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Planta Med 2023; 89(13): 1250-1258
DOI: 10.1055/a-2072-2177
Natural Product Chemistry and Analytical Studies
Original Papers

Phytochemical Analysis of Nothapodytes tomentosa and Distribution and Content of Camptothecin and its Analogues in Four Plants

Junheng Li‡
1   State Key Laboratory of Southwestern Chinese Medicine Resources, and School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Yin Chen‡
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Lei Wu
2   Institute of Applied Chemistry, Jiangxi Academy of Sciences, Nanchang, China
,
Xiaotao Tuo
1   State Key Laboratory of Southwestern Chinese Medicine Resources, and School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Li Wang
1   State Key Laboratory of Southwestern Chinese Medicine Resources, and School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Guanglian Zhou
1   State Key Laboratory of Southwestern Chinese Medicine Resources, and School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Sheng-Xiong Huang
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
,
Wei Xiong
2   Institute of Applied Chemistry, Jiangxi Academy of Sciences, Nanchang, China
,
Jian-Ping Huang 
1   State Key Laboratory of Southwestern Chinese Medicine Resources, and School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, China
3   State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
› Author AffiliationsThis research was supported by the National Key R&D Program of China (2018YFA0900600), the National Natural Science Foundation of China (32000239 to J.-P. H.), the China Postdoctoral Science Foundation (2022M710497 to L. W.), and the Xinglin Scholar Research Promotion Project of Chengdu University of TCM (BSH2021013 to L. W.).
› Further Information
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Abstract

Camptothecin (CPT) and its derivatives have attracted worldwide attention because of their notable anticancer activity. However, the growing demand for CPT in the global pharmaceutical industry has caused a severe shortage of CPT-producing plant resources. In this study, phytochemical analysis of Nothapodytes tomentosa results in the isolation and identification of CPT (13) and 16 analogues (1 – 12, 14 – 17), including a new (1) and five known (9, 10, 12, 15, and 17) CPT analogues with an open E-ring. In view of the potential anticancer activity of CPT analogues with an open E-ring, the fragmentation pathways and mass spectra profiles of these six CPT analogues (1, 9, 10, 12, 15, and 17) are investigated, providing a reference for the rapid detection of these compounds in other plants. Furthermore, based on the fragmentation patterns of CPT (13) and known analogues (2 – 8, 11, 14, 16, 18 – 26), the distribution and content of these compounds in different tissues of N. tomentosa, N. nimmoniana, Camptotheca acuminata, and Ophiorrhiza japonica are further studied. Our findings not only provide an alternative plant resource for further expanding the development and utilization of CPT and its analogues, but also lay a foundation for improving the utilization of known CPT-producing plant resources.

Key words

Nothapodytes tomentosa - Nothapodytes nimmoniana - Camptotheca acuminata - Ophiorrhiza japonica - Icacinaceae - camptothecin derivatives

Supporting Information

    Methods for ECD calculations, methods for optimization of extraction conditions, methods for qualitative and quantitative analysis of CPT and its analogues in four plants by UHPLC-Q-ESI-TOF-MS/MS and HPLC-Q-ESI-TOF-MS, NMR data of compounds 2 – 17, spectra of compound 1, ECD spectra of compounds 1, 9, and 12, structure of CPT and its analogues analyzed in this study, data on distribution of CPT and its analogues in different tissues of four plants, MS/MS spectra of compounds 1, 9, 12, 10, 15, and 17, proposed MS/MS fragmentation pathway of compounds 1, 9, and 12, data obtained by the single factor experiments and RSM, important thermodynamic parameters (a. u.) and Boltzmann distributions of the optimized compound 1, and optimized Z-matrixes of compound 1 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 15 December 2022

Accepted after revision: 11 April 2023

Accepted Manuscript online:
12 April 2023

Article published online:
28 July 2023

© 2023. Thieme. All rights reserved.

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