Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

doi:10.1007/s13659-020-00273-x

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (1): 73-79.DOI: 10.1007/s13659-020-00273-x

• ORIGINAL ARTICLES • Previous Articles Next Articles

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Yi Chen^2,3, Song-Wei Li¹, Fang-Zhou Yin¹, Min Yang¹, Xia-Juan Huan¹, Ze-Hong Miao¹, Xiao-Ming Wang^2,3, Yue-Wei Guo^1,4

1 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;
2 Hunan Academy of Forestry, 658 South Shao shan Road, Changsha 410004, Hunan, China;
3 Changsha Engineering Technology Research Center of Woody Flower, 658 South shao shan Road, Changsha 410004, Hunan, China;
4 College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shao shan Road, Changsha 410004, Hunan, China

Received:2020-08-13 Revised:2020-10-12 Online:2021-03-11 Published:2021-02-24
Contact: Xiao-Ming Wang, Yue-Wei Guo
Supported by:
This research work was financially supported by the National Natural Science Foundation of China (NSFC) (Nos. 81991521, 41676073), the National Key Research and Development Program of China (No. 2018YFC0310903), the Drug Innovation Major Project (No. 2018ZX09711-001-001-009), and the SKLDR/ SIMM Project (No. SIMM1903ZZ-04). Changsha Engineering Technology Research Center of Woody flower (kq1907081).

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Yi Chen^2,3, Song-Wei Li¹, Fang-Zhou Yin¹, Min Yang¹, Xia-Juan Huan¹, Ze-Hong Miao¹, Xiao-Ming Wang^2,3, Yue-Wei Guo^1,4

1 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;
2 Hunan Academy of Forestry, 658 South Shao shan Road, Changsha 410004, Hunan, China;
3 Changsha Engineering Technology Research Center of Woody Flower, 658 South shao shan Road, Changsha 410004, Hunan, China;
4 College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shao shan Road, Changsha 410004, Hunan, China

通讯作者: Xiao-Ming Wang, Yue-Wei Guo
基金资助:
This research work was financially supported by the National Natural Science Foundation of China (NSFC) (Nos. 81991521, 41676073), the National Key Research and Development Program of China (No. 2018YFC0310903), the Drug Innovation Major Project (No. 2018ZX09711-001-001-009), and the SKLDR/ SIMM Project (No. SIMM1903ZZ-04). Changsha Engineering Technology Research Center of Woody flower (kq1907081).

Abstract

Abstract: A phytochemical investigation of the EtOH extract of the flowers of Lagerstroemia indica L. led to the isolation and characterization of a new pyrrole alkaloid, named lagerindicine (1), along with four known compounds (2-5). Their structures were elucidated by the detailed spectroscopic analysis and comparison with literature data, whereas the structure, in particularly, the absolute configuration (AC) of 1, was firmly determined by total synthesis. All the isolates were evaluated for their cytotoxic effects against human colon cancer cell (HCT-116), and compound 3 exhibited weak cytotoxicity with IC₅₀ value of 28.4 μM.

Key words: Lagerstroemia indica Linnaeus, Pyrrole alkaloid, Total synthesis, Stereochemistry, Cytotoxicity

摘要： A phytochemical investigation of the EtOH extract of the flowers of Lagerstroemia indica L. led to the isolation and characterization of a new pyrrole alkaloid, named lagerindicine (1), along with four known compounds (2-5). Their structures were elucidated by the detailed spectroscopic analysis and comparison with literature data, whereas the structure, in particularly, the absolute configuration (AC) of 1, was firmly determined by total synthesis. All the isolates were evaluated for their cytotoxic effects against human colon cancer cell (HCT-116), and compound 3 exhibited weak cytotoxicity with IC₅₀ value of 28.4 μM.

关键词: Lagerstroemia indica Linnaeus, Pyrrole alkaloid, Total synthesis, Stereochemistry, Cytotoxicity

Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus[J]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.

