Abstract
Five terpenoids, including two new cyathane diterpenoids neocyathin S (1) and neocyathin T (2), together with three drimane sesquiterpenoids, one known 3β,6β-dihydroxycinnamolide (3), two new ones 3β,6α-dihydroxycinnamolide (4) and 2-keto-3β,6β-dihydroxycinnamolide (5), were isolated from the cultures of the basidiomycete Cyathus africanus. Their structures were established based on extensive spectroscopic methods including 2D NMR (HSQC, 1H‒1H-COSY, HMBC, ROESY) and HRESIMS experiments. The absolute configurations of two pairs of epimers, 1 and 2 as well as 3 and 4, were determined by ECD quantum chemical calculation. All the five compounds enhanced nerve growth factor (NGF)-mediated neurite outgrowth using rat pheochromocytoma (PC12) cells at concentration 10 µM.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Tang HY, Yin X, Zhang CC, Jia Q, Gao JM. Structure diversity, synthesis, and biological activity of cyathane diterpenoids in higher fungi. Curr Med Chem. 2015;22:2375–91.
Kita T, Takaya Y, Tomihisa YO. Scabronines B, C, D, E and F, novel diterpenoids showing stimulating activity of the nerve growth factor synthesis, from the mushroom Sarcodon scabrosus. Tetrahedron. 1998;54:11886–7.
Hitro M, Morimura K, Shibata H. Anti-inflammatory compounds from the bitter mushroom, Sarcodon scabrosus. Biosci Biotechnol Biochem. 2002;68:1362–5.
Obara Y, Nakahata N, Kita T, Takaya Y, Kobayashi H, Hosoi S, et al. Stimulation of neurotrophic factor secretion from 1321N1human astrocytoma cells by novel diterpenoids, scabronines A and G. Eur J Pharmacol. 1999;370:79–84.
Bai R, Zhang CC, Yin X, Wei J, Gao JM, Striatoids A-F. cyathane diterpenoids with neurotrophic activity from cultures of the fungus Cyathus striatus. J Nat Prod. 2015;78:783–8.
Wei J, Cheng YY, Guo WH, Wang DC, Zhang Q, Li D, et al. Molecular diversity and potential anti-neuroinflammatory activities of cyathane diterpenoids from the basidiomycete Cyathus africanus. Sci Rep. 2017;7:8883.
Wei J, Guo WH, Cao CY, Kou RW, Xu YZ, Gorecki M, et al. Polyoxygenated cyathane diterpenoids from the mushroom Cyathus africanus, and their neurotrophic and anti-neuroinflammatory activities. Sci Rep. 2018;8:2175.
Shi XW, Liu L, Gao JM, Zhang AL. Cyathane diterpenes from Chinese mushroom Sarcodon scabrosus and their neurite outgrowth-promoting activity. Eur J Med Chem. 2011;46:3112.
Zhang C-C, Cao C-Y, Kubo M, Harada K, Yan X-T, Fukuyama Y, et al. Chemical constituents from Hericium erinaceus promote neuronal survival and potentiate neurite outgrowth via the TrkA/Erk1/2 pathway. Int J Mol Sci. 2017;18:1659.
Cao CY, Zhang CC, Shi XW, Li D, Cao W, Yin X, et al., Sarcodonin G derivatives exhibit distinctive effects on neurite outgrowth by modulating NGF signaling in PC12 cells. ACS Chem. Neurosci. https://doi.org/10.1021/acschemneuro.7b00488.
Guo HY, Lu TD, Li ZH, Wang G, Liu JK. A new drimane-type sesquiterpenoid from fermentation broth of Fomitiporia punicata. Nat Prod Res Dev. 2014;26:6–10.
Shiono Y, Hiramatsu F, Murayama T, Koseki T, Funakoshi T. Two cyathane-type diterpenoids from the liquid culture of Strobilurus tenacellu. Chem Biodivers. 2008;5:1811–6.
Xu Z, Yan S, Bi K, Han J, Chen Y, Wu Z, et al. Anti-inflammatory and cytotoxic cyathane diterpenoids from the medicinal fungus Cyathus hookeri Berk. Fitoterapia. 2013;86:159–62.
Wang B, Han J, Xu W, Chen Y, Liu H. Production of bioactive cyathane diterpenes by a bird’s nest fungus Cyathus gansuensis growing on cooked rice. Food Chem. 2014;152:169–76.
Conflex 6.7, Conflex Corp: Tokyo Yokohama, Japan, 2010.
Frisc MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09 revision D.01; Gaussian Inc.: Wallingford CT, 2013.
Bruhn T, Schaumloeffel A, Hemberger Y, Bringmann G. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality. 2013;25:243–9.
Lin CW, Wu MJ, Liu IYC, Su JD, Yen JH. Neurotrophic and cytoprotective action of luteolin in PC12 cells through ERL-dependent induction of Nrf2-deiven HO-1 expression. J Agric Food Chem. 2010;58:4477–86.
Suzuki-Mizushima Y, Gohda E, Okamura T, Kanasaki K, Yamamoto I. Enhancement of NGF- and cholera toxin-induced neurite outgrouth by butyrate in PC12 cells. Brain Res. 2002;951:209–17.
Acknowledgements
This work was financially supported by National Natural Science Foundation of China (81502938, 21572182, 21503168), and the Fundamental Research Funds for the Central Universities (No. 2452016094).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Electronic supplementary material
41429_2018_106_MOESM1_ESM.docx
Cyathane diterpenoids and drimane sesquiterpenoids with neurotrophic activity from cultures of the fungus Cyathus africanus
Rights and permissions
About this article
Cite this article
Kou, RW., Du, ST., Li, YX. et al. Cyathane diterpenoids and drimane sesquiterpenoids with neurotrophic activity from cultures of the fungus Cyathus africanus. J Antibiot 72, 15–21 (2019). https://doi.org/10.1038/s41429-018-0106-3
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/s41429-018-0106-3
This article is cited by
-
A new antibiotic from the culture broth of Dentipellis fragilis
The Journal of Antibiotics (2023)
