薄壳山核桃酚类代谢物研究进展

doi:10.11983/CBB19008

摘要/Abstract

摘要： 薄壳山核桃(Carya illinoensis)富含酚类代谢物, 具有显著的抗氧化活性。近年来, 我国薄壳山核桃产业快速发展, 种植面积迅速扩大。明确薄壳山核桃中的酚类代谢物组成及保健功效对于促进健康产业发展具有重要意义。迄今为止, 从薄壳山核桃中已检测出酚类代谢物67个, 其中包括单宁36个、类黄酮22个、酚酸9个, 水解后检测出酚类代谢物苷元34个。该文主要对薄壳山核桃酚类代谢物的组成、提取方法、含量、药理活性及与采后贮藏特性的关系进行综述, 以期为今后深入研究薄壳山核桃酚类代谢物与其生理活性的关系及挖掘薄壳山核桃酚类代谢物的保健价值提供依据。

关键词: 薄壳山核桃, 酚类, 代谢物, 研究进展

Abstract: Pecan (Carya illinoensis) is enriched in phenolic metabolites, which have significant antioxidant activity. In recent years, the pecan industry has developed rapidly in China, with drastic increase of planting area. It is of great significance to clarify the composition and health benefits of phenolic metabolites in pecan for promoting the healthy development of the industry. So far, a total of 67 phenolic metabolites have been detected from pecan, including 36 tannins, 22 flavonoids, and 9 phenolic acids. And 34 phenolic metabolite aglycones have been detected after hydrolysis. This paper summarizes the recent progresses in the composition, extraction method, content, pharmacological activity, and relationship with postharvest of phenolic metabolites in pecan. These data are of great significance to further study the relationship between the phenolic metabolites and their physiological activities, and explore the health benefits of the phenolic metabolites in pecan.

Key words: Carya illinoensis, phenolic, metabolite, advances

贾晓东,许梦洋,莫正海,宣继萍,翟敏,郭忠仁. 薄壳山核桃酚类代谢物研究进展. 植物学报, 2020, 55(1): 106-119.

Xiaodong Jia,Mengyang Xu,Zhenghai Mo,Jiping Xuan,Min Zhai,Zhongren Guo. Recent Advances in Phenolic Metabolites in Pecan. Chinese Bulletin of Botany, 2020, 55(1): 106-119.

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.chinbullbotany.com/CN/10.11983/CBB19008

