Coumarin Compounds of Genus Heracleum L. and Their Bioactivity: A Review

doi:10.11924/j.issn.1000-6850.casb2023-0299

Abstract

Abstract:

To provide a reference for the in-depth research and utilization of coumarin compounds in the genus Heracleum, this review summarized the types and chemical structures of the identified coumarin compounds in the genus Heracleum, concluded the research progress in aspects of anti-bacteria, anti-oxidation, anti-cell proliferation, anti-inflammation, toxicity, etc, and comparatively analyzed the difference between relevant domestic and foreign researches. It revealed the diversity of coumarin compounds in the genus Heracleum and their values in medical and food industries. It proposed during the drug development process, there are problems, such as the research in its function is not deep or systemic enough, active ingredients are unclear, etc. It suggested fortifying research on its toxicity and efficacy and promoting the development and utilization of the genus Heracleum as a plant resource for foods and medicine.

Key words: genus Heracleum, coumarin compounds, bioactivities, plant utilization

PAN Yan, FAN Lili, SUN Haixia, SUN Yan, LI Sining. Coumarin Compounds of Genus Heracleum L. and Their Bioactivity: A Review[J]. Chinese Agricultural Science Bulletin, 2023, 39(29): 14-23.

Figures/Tables 2

References 82

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编号		拉丁学名（中文名）	化合物中英文名称									化学式			提取部位				参考文献
1		H. brunonis （阔翅芹）	Isopsoralen					异补骨脂素				C₁₁H₆O₃			根				[20]
			Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[20]
			Isopimpinellin					异茴芹内酯				C₁₃H₁₀O₅			根				[20]
			Pimpinellin					茴芹内酯				C₁₃H₁₀O₅			根				[20]
			Xanthotoxin					花椒毒素				C₁₂H₈O₄			根				[20]
2		H. candicans （白亮独活）	Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[21]
			Candinol A					白亮素A				C₂₁H₁₆O₆			根				[22]
			Candibirin A					白亮二聚香豆素A				C₃₂H₂₈O₁₀			根				[23]
			Canditririn A					白亮三聚香豆素A				C₄₈H₄₂O₁₅			根				[22]
			Canditetrarin A					白亮四聚香豆素A				C₆₄H₅₈O₂₁			根				[24]
			Candinoside A					白亮糖苷A				C₃₈H₄₀O₁₆			根				[25]
			Psoralen					补骨脂素				C₁₁H₆O₃			根				[24]
3		H. canescens （灰白独活）	Alloimperatorin					别欧前胡素				C₁₆H₁₄O₄			根				[26]
			Alloisoimperatorin					别异欧前胡素				C₁₆H₁₄O₄			根				[26]
			Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[26]
			Isogosferol					异栓翅芹醇				C₁₆H₁₄O₅			根				[26]
			Osthol					蛇床子素				C₁₅H₁₆O₃			根				[26]
			Psoralen					补骨脂素				C₁₁H₆O₃			根				[26]
			Xanthotoxin					花椒毒素				C₁₂H₈O₄			根				[26]
4		H. crenatifolium	Isobergapten					异佛手苷内酯				C₁₂H₈O₄			果实				[27]
			Isopimpinellin					异茴芹内酯				C₁₃H₁₀O₅			果实				[27]
			Pimpinellin					茴芹内酯				C₁₃H₁₀O₅			果实				[27]
			Sphondin					牛防风素				C₁₂H₈O₄			果实				[27]
5		H. dissectum （兴安独活）			Imperatorin		欧前胡素			C₁₆H₁₄O₄			根			[5]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			根			[5]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			根			[5]
					Apterin		醚菌酯			C₂₀H₂₄O₁₀			根			[5]
					Bergapten		佛手苷内酯			C₁₂H₈O₄			根			[5]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			根			[14]
6		H. grandiflorum			Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			地上部分			[28]
					Marmesin		异紫花前胡苷			C₁₄H₁₄O₄			地上部分			[28]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			地上部分			[28]
					Psoralen		补骨脂素			C₁₁H₆O₃			地上部分			[28]
					Scopoletin		东莨菪素			C₁₀H₈O₄			地上部分			[28]
					Umbelliferone		伞形酮			C₉H₆O₃			地上部分			[28]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			地上部分			[28]
7		H. leskovii			Isopsoralen		异补骨脂素			C₁₁H₆O₃			果实			[29]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			果实			[29]
					Isoimperatorin		异欧前胡素			C₁₆H₁₄O₄			果实			[29]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			果实			[29]
					Umbelliferone		伞形酮			C₉H₆O₃			果实			[29]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			果实			[29]
8		H. mantegazzianum （巨型猪草）			Bergapten		佛手苷内酯			C₁₂H₈O₄			果实			[18]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			果实			[18]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			果实			[18]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			果实			[18]
