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Recent studies on terpenoids in Aspergillus fungi: Chemical diversity, biosynthesis, and bioactivity
- 1. * & ** & Dalian Key Laboratory of Metabolic Target Characterization and Traditional Chinese Medicine Intervention, College of Pharmacy, College (Institute) of Integrative Medicine, Dalian Medical University, Dalian, China
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Zhao, Wen-Yu, Yi, Jing, Chang, Yi-Bo, Sun, Cheng-Peng, Ma, Xiao-Chi (2022): Recent studies on terpenoids in Aspergillus fungi: Chemical diversity, biosynthesis, and bioactivity. Phytochemistry (113011) 193: 1-25, DOI: 10.1016/j.phytochem.2021.113011, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113011
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References
- Afiyatullov, S.S., Zhuravleva, O.I., Antonov, A.S., Kalinovsky, A.I., Aminin, D.L., 2012. New metabolites from the marine-derived fungus Aspergillus fumigatus. Nat. Prod. Commun. 7, 497-500. https://doi.org/10.1177/1934578X1200700421.
- An, C.L., Kong, F.D., Li, Y., Ma, Q.Y., Zhao, Y.X., 2020. Asperpenes D and E from the fungus Aspergillus sp. SCS-KFD66 isolated from a bivalve mollusk, Sanguinolaria chinensis. J. Asian Nat. Prod. Res. 23, 117-122. https://doi.org/10.1080/ 10286020.2019.1709450.
- Bai, Z.Q., Lin, X.P., Wang, J.F., Zhou, X.F., Liu, J., Yang, B., Yang, X.W., Liao, S.R., Wang, L.S., Liu, Y.H., 2015. New meroterpenoids from the endophytic fungus Aspergillus flavipes AIL8 derived from the mangrove plant Acanthus ilicifolius. Mar. Drugs 13, 237-248. https://doi.org/10.3390/md13010237.
- Boruta, T., Bizukojc, M., 2017. Production of lovastatin and itaconic acid by Aspergillus terreus: a comparative perspective. World J. Microbiol. Biotechnol. 33, 34. https:// doi.org/10.1007/s11274-017-2206-9.
- Cai, R.L., Jiang, H.M., Mo, Y.L., Guo, H.X., She, Z.G., 2019. Ophiobolin-type sesterterpenoids from the mangrove endophytic fungus Aspergillus sp. ZJ-68. J. Nat. Prod. 82, 2268-2278. https://doi.org/10.1021/acs.jnatprod.9b00462.
- Chai, H., Yin, R., Liu, Y., Meng, H., Zhou, X., Zhou, G., Bi, X., Yang, X., Zhu, T., Zhu, W., 2016. Sesterterpene ophiobolin biosynthesis involving multiple gene clusters in Aspergillus ustus. Sci. Rep. 6, 27181. https://doi.org/10.1038/srep27181.
- Chen, L.F., Fu, W.T., Zheng, L.L., Wang, Y., Liang, G., 2018. Recent progress in the discovery of myeloid differentiation 2 (MD2) modulators for inflammatory diseases. Drug Discov. Today 23, 1187-1202. https://doi.org/10.1016/j.drudis.2018.01.015.
- Chiba, R., Minami, A., Gomi, K., Oikawa, H., 2013. Identification of ophiobolin F synthase by a genome mining approach: a sesterterpene synthase from Aspergillus clavatus. Org. Lett. 15, 594-597. https://doi.org/10.1021/ol303408a.
- Choi, B.K., Trinh, P.T.H., Lee, H.S., Choi, B.W., Shin, H.J., 2019. New ophiobolin derivatives from the marine fungus Aspergillus flocculosus and their cytotoxicities against cancer cells. Mar. Drugs 17, 346. https://doi.org/10.3390/md17060346.
- Chung, Y.M., Wei, C.K., Chuang, D.W., El-Shazly, M., Hsieh, C.T., Asai, T., Oshima, Y., Hsieh, T.J., Hwang, T.L., Wu, Y.C., 2013. An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii. Bioorg. Med. Chem. 21, 3866-3872. https://doi.org/10.1016/j. bmc.2013.04.004.
- Cohen, E., Koch, L., Thu, K.M., Rahamim, Y., Aluma, Y., Ilan, M., Yarden, O., Carmeli, S., 2011. Novel terpenoids of the fungus Aspergillus insuetus isolated from the Mediterranean sponge Psammocinia sp. collected along the coast of Israel. Bioorg. Med. Chem. 19, 6587-6593. https://doi.org/10.1016/j.bmc.2011.05.045.
- Cueto, M., Jensen, P.R., Fenical, W., 2002. Aspergilloxide, a novel sesterterpene epoxide from a marine-derived fungus of the genus Aspergillus. Org. Lett. 4, 1583-1585. https://doi.org/10.1021/ol0258076.
- Davies, F.K., Work, V.H., Beliaev, A.S., Posewitz, M.C., 2014. Engineering limonene and bisabolene production in eild type and a glycogen-deficient mutant of Synechococcus sp. PCC 7002. Front. Bioeng. Biotechnol. 19, 21. https://doi.org/10.3389/ fbioe.2014.00021.