https://www.chinbullbotany.com/CN/Y2020/V55/I1/106

图/表 5

参考文献 58

[1]	李珊珊, 吴倩, 袁茹玉, 邵帅, 张会金, 王亮生 (2014). 莲属植物类黄酮代谢产物的研究进展. 植物学报 49, 738-750.
[2]	柳鎏, 孙醉君 (1986). 中国重要经济树种. 南京: 江苏科学技术出版社. pp. 78-89.
[3]	罗会婷, 贾晓东, 翟敏, 宣继萍, 张计育, 王刚, 贾展慧, 黄胜男, 郭忠仁, 翁文昕 (2017). 薄壳山核桃营养成分的研究进展. 中国农学通报 33(8), 39-46.
[4]	裴东, 鲁新政 (2011). 中国核桃种质资源. 北京: 中国林业出版社. pp. 41-43.
[5]	石碧, 狄莹 (2000). 植物多酚. 北京: 科学出版社. pp. 5-18.
[6]	孙达旺 (1992). 植物单宁化学. 北京: 中国林业出版社. pp. 3.
[7]	Abdallah HM, Salama MM, Abd-Elrahman EH, El-Maraghy SA (2011). Antidiabetic activity of phenolic compounds from pecan bark in streptozotocin-induced diabetic rats. Phytochem Lett 4, 337-341.
[8]	Alasalvar C, Shahidi F (2009). Natural antioxidants in tree nuts. Eur J Lipid Sci Technol 111, 1056-1062.
[9]	Anzaldúa-Morales A, Brusewitz GH, Anderson JA (1999). Pecan texture as affected by freezing rates, storage temperature, and thawing rates. J Food Sci 64, 332-335.
[10]	Blomhoff R, Carlsen MH, Andersen LF, Jacobs Jr DR (2006). Health benefits of nuts: potential role of antioxidants. Br J Nutr 96, S52-S60.
[11]	Bonner FT, Karrfalt RP (2008). The Woody Plant Seed Manual. Washington: Government Printing Office. pp. 333.
[12]	Chun OK, Kim DO (2004). Consideration on equivalent chemicals in total phenolic assay of chlorogenic acid-rich plums. Food Res Int 37, 337-342.
[13]	de la Rosa LA, Alvarez-Parrilla E, Shahidi F (2011). Phenolic compounds and antioxidant activity of kernels and shells of Mexican pecan ( Carya illinoinensis). J Agric Food Chem 59, 152-162.
[14]	de la Rosa LA, Vazquez-Flores AA, Alvarez-Parrilla E, Rodrigo-Garc AJN, Medina-Campos ON, Vila-Nava A, González-Reyes S, Pedraza-Chaverri J (2014). Content of major classes of polyphenolic compounds, antioxidant, antiproliferative, and cell protective activity of pecan crude extracts and their fractions. J Funct Foods 7, 219-228.
[15]	do Prado ACP, da Silva HS, da Silveira SM, Barreto PLM, Vieira CRW, Maraschin M, Ferreira SRS, Block JM (2014). Effect of the extraction process on the phenolic compounds profile and the antioxidant and antimicrobial activity of extracts of pecan nut [Carya illinoinensis(Wangenh) C. Koch] shell. Ind Crops Prod 52, 552-561.
[16]	do Prado ACP, Manion BA, Seetharaman K, Deschamps FC, Arellano DB, Block JM (2013). Relationship between antioxidant properties and chemical composition of the oil and the shell of pecan nuts [Carya illinoinensis(Wangenh) C. Koch]. Ind Crops Prod 45, 64-73.
[17]	Domínguez-Avila JA, Alvarez-Parrilla E, López-Díaz JA, Maldonado-Mendoza IE, del Consuelo Gómez-García M, de la Rosa LA (2015). The pecan nut (Carya illinoinensis) and its oil and polyphenolic fractions differentially modulate lipid metabolism and the antioxidant enzyme activities in rats fed high-fat diets. Food Chem 168, 529-537.
[18]	Dull GEG, Kays STJ (1988). Quality and mechanical stability of pecan kernels with different packaging protocols. J Food Sci 53, 565-567.
[19]	Flores-Córdova MA, Sánchez E, Muñoz-Márquez E, Ojeda-Barrios DL, Soto-Parra JM, Preciado-Rangel P (2017). Phytochemical composition and antioxidant capacity in Mexican pecan nut. Emir J Food Agr 29, 346-350.
[20]	Gad HA, Ayoub NA, Al-Azizi MM (2007). Phenolic constituents with promising antioxidant and hepatoprotective activities from the leaves extract of Carya illinoinensis. Nat Prod Indian J 3, 151-158.
[21]	Gong Y, Pegg RB (2017). Separation of ellagitannin-rich phenolics from U.S. pecans and Chinese hickory nuts using fused-core HPLC columns and their characterization. J Agric Food Chem 65, 5810-5820.