References

1. H.N. Qin, S. Graham, Flora of China 13, 277-281 (2007)
2. R.M. Labib, N.A. Ayoub, A.B. Singab, M.M. Al-Azizi, A. Sleem, Phytopharmacology 4, 373-389 (2013)
3. J.P. Ferris, J. Org. Chem. 27, 2985-2990 (1962)
4. J.P. Ferris, J. Org. Chem. 28, 817-822 (1963)
5. J.P. Ferris, C.B. Boyce, R.C. Briner, J. Am. Chem. Soc. 93, 2942-2953 (1971)
6. J.P. Ferris, C.B. Boyce, R.C. Briner, J. Am. Chem. Soc. 93, 2953-2957 (1971)
7. J.P. Ferris, C.B. Boyce, R.C. Briner, J. Am. Chem. Soc. 93, 2958-2962 (1971)
8. J.P. Ferris, C.B. Boyce, R.C. Briner, U. Weiss, I.H. Qureshi, N.E. Sharpless, J. Am. Chem. Soc. 93, 2963-2968 (1971)
9. H.J. Kim, I.S. Lee, U.J. Youn, Q.C. Chen, T.M. Ngoc, D.T. Ha, H. Liu, B.S. Min, J.Y. Lee, R.S. Seong, K.H. Bae, J. Nat. Prod. 72, 749-752 (2009)
10. I.S. Lee, U.J. Youn, H.J. Kim, B.S. Min, J.S. Kim, K.H. Bae, Planta Med. 77, 2037-2041 (2011)
11. Y.S. Cai, T. Kurtán, Z.H. Miao, A. Mándi, I. Komáromi, H.L. Liu, J. Ding, Y.W. Guo, J. Org. Chem. 76, 1821-1828 (2011)
12. X.L. Chen, H.L. Liu, J. Li, G.R. Xin, Y.W. Guo, Org. Lett. 13, 5032-5035 (2011)
13. Z.F. Zhou, W. Zhang, T. Kurtan, A. Mandi, A. Bényei, J. Li, O. Taglialatela-Scafati, Y.W. Guo, Tetrahedron 70, 6444-6449 (2014)
14. J.R. Wang, S.T. Kurtán, A. Mándi, Y.W. Guo, Eur. J. Org. Chem. 2012, 5471-5482 (2012)
15. M.C. Song, H.J. Yang, T.S. Jeong, K.T. Kim, N.I. Beak, Arch. Pharm. Res. 31, 573-578 (2008)
16. S. Khaliq, F. Volk, A.W. Frahm, Planta Med. 73, 77-83 (2007)
17. A. Ikuta, H. Itokawa, J. Nat. Prod. 52, 623-628 (1989)
18. K. Yoshida, Y. Hirose, Y. Imai, T. Kondo, Agric. Biol. Chem. 53, 1901-1912 (1989)
19. N. Trombach, O. Hild, D. Schlettwein, D. Wohrle, J. Mater. Chem. 12, 879-885 (2002)
20. M.N. Alberti, G.C. Vougioukalakis, M. Orfanopoulos, J. Org. Chem. 74, 7274-7282 (2009)
21. J.K. Gawronski, A.V. Oeveren, H.V.D. Deen, C.W. Leung, B.L. Feringa, J. Org. Chem. 61, 1513-1515 (1996)
22. A.E. Dascalu, A. Ghinet, E. Lipka, C. Furman, B. Rigo, A. Fayeulle, M. Billamboz, Fitoterapia 143, 104581 (2020)
23. S. Li, F. Ye, Z. Zhu, H. Huang, S. Mao, Y. Guo, Acta Pharm. Sin. B 8, 944-955 (2018)

[1]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways [J]. Natural Products and Bioprospecting, 2025, 15(2): 17-17.
[2]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb. [J]. Natural Products and Bioprospecting, 2025, 15(1): 9-9.
[3]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia [J]. Natural Products and Bioprospecting, 2025, 15(1): 5-5.
[4]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family [J]. Natural Products and Bioprospecting, 2024, 14(6): 51-51.
[5]	Song-Yu Hou, Bing-Chao Yan, Han-Dong Sun, Pema-Tenzin Puno. Recent advances in the application of [2+2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products [J]. Natural Products and Bioprospecting, 2024, 14(5): 37-37.
[6]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus [J]. Natural Products and Bioprospecting, 2024, 14(5): 45-45.
[7]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti [J]. Natural Products and Bioprospecting, 2023, 13(3): 17-17.
[8]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta [J]. Natural Products and Bioprospecting, 2023, 13(2): 7-7.
[9]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron [J]. Natural Products and Bioprospecting, 2022, 12(6): 38-38.
[10]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha [J]. Natural Products and Bioprospecting, 2022, 12(3): 16-16.
[11]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations [J]. Natural Products and Bioprospecting, 2022, 12(2): 9-9.
[12]	Ding Lin, Senze Jiang, Ailian Zhang, Tong Wu, Yongchang Qian, Qingsong Shao. Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis [J]. Natural Products and Bioprospecting, 2022, 12(2): 8-8.
[13]	Aluru Rammohan, Albert F. Khasanov, Dmitry S. Kopchuk, Duvvuru Gunasekar, Grigory V. Zyryanov, Oleg N. Chupakhin. Assessment on facile Diels–Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds [J]. Natural Products and Bioprospecting, 2022, 12(2): 12-12.
[14]	Pan-Pan Wei, Jia-Cheng Ji, Xu-Jun Ma, Zheng-Hui Li, Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu. Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis [J]. Natural Products and Bioprospecting, 2022, 12(1): 1-5.
[15]	Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity [J]. Natural Products and Bioprospecting, 2021, 11(6): 651-658.

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments