汉麻黄酮类成分研究进展

doi:10.11924/j.issn.1000-6850.casb2020-0480

中国农学通报 ›› 2021, Vol. 37 ›› Issue (17): 120-128.doi: 10.11924/j.issn.1000-6850.casb2020-0480

• 食品·营养·检测·安全 • 上一篇下一篇

汉麻黄酮类成分研究进展

姜硕¹^,²(), 万璐¹^,², 许哲祥¹^,², 闫佳佳¹^,², 郑春英¹^,²()

¹黑龙江大学农业微生物技术教育部工程研究中心,哈尔滨 150500
²黑龙江大学生命科学学院/黑龙江省普通高校微生物重点实验室,哈尔滨 150080

收稿日期:2020-09-20 修回日期:2020-12-08 出版日期:2021-06-15 发布日期:2021-06-29
通讯作者: 郑春英
作者简介:姜硕,女,1997年出生,黑龙江大庆人,硕士研究生,研究方向：食品和药物生物活性挖掘及研发。通信地址：150080 黑龙江省哈尔滨市南岗区学府路74号黑龙江大学生命科学学院,Tel：0451-86608586,E-mail：2535794649@qq.com。
基金资助:
黑龙江省现代农业产业技术协同创新体系项目“麻类食品与药物研发协同创新项目”(YYM19STX-1)

Research Progress on Flavonoids of Cannabis sativa L

Jiang Shuo¹^,²(), Wan Lu¹^,², Xu Zhexiang¹^,², Yan Jiajia¹^,², Zheng Chunying¹^,²()

¹Engineering Research Center of Agricultural Microbiology Technology, Ministry of Education, Heilongjiang University, Harbin 150500
²Key Laboratory of Microbiology, College of Heilongjiang Province/School of Life Sciences, Heilongjiang University, Harbin 150080

Received:2020-09-20 Revised:2020-12-08 Online:2021-06-15 Published:2021-06-29
Contact: Zheng Chunying

摘要/Abstract

摘要：

为了高效利用汉麻黄酮类成分及系统开展汉麻黄酮类化合物的研究,本文综述了汉麻黄酮类化合物的结构、合成途径、生物活性及分析方法。归纳总结出汉麻中共含有26种黄酮类化合物,其主要结构类型以黄酮和黄酮醇为主;此外,在黄酮类化合物经典合成途径的基础上,明确了2种特征性汉麻黄酮成分-大麻黄素A和大麻黄素B的生物合成途径;同时,也总结了汉麻黄酮类化合物具有抗肿瘤、神经保护、抗抑郁等生物活性,并针对其结构特点和活性作用,建立了汉麻黄酮类化合物高效、快速的分析方法为LC-MS等功效。上述归纳可为开展汉麻黄酮类化合物的研究及应用提供参考。

关键词: 汉麻, 黄酮类化合物, 结构, 生物活性, 合成途径, 分析方法

Abstract:

To efficiently utilize the flavonoids of Cannabis sativa L and systematically carry out research on flavonoids of Cannabis sativa L, in this study, the structures, synthesis pathways, biological activities and analysis methods of flavonoids of Cannabis sativa L were reviewed. The results showed that 26 flavonoids compounds of Cannabis sativa L were contained in the Cannabis sativa L, and the main structure types of these flavonoids compounds were flavonoids and flavonols. Moreover, based on the classical synthetic pathway of flavonoids, the biosynthesis pathway of cannflavins A and cannflavins B, which were the characteristic flavonoids of Cannabis sativa L., were identified. Meanwhile, the biological activities of Cannabis sativa L, such as anti-tumor, neuroprotective, antidepressant and so on, were also summarized. According to the structural characteristics and biological activities, LC-MS was established as the efficient and rapid method to analyze the flavonoids in Cannabis sativa L. The study could provide certain reference for the research and application of the flavonoids in Cannabis sativa L.

Key words: Cannabis sativa L, flavonoids, structure, biological activity, synthetic pathway, analysis method

中图分类号:

R931

姜硕, 万璐, 许哲祥, 闫佳佳, 郑春英. 汉麻黄酮类成分研究进展[J]. 中国农学通报, 2021, 37(17): 120-128.

Jiang Shuo, Wan Lu, Xu Zhexiang, Yan Jiajia, Zheng Chunying. Research Progress on Flavonoids of Cannabis sativa L[J]. Chinese Agricultural Science Bulletin, 2021, 37(17): 120-128.