[22]	Grauke LJ, Iqbal MJ, Reddy AS, Thompson TE (2003). Developing microsatellite DNA markers in pecan. J Am Soc Hortic Sci 128, 374-380.
[23]	Grauke LJ, Thompson TE, Young EF, Petersen HD (1998). The effect of year, cultivar, location, and storage regime on pecan kernel color. J Am Soc Hortic Sci 123, 681-686.
[24]	Grimmer HR, Parbhoo V, McGrath RM (1992). Antimutagenicity of polyphenol-rich fractions from sorghum-bicolor grain. J Sci Food Agric 59, 251-256.
[25]	Gu LW, Kelm M, Hammerstone JF, Beecher G, Cunningham D, Vannozzi S, Prior RL (2002). Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. J Agric Food Chem 50, 4852-4860.
[26]	Gu LW, Kelm MA, Hammerstone JF, Beecher G, Holden J, Haytowitz D, Gebhardt S, Prior RL (2004). Concentrations of proanthocyanidins in common foods and estimations of normal consumption. J Nutr 134, 613-617.
[27]	Heaton EK, Shewfelt AL (1976). Pecan quality effect of light exposure on kernel color and flavor. Lebensm Wiss U Technol 9, 201-206.
[28]	Hilbig J, Alves VR, Müller CMO, Micke GA, Vitali L, Pedrosa RC, Block JM (2018a). Ultrasonic-assisted extraction combined with sample preparation and analysis using LC-ESI-MS/MS allowed the identification of 24 new phenolic compounds in pecan nut shell [Carya illinoinensis(Wangenh) C. Koch] extracts. Food Res Int 106, 549-557.
[29]	Hilbig J, de Britto Policarpi P, de Souza Grinevicius VMA, Mota NSRS, Toaldo IM, Luiz MTB, Pedrosa RC, Block JM (2018b). Aqueous extract from pecan nut [Carya illinoinensis(Wangenh) C. Koch] shell show activity against breast cancer cell line MCF-7 and Ehrlich ascites tumor in Balb-C mice. J Ethnopharmacol 211, 256-266.
[30]	Holton TA, Cornish EC (1995). Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 7, 1071-1083.
[31]	Ishak MS, Ahmed AA, Abd-Alla MF, Saleh NAM (1980). Flavonol glycosides of Carya pecan. Phytochemistry 19, 2512-2513.
[32]	Jia XD, Luo HT, Xu MY, Zhai M, Guo ZR, Qiao YS, Wang LJ (2018). Dynamic changes in phenolics and antioxidant capacity during pecan (Carya illinoinensis) kernel ripening and its phenolics profiles. Molecules 23, 435.
[33]	Kays SJ (1979). Pecan kernel color changes during maturation, harvest, storage and distribution. Pecan Quart 13, 4-12, 34.
[34]	Kornsteiner M, Wagner KH, Elmadfa I (2006). Tocopherols and total phenolics in 10 different nut types. Food Chem 98, 381-387.
[35]	Lei ZT, Kranawetter C, Sumner BW, Huhman D, Wherritt DJ, Thomas AL, Rohla C, Sumner LW (2018). Metabolo- mics of two pecan varieties provides insights into scab resistance. Metabolites 8, 56.
[36]	Malik NS, Perez JL, Lombardini L, Cornacchia R, Cisneros-Zevallos L, Braford J (2009). Phenolic compounds and fatty acid composition of organic and conventional grown pecan kernels. J Sci Food Agric 89, 2207-2213.
[37]	Mo ZH, He HY, Su WC, Peng FR (2017). Analysis of differentially accumulated proteins associated with graft union formation in pecan ( Carya illinoensis). Sci Hortic 224, 126-134.
[38]	Morgan WA, Clayshulte BJ (2000). Pecans lower low density lipoprotein cholesterol in people with normal lipid levels. J Am Diet Assoc 100, 312-318.
[39]	Müller LG, Pase CS, Reckziegel P, Barcelos RCS, Boufleur N, Prado ACP, Fett R, Block JM, Pavanato MA, Bauermann LF, da Rocha JBT, Burger ME (2013). Hepatoprotective effects of pecan nut shells on ethanol-induced liver damage. Exp Toxicol Pathol 65, 165-171.
[40]	Nelson SO, Senter SD, Forbus Jr WR (1985). Dielectric and steam heating treatments for quality maintenance in stored pecans. J Microwave Power 20, 71-74.
