Nitric Oxide Inhibitory Carbazole Alkaloids from the Folk Medicine Murraya tetramera C.C. Huang.


Journal

Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449

Informations de publication

Date de publication:
Nov 2020
Historique:
received: 23 06 2020
accepted: 22 09 2020
pubmed: 23 9 2020
medline: 26 5 2021
entrez: 22 9 2020
Statut: ppublish

Résumé

The phytochemical investigation of the leaves and stems of Murraya tetramera C.C. Huang, a traditional folk medicine used as an anti-inflammatory agent, yielded 19 simple carbazole alkaloids, two of which (1-ethoxy-3-methyl-9H-carbazol-2-ol (1) and 7-hydroxy-2,8-dimethoxy-6-methyl-9H-carbazole-1-carbaldehyde (2)) are new ones. The structures of the new compounds were determined by extensive spectroscopic analysis including NMR and HR-EI-MS experiments, as well as comparison with the reported data. Most of the isolates showed potent inhibitory effects on NO production in LPS-stimulated BV-2 microglial cells with IC

Identifiants

pubmed: 32960486
doi: 10.1002/cbdv.202000490
doi:

Substances chimiques

Alkaloids 0
Anti-Inflammatory Agents 0
Carbazoles 0
Lipopolysaccharides 0
Nitric Oxide 31C4KY9ESH

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

e2000490

Subventions

Organisme : National Natural Science Foundation of China
ID : 81973199
Organisme : National Natural Science Foundation of China
ID : 81773864
Organisme : National Natural Science Foundation of China
ID : 81473106
Organisme : Fundamental Research Funds for the Central Public Welfare Research Institutes
ID : ZXKT19025
Organisme : The Drug Innovation Project of China
ID : 2018ZX09711001-008-003

Informations de copyright

© 2020 Wiley-VHCA AG, Zurich, Switzerland.