					Limettin		柠檬内酯			C₁₁H₁₀O₄			果实			[18]
					Phellopterin		珊瑚菜内酯			C₁₇H₁₆O₅			果实			[18]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			果实			[18]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			果实			[18]
9		H. maximum （川白芷）			Bergapten		佛手苷内酯			C₁₂H₈O₄			全株			[30-31]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			全株			[31]
					Isoimperatorin		异欧前胡素			C₁₆H₁₄O₄			全株			[31]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			根			[30]
					Isobergapten		异佛手苷内酯			C₁₂H₈O₄			根			[30]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			根			[30]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			根			[30]
					Sphondin		牛防风素			C₁₂H₈O₄			根			[30]
10		H. moellendorfﬁi （短毛独活）			Geijerin		吉枝素			C₁₅H₁₅O₄			叶			[32]
					Isobergapten		异佛手苷内酯			C₁₂H₈O₄			叶			[32]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			叶			[32]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			叶			[32]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			叶			[32]
11	H. orphanidis		Bergapten						佛手苷内酯		C₁₂H₈O₄		地上部分、根				[33]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		地上部分、根				[33]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		地上部分、根				[33]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		地上部分、根				[33]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分、根				[33]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		地上部分、根				[33]
12	H. pastinacifolium		Allobergapten						别佛手苷内酯		C₁₂H₈O₄		根				[34]
			Bergapten						佛手苷内酯		C₁₂H₈O₄		根				[34]
			Umbelliferone						伞形酮		C₉H₆O₃		根				[34]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		根				[34]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		根				[34]
			Osthol						蛇床子素		C₁₅H₁₆O₃		根				[34]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根				[34]
			Sphondin						牛防风素		C₁₂H₈O₄		根				[34]
13	H. persicum （波斯独活）		Isopsoralen						异补骨脂素		C₁₁H₆O₃		果实				[35]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		果实				[35]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		果实				[35]
14	H. platytaenium		Apterin						醚菌酯		C₂₀H₂₄O₁₀		地上部分				[36]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		地上部分				[36]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		地上部分				[36]
			Psoralen						补骨脂素		C₁₁H₆O₃		地上部分				[36]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分				[36]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		地上部分				[36]
15	H. rapula （鹤庆独活）		Rapultririn A						鹤庆三聚素A		C₃₃H₄₆O₁₉		根				[37]
16	H. rawianum		Allobergapten						别佛手苷内酯		C₁₂H₈O₄		地上部分				[38]
			Angelicin						异补骨脂素		C₁₁H₆O₃		地上部分				[38]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分				[38]
17	H. sibiricum （西伯利亚大猪草）		Imperatorin						欧前胡素		C₁₆H₁₄O₄		果实				[39]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		果实、根				[39-40]
			Phellopterin						珊瑚菜内酯		C₁₇H₁₆O₅		果实				[39]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根				[40]
			Sphondin						牛防风素		C₁₂H₈O₄		根				[40]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		果实				[39]
18	H. stenopterum （狭翅独活）		6-hydroxycoumurrayin						6-羟基香豆素		C₁₆H₁₈O₅		全株				[41]
19	H. transcaucasicum		Furomethoxyheraclin						呋喃甲氧基佛手苷内酯		C₁₂H₈O₄		果实				[42]
20	H. verticillatum		Bergapten						佛手苷内酯		C₁₂H₈O₄		根、叶、果实				[43]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		根、叶、果实				[43]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		根、叶、果实				[43]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根、叶、果实				[43]
			Osthol						蛇床子素		C₁₅H₁₆O₃		根、叶、果实				[43]
21		H. yunngningense （永宁独活）		Yunngnin A		永宁素A					C₁₂H₁₀O₆			根				[44]
21		H. yunngningense （永宁独活）		Yunngnoside A		永宁葡萄糖苷A					C₂₁H₁₆O₁₁			根				[44]
22		H. dulce		Bergapten		佛手苷内酯					C₁₂H₈O₄			地上部分				[45]
				Psoralen		补骨脂素					C₁₁H₆O₃			地上部分				[45]
				Xanthotoxin		花椒毒素					C₁₂H₈O₄			地上部分				[45]
23		H. nepalense （尼泊尔独活）		Bergapten		佛手苷内酯					C₁₂H₈O₄			根				[46]
24		H. sosnowskyi （索斯诺夫斯基独活）		Bergapten		佛手苷内酯					C₁₂H₈O₄			地上部分				[47]
24		H. sosnowskyi （索斯诺夫斯基独活）		Psoralen		补骨脂素					C₁₁H₆O₃			地上部分				[47]