图/表 4

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序号	名称	分子式	结构式	文献来源
1	芹菜素 (Apigenin)	C₁₅H₁₀O₅		Delgado, et al.^[21]
2	槲皮素 (Quercetin)	C₁₅H₁₀O₇		Delgado, et al.^[21]
3	槲皮素-3-半乳糖苷 (Quercetin-3-galactoside)	C₂₁H₂₀O₁₂		Delgado, et al.^[21]
4	山奈酚-7-O-葡萄糖苷 (Kaempferol-7-O-glucoside)	C₂₁H₂₀O₁₀		Delgado, et al.^[21]
5	原花青素B₂ (Procyanidin B₂)	C₃₀H₂₆O₁₂		Delgado, et al.^[21]
6	牡荆素-2"-O-α-L-鼠李糖苷 (vitexin-2"-O-α-L-rhamnoside)	C₂₇H₃₀O₁₄		Delgado, et al.^[21]
7	异荭草素 (Luteolin-6-C-glucoside)	C₂₁H₂₀O₁₁		Delgado, et al.^[21]
序号	名称	分子式	结构式	文献来源
8	香叶木素 (Diosmetin)	C₁₆H₁₂O₆		Delgado, et al.^[21]
9	牡荆素 (Vitexin)	C₂₁H₂₀O₁₀		Delgado, et al.^[21]
10	大麻黄素C (Cannflavin C)	C₂₆H₂₈O₆		Radwan, et al.^[24]
11	异戊烯基芹菜素 (6-Prenylapigenin)	C₂₀H₁₈O₅		Radwan, et al.^[24]
12	金圣草黄素 (Chrysoeriol)	C₁₆H₁₂O₆		Kevin, et al.^[25]
13	大麻黄素A (Cannflavin A)	C₂₆H₂₈O₆		Kevin, et al.^[25]
14	大麻黄素B (Cannflavin B)	C₂₁H₂₀O₆		Kevin, et al.^[25]
15	木犀草素 (Luteolin)	C₁₅H₁₀O₆		Kevin, et al.^[25]
16	芹菜素7-O-葡萄糖苷 (Apigenin 7-O-glucoside)	C₂₁H₂₀O₁₀		成亮,等.^[26]
17	木犀草素-7-O-β-D-吡喃葡萄糖苷 (Luteolin-7-O-β-D-glucopyranoside)	C₂₁H₂₀O₁₁		成亮,等.^[26]
18	芦丁 (Rutin)	C₂₇H₃₀O₁₆		成亮,等.^[26]
序号	名称	分子式	结构式	文献来源
19	槲皮素-3-O-α-L-鼠李糖苷 (Quercetin-3-O-α-L-rhamnoside)	C₂₇H₃₀O₁₆		成亮,等.^[26]
20	芹菜素-6,8-二-C-β-D-吡喃葡萄糖苷 (Apigenin-6,8-di-C-β-D-glucopyranoside)	C₂₇H₃₀O₁₆		成亮,等.^[26]
21	山奈酚-3-O-α-L-鼠李糖苷 (Kaempferol-3-O-α-L-rhamnoside)	C₂₁H₂₀O₁₀		成亮, 等.^[26]
22	荭草素 (Orientin)	C₂₁H₂₀O₁₁		成亮,等.^[26]
23	异牡荆素 (Isovitexi)	C₂₁H₂₀O₁₀		Amany, et al.^[27]