- Deng, C., Huang, C., Wu, Q., Pang, J., Lin, Y., 2013. A new sesquiterpene from the mangrove endophytic fungus Aspergillus terreus (No. GX7-3B). Nat. Prod. Res. 27, 1882-1887. https://doi.org/10.1080/14786419.2013.778847.
- Dickschat, J.S., Brock, N.L., Citron, C.A., Tudzynski, B., 2011. Biosynthesis of sesquiterpenes by the fungus Fusarium verticillioides. Chembiochem 12, 2088-2095. https://doi.org/10.1002/cbic.201100268.
- Ding, C.H., Wu, X.D., Auckloo, B.N., Chen, C.T.A., Wu, B., 2016. An unusual stress metabolite from a hydrothermal vent fungus Aspergillus sp. Wu 243 induced by cobalt. Molecules 21, 105. https://doi.org/10.3390/molecules21010105.
- Ebrahim, W., El-Neketi, M., Lewald, L.I., Orfali, R.S., Lin, W.H., Rehberg, N., Kalscheuer, R., Daletos, G., Proksch, P., 2017. Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal-bacterial mixed cultures. J. Nat. Prod. 79, 914-922. https://doi.org/10.1021/acs.jnatprod.5b00975.
- Edwards, M., 2009. Penicillin: triumph and tragedy. Ann. Sci. 66, 295-297. https://doi. org/10.1080/00033790701832260.
- Elena, I., Anton, Y., Olga, S., Anton, R., Olesya, Z., Mikhail, P., Roman, P., Gunhild, V.A., Shamil, A., Sergey, D., 2018. Asperindoles A-D and a p-terphenyl derivative from the ascidian-derived fungus Aspergillus sp. KMM 4676. Mar. Drugs 16, 232. https://doi. org/10.3390/md16070232.
- Elsbaey, M., Sallam, A., El-Metwally, M., Nagata, M., Tanaka, C., Shimizu, K., Miyamoto, T., 2019a. Melanogenesis inhibitors from the endophytic fungus Aspergillus amstelodami. Chem. Biodivers. 16, 1900237. https://doi.org/10.1002/ cbdv.201900237.
- Elsbaey, M., Tanaka, C., Miyamoto, T., 2019b. New secondary metabolites from the mangrove endophytic fungus Aspergillus versicolor. Phytochem. Lett. 32, 70-76. https://doi.org/10.1016/j.phytol.2019.04.023.
- Fang, W., Lin, X.P., Zhou, X.F., Wan, J.T., Lu, X., Yang, B., Ai, W., Lin, J., Zhang, T.Y., Tu, Z.C., 2014. Cytotoxic and antiviral nitrobenzoyl sesquiterpenoids from the marine-derived fungus Aspergillus ochraceus Jcma1F17. MedChemComm 5, 701. https://doi.org/10.1039/C3MD00371J.
- Felix, S., Sandjo, L.P., Opatz, T., Erkel, G., 2013. SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression. Beilstein J. Org. Chem. 9, 2866-2876. https://doi.org/10.3762/bjoc.9.323.
- Felix, S., Sandjo, L.P., Opatz, T., Erkel, G., 2014. Anti-inflammatory drimane sesquiterpene lactones from an Aspergillus species. Bioorg. Med. Chem. 22, 2912-2918. https://doi.org/10.1016/j.bmc.2014.04.015.
- Gao, Y.Q., Guo, C.J., Zhang, Q., Zhou, W.M., Wang, C.C., Gao, J.M., 2014. Asperaculanes A and B, two sesquiterpenoids from the fungus Aspergillus aculeatus. Molecules 20, 325-334. https://doi.org/10.3390/molecules20010325.
- Guo, C.J., Knox, B.P., Chiang, Y.M., Lo, H.C., Wang, C.C.C., 2012. Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin. Org. Lett. 14, 5684-5687. https://doi.org/10.1021/ol302682z.
- Guo, Z.K., Wang, R., Huang, W., Li, X.N., Jiang, R., Tan, R.X., Ge, H.M., 2014. Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3. Beilstein J. Org. Chem. 10, 2677-2682. https://doi.org/10.3762/bjoc.10.282.
- Han, J.J., Lu, F.M., Bao, L., Wang, H.Y., Chen, B.S., Li, E.W., Wang, Z.D., Xie, L.P., Guo, C.B., Xue, Y.F., 2020. Terphenyl derivatives and terpenoids from a wheat-born mold Aspergillus candidus. J. Antibiot. 73, 189-193. https://doi.org/10.1038/ s41429-019-0266-9.
- Harmer, C.J., Duman, R.S., Cowen, P.J., 2017. How do antidepressants work? New perspectives for refining future treatment approaches. Lancet. Psychiatr. 4, 409-418. https://doi.org/10.1016/s2215-0366(17)30015-9.
- He, F., Sun, Y.L., Liu, K.S., Zhang, X.Y., Qian, P.Y., Wang, Y.F., Qi, S.H., 2012. Indole alkaloids from marine-derived fungus Aspergillus sydowii SCSIO 00305. J. Antibiot. 65, 109-111. https://doi.org/10.1038/ja.2011.117.
