, H.-W.; Yu, X.; Zhang, X.-X.; Zhang, J.-L.; Wang, W. Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus Penicillium chrysogenum LD-201810. Mar. Drugs 2020, 18, 276.

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