Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Sep 20

PMID 30227613

Citations 17

Authors

Zhao-Xia Li

Xiu-Fang Wang

Guang-Wei Ren

Xiao-Long Yuan

Ning Deng

Gui-Xia Ji

Wei Li

Peng Zhang

Affiliations

Soon will be listed here.

Abstract

Considerable attention has been paid to marine derived endophytic fungi, owing to their capacity to produce novel secondary metabolites with potent bioactivities. In this study, two new compounds with a prenylated diphenyl ether structure-diorcinol L () and ()-diorcinol B ()-were isolated from the marine algal-derived endophytic fungus , along with seven known compounds: ()-diorcinol B (), 9-acetyldiorcinol B (), diorcinol C (), diorcinol D (), diorcinol E (), diorcinol J (), and a dihydrobenzofuran derivative . Their structures were elucidated by extensive NMR spectroscopy studies. Compound represents the first example of an -configuration in the prenylated moiety. All these isolated compounds were examined for antimicrobial and cytotoxic activities. Compounds ⁻ exhibited antimicrobial activities against some human- and plant-pathogenic microbes with MIC values ranging from 2 to 64 μg/mL. Moreover, compound displayed considerable inhibitory activity against the THP-1 cell line in vitro, with an IC value of 7.0 μg/mL.

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References

Wang S, Li X, Teuscher F, Li D, Diesel A, Ebel R . Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J Nat Prod. 2006; 69(11):1622-5. DOI: 10.1021/np060248n. View

Bunyapaiboonsri T, Yoiprommarat S, Intereya K, Kocharin K . New diphenyl ethers from the insect pathogenic fungus Cordyceps sp. BCC 1861. Chem Pharm Bull (Tokyo). 2007; 55(2):304-7. DOI: 10.1248/cpb.55.304. View

Zhao D, Shao C, Wang C, Wang M, Yang L, Wang C . Naphthalenones and Depsidones from a Sponge-Derived Strain of the Fungus Corynespora cassiicola. Molecules. 2016; 21(2):160. PMC: 6273126. DOI: 10.3390/molecules21020160. View

Zhang Y, Li X, Shang Z, Li C, Ji N, Wang B . Meroterpenoid and diphenyl ether derivatives from Penicillium sp. MA-37, a fungus isolated from marine mangrove rhizospheric soil. J Nat Prod. 2012; 75(11):1888-95. DOI: 10.1021/np300377b. View

Blunt J, Carroll A, Copp B, Davis R, Keyzers R, Prinsep M . Marine natural products. Nat Prod Rep. 2018; 35(1):8-53. DOI: 10.1039/c7np00052a. View

Xu X, Yang H, Xu H, Yin L, Chen Z, Shen H . Diphenyl ethers from a marine-derived isolate of Aspergillus sp. CUGB-F046. Nat Prod Res. 2017; 32(7):821-825. DOI: 10.1080/14786419.2017.1363754. View

Al-Burtamani S, Fatope M, Marwah R, Onifade A, Al-Saidi S . Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J Ethnopharmacol. 2004; 96(1-2):107-12. DOI: 10.1016/j.jep.2004.08.039. View

Yang G, Yun K, Nenkep V, Choi H, Kang J, Son B . Induced production of halogenated diphenyl ethers from the marine-derived fungus Penicillium chrysogenum. Chem Biodivers. 2010; 7(11):2766-70. DOI: 10.1002/cbdv.201000067. View

Gao H, Zhou L, Cai S, Zhang G, Zhu T, Gu Q . Diorcinols B-E, new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60. J Antibiot (Tokyo). 2013; 66(9):539-42. DOI: 10.1038/ja.2013.40. View

10.

Fu X, Schmitz F, Govindan M, Abbas S, Hanson K, Horton P . Enzyme inhibitors: new and known polybrominated phenols and diphenyl ethers from four Indo-Pacific Dysidea sponges. J Nat Prod. 1995; 58(9):1384-91. DOI: 10.1021/np50123a008. View

11.

Yuan X, Zhang P, Liu X, Du Y, Hou X, Cheng S . Cytological Assessments and Transcriptome Profiling Demonstrate that Evodiamine Inhibits Growth and Induces Apoptosis in a Renal Carcinoma Cell Line. Sci Rep. 2017; 7(1):12572. PMC: 5626725. DOI: 10.1038/s41598-017-12918-y. View

12.

Jang J, Kanoh K, Adachi K, Shizuri Y . New dihydrobenzofuran derivative, awajanoran, from marine-derived Acremonium sp. AWA16-1. J Antibiot (Tokyo). 2006; 59(7):428-31. DOI: 10.1038/ja.2006.60. View

13.

Zhuravleva O, Afiyatullov S, Yurchenko E, Denisenko V, Kirichuk N, Dmitrenok P . New metabolites from the algal associated marine-derived fungus Aspergillus carneus. Nat Prod Commun. 2013; 8(8):1071-4. View

14.

Zhao H, Wang G, Tong X, Chen G, Huang Y, Cui J . Diphenyl ethers from Aspergillus sp. and their anti-Aβ₄₂ aggregation activities. Fitoterapia. 2014; 98:77-83. DOI: 10.1016/j.fitote.2014.07.007. View

15.

Imhoff J . Natural Products from Marine Fungi--Still an Underrepresented Resource. Mar Drugs. 2016; 14(1):19. PMC: 4728516. DOI: 10.3390/md14010019. View