- He, Y., Wang, B., Chen, W., Cox, R.J., He, J., Chen, F., 2018. Recent advances in reconstructing microbial secondary metabolites biosynthesis in Aspergillus sp. Biotechnol. Adv. 36, 739-783. https://doi.org/10.1016/j.biotechadv.2018.02.001.
- Hu, X., Li, X., Meng, L., Wang, B., 2020. Antioxidant bisabolane-type sesquiterpenoids from algal-derived fungus Aspergillus sydowii EN-434. J. Oceanol. Limnol. 38, 1-5. https://doi.org/10.1007/s00343-020-0049-y.
- Huang, X.S., Huang, H.B., Li, H.X., Sun, X.F., She, Z.G., 2013. Asperterpenoid A, a new sesterterpenoid as an inhibitor of mycobacterium tuberculosis protein tyrosine phosphatase B from the culture of Aspergillus sp. 16-5c. Org. Lett. 15, 721-723. https://doi.org/10.1021/ol303549c.
- Itoh, T., Tokunaga, K., Matsuda, Y., Fujii, I., Abe, I., Ebizuka, Y., Kushiro, T., 2010. Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases. Nat. Chem. 2, 858-864. https://doi.org/10.1038/ nchem.764.
- Kato, H., Sebe, M., Nagaki, M., Eguchi, K., Kagiyama, I., 2019. Taichunins A-D, norditerpenes from Aspergillus taichungensis (IBT 19404). J. Nat. Prod. 82, 1377-1381. https://doi.org/10.1021/acs.jnatprod.8b01032.
- King, A.M., Reid-Yu, S.A., Wang, W., King, D.T., Pascale, G.D., Strynadka, N.C., Walsh, T. R., Coombes, B.K., Wright, G.D., 2014. Aspergillomarasmine A overcomes metalloβ -lactamase antibiotic resistance. Nature 510, 503-506. https://doi.org/10.1038/ nature13445.
- Kishi, T., Meltzer, H.Y., Matsuda, Y., Iwata, N., 2014. Azapirone 5-HT1A receptor partial agonist treatment for major depressive disorder: systematic review and metaanalysis. Psychol. Med. 44, 2255-2269. https://doi.org/10.1017/ s0033291713002857.
- Kong, F.D., Huang, X.L., Ma, Q.Y., Xie, Q.Y., Wang, P., 2018. Helvolic acid derivatives with antibacterial activities against Streptococcus agalactiae from the marine-derived fungus Aspergillus fumigatus HNMF0047. J. Nat. Prod. 81, 1869-1876. https://doi. org/10.1021/acs.jnatprod.8b00382.
- Kwon, J., Seo, Y.H., Lee, J.E., Seo, E.K., Lee, D., 2015. Spiroindole alkaloids and spiroditerpenoids from Aspergillus duricaulis and their potential neuroprotective effects. J. Nat. Prod. 78, 2572-2579. https://doi.org/10.1021/acs. jnatprod.5b00508.
- Lane, R.M., Kivipelto, M., Greig, N.H., 2004. Acetylcholinesterase and its inhibition in Alzheimer disease. Clin. Neuropharmacol. 27, 141-149. https://doi.org/10.1097/ 00002826-200405000-00011.
- Li, D., Xu, Y., Shao, C.L., Yang, R.Y., Zheng, C.J., 2012. Antibacterial bisabolane-type sesquiterpenoids from the Sponge-derived fungus Aspergillus sp. Mar. Drugs 10, 234-241. https://doi.org/10.3390/md10010234.
- Li, H.L., Li, X.M., Li, X., Yang, S.Q., Wang, B.G., 2019a. Structure, absolute configuration and biological evaluation of polyoxygenated meroterpenoids from the marine algal-derived Aspergillus terreus EN-539. Phytochem. Lett. 32, 138-142. https://doi.org/ 10.1016/j.phytol.2019.05.017.
- Li, X.B., Zhou, Y.H., Zhu, R.X., Chang, W.Q., Lou, H.X., 2015. Identification and biological evaluation of secondary metabolites from the endolichenic fungus Aspergillus versicolor. Chem. Biodivers. 12, 575-592. https://doi.org/10.1002/ cbdv.201400146.
- Li, X.D., Li, X., Li, X.M., Xu, G.M., Liu, Y., Wang, B.G., 2018. 20-Nor-isopimarane epimers produced by Aspergillus wentii SD-310, a fungal strain obtained from deep sea sediment. Mar. Drugs 16, 440. https://doi.org/10.3390/md16110440.
- Li, X.D., Li, X.M., Li, X., Xu, G.M., Liu, Y., Wang, B.C., 2016. Aspewentins D-H, 20-nor-isopimarane derivatives from the deep sea sediment-derived fungus Aspergillus wentii SD-310. J. Nat. Prod. 79, 1347-1353. https://doi.org/10.1021/acs. jnatprod.5b01153.
- Li, X.D., Li, X.M., Yin, X.L., Li, X., Wang, B.G., 2019b. Antimicrobial sesquiterpenoid derivatives and monoterpenoids from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. Mar. Drugs 17, 563. https://doi.org/10.3390/ md17100563.