编号		拉丁学名（中文名）	化合物中英文名称									化学式			提取部位				参考文献
1		H. brunonis （阔翅芹）	Isopsoralen					异补骨脂素				C₁₁H₆O₃			根				[20]
			Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[20]
			Isopimpinellin					异茴芹内酯				C₁₃H₁₀O₅			根				[20]
			Pimpinellin					茴芹内酯				C₁₃H₁₀O₅			根				[20]
			Xanthotoxin					花椒毒素				C₁₂H₈O₄			根				[20]
2		H. candicans （白亮独活）	Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[21]
			Candinol A					白亮素A				C₂₁H₁₆O₆			根				[22]
			Candibirin A					白亮二聚香豆素A				C₃₂H₂₈O₁₀			根				[23]
			Canditririn A					白亮三聚香豆素A				C₄₈H₄₂O₁₅			根				[22]
			Canditetrarin A					白亮四聚香豆素A				C₆₄H₅₈O₂₁			根				[24]
			Candinoside A					白亮糖苷A				C₃₈H₄₀O₁₆			根				[25]
			Psoralen					补骨脂素				C₁₁H₆O₃			根				[24]
3		H. canescens （灰白独活）	Alloimperatorin					别欧前胡素				C₁₆H₁₄O₄			根				[26]
			Alloisoimperatorin					别异欧前胡素				C₁₆H₁₄O₄			根				[26]
			Imperatorin					欧前胡素				C₁₆H₁₄O₄			根				[26]
			Isogosferol					异栓翅芹醇				C₁₆H₁₄O₅			根				[26]
			Osthol					蛇床子素				C₁₅H₁₆O₃			根				[26]
			Psoralen					补骨脂素				C₁₁H₆O₃			根				[26]
			Xanthotoxin					花椒毒素				C₁₂H₈O₄			根				[26]
4		H. crenatifolium	Isobergapten					异佛手苷内酯				C₁₂H₈O₄			果实				[27]
			Isopimpinellin					异茴芹内酯				C₁₃H₁₀O₅			果实				[27]
			Pimpinellin					茴芹内酯				C₁₃H₁₀O₅			果实				[27]
			Sphondin					牛防风素				C₁₂H₈O₄			果实				[27]
5		H. dissectum （兴安独活）			Imperatorin		欧前胡素			C₁₆H₁₄O₄			根			[5]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			根			[5]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			根			[5]
					Apterin		醚菌酯			C₂₀H₂₄O₁₀			根			[5]
					Bergapten		佛手苷内酯			C₁₂H₈O₄			根			[5]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			根			[14]
6		H. grandiflorum			Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			地上部分			[28]
					Marmesin		异紫花前胡苷			C₁₄H₁₄O₄			地上部分			[28]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			地上部分			[28]
					Psoralen		补骨脂素			C₁₁H₆O₃			地上部分			[28]
					Scopoletin		东莨菪素			C₁₀H₈O₄			地上部分			[28]
					Umbelliferone		伞形酮			C₉H₆O₃			地上部分			[28]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			地上部分			[28]
7		H. leskovii			Isopsoralen		异补骨脂素			C₁₁H₆O₃			果实			[29]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			果实			[29]
					Isoimperatorin		异欧前胡素			C₁₆H₁₄O₄			果实			[29]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			果实			[29]
					Umbelliferone		伞形酮			C₉H₆O₃			果实			[29]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			果实			[29]
8		H. mantegazzianum （巨型猪草）			Bergapten		佛手苷内酯			C₁₂H₈O₄			果实			[18]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			果实			[18]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			果实			[18]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			果实			[18]
					Limettin		柠檬内酯			C₁₁H₁₀O₄			果实			[18]
					Phellopterin		珊瑚菜内酯			C₁₇H₁₆O₅			果实			[18]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			果实			[18]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			果实			[18]
9		H. maximum （川白芷）			Bergapten		佛手苷内酯			C₁₂H₈O₄			全株			[30-31]
					Imperatorin		欧前胡素			C₁₆H₁₄O₄			全株			[31]
					Isoimperatorin		异欧前胡素			C₁₆H₁₄O₄			全株			[31]
					Isopsoralen		异补骨脂素			C₁₁H₆O₃			根			[30]
					Isobergapten		异佛手苷内酯			C₁₂H₈O₄			根			[30]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			根			[30]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			根			[30]