[41]	Polles SG, Hanny BW, Harvey AJ (1981). Condensed tannins in kernels of thirty-one pecan [Carya illinoensis(Wangenh) K. Koch] cultivars. J Agric Food Chem 29, 196-197.
[42]	Rajaram S, Burke K, Connell B, Myint T, Sabaté J (2001). A monounsaturated fatty acid-rich pecan-enriched diet favorably alters the serum lipid profile of healthy men and women. J Nutr 131, 2275-2279.
[43]	Reckziegel P, Boufleur N, Barcelos RCS, Benvegnú DM, Pase CS, Muller LG, Teixeira AM, Zanella R, Prado ACP, Fett R, Block JM, Burger ME (2011). Oxidative stress and anxiety-like symptoms related to withdrawal of passive cigarette smoke in mice: beneficial effects of pecan nut shells extract, a by-product of the nut industry. Ecotoxicol Environ Saf 74, 1770-1778.
[44]	Ribeiro PCE, de Britto Policarpi P, dal Bo A, Barbetta PA, Block JM (2017). Impact of pecan nut shell aqueous extract on the oxidative properties of margarines during storage. J Sci Food Agric 97, 3005-3012.
[45]	Robbins KS, Gong Y, Wells ML, Greenspan P, Pegg RB (2015). Investigation of the antioxidant capacity and phenolic constituents of U.S. pecans. J Funct Foods 15, 11-22.
[46]	Robbins KS, Greenspan P, Pegg RB (2016). Effect of pecan phenolics on the release of nitric oxide from murine RAW 264.7 macrophage cells. Food Chem 212, 681-687.
[47]	Robbins KS, Ma YY, Wells ML, Greenspan P, Pegg RB (2014). Separation and characterization of phenolic compounds from U.S. pecans by liquid chromatography- tandem mass spectrometry. J Agric Food Chem 62, 4332-4341.
[48]	Rudolph CJ, Odell GV, Hinrichs HA, Hopfer DA, Kays SJ (1992). Genetic, environmental, and maturity effects on pecan kernel lipid, fatty acid, tocopherol, and protein composition. J Food Qual 15, 263-278.
[49]	Senter SD, Forbus Jr WR (1979). Effects of acetylated monoglyceride coatings on pecan kernel shelf-life. J Food Sci 44, 1752-1755.
[50]	Senter SD, Forbus Jr WR, Smit CJB (1978). Leucoanthocyanidin oxidation in pecan kernels: relation to discoloration and kernel quality. J Food Sci 43, 128-134.
[51]	Senter SD, Horvat RJ, Forbus Jr WR (1980). Relation between phenolic acid content and stability of pecans in accelerated storage. J Food Sci 45, 1380-1382.
[52]	Sumner LW, Amberg A, Barrett D, Beale MH, Beger R, Daykin CA, Fan TWM, Fiehn O, Goodacre R, Griffin JL, Hankemeier T, Hardy N, Harnly J, Higashi R, Kopka J, Lane AN, Lindon JC, Marriott P, Nicholls AW, Reily MD, Thaden JJ, Viant MR (2007). Proposed minimum reporting standards for chemical analysis: Chemical Analysis Working Group (CAWG) Metabolomics Standards Initiative (MSI). Metabolomics 3, 211-221.
[53]	Villarreal-Lozoya JE, Lombardini L, Cisneros-Zevallos L (2007). Phytochemical constituents and antioxidant capacity of different pecan [Carya illinoinensis(Wangenh.) K. Koch] cultivars. Food Chem 102, 1241-1249.
[54]	Woodroof JG, Heaton EK (1953). Year round on pecans by refrigerated storage. Food Engr 25, 83-85, 141.
[55]	Wu XL, Beecher GR, Holden JM, Haytowitz DB, Gebhardt SE, Prior RL (2004). Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. J Agric Food Chem 52, 4026-4037.
[56]	Yang J, Liu RH, Halim L (2009). Antioxidant and antiproliferative activities of common edible nut seeds. LWT-Food Sci Technol 42, 1-8.
[57]	Yao F, Dull G, Eitenmiller R (1992). Tocopherol quantification by HPLC in pecans and relationship to kernel quality during storage. J Food Sci 57, 1194-1197.
[58]	Zhang JY, Guo ZR, Zhang R, Li YR, Cao L, Liang YW, Huang LB (2015). Auxin type, auxin concentration, and air and substrate temperature difference play key roles in the rooting of juvenile hardwood pecan cuttings. HortTechnology 25, 209-213.

