吲哚生物碱Catharanthine合成研究进展

doi:10.6023/cjoc202509026

有机化学 ›› 2026, Vol. 46 ›› Issue (3): 725-742.DOI: 10.6023/cjoc202509026 上一篇下一篇

综述与进展

吲哚生物碱Catharanthine合成研究进展

王雪倩^a^,^b, 段宝忠^b^,^*(), 田红畅^a^,^*(), 张磊^a^,^*()

^a 海军军医大学药学院教育部真菌感染性疾病医药基础研究创新中心教育部真菌感染性疾病医药基础研究创新中心上海 200433
^b 大理大学药学院云南大理 671000

收稿日期:2025-09-22 修回日期:2025-10-24 发布日期:2025-12-09
基金资助:
国家自然科学基金(82504962); 国家自然科学基金(82225047); 国家自然科学基金(82170274); 教育部真菌感染性疾病医药基础研究创新中心开放课题(YXX2024-KF02-02); 国家重点研发计划(2024YFC3506500); 国家重点研发计划(2024YFC3506400); 浙江省自然科学基金(LZ24H280003)

Research Progress in Synthesis of Indole Alkaloid Catharanthine

Xueqian Wang^a^,^b, Baozhong Duan^b^,^*(), Hongchang Tian^a^,^*(), Lei Zhang^a^,^*()

^a The Center for Basic Research and Innovation of Medicine and Pharmacy (MOE), School of Pharmacy, Naval Medical University, Shanghai 200433
^b College of Pharmaceutical Science, Dali University, Dali, Yunnan 671000

Received:2025-09-22 Revised:2025-10-24 Published:2025-12-09
Contact: *bzduan@126.com; tianhc8023@163.com; leizhang100@163.com
Supported by:
National Natural Science Foundation of China(82504962); National Natural Science Foundation of China(82225047); National Natural Science Foundation of China(82170274); Open Research Project of the Ministry of Education Innovation Center for Basic Medical Research on Fungal Infectious Diseases(YXX2024-KF02-02); National Key Research and Development Program of China(2024YFC3506500); National Key Research and Development Program of China(2024YFC3506400); Zhejiang Provincial Natural Science Foundation(LZ24H280003)

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摘要/Abstract

长春质碱(Catharanthine)是从长春花中分离得到的Iboga型吲哚生物碱, 具有五环结构, 三个手性中心, 是抗癌药物长春碱及其类似物长春新碱的重要结构片段, 因其复杂独特的化学结构成为合成研究的热点. 近年来, 其完整的生物合成途径已被解析, 并在酵母和本氏烟草等异源系统中实现了功能性重建. 自1969年以来, 已有18个研究团队报道了Catharanthine的化学合成路线, 涵盖消旋合成、不对称合成、仿生合成及多种过渡金属催化方法. 按照时间顺序综述了Catharanthine的生物合成与化学合成研究进展, 并对其未来发展方向进行了展望.

关键词: 长春质碱, 吲哚生物碱, 生物合成, 全合成

Catharanthine, an iboga-type indole alkaloid isolated from Catharanthus roseus, features a pentacyclic framework with three stereocenters. As a key structural fragment of the anticancer drugs vinblastine and its analogue vincristine, its complex and unique chemical architecture has made it a hotspot in synthetic studies. In recent years, its complete biosynthetic pathway has been elucidated and functionally reconstructed in heterologous systems, such as yeast and Nicotiana benthamiana. Since 1969, 18 research groups have reported chemical syntheses of catharanthine, encompassing racemic, asymmetric, and biomimetic syntheses, as well as various transition-metal-catalyzed approaches. This review chronologically summarizes the advances in both the biosynthesis and chemical synthesis of catharanthine and offers perspectives on future research directions.

Key words: catharanthine, indole alkaloid, biosynthesis, total synthesis

引用此文

王雪倩, 段宝忠, 田红畅, 张磊. 吲哚生物碱Catharanthine合成研究进展[J]. 有机化学, 2026, 46(3): 725-742.

Xueqian Wang, Baozhong Duan, Hongchang Tian, Lei Zhang. Research Progress in Synthesis of Indole Alkaloid Catharanthine[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 725-742.

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图/表 23

图1. 长春质碱的结构

Figure 1. Structures of catharanthine

图式1. Catharanthine的生源合成途径

Scheme 1. Biosynthesis route of Catharanthine GES, Geraniol synthase; G8H, Geraniol 8-hydroxylase; CPR, Cytochrome P450 reductase; GOR, 8-Hydroxygeraniol oxidoreductase; ISY, Isopiperitenone synthase; MLPL, Monoterpenyl phosphate phosphatase; IO, Iridoid oxidase; CYPADH2, Cytochrome P450-dependent alcohol dehydrogenase 2; 7DLGT, 7-Deoxyloganic acid glucosyltransferase; LAMT, Loganic acid O-methyl-transferase; SLS, Secologanin synthase; TDC, Tryptophan decarboxylase; STR, Strictosidine synthase; SGD, Strictosidine β-D-glucosidase; GS, Geissoschizine synthase; GO, Geissoschizine oxidase; Redox 1, Redoxase 1; Redox 2, Redoxase 2; SAT, Coronaridine-O-acetyltransferase; PAS, precondylocarpine acetate synthase; DPAS, Dihydroprecondylocarpine synthase; CS, Catharanthine synthase.