- Li, Y.L., Gao, Y., Liu, C.Y., Sun, C.J., Zhao, Z.T., Lou, H.X., 2019c. Asperunguisins A-F, cytotoxic asperane sesterterpenoids from the endolichenic fungus Aspergillus unguis. J. Nat. Prod. 82, 1527-1534. https://doi.org/10.1021/acs.jnatprod.8b01066.
- Li, Y.L., Liu, W., Xu, W., Zeng, X., Cheng, Z.B., Li, Q., 2019d. Aspterrics A and B, new sesquiterpenes from deep sea-derived fungus Aspergillus terreus YPGA10. Record Nat. Prod. 14, 18-22. https://doi.org/10.25135/rnp.131.19.04.1247.
- Liaw, C.C., Yang, Y.L., Lin, C.K., Lee, J.C., Liao, W.Y., 2015. New meroterpenoids from Aspergillus terreus with inhibition of cyclooxygenase-2 expression. Org. Lett. 17, 2330-2333. https://doi.org/10.1021/acs.orglett.5b00739.
- Limbadri, S., Luo, X.W., Lin, X.P., Liao, S.R., Wang, J.F., Zhou, X.F., Yang, B., Liu, Y.H., 2018. Bioactive novel indole alkaloids and steroids from deep sea-derived fungus Aspergillus fumigatus SCSIO 41012. Molecules 23, 2379. https://doi.org/10.3390/ molecules23092379.
- Liu, C., Minami, A., Dairi, T., Gomi, K., Scott, B., Oikawa, H., 2016a. Biosynthesis of shearinine: diversification of a tandem prenyl moiety of fungal indole diterpenes. Org. Lett. 18, 5026-5029. https://doi.org/10.1021/acs.orglett.6b02482.
- Liu, D.S., Huang, Y.L., Li, C.M., Ma, L.Y., Pan, X.H., Ferreira, D., Liu, W.Z., 2016b. A new sesquiterpenoid derivative from the coastal saline soil fungus Aspergillus fumigatus. Record Nat. Prod. 10, 708-713.
- Liu, H.B., Edrada-Ebel, R.A., Ebel, R., Yao, E., Schulz, B., Draeger, S., Muller, W.E.G., Wray, V., Lin, W.H., Proksch, P., 2011. Ophiobolin sesterterpenoids and pyrrolidine alkaloids from the sponge-derived fungus Aspergillus ustus. Helv. Chim. Acta 94, 623-631. https://doi.org/10.1002/hlca.201000283.
- Liu, N.Z., Peng, S., Yang, J., Cong, Z.W., Lin, X.P., 2019a. Structurally diverse sesquiterpenoids and polyketides from a sponge-associated fungus Aspergillus sydowii SCSIO41301. Fitoterapia 135, 27-32. https://doi.org/10.1016/j.fitote.2019.03.031.
- Liu, S., Dai, H.F., Konuklugil, B., Orfali, R.S., Lin, W.H., Kalscheuer, R., Liu, Z., Proksch, P., 2016c. Phenolic bisabolanes from the sponge-derived fungus Aspergillus sp. Phytochem. Lett. 18, 187-191. https://doi.org/10.1016/j.phytol.2016.10.015.
- Liu, S., Wang, H.B., Su, M.B., Hwang, G.J., Jung, J.H., 2017a. New metabolites from the sponge-derived fungus Aspergillus sydowii J05B-7F-4. Nat. Prod. Res. 31, 1-5. https://doi.org/10.1080/14786419.2017.1289205.
- Liu, X.H., Miao, F.P., Li, X.D., Yin, X.L., Ji, N.Y., 2012. A new sesquiterpene from an endophytic Aspergillus versicolor strain. Nat. Prod. Commun. 7, 819-820. https://doi. org/10.1177/1934578X1200700702.
- Liu, X.H., Miao, F.P., Qiao, M.F., Cichewicz, R.H., Ji, N.Y., 2013. Terretonin, ophiobolin, and drimane terpenes with absolute configurations from an algicolous Aspergillus ustus. RSC Adv. 3, 588-595. https://doi.org/10.1039/C2RA22701K.
- Liu, Y., Jing, S.-X., Luo, S.-H., Li, S.-H., 2019b. Non-volatile natural products in plant glandular trichomes: chemistry, biological activities and biosynthesis. Nat. Prod. Rep. 36, 626-665. https://doi.org/10.1039/C8NP00077H.
- Liu, Z., Zhao, J.Y., Sun, S.F., Li, Y., Qu, J., 2019c. Sesquiterpenes from an endophytic Aspergillus flavus. J. Nat. Prod. 82, 1063-1071. https://doi.org/10.1021/acs. jnatprod.8b01084.
- Liu, Z.M., Chen, Y., Chen, S.H., Liu, Y.Y., She, Z.G., 2016d. Aspterpenacids A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010. Org. Lett. 18, 1406. https://doi.org/10.1021/acs.orglett.6b00336.
- Liu, Z.M., Liu, H.J., Chen, Y., She, Z.G., 2018. A new anti-inflammatory meroterpenoid from the fungus Aspergillus terreus H010. Nat. Prod. Res. 32, 2652-2656.
- Long, Y.H., Hui, C., Liu, X.L., Xiao, Z.E., Wen, S.T., She, Z.G., Huang, X.H., 2017. Acetylcholinesterase inhibitory meroterpenoid from a mangrove endophytic fungus Aspergillus sp. 16-5c. Molecules 22, 727. https://doi.org/10.3390/ molecules22050727.
- Luo, S.L., Li, G.H., Liu, F.F., Lei, L.P., Zhang, K.Q., 2011. A new sesquiterpene from endophytic fungus Aspergillus sp. Nat. Prod. Res. 26, 1334-1338. https://doi.org/ 10.1080/14786419.2011.583242.
- Marc, K., 2017. Viral infection and apoptosis. Viruses 9, 356. https://doi.org/10.3390/ v9120356.
- Matsuda, Y., Abe, I., 2016. Biosynthesis of fungal meroterpenoids. Nat. Prod. Rep. 33, 26-53. https://doi.org/10.1039/C5NP00090D.
- Matsuda, Y., Awakawa, T., Wakimoto, T., Abe, I., 2013. Spiro-ring frmation is catalyzed by a multifunctional dioxygenase in austinol biosynthesis. J. Am. Chem. Soc. 135, 10962-10965. https://doi.org/10.1021/ja405518u.
- Matsuda, Y., Iwabuchi, T., Fujimoto, T., Awakawa, T., Yu, N., Mori, T., Zhang, H.P., Hayashi, F., Abe, I., 2016. Discovery of key dioxygenases that diverged the paraherquonin and acetoxydehydroaustin pathways in Penicillium brasilianum. J. Am. Chem. Soc. 138, 12671-12677. https://doi.org/10.1021/jacs.6b08424.
- Meghan, N.J., 2017. The whole price of vancomycin: toxicities, troughs, and time. Drugs 77, 1143-1154. https://doi.org/10.1007/s40265-017-0764-7.
- Miao, F.P., Liang, X.R., Liu, X.H., Ji, N.Y., 2014. Aspewentins A-C, norditerpenes from a cryptic pathway in an algicolous strain of Aspergillus wentii. J. Nat. Prod. 77, 429-432. https://doi.org/10.1021/np401047w.
- Nasr, S.H., Radhakrishnan, J., D' agati, V.D., 2013. Bacterial infection-related glomerulonephritis in adults. Kidney Int. 83, 792-803. https://doi.org/10.1038/ ki.2012.407.
- Newman, D.J., Cragg, G.M., 2020. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J. Nat. Prod. 83, 770-803. https:// doi.org/10.1021/acs.jnatprod.9b01285.
- Nicolatalesa, V., 2001. Acetylcholinesterase in Alzheimer' s disease. Mech. Ageing Dev. 122, 1961-1969. https://doi.org/10.1016/S0047-6374(01)00309-8.
- Nong, X.H., Wang, Y.F., Zhang, X.Y., Zhou, M.P., Xu, X.Y., Qi, S.H., 2014. Territrem and butyrolactone derivatives from a marine-derived fungus Aspergillus Terreus. Mar. Drugs 12, 6113-6124. https://doi.org/10.3390/md12126113.
- Ogata, M., Ueda, J.Y., Hoshi, M., Hashimoto, J., Nakashima, T., 2007. A novel indole-diterpenoid, JBIR-03 with anti-MRSA activity from Dichotomomyces cejpii var. cejpii NBRC 103559. J. Antibiot. https://doi.org/10.1038/ja.2007.83.
- Oleinikova, G.K., Denisenko, V.A., Berdyshev, D.V., Pushilin, M.A., Kirichuk, N.N., Menzorova, N.I., Kuzmich, A.S., Yurchenko, E.A., Zhuravleva, O.I., Afiyatullov, S.S., 2016. Two new sesterterpenoids, terretonins H and I, from the marine-derived fungus Aspergillus ustus. Phytochem. Lett. 17, 135-139. https://doi.org/10.1016/j. phytol.2016.07.002.
- Pang, X.Y., Lin, X.P., Zhou, X.F., Yang, B., Tian, X.P., Wang, J.F., Xu, S.H., Liu, Y.H., 2020. New quinoline alkaloid and bisabolane-type sesquiterpenoid derivatives from the deep-sea-derived fungus Aspergillus sp. SCSIO06786. Fitoterapia 140, 104406. https://doi.org/10.1016/j.fitote.2019.104406.
- Panpetch, W., Hiengrach, P., Nilgate, S., Tumwasorn, S., Somboonna, N., Wilantho, A., Chatthanathon, P., Prueksapanich, P., Leelahavanichkul, A., 2020. Additional Candida albicans administration enhances the severity of dextran sulfate solution induced colitis mouse model through leaky gut-enhanced systemic inflammation and gut-dysbiosis but attenuated by Lactobacillus rhamnosus L34. Gut Microb. 11, 465-480. https://doi.org/10.1080/19490976.2019.1662712.
- Patrick, K.L., Bell, S.L., Weindel, C.G., Watson, R.O., 2019. Exploring the "Multiple-Hit Hypothesis" of neurodegenerative disease: bacterial infection comes up to bat. Front. Cell Infect. Microbiol. 9, 138. https://doi.org/10.3389/fcimb.2019.00138.