编号	名称		母核	取代基																部位			参考文献
编号	名称		母核	R1			R2			R3		R4		R5			R6			部位			参考文献
单宁-水解单宁-鞣花单宁
1	鞣花酸		A	H			H			-		H		-			-			种仁, 叶			Villarreal-Lozoya et al., 2007
2	鞣花酸六碳糖		A	hexose, H, H, H										-			-			种仁			Robbins et al., 2014
3	鞣花酸五碳糖		A	pentose, H, H, H										-			-			种仁			Robbins et al., 2014
4	鞣花酸鼠李糖		A	rhamnose, H, H, H										-			-			种仁			de la Rosa et al., 2011
5	鞣花酸芸香糖		A	rutinose, H, H, H										-			-			种仁			Jia et al., 2018
6	鞣花酰基鞣花酸葡萄糖		A	HHDP, glucose, H, H										-			-			种仁			Robbins et al., 2014
7	乙酰基鞣花酸六碳糖		A	CH₃CO, hexose, H, H										-			-			种仁			Gong and Pegg, 2017
8	甲基鞣花酸		A	CH₃, H, H, H										-			-			种仁			de la Rosa et al., 2011
9	甲基鞣花酸六碳糖		A	CH₃, hexose, H, H										-			-			种仁			Robbins et al., 2014
10	甲基鞣花酸五碳糖		A	CH₃, pentose, H, H										-			-			种仁			Robbins et al., 2014
11	二甲基鞣花酸		A	CH₃, CH₃, H, H										-			-			种仁, 叶			Gad et al., 2007
12	二甲基鞣花酸六碳糖		A	CH₃, CH₃, hexose, H										-			-			种仁			Robbins et al., 2014
13	二甲基鞣花酸五碳糖		A	CH₃, CH₃, pentose, H										-			-			种仁			Robbins et al., 2014
编号	名称	母核				取代基															部位			参考文献
编号	名称	母核				R1		R2		R3			R4			R5		R6			部位			参考文献
14	鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					H			H		-			种仁			Robbins et al., 2014
15	橡椀酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-valoneoyl					H			H		-			种仁			Jia et al., 2018
16	二鞣花酰基葡萄糖	B				OH		R2-R3=(S)-HHDP					R4-R5=(S)-HHDP					-			-			Jia et al., 2018
17	鞣花酰基橡椀酰基葡萄糖	B				OH		R2-R3=(S)-HHDP/(S)-valoneoyl					R4-R5=(S)-valoneoyl/(S)-HHDP					-			-			Jia et al., 2018
单宁-水解单宁-棓单宁
18	没食子酸	C				OH		OH		OH			-			-		-			种仁, 叶			Malik et al., 2009
19	没食子酸六碳糖	C				Ohexose, OH, OH							-			-		-			种仁			de la Rosa et al., 2011
20	甲基没食子酸	C				OCH₃, OH, OH							-			-		-			种仁, 叶			Jia et al., 2018
21	乙基没食子酸	C				OCH₃CH₂, OH, OH							-			-		-			种仁			Robbins et al., 2014
22	2, 3-双没食子酰基葡萄糖	B				OH		G		G			H			H		-			种仁, 叶			Gong and Pegg, 2017
单宁-水解单宁-鞣花单宁和棓单宁混合结构
23	双没食子酰基鞣花酸	A				G, G, H, H										-		-			种仁			Robbins et al., 2014
24	没食子酰基鞣花酸五碳糖	A				G, pentose, H, H										-		-			种仁			Robbins et al., 2015
25	没食子酰基甲基鞣花酸五碳糖	A				G, pentose, CH₃, H										-		-			种仁			Robbins et al., 2014
26	没食子酰基鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					G, H					-			种仁			Gong and Pegg, 2017
27	双没食子酰基鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					G			G		-			种仁			Gong and Pegg, 2017
28	戊烯酸双内酯	-				-		-		-			-			-		-			种仁			Robbins et al., 2015
29	戊烯酸双内酯水合物	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
单宁-缩合单宁-单体黄烷及其衍生物
30	(表)儿茶素	D				H		H		H			H			H		H			种仁			Robbins et al., 2014
31	儿茶素六碳糖	D				hexose, H, H, H, H												H			种仁			Gong and Pegg, 2017
32	(表)儿茶素没食子酸酯	D				G		H		H			H			H		H			种仁			Robbins et al., 2014
33	(表)没食子儿茶素	D				H		H		H			H			H		OH			种仁			de la Rosa et al., 2011
34	(表)没食子酸儿茶素没食子酸酯	D				G		H		H			H			H		OH			种仁, 叶			Gad et al., 2007
单宁-缩合单宁-原花青素
35	原花青素的A型二聚体	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
36	原花青素的B型二聚体	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
类黄酮