图式2. Büchi团队对(±)-Catharanthine的消旋合成路线

Scheme 2. Synthetic route to (±)-Catharanthine from the Büchi group

图式3. Kutney团队(±)-Catharanthine的合成路线

Scheme 3. Synthetic route to (±)-Catharanthine from the Kutney group

图式4. Trost团队对(±)-Catharanthine的形式合成路线

Scheme 4. Synthetic route to (±)-Catharanthine from the Trost group

图式5. Beisler团队对(±)-Catharanthine的形式合成路线

Scheme 5. Formal synthetic route to (±)-Catharanthine from the Beisler group

图式6. Tmanishi团队对(±)-Catharanthine的合成路线

Scheme 6. Synthetic route to (±)-Catharanthine from the Tmanishi group

图式7. Das团队对(±)-Catharanthine的仿生合成路线

Scheme 7. Biomimetic synthesis of (±)-Catharanthine by the Das group

图式8. Raucher团队对(±)-Catharanthine的全合成路线

Scheme 8. Total synthesis of (±)-Catharanthine by the Raucher group

图式9. 1986年Kuehne团队的(±)-Catharanthine合成路线

Scheme 9. Synthesis of (±)-Catharanthine by the Kuehne group in 1986

图式10. 2008年Kuehne团队对(±)-Catharanthine的选择性合成路线

Scheme 10. Selective synthesis of (±)-Catharanthine by the Kuehne group in 2008

图式11. Szántay团队对(＋)-Catharanthine的不对称合成路线

Scheme 11. Asymmetric synthesis of (＋)-Catharanthine by the Szántay group

图式12. Fukuyam团队对(±)-Catharanthine的立体控制全合成路线

Scheme 12. Stereocontrolled total synthesis of (±)-Catharanthine by the Fukuyam group

图式13. Doris团队对(＋)-Catharanthine的形式合成路线

Scheme 13. Formal synthesis of (＋)-Catharanthine by the Doris group

图式14. Oguri团队对(－)-Catharanthine的不对称合成路线

Scheme 14. Asymmetric synthesis of (－)-Catharanthine by the Oguri group

图式15. 2014年Ishihara团队对(－)-Catharanthine的形式合成路线

Scheme 15. Formal synthesis of (－)-Catharanthine by the Ishihara group in 2014

图式16. 2015年Ishihara团队对(＋)-Catharanthine的不对称合成路线

Scheme 16. Asymmetric synthesis of (＋)-Catharanthine by the Ishihara group in 2025

图式17. 罗佗平团队对(＋)-Catharanthine的形式合成路线

Scheme 17. Formal synthesis of (＋)-Catharanthine by the Tuopin Luo group

图式18. Batey团队对(＋)-Catharanthine的全合成路线

Scheme 18. Total synthesis of (＋)-Catharanthine by the Batey Group

图式19. Nemoto团队对(＋)-Catharanthine的不对称合成路线

Scheme 19. Asymmetric synthesis of (＋)-Catharanthine by the Nemoto group

图式20. Dixon团队对(±)-Catharanthine合成路线

Scheme 20. Synthesis of (±)-Catharanthine by the Dixon group

图式21. Gröger团队对(－)-Catharanthine对映选择性合成路线

Scheme 21. Enantioselective synthesis of (－)-Catharanthine by the Gröger group

Entry	Research group	Year	(±/＋/－)-Catharanthine	Steps	Yield/%	Reference
1	Büchiʼ group	1969	(±)-Catharanthine	17	1.4	[19]
2	Kutneyʼ group	1975	(±)-Catharanthine	12	<1	[20]
3	Trostʼ group	1979	(±)-Catharanthine	12	13	[22]
4	Beislerʼ group	1980	(±)-Catharanthine	14	<1	[23]
5	Tmanishiʼ group	1980	(±)-Catharanthine	19	<1	[26]
6	Dasʼ group	1981	(±)-Catharanthine	10	1.4	[27]
7	Raucherʼ group	1985	(±)-Catharanthine	10	13	[29]
8	Kuehneʼ group	1986	(±)-Catharanthine	9	11	[30a]
9	Kuehneʼ group	2008	(±)-Catharanthine	12	2.6	[30b]
10	Szántayʼ group	1990	(＋)-Catharanthine	9	6.3	[31]
11	Fukuyamaʼ group	1999	(±)-Catharanthine	13	12.4	[32a]
12	Dorisʼ group	2006	(＋)-Catharanthine	24	<1	[33]
13	Oguriʼ group	2013	(－)-Catharanthine	10	3.2	[34]
14	Ishiharaʼ group	2014	(－)-Catharanthine	17	<1	[35]
15	Ishiharaʼ group	2015	(＋)-Catharanthine	19	<1	[36]
16	Tuoping Luoʼ group	2016	(＋)-Catharanthine	13	<1	[37]
17	Bateyʼ group	2018	(＋)-Catharanthine	15	<1	[39]
18	Nemotoʼ group	2019	(＋)-Catharanthine	27	<1	[40]
19	Dixonʼ group	2021	(±)-Catharanthine	5	2.1	[42]
20	Grögerʼ group	2023	(－)-Catharanthine	22	<1	[43]

表1. Catharanthine的全合成研究工作总结

Table 1. Summary of total synthesis of Catharanthine

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吲哚生物碱Catharanthine合成研究进展

Research Progress in Synthesis of Indole Alkaloid Catharanthine

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