- Peng, J., Zhang, X., Wang, W., Zhu, T., Gu, Q., Li, D., 2016. Austalides S-U, new meroterpenoids from the sponge-derived fungus Aspergillus aureolatus HDN14-107. Mar. Drugs 14, 131. https://doi.org/10.3390/md14070131.
- Petersen, L.M., Frisvad, J.C., Knudsen, P.B., Rohlfs, M., Gotfredsen, C.H., Larsen, T.O., 2015. Induced sclerotium formation exposes new bioactive metabolites from Aspergillus sclerotiicarbonarius. J. Antibiot. 68, 603-608. https://doi.org/10.1038/ ja.2015.40.
- Petersen, L.M., Holm, D.K., Knudsen, P.B., Nielsen, K.F., Gotfredsen, C.H., Mortensen, U. H., Larsen, T.O., 2014. Characterization of four new antifungal yanuthones from Aspergillus niger. J. Antibiot. 68, 201-205. https://doi.org/10.1038/ja.2014.130.
- Prompanya, C., Dethoup, T., Bessa, L.J., Pinto, M., Gales, L., Costa, P.M.D., Silva, A.M.S., Kijjoa, A., 2014. New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013. Mar. Drugs 12, 5160-5173. https://doi.org/10.3390/md12105160.
- Qi, C.X., Zhou, Q., Gao, W.X., Liu, M.T., Zhang, Y.H., 2019. Anti-BACE1 and anti-AchE activities of undescribed spiro-dioxolane-containing meroterpenoids from the endophytic fungus Aspergillus terreus Thom. Phytochemistry 165, 112041. https:// doi.org/10.1016/j.phytochem.2019.05.014.
- Qiao, M.F., Ji, N.Y., Liu, X.H., Li, K., Zhu, Q.M., Xue, Q.Z., 2010. Indoloditerpenes from an algicolous isolate of Aspergillus oryzae. Bioorg. Med. Chem. Lett 20, 5677-5680. https://doi.org/10.1016/j.bmcl.2010.08.024.
- Qiao, Y.B., Zhang, X.T., He, Y., Sun, W.G., Feng, W.Y., Liu, J.J., Hu, Z.X., Xu, Q.Q., Zhu, H.C., Zhang, J.W., 2018. Aspermerodione, a novel fungal metabolite with an unusual 2,6-dioxabicyclo[2.2.1]heptane skeleton, as an inhibitor of penicillin-binding protein 2a. Sci. Rep. 8, 5454. https://doi.org/10.1038/s41598-018-23817- 1.
- Qiu, R.M., Luo, G.S., Cai, X.R., Liu, L.Y., Chen, M.Q., Chen, D.Y., You, Q.D., Xiang, H., 2018. Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities. Bioorg. Med. Chem. Lett 28, 3726-3730. https://doi.org/10.1016/j.bmcl.2018.10.021.
- Ren, R., Chen, C.J., Hu, S.S., Ge, H.M., Jiao, R.H., 2015. Drimane sesquiterpenoids from the Aspergillus oryzae QXPC-4. Chem. Biodivers. 12, 371-379. https://doi.org/ 10.1002/cbdv.201400119.
- Romsdahl, J., Wang, C.C.C., 2019. Recent advances in the genome mining of Aspergillus secondary metabolites (covering 2012-2018). MedChemComm 10, 840-866. https://doi.org/10.1039/C9MD00054B.
- Saleem, M., Ali, M.S., Hussain, S., Jabbar, A., Ashraf, M., Lee, Y.S., 2007. Marine natural products of fungal origin. Nat. Prod. Rep. 24, 1142. https://doi.org/10.1039/ B607254M.
- Saleem, M., Nazir, M., Ali, M.S., Hussain, H., Lee, Y.S., Riaz, N., Jabbar, A., 2010. Antimicrobial natural products: an update on future antibiotic drug candidates. Nat. Prod. Rep. 27, 238-254. https://doi.org/10.1039/B916096E.
- Sanchez, J.F., Somoza, A.D., Keller, N.P., Wang, C.C., 2012. Advances in Aspergillus secondary metabolite research in the post-genomic era. Nat. Prod. Rep. 29, 351. https://doi.org/10.1039/c2np00084a.
- Shaaban, M., El-Metwally, M.M., Abdel-Razek, A.A., Laatsch, H., 2018. Terretonin M: a new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat. Prod. Res. 32, 2437-2446. https://doi. org/10.1080/14786419.2017.1419230.
- Shin, H.J., Choi, B., Trinh, P.T.H., Lee, H., Kang, J.S., Van, T.T.T., Lee, H., Lee, J.S., Lee, Y., Lee, J., 2018. Suppression of RANKL-induced osteoclastogenesis by the metabolites from the marine fungus Aspergillus flocculosus isolated from a sponge Stylissa sp. Mar. Drugs 16, 14. https://doi.org/10.3390/md16010014.