					Sphondin		牛防风素			C₁₂H₈O₄			根			[30]
10		H. moellendorfﬁi （短毛独活）			Geijerin		吉枝素			C₁₅H₁₅O₄			叶			[32]
					Isobergapten		异佛手苷内酯			C₁₂H₈O₄			叶			[32]
					Isopimpinellin		异茴芹内酯			C₁₃H₁₀O₅			叶			[32]
					Pimpinellin		茴芹内酯			C₁₃H₁₀O₅			叶			[32]
					Xanthotoxin		花椒毒素			C₁₂H₈O₄			叶			[32]
11	H. orphanidis		Bergapten						佛手苷内酯		C₁₂H₈O₄		地上部分、根				[33]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		地上部分、根				[33]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		地上部分、根				[33]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		地上部分、根				[33]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分、根				[33]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		地上部分、根				[33]
12	H. pastinacifolium		Allobergapten						别佛手苷内酯		C₁₂H₈O₄		根				[34]
			Bergapten						佛手苷内酯		C₁₂H₈O₄		根				[34]
			Umbelliferone						伞形酮		C₉H₆O₃		根				[34]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		根				[34]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		根				[34]
			Osthol						蛇床子素		C₁₅H₁₆O₃		根				[34]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根				[34]
			Sphondin						牛防风素		C₁₂H₈O₄		根				[34]
13	H. persicum （波斯独活）		Isopsoralen						异补骨脂素		C₁₁H₆O₃		果实				[35]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		果实				[35]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		果实				[35]
14	H. platytaenium		Apterin						醚菌酯		C₂₀H₂₄O₁₀		地上部分				[36]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		地上部分				[36]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		地上部分				[36]
			Psoralen						补骨脂素		C₁₁H₆O₃		地上部分				[36]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分				[36]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		地上部分				[36]
15	H. rapula （鹤庆独活）		Rapultririn A						鹤庆三聚素A		C₃₃H₄₆O₁₉		根				[37]
16	H. rawianum		Allobergapten						别佛手苷内酯		C₁₂H₈O₄		地上部分				[38]
			Angelicin						异补骨脂素		C₁₁H₆O₃		地上部分				[38]
			Sphondin						牛防风素		C₁₂H₈O₄		地上部分				[38]
17	H. sibiricum （西伯利亚大猪草）		Imperatorin						欧前胡素		C₁₆H₁₄O₄		果实				[39]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		果实、根				[39-40]
			Phellopterin						珊瑚菜内酯		C₁₇H₁₆O₅		果实				[39]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根				[40]
			Sphondin						牛防风素		C₁₂H₈O₄		根				[40]
			Xanthotoxin						花椒毒素		C₁₂H₈O₄		果实				[39]
18	H. stenopterum （狭翅独活）		6-hydroxycoumurrayin						6-羟基香豆素		C₁₆H₁₈O₅		全株				[41]
19	H. transcaucasicum		Furomethoxyheraclin						呋喃甲氧基佛手苷内酯		C₁₂H₈O₄		果实				[42]
20	H. verticillatum		Bergapten						佛手苷内酯		C₁₂H₈O₄		根、叶、果实				[43]
			Isobergapten						异佛手苷内酯		C₁₂H₈O₄		根、叶、果实				[43]
			Isopimpinellin						异茴芹内酯		C₁₃H₁₀O₅		根、叶、果实				[43]
			Pimpinellin						茴芹内酯		C₁₃H₁₀O₅		根、叶、果实				[43]
			Osthol						蛇床子素		C₁₅H₁₆O₃		根、叶、果实				[43]
21		H. yunngningense （永宁独活）		Yunngnin A		永宁素A					C₁₂H₁₀O₆			根				[44]
21		H. yunngningense （永宁独活）		Yunngnoside A		永宁葡萄糖苷A					C₂₁H₁₆O₁₁			根				[44]
22		H. dulce		Bergapten		佛手苷内酯					C₁₂H₈O₄			地上部分				[45]
				Psoralen		补骨脂素					C₁₁H₆O₃			地上部分				[45]
				Xanthotoxin		花椒毒素					C₁₂H₈O₄			地上部分				[45]
23		H. nepalense （尼泊尔独活）		Bergapten		佛手苷内酯					C₁₂H₈O₄			根				[46]
24		H. sosnowskyi （索斯诺夫斯基独活）		Bergapten		佛手苷内酯					C₁₂H₈O₄			地上部分				[47]
24		H. sosnowskyi （索斯诺夫斯基独活）		Psoralen		补骨脂素					C₁₁H₆O₃			地上部分				[47]