Lycopodium Alkaloids from Phlegmariurus carinatus with Cytotoxic and Neuroprotective Effects.
Huperziaceae
Lycopodium alkaloids
Phlegmariurus carinatus
cytotoxicity
neuroprotective activity
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
15 Nov 2023
15 Nov 2023
Historique:
received:
18
09
2023
accepted:
14
11
2023
pubmed:
15
11
2023
medline:
15
11
2023
entrez:
15
11
2023
Statut:
aheadofprint
Résumé
One new fawcettimine-type alkaloid, phlecarinadine A (1), and twelve known ones (2-13) were isolated from the whole plant of Phlegmariurus carinatus. Their chemical structures were unambiguously established by extensive spectroscopic analyses, including nuclear magnetic resonance (NMR) spectroscopic and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configuration of 1 was elucidated by the electronic circular dichroism (ECD) technique. These compounds were tested for their cytotoxic and neuroprotective activities. None of these compounds revealed cytotoxic activity against five tumor cells. Phlegmariurine B (2) exhibited potential neuroprotective effects against hemin-induced HT22 cell damage, with a 17.76 % increase in cell survival at 10 μM. In further study, 2 can ameliorate hemin-induced neuronal cell death via an anti-apoptotic pathway. These findings suggest that 2 might be a valuable lead compound with neuroprotective activity.
Identifiants
pubmed: 37966166
doi: 10.1002/cbdv.202301449
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301449Subventions
Organisme : National Natural Science Foundation of China
ID : 32260109
Organisme : Science and Technology Plan Project of Jiangxi Provincial Administration of Traditional Chinese Medicine
ID : 2021A325
Organisme : Jiangxi Province Department of Education Science and Technology Research Projects
ID : GJJ211540
Organisme : Jiangxi Province Department of Education Science and Technology Research Projects
ID : GJJ211547
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
X. Q. Ma, D. R. Gang, Nat. Prod. Rep. 2004, 21, 752-772.
Y. Hirasawa, J. Kobayashi, H. Morita, Heterocycles 2009, 77, 679-729.
G. Cordell, A. Brossi, The Alkaloids: Chemistry and Pharmacology, Elsevier, Amsterdam, 1994, p. 233.
J. S. Liu, Y. L. Zhu, C. M. Yu, Y. Z. Zhou, Y. Y. Han, F. W. Wu, B. F. Qi, Can. J. Chem. 1986, 64, 837-839.
X. Ma, D. R. Gang, Phytochemistry 2008, 69, 2022-2028.
X. Ma, C. Tan, D. Zhu, D. R. Gang, P. Xiao, J. Ethnopharmacol. 2007, 113, 15-34.
Y. G. Chen, Q. Yang, Y. Zhang, Arab. J. Chem. 2020, 13, 5438-5450.
R. C. Ching, Acta Bot. Yunnan. 1982, 4, 119-128.
Y. G. Wu, L. R. Song, Chinese materia medica, Shanghai Science and Technology Press, Shanghai, 1998, p. 357.
X. C. Zhang, L. B. Zhang, Flora of China, Science Press, Beijing, 2004, p. 53.
F. Liu, Y. C. Liu, W. W. Jiang, J. He, X. D. Wu, L. Y. Peng, J. Xu, X. Cheng, Q. S. Zhao, Nat. Prod. Bioprospect. 2014, 4, 221-225.
W. Thamnarak, W. Thaisaeng, P. Batsomboon, C. Eurtivong, N. Wannarit, S. Ruchirawat, N. Thasana, Phytochemistry 2023, 206, 113553.
C. Wang, X. Z. Yang, G. Mellick, Y. J. Feng, J. Nat. Prod. 2022, 85, 899-909.
W. Thaisaeng, W. Thamnarak, S. Ruchirawat, K. Chainok, N. Thasana, Nat. Prod. Res. 2023, online, https://doi.org/10.1080/14786419.2023.2188587.
Y. Liu, Q. Wang, D. K. Zheng, D. Zhang, Z. Xie, J. W. Hu, X. H. Xie, J. Li, S. P. Jiang, Nat. Prod. Res. 2022, 36, 6006-6011.
J. W. Hu, Q. Wang, L. Liu, Y. M. Hu, M. Xie, D. K. Zheng, Z. Xie, Y. Liu, Phytochemistry 2022, 204, 113457.
K. Ishiuchi, T. Kubota, T. Hoshino, Y. Obara, N. Nakahata, J. Kobayashi, Bioorg. Med. Chem. 2006, 4, 5995-6000.
C. H. Tan, B. D. Wang, S. H. Jiang, D. Y. Zhu, Planta Med. 2002, 68, 188-190.
H. Morita, Y. Hirasawa, J. Kobayashi, J. Nat. Prod. 2005, 68, 1809-1812.
H. Takayama, K. Katakawa, M. Kitajima, K. Yamaguchi, N. Aimi, Chem. Pharm. Bull. 2003, 51, 1163-1169.
J. M. Jiang, D. Xia, X. L. Zhu, D. Zhu, X. W. Yang, K. Pan, Tetrahedron 2022, 114, 132782.
J. S. Liu, M. F. Huang, Phytochemistry 1994, 37, 1759-1761.
X. J. Wang, L. Li, S. S. Yu, S. G. Ma, J. Qu, Y. B. Liu, Y. Li, Y. D. Wang, W. B. Tang, Fitoterapia 2013, 91, 74-81.
C. C. Tan, X. Q. Ma, G. F. Chen, S. H. Jiang, D. Y. Zhu, Chin. Chem. Lett. 2002, 13, 331-332.
C. Peng, X. Gong, Z. Hu, C. Chen, Z. Jiang, PeerJ 2023,11, e15293.
J. Li, L. Q. Li, H. P. Long, J. Liu, Y. P. Jiang, Y. Xue, W. X. Wang, G. S. Tan, Z. C. Gon, J. K. Liu, Phytochemistry 2021, 186, 112729.
Z. X. He, H. F. Song, T. Y. Liu, J. Ma, Z. K. Xing, Y. Y. Yin, L. Liu, Y. N. Zhang, Y. .F. Zhao, H. L. Yu, X. X. He, W. X. Guo, X. J. Zhu, Cereb. Cortex 2019, 29, 2737-2747.