37	杜鹃黄素	E				OH		OCH₃		OH			OH			OH		-			树皮			Abdallah et al., 2011
38	杜鹃黄素-3-葡萄糖苷	E				OGlu		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
39	杜鹃黄素-3-鼠李糖苷	E				ORha		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
40	杜鹃黄素-3-阿拉伯糖苷	E				OAra		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
41	杜鹃黄素-3-双葡萄糖苷	E				OGluGlu		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
42	杜鹃黄素-3-芸香糖苷	E				ORut		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
43	槲皮素	E				OH		OH		OH			OH			OH		-			叶, 树皮			Abdallah et al., 2011
44	槲皮素-3-葡萄糖苷(异槲皮苷)	E				OGlu		OH		OH			OH			OH		-			叶			Gad et al., 2007
编号	名称	母核			取代基																	部位			参考文献
编号	名称	母核			R1				R2		R3		R4		R5				R6			部位			参考文献
45	槲皮素-3-鼠李糖苷	E			ORha				OH		OH		OH		OH				-			叶			Gad et al., 2007
46	槲皮素-3-阿拉伯糖苷	E			OAra				OH		OH		OH		OH				-			叶			Ishak et al., 1980
47	槲皮素-3-半乳糖苷	E			OGal				OH		OH		OH		OH				-			叶			Ishak et al., 1980
48	槲皮素-3-(6''-没食子酰基)半乳糖苷	E			OGal-6''-G				OH		OH		OH		OH				-			叶			Gad et al., 2007
49	山核桃黄素	E			OCH₃				OCH₃		OH		OH		OH				-			树皮			Abdallah et al., 2011
50	山核桃黄素-3'-/4'-葡萄糖苷	E			OCH3				OCH3		OH		OGlu/OH		OH/OGlu				-			树皮			Abdallah et al., 2011
51	山核桃黄素-3'-/4'-鼠李糖苷	E			OCH₃				OCH₃		OH		ORha/OH		OH/ORha				-			树枝			Ishak et al., 1980
52	山核桃黄素-3'-硫酸盐	E			OCH₃				OCH₃		OH		OSO₃H		OH				-			树皮			Abdallah et al., 2011
53	3'-甲氧基山核桃黄素	E			OCH₃				OCH₃		OH		OCH₃		OH				-			树皮			Abdallah et al., 2011
54	3'-甲氧基山核桃黄素- 7-葡萄糖苷	E			OCH₃				OCH₃		OGlu		OCH₃		OH				-			树皮			Abdallah et al., 2011
55	山奈酚	E			OH				OH		OH		H		OH				-			叶			Gad et al., 2007
56	3-甲氧基山奈酚	E			OCH₃				OH		OH		H		OH				-			叶			Ishak et al., 1980
57	山奈酚-3-半乳糖苷(三叶豆苷)	E			OGal				OH		OH		H		OH				-			叶			Gad et al., 2007
58	山奈酚-3-(6''-没食子酰基)半乳糖苷	E			OGal-6''-G				OH		OH		H		OH				-			叶			Gad et al., 2007
酚酸类
59	对香豆酸	F			H				OH		-		-		-				-			种仁			Senter et al., 1980
60	咖啡酸	F			OH				OH		-		-		-				-			种仁			Malik et al., 2009
61	咖啡酸六碳糖	F			OH/Ohexose				Ohexose/ OH		-		-		-				-			种仁			Malik et al., 2009
62	原儿茶酸六碳糖	C			OH/Ohexose				Ohexose/ OH		H		-		-				-			种仁, 树皮			Gong and Pegg, 2017
63	对羟基苯甲酸	C			H				OH		H		-		-				-			种仁, 叶			Gad et al., 2007
64	儿茶酚	-			-				-		-		-		-				-			种仁			Malik et al., 2009
65	原儿茶醛	-			-				-		-		-		-				-			种仁			de la Rosa et al., 2011
66	绿原酸	-			-				-		-		-		-				-			种仁			Malik et al., 2009
67	短叶苏木酚酸	-			-				-		-		-		-				-			种仁			Robbins et al., 2015

编号	名称		母核	取代基																部位			参考文献
编号	名称		母核	R1			R2			R3		R4		R5			R6			部位			参考文献
单宁-水解单宁-鞣花单宁
1	鞣花酸		A	H			H			-		H		-			-			种仁, 叶			Villarreal-Lozoya et al., 2007
2	鞣花酸六碳糖		A	hexose, H, H, H										-			-			种仁			Robbins et al., 2014
3	鞣花酸五碳糖		A	pentose, H, H, H										-			-			种仁			Robbins et al., 2014
4	鞣花酸鼠李糖		A	rhamnose, H, H, H										-			-			种仁			de la Rosa et al., 2011
5	鞣花酸芸香糖		A	rutinose, H, H, H										-			-			种仁			Jia et al., 2018
6	鞣花酰基鞣花酸葡萄糖		A	HHDP, glucose, H, H										-			-			种仁			Robbins et al., 2014
7	乙酰基鞣花酸六碳糖		A	CH₃CO, hexose, H, H										-			-			种仁			Gong and Pegg, 2017
8	甲基鞣花酸		A	CH₃, H, H, H										-			-			种仁			de la Rosa et al., 2