序号	名称	分子式	结构式	文献来源
1	芹菜素 (Apigenin)	C₁₅H₁₀O₅		Delgado, et al.^[21]
2	槲皮素 (Quercetin)	C₁₅H₁₀O₇		Delgado, et al.^[21]
3	槲皮素-3-半乳糖苷 (Quercetin-3-galactoside)	C₂₁H₂₀O₁₂		Delgado, et al.^[21]
4	山奈酚-7-O-葡萄糖苷 (Kaempferol-7-O-glucoside)	C₂₁H₂₀O₁₀		Delgado, et al.^[21]
5	原花青素B₂ (Procyanidin B₂)	C₃₀H₂₆O₁₂		Delgado, et al.^[21]
6	牡荆素-2"-O-α-L-鼠李糖苷 (vitexin-2"-O-α-L-rhamnoside)	C₂₇H₃₀O₁₄		Delgado, et al.^[21]
7	异荭草素 (Luteolin-6-C-glucoside)	C₂₁H₂₀O₁₁		Delgado, et al.^[21]
序号	名称	分子式	结构式	文献来源
8	香叶木素 (Diosmetin)	C₁₆H₁₂O₆		Delgado, et al.^[21]
9	牡荆素 (Vitexin)	C₂₁H₂₀O₁₀		Delgado, et al.^[21]
10	大麻黄素C (Cannflavin C)	C₂₆H₂₈O₆		Radwan, et al.^[24]
11	异戊烯基芹菜素 (6-Prenylapigenin)	C₂₀H₁₈O₅		Radwan, et al.^[24]
12	金圣草黄素 (Chrysoeriol)	C₁₆H₁₂O₆		Kevin, et al.^[25]
13	大麻黄素A (Cannflavin A)	C₂₆H₂₈O₆		Kevin, et al.^[25]
14	大麻黄素B (Cannflavin B)	C₂₁H₂₀O₆		Kevin, et al.^[25]
15	木犀草素 (Luteolin)	C₁₅H₁₀O₆		Kevin, et al.^[25]
16	芹菜素7-O-葡萄糖苷 (Apigenin 7-O-glucoside)	C₂₁H₂₀O₁₀		成亮,等.^[26]
17	木犀草素-7-O-β-D-吡喃葡萄糖苷 (Luteolin-7-O-β-D-glucopyranoside)	C₂₁H₂₀O₁₁		成亮,等.^[26]
18	芦丁 (Rutin)	C₂₇H₃₀O₁₆		成亮,等.^[26]
序号	名称	分子式	结构式	文献来源
19	槲皮素-3-O-α-L-鼠李糖苷 (Quercetin-3-O-α-L-rhamnoside)	C₂₇H₃₀O₁₆		成亮,等.^[26]
20	芹菜素-6,8-二-C-β-D-吡喃葡萄糖苷 (Apigenin-6,8-di-C-β-D-glucopyranoside)	C₂₇H₃₀O₁₆		成亮,等.^[26]
21	山奈酚-3-O-α-L-鼠李糖苷 (Kaempferol-3-O-α-L-rhamnoside)	C₂₁H₂₀O₁₀		成亮, 等.^[26]
22	荭草素 (Orientin)	C₂₁H₂₀O₁₁		成亮,等.^[26]
23	异牡荆素 (Isovitexi)	C₂₁H₂₀O₁₀		Amany, et al.^[27]

序号	方法	条件	文献来源
1	HPLC-UV (梯度洗脱)	流动相：溶剂A：水(0.1%TFA);溶剂B：水-乙腈(65:35,TFA 0.1%) 溶剂C：乙腈;检测波长：254 nm	Wieland, et al^[46]
2	HPLC-MS (梯度洗脱)	流动相：溶剂A：5%乙腈-0.1% FA;溶剂B：乙腈-5%水-0.1% FA; 离子源：电喷雾离子源(ESI);检测方式：正负离子模式检测	Delgado, et al^[21]
3	HPLC-MS (梯度洗脱)	流动相：溶剂A：1%甲酸-水;溶剂B：5%乙腈-甲醇; 离子源：大气压电喷雾离子源(API-ESI);检测方式：正离子模式检测	Vanhoenacke, et al^[50]

序号	方法	条件	文献来源
1	HPLC-UV (梯度洗脱)	流动相：溶剂A：水(0.1%TFA);溶剂B：水-乙腈(65:35,TFA 0.1%) 溶剂C：乙腈;检测波长：254 nm	Wieland, et al^[46]
2	HPLC-MS (梯度洗脱)	流动相：溶剂A：5%乙腈-0.1% FA;溶剂B：乙腈-5%水-0.1% FA; 离子源：电喷雾离子源(ESI);检测方式：正负离子模式检测	Delgado, et al^[21]
3	HPLC-MS (梯度洗脱)	流动相：溶剂A：1%甲酸-水;溶剂B：5%乙腈-甲醇; 离子源：大气压电喷雾离子源(API-ESI);检测方式：正离子模式检测	Vanhoenacke, et al^[50]

汉麻黄酮类成分研究进展

Research Progress on Flavonoids of Cannabis sativa L

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