- Song, Y.X., Qiao, L.T., Wang, J.J., Zeng, H.M., She, Z.G., Miao, C.D., Hong, K., Gu, Y.C., Lan, L., Lin, Y.C., 2011. Two new meroterpenes from the mangrove endophytic fungus Aspergillus sp. 085241B. Helv. Chim. Acta 94, 1875-1880. https://doi.org/ 10.1002/hlca.201100111.
- Spiteller, P., 2015. Chemical ecology of fungi. Nat. Prod. Rep. 32, 971-993. https://doi. org/10.1039/C4NP00166D.
- Sun, H.F., Li, X.M., Meng, L., Cui, C.M., Gao, S.S., Li, C.S., Huang, C.G., Wang, B.G., 2012a. Asperolides A-C, tetranorlabdane diterpenoids from the marine alga-derived endophytic fungus Aspergillus wentii EN-48. J. Nat. Prod. 75, 148-152. https://doi. org/10.1021/np2006742.
- Sun, K.L., Li, Y., Guo, L., Wang, Y., Liu, P.P., Zhu, W.M., 2014. Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar. Drugs 12, 3970-3981. https://doi.org/10.3390/md12073970.
- Sun, L.L., Shao, C.L., Chen, J.F., Guo, Z.Y., Fu, X.M., Chen, M., Chen, Y.Y., Li, R., Voogd, N.J.D., She, Z.G., 2012b. New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from the sponge Xestospongia testudinaria. Bioorg. Med. Chem. Lett 22, 1326-1329. https://doi.org/10.1016/j. bmcl.2011.12.083.
- Tagami, K., Liu, C., Minami, A., Noike, M., Oikawa, H., 2013. Reconstitution of biosynthetic machinery for indole-diterpene paxilline in Aspergillus oryzae. J. Am. Chem. Soc. 135, 1260-1263. https://doi.org/10.1021/ja3116636.
- Tagami, K., Minami, A., Fujii, R., Liu, C., Tanaka, M., Gomi, K., Dairi, T., Oikawa, H., 2014. Rapid reconstitution of biosynthetic machinery for fungal metabolites in Aspergillus oryzae: total biosynthesis of Aflatrem. Chembiochem 15, 2076-2080. https://doi.org/10.1002/cbic.201402195.
- Tan, Y.H., Yang, B., Lin, X.P., Luo, X.W., Zhou, X.F., 2018. Nitrobenzoyl sesquiterpenoids with cytotoxic activities from a marine-derived Aspergillus ochraceus fungus. J. Nat. Prod. 81, 92-97. https://doi.org/10.1021/acs.jnatprod.7b00698.
- Thapa, S., Lv, M., Xu, H., 2017. Acetylcholinesterase: a primary target for drugs and insecticides. Mini Rev. Med. Chem. 17, 1665-1676. https://doi.org/10.2174/ 1389557517666170120153930.
- Tsunematsu, Y., Namiki, T., Kishimoto, S., Noguchi, H., Watanabe, K., 2016. New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145. J. Antibiot. 69, 561-566. https://doi.org/10.1038/ja.2016.54.
- Wang, J.F., He, W.J., Kong, F.D., Tian, X.P., Wang, P., Zhou, X.J., Liu, Y.H., 2017a. Ochracenes A-I, humulane-derived sesquiterpenoids from the antarctic fungus Aspergillus ochraceopetaliformis. J. Nat. Prod. 80, 1725-1733. https://doi.org/ 10.1021/acs.jnatprod.6b00810.
- Wang, J.F., Wei, X.Y., Qin, X.C., Tian, X.P., Liao, L., Li, K.M., Zhou, X.F., Yang, X.W., Wang, F.Z., Zhang, T.Y., 2016a. Antiviral merosesquiterpenoids produced by the antarctic fungus Aspergillus ochraceopetaliformis SCSIO 05702. J. Nat. Prod. 79, 59-65. https://doi.org/10.1021/acs.jnatprod.5b00650.
- Wang, J.M., Bai, G., Liu, Y.H., Wang, H.B., Li, Y., 2016b. Cytotoxic metabolites produced by the endophytic fungus Aspergillus clavatus. Chem. Lett. 44, 1148-1149. https:// doi.org/10.1246/cl.150417.
- Wang, P., Yu, J.H., Zhu, K.K., Wang, Y.Y., Cheng, Z.Q., Jiang, C.S., Dai, J.G., Wu, J., Zhang, H., 2018. Phenolic bisabolane sesquiterpenoids from a Thai mangrove endophytic fungus, Aspergillus sp. xy02. Fitoterapia 127, 322-327. https://doi.org/ 10.1016/j.fitote.2018.02.031.
- Wang, Y., Li, D.H., Li, Z.L., Sun, Y.J., Hua, H.M., Liu, T., Bai, J., 2015a. Terpenoids from the marine-derived fungus Aspergillus fumigatus YK-7. Molecules 21, 31. https://doi. org/10.3390/molecules21010031.
- Wang, Y.Z., Qi, S., Zhan, Y., Zhang, N.W., Deng, X.M., 2015b. Aspertetranones A-D, putative meroterpenoids from the marine algal-associated fungus Aspergillus sp. ZL0- 1b14. J. Nat. Prod. 78, 2405-2410. https://doi.org/10.1021/acs.jnatprod.5b00487.