Références

Editorial Committee of Flora of China, ‘Flora of China’, Science Press, Beijing, 1977, Vol. 43, p. 145.
H. N. Lv, R. Wen, Y. Zhou, K. W. Zeng, J. Li, X. Y. Guo, P. F. Tu, Y. Jiang, ‘Nitrogen oxide inhibitory trimeric and dimeric carbazole alkaloids from Murraya tetramera’, J. Nat. Prod. 2015, 78, 2432-2439.
H. N. Lv, Y. Zhou, R. Wen, M. L. Shi, K. W. Zeng, F. Xia, P. F. Tu, Y. Jiang, ‘Murradiate and murradiol, two structurally unique heterodimers of carbazole-monoterpene and carbazole-phenylethanol from Murraya tetramera’, Phytochem. Lett. 2016, 15, 113-115.
X. L. Ma, J. Li, J. Zheng, X. P. Gu, D. Ferreira, J. K. Zjawiony, M. B. Zhao, X. Y. Guo, P. F. Tu, Y. Jiang, ‘LC/MS-guided isolation of insulin-secretion-promoting monoterpenoid carbazole alkaloids from Murraya microphylla’, J. Nat. Prod. 2018, 81, 2371-2380.
X. Ma, N. Cao, C. Zhang, X. Guo, M. Zhao, P. Tu, Y. Jiang, ‘Cytotoxic carbazole alkaloid derivatives from the leaves and stems of Murraya microphylla’, Fitoterapia 2018, 127, 334-340.
O. P. Patel, A. Mishra, R. Maurya, D. Saini, J. Pandey, I. Taneja, K. S. Raju, S. Kanojiya, S. K. Shukla, M. N. Srivastava, M. Wahajuddin, A. K. Tamrakar, A. K. Srivastava, P. P. Yadav, ‘Naturally occurring carbazole alkaloids from Murraya koenigii as potential antidiabetic agents’, J. Nat. Prod. 2016, 79, 1276-1284.
Y. Nalli, V. Khajuria, S. Gupta, P. Arora, S. Riyaz-Ul-Hassan, Z. Ahmed, A. Ali, ‘Four new carbazole alkaloids from Murraya koenigii that display anti-inflammatory and anti-microbial activities’, Org. Biomol. Chem. 2016, 14, 3322-3332.
R. Wei, Q. Ma, G. Zhong, Y. Su, J. Yang, A. Wang, T. Ji, H. Guo, M. Wang, P. Jiang, H. Wu, ‘Structural characterization, hepatoprotective and antihyperlipidemic activities of alkaloid derivatives from Murraya koenigii’, Phytochem. Lett. 2020, 35, 135-140.
A. W. Schmidt, K. R. Reddy, H. J. Knölker, ‘Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids’, Chem. Rev. 2012, 112, 3193-3328.
Editorial Committee of the Administration Bureau of Traditional Chinese Medicine, ‘Chinese Materia Medica (Zhong Hua Ben Cao)’, Shanghai Science & Technology Press, Shanghai, 1999, Vol. 12, p. 947.
Y. P. Liu, J. M. Guo, Y. Y. Liu, S. Hu, G. Yan, L. Qiang, Y. H. Fu, ‘Carbazole alkaloids with potential neuroprotective activities from the fruits of Clausena lansium’, J. Agric. Food Chem. 2019, 67, 5764-5771.
C. Ito, M. Nakagawa, T. S. Wu, H. Furukawa, ‘New carbazole alkaloids from Murraya euchrestifolia’, Chem. Pharm. Bull. 1991, 39, 2525-2528.
R. Hesse, M. P. Krahl, A. Jäger, O. Kataeva, A. W. Schmidt, H. J. Knölker, ‘Palladium(II)-catalyzed synthesis of the formylcarbazole alkaloids murrayaline A-C, 7-methoxymukonal, and 7-methoxy-O-methylmukonal’, Eur. J. Org. Chem. 2014, 2014, 4014-4028.
S. Roy, P. Bhattacharyya, D. P. Chakraborty, ‘3-Methylcarbazole from Clausena heptaphylla’, Phytochemistry 1974, 13, 1017.
M. Chakrabarty, A. C. Nath, S. Khasnobis, M. Chakrabarty, Y. Konda, Y. Harigaya, K. Komiyama, ‘Carbazole alkaloids from Murraya koenigii’, Phytochemistry 1997, 46, 751-755.
H. J. Knölker, M. Bauermeister, J. B. Pannek, ‘Transition-Metal-Diene complexes in organic synthesis, 12. Regio- and stereoselectivity of electrophilic substitutions of arylamines by tricarbonyliron-complexed cyclohexadienylium cations and oxidative cyclizations to carbazoles’, Chem. Ber. 1992, 125, 2783-2793.
H. Furukawa, T. S. Wu, T. Ohta, C. Kuoh, ‘Chemical constituents of Murraya euchrestifolia Hayata. Structures of novel carbazolequinones and other new carbazole alkaloids’, Chem. Pharm. Bull. 1985, 33, 4132-4138.
B. Liégault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, ‘Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: reaction development and scope’, J. Org. Chem. 2008, 73, 5022-5028.
H. J. Knölker, M. Bauermeister, ‘Transition metal-diene complexes in organic synthesis-16. 1: Iron-mediated total synthesis of 1-oxygenated carbazole alkaloids’, Tetrahedron 1993, 49, 11221-11236.
B. S. Joshi, V. N. Kamat, D. H. Gawad, ‘Structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine, and murrayacine’, Tetrahedron 1970, 26, 1475-1482.
R. Hesse, K. K. Gruner, O. Kataeva, A. W. Schmidt, H. J. Knölker, ‘Efficient construction of pyrano[3,2-a]carbazoles: application to a biomimetic total synthesis of cyclized monoterpenoid pyrano[3,2-a]carbazole alkaloids’, Chem. Eur. J. 2013, 19, 14098-14111.
K. Sravanthi, S. K. Agrawal, C. N. Rao, F. A. Khan, ‘Synthesis of carbazole analogs via Grob fragmentation of norbornyl α-diketones’, Tetrahedron Lett. 2016, 57, 3449-3452.
C. Ito, N. Okahana, T. S. Wu, M. L. Wang, J. S. Lai, C. S. Kuoh, H. Furukawa, ‘New carbazole alkaloids from Murraya euchrestifolia’, Chem. Pharm. Bull. 1992, 40, 230-232.
M. Fiebig, J. M. Pezzuto, D. D. Soejarto, A. D. Kinghorn, ‘Plant anticancer agents. Part 40. Koenoline, a further cytotoxic carbazole alkaloid from Murraya koenigii’, Phytochemistry 1985, 24, 3041-3043.
H. J. Knölker, M. Bauermeister, ‘Iron-mediated total synthesis of the cytotoxic carbazole koenoline and related alkaloids’, J. Chem. Soc. Chem. Commun. 1990, 664-665.
C. Cui, B. Cai, S. Yan, X. Yao, ‘Carbazole alkaloids and their isolation and use’, Faming Zhuanli Shenqing Gongkai Shuomingshu, 2002, CN 1332157A 20020123.
C. Ito, T. S. Wu, H. Furukawa, ‘New carbazole alkaloids from Murraya euchrestifolia’, Chem. Pharm. Bull. 1988, 36, 2377-2380.
D. P. Chakraborty, B. K. Barman, P. K. Bose, ‘Constitution of murrayanine, a carbazole derivative isolated from Murraya koenigii’, Tetrahedron 1965, 21, 681-685.
P. Bernal, J. Tamariz, ‘Total synthesis of murrayanine Involving 4,5-dimethyleneoxazolidin-2-ones and a palladium(0)-catalyzed diaryl insertion’, Helv. Chim. Acta 2007, 90, 1449-1454.
W. S. Li, D. M. James, S. E. Farouk, ‘Carbazole alkaloids from Clausena lansium’, Phytochemistry 1991, 30, 343-346.
S. Rasheed, D. N. Rao, K. R. Reddy, S. Aravinda, R. A. Vishwakarma, P. Das, ‘C-N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids’, RSC Adv. 2014, 4, 4960-4969.
D. P. Chakraborty, P. Bhattacharyya, S. Roy, S. P. Bhattacharyya, A. K. Biswas, ‘Structure and synthesis of mukonine, a new carbazole alkaloid from Murraya koenigii’, Phytochemistry 1978, 17, 834-835.
H. J. Knölker, M. Wolpert, ‘Transition metal complexes in organic synthesis. Part 68: Iron-mediated total synthesis of mukonine and mukonidine by oxidative cyclization with air as the oxidizing agent’, Tetrahedron 2003, 59, 5317-5322.
C. Ito, M. Nakagawa, T. S. Wu, H. Furukawa, ‘New carbazole alkaloids from Murraya euchrestifolia Hayata’, Chem. Pharm. Bull. 1991, 39, 1668-1671.
R. Hesse, A. Jäger, A. W. Schmidt, H. J. Knölker, ‘Palladium(II)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids’, Org. Biomol. Chem. 2014, 12, 3866-3876.

Auteurs

Hai-Ning Lyu (HN)

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P. R. China.
Artemisinin Research Center, Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, P. R. China.

Ying Zhou (Y)

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P. R. China.
Zhejiang Institute for Food and Drug Control, Hangzhou, 310004, P. R. China.

Ran Wen (R)

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P. R. China.
School of Pharmacy, Hebei Medical University, Shijiazhuang, 050017, P. R. China.

Peng-Fei Tu (PF)

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P. R. China.

Yong Jiang (Y)

State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, 100191, P. R. China.

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