Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus
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ORIGINAL ARTICLE
Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus Yi Chen2,3 · Song‑Wei Li1 · Fang‑Zhou Yin1 · Min Yang1 · Xia‑Juan Huan1 · Ze‑Hong Miao1 · Xiao‑Ming Wang2,3 · Yue‑Wei Guo1,4 Received: 13 August 2020 / Accepted: 12 October 2020 © The Author(s) 2020
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 I C50 value of 28.4 μM. Graphic Abstract
Keywords Lagerstroemia indica Linnaeus · Pyrrole alkaloid · Total synthesis · Stereochemistry · Cytotoxicity
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13659-020-00273-x) contains supplementary material, which is available to authorized users. * Xiao‑Ming Wang [email protected]
2
Hunan Academy of Forestry, 658 South Shao shan Road, Changsha 410004, Hunan, China
* Yue‑Wei Guo [email protected]
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
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
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1 Introduction Terrestrial plants of Lythracea is a large family, widely used in architecture, landscaping, food and drug applications. The plants of genus Lagerstroemia comprise more than 15 species, which are either small trees or shrubs with colourful flowers distributed in warm temperate regions of China [1]. Earlier chemical investigation of the different species of Lythracea can trace back to decades, and a lot of structurally diverse and complex compounds, such as alkaloids, sesqui-, triterpenoids, steroids and flavonoids [2] were reported. Especially, alkaloids have attracted much attention of natural product chemists and pharmacologists due to their extensive biological activities, ranging from antifungal activities to cytotoxicity. The earlier phytochemical studies on the plants of the Lagerstroemia indica initiated in 1962. Ferris et al. had reported a series of phenylquinolizidine alkaloids from the aerial of title species [3–8]. Recently, several new biphenylquinolizidine alkaloids were also isolated from the aerial parts of L. indica by Bae et al. [9, 10]. It is interesting to note that the chemical constitu
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