Research Progress on Flavonoids of Cannabis sativa L

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

Abstract

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

CLC Number:

R931

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.

Figures/Tables 4

References 59

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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]