Abstract
A new aromatic bisabolene-type sesquiterpenoid (7S-8S)-8-hydroxysydowic acid (1), together with a pair of new bisabolene derivative (±)-(7R*,10R*)-10-hydroxysydowic acid (2), as well as two known analogues hydroxysydonic acid (3) and sydowic acid (4) were isolated and identified from the endophytic fungal strain Aspergillus sydowii EN-434 that was obtained from the marine red alga Symphyocladia latiuscula. Their structures were elucidated by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), and quantum chemical electronic circular dichroism (ECD) calculations as well as comparison of the data with literature reports. Compound 1 exhibited potent DPPH free radical scavenging activity with IC50 value of 113.5 µmol/L.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Barzkar N, Jahromi S T, Poorsaheli H B, Vianello F. 2019. Metabolites from marine microorganisms, micro, and macroalgae: immense scope for pharmacology. Mar. Drugs, 17(8): 464, https://doi.org/10.3390/md17080464.
Blunt J W, Copp B R, Keyzers R A, Munro M H G, Prinsep M R. 2015. Marine natural products. Nat. Prod. Rep., 32(2): 116–211, https://doi.org/10.1039/C4NP00144C.
Cho K H, Sohn J H, Oh H. 2018. Isolation and structure determination of a new diketopiperazine dimer from marine-derived fungus Aspergillus sp. SF-5280. Nat. Prod. Res., 32(2): 214–221, https://doi.org/10.1080/14786419.2017.1346642.
Frisch M J, Trucks G W, Schlegel H B et al. 2013. Gaussian 09, Revision D.01. Wallingford, CT: Gaussian, Inc.
Hamasaki T, Nagayama K, Hatsuda Y. 1978. Two new metabolites, sydonic acid and hydroxysydonic acid, from Aspergillus sydowi. Agrie Biol. Chem., 42(1): 37–40, https://doi.org/10.1271/bbb1961.42.37.
Hamasaki T, Sato Y, Hatsuda Y, Tanabe M, Cary L W. 1975. Sydowic acid, a new metabolite from Aspergillus sydowi. Tetrahedron Lett., 16(9): 659–660, https://doi.org/10.1016/S0040-4039(00)71947-2.
Li W T, Luo D, Huang J N, Wang L L, Zhang F G, Xi T, Liao J M, Lu Y Y. 2018. Antibacterial constituents from Antarctic fungus, Aspergillus sydowii SP-1. Nat. Prod. Res., 32(6): 662–667, https://doi.org/10.1080/14786419.2017.1335730.
Liu S, Wang H B, Su M Z, Hwang G J, Hong J K, Jung J H. 2017. New metabolites from the sponge-derived fungus Aspergillus sydowii J05B-7F-4. Nat. Prod. Res., 31(14): 1682–1686, https://doi.org/10.1080/14786419.2017.1289205.
Liu X R, Song F H, Ma L, Chen C X, Xiao X, Ren B, Liu X T, Dai H Q, Piggott A M, Av-Gay Y, Zhang L X, Capon R J. 2013. Sydowiols A-C: Mycobacterium tuberculosis protein tyrosine phosphatase inhibitors from an East China Sea marine-derived fungus, Aspergillus sydowii. Tetrahedron Lett, 54(45): 6081–6083, https://doi.org/10.1016/j.tetlet.2013.08.137.
Schinke C, Martins T, Queiroz S C N, Melo I S, Reyes F G R. 2017. Antibacterial compounds from marine bacteria, 2010–2015. J. Nat. Prod, 80(4): 1215–1228, https://doi.org/10.1021/acs.jnatprod.6b00235.
Tasdemir D. 2017. Marine fungi in the spotlight: opportunities and challenges for marine fungal natural product discovery and biotechnology. Fungal Biol. Biotechnol., 4(1): 5, https://doi.org/10.1186/s40694-017-0034-1.
Teuscher F, Lin W H, Wray V, Edrada R, Padmakumar K Proksch P, Ebel R. 2006. Two new cyclopentanoids from the endophytic fungus Aspergillus sydowii associated with the marine alga Acanthophora spicifera. Nat. Prod. Comm., 1(11): 927–933, https://doi.org/10.1177/1934578X0600101103.
Trisuwan K, Rukachaisirikul V, Kaewpet M, Phongpaichit S, Hutadilok-Towatana N, Preedanon S, Sakayaroj J. 2011. Sesquiterpene and xanthone derivatives from the sea fanderived fungus Aspergillus sydowii PSU-F154. J. Nat. Prod, 74(7): 1663–1667, https://doi.org/10.1021/np200374j.
Wang S, Li X M, Teuscher F, Li D L, Diesel A, Ebel R, Proksch P, Wang B G. 2006. 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., 69(11): 1622–1625, https://doi.org/10.1021/np060248n.
Wang W L, Lu Z Y, Tao H W, Zhu T J, Fang Y C, Gu Q Q, Zhu W M. 2007. Isoechinulin-type alkaloids, Variecolorins A-L, from halotolerant Aspergillus variecolor. J. Nat. Prod., 70(10): 1558–1564, https://doi.org/10.1021/np070208z.
Wang Y N, Mou Y H, Dong Y, Wu Y, Liu B Y, Bai J, Yan D J, Zhang L, Feng D Q, Pei Y H, Hu Y C. 2018. Diphenyl ethers from a marine-derived Aspergillus sydowii. Mar. Drugs, 16(11): 451, https://doi.org/10.3390/md16110451.
Xu X L, Zhao S J, Yin L Y, Yu Y, Chen Z K, Shen H H, Zhou L. 2017. A new sydonic acid derivative from a marine derived-fungus Aspergillus sydowii. Chem. Nat. Compd., 53(6): 1056–1058, https://doi.org/10.1007/s10600-017-2200-3.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Data Availability Statement
All the data supporting the results of this study are available within the article and the supplementary material.
Supported by the National Natural Science Foundation of China (Nos. 31330009, 31600267)
Electronic Supplementary Material
Rights and permissions
About this article
Cite this article
Hu, X., Li, X., Meng, L. et al. Antioxidant bisabolane-type sesquiterpenoids from algal-derived fungus Aspergillus sydowii EN-434. J. Ocean. Limnol. 38, 1532–1536 (2020). https://doi.org/10.1007/s00343-020-0049-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00343-020-0049-y