Penispirozines A-H, Three Classes of Dioxopiperazine Alkaloids with Spirocyclic Skeletons Isolated from the Mangrove-Derived Penicillium janthinellum.

Eight new dioxopiperazine alkaloids, penispirozines A-H (1-8), were discovered from the mangrove-derived fungus Penicillium janthinellum HDN13-309. Their structures were elucidated by spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Compound 1 had an unusual pyrazino[1,2]oxazadecaline coupled with a thiophane ring system, and compound 2 possessed a 6/5/6/5/6 pentacyclic ring system with two rare spirocyclic centers. Interestingly, compounds 3-8 were distinguished by not only the existence of a spiro-thiophane or spiro-furan ring system but also the chirality of the pentacyclic moiety. Compounds 3 and 4 increased the expression of the two relevant phase II detoxifying enzymes SOD2 and HO-1 at 10 μM.

[1]  Meilin Zhu,et al.  N-Me-trichodermamide B isolated from Penicillium janthinellum, with antioxidant properties through Nrf2-mediated signaling pathway. , 2017, Bioorganic & medicinal chemistry.

[2]  P. Proksch,et al.  Eutypellazines N−S, new thiodiketopiperazines from a deep sea sediment derived fungus Eutypella sp. with anti-VRE activities , 2017 .

[3]  Meilin Zhu,et al.  Penicisulfuranols A-F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309. , 2017, Journal of natural products.

[4]  O. Takahashi,et al.  Induced production of a new dipeptide with a disulfide bridge by long-term fermentation of marine-derived Trichoderma cf. brevicompactum , 2016 .

[5]  Xiao‐Ming Li,et al.  Three Diketopiperazine Alkaloids with Spirocyclic Skeletons and One Bisthiodiketopiperazine Derivative from the Mangrove-Derived Endophytic Fungus Penicillium brocae MA-231. , 2016, Organic letters.

[6]  Xiao‐Ming Li,et al.  Bisthiodiketopiperazines and Acorane Sesquiterpenes Produced by the Marine-Derived Fungus Penicillium adametzioides AS-53 on Different Culture Media. , 2015, Journal of natural products.

[7]  Xiao‐Ming Li,et al.  Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides , 2015, Marine drugs.

[8]  Ming Liu,et al.  Identification of epipolythiodioxopiperazines HDN-1 and chaetocin as novel inhibitor of heat shock protein 90 , 2015, Oncotarget.

[9]  Chenghai Gao,et al.  An Update on 2,5-Diketopiperazines from Marine Organisms , 2014, Marine drugs.

[10]  Kristina M. Cook,et al.  Epidithiodiketopiperazines (ETPs) exhibit in vitro antiangiogenic and in vivo antitumor activity by disrupting the HIF-1α/p300 complex in a preclinical model of prostate cancer , 2014, Molecular Cancer.

[11]  H. Yeh,et al.  Biosynthetic pathway for the epipolythiodioxopiperazine acetylaranotin in Aspergillus terreus revealed by genome-based deletion analysis. , 2013, Journal of the American Chemical Society.

[12]  A. D. Borthwick.  2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. , 2012, Chemical reviews.

[13]  J. Hyun,et al.  Antioxidant mechanism of isoflavone metabolites in hydrogen peroxide‐stimulated rat primary astrocytes: critical role of hemeoxygenase‐1 and NQO1 expression , 2011, Journal of neurochemistry.

[14]  H. Kwon,et al.  Apoptosis‐inducing effect of diketopiperazine disulfides produced by Aspergillus sp. KMD 901 isolated from marine sediment on HCT116 colon cancer cell lines , 2011, Journal of applied microbiology.

[15]  Yonghong Liu,et al.  Diketopiperazines from Marine Organisms , 2010, Chemistry & biodiversity.

[16]  K. Parkin,et al.  Limited contribution of isoflavones to hepatocellular phase II enzyme-inducing activity of soybean (Glycine max) extracts , 2009 .