- Wang, Z., Wang, S., Qin, B., 2017b. An LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and 1-O-acetylbritannilactone in rat plasma and its application to a pharmacokinetic study. Biomed. Chromatogr. 31, 12. https://doi.org/10.1002/bmc.3811.
- Wen, H.L., Yang, X.L., Liu, Q., Li, S.J., Zhang, Y.H., 2019. Structurally diverse meroterpenoids from a marine-derived Aspergillus sp. fungus. J. Nat. Prod. 83, 99-104. https://doi.org/10.1021/acs.jnatprod.9b00878.
- Wu, C.J., Cui, X., Xiong, B., Yang, M.S., Liu, X.M., 2018a. Terretonin D1, a new meroterpenoid from marine-derived Aspergillus terreus ML-44. Nat. Prod. Res. 33, 2262-2265. https://doi.org/10.1080/14786419.2018.1493583.
- Wu, Y.N., Chen, Y., Huang, X.S., Pan, Y.H., Liu, Z.M., 2018b. α- Glucosidase inhibitors: diphenyl ethers and phenolic bisabolane sesquiterpenoids from the mangrove endophytic fungus Aspergillus flavus QQSG-3. Mar. Drugs 16, 307. https://doi.org/ 10.3390/md16090307.
- Xiao, Z.E., Huang, H.R., Shao, C.L., Xia, X.K., She, Z.G., 2013. Asperterpenols A and B, new sesterterpenoids isolated from a mangrove endophytic fungus Aspergillus sp. 085242. Org. Lett. 15, 2522-2525. https://doi.org/10.1021/ol401005j.
- Xu, Y., Wang, L.P., Gong, Q.Y., Zhu, G.L., Yuan, C.M., Zuo, M.X., Rao, Q., Zhu, W.M., Hao, X.J., 2018. Kojic acid derivatives and sesquiterpenes from the Aspergillus flavus GZWMJZ-288, a fungal endophyte of Garcinia multiflora. Nat. Prod. Commun. 13, 1421-1424. https://doi.org/10.1177/1934578X1801301102.
- Yan, T., Guo, Z.K., Jiang, R., 2013. New flavonol and diterpenoids from the endophytic fungus Aspergillus sp. YXf3. Planta Med. 79, 348-352. https://doi.org/10.1055/s- 0032-1328260.
- Yang, C., Wang, C.M., Jia, Z.-J., 2003. Sesquiterpenes and other constituents from the aerial parts of Inula japonica. Planta Med. 69, 662-666. https://doi.org/10.1055/s- 2003-41123.
- Yurchenko, A.N., Smetanina, O.F., Kalinovsky, A.I., Pivkin, M.V., Dmitrenok, P.S., Kuznetsova, T.A., 2010. A new meroterpenoid from the marine fungus Aspergillus versicolor (Vuill.) Tirab. Russ. Chem. Bull. 59, 852-856. https://doi.org/10.1007/ s11172-010-0173-5.
- Yurchenko, A.N., Trinh, P.T.H., Girich, E.V., Smetanina, O.F., Afiyatullov, S.S., 2019. Biologically active metabolites from the marine sediment-derived fungus Aspergillus flocculosus. Mar. Drugs 17, 579. https://doi.org/10.3390/md17100579.
- Zhang, D.H., Fukuzawa, S., Satake, M., Li, X.G., Kuranaga, T., Niitsu, A., Yoshizawa, K., Tachibana, K., 2012. Ophiobolin O and 6-epi-ophiobolin O, two new cytotoxic sesterterpenes from the marine derived fungus Aspergillus sp. Nat. Prod. Commun. 7, 1411. https://doi.org/10.1177/1934578X1200701102.
- Zhang, J., Sun, Y., Kang, Y., Shang, D.J., 2021a. Antimicrobial peptide temporin-1CEa isolated from frog skin secretions inhibits the proinflammatory response in lipopolysaccharide-stimulated RAW264.7 murine macrophages through the MyD88- dependent signaling pathway. Mol. Immunol. 132, 227-235. https://doi.org/ 10.1016/j.molimm.2021.01.007.
- Zhang, P., Li, X.M., Li, X., Wang, B.G., 2015. New indole-diterpenoids from the algal-associated fungus Aspergillus nidulans Phytochem. Lett 12, 182-185. https://doi.org/ 10.1016/j.phytol.2015.03.017.
- Gao, J.M., 2013. Potential allelopathic indole diketopiperazines produced by the plant endophytic Aspergillus fumigatus using the one strain-many compounds method. J. Agric. Food Chem. 61, 11447-11452. https://doi.org/10.1021/
- Zhang, X., Guo, J., Cheng, F., Li, S., 2021b. Cytochrome P450 enzymes in fungal natural product biosynthesis. Nat. Prod. Rep. https://doi.org/10.1039/D1NP00004G.
- Zhang, D., Yi, W.W., Ge, H.J., Zhang, Z.Z., Wu, B., 2021. A new antimicrobial indoloditerpene from a marine-sourced fungus aspergillus versicolor ZZ761. Nat. Prod.
- Zheng, W.F., 2011. Drug discovery from fungal metabolites: a review of the papers in this monographical issue of mycosystema concerned with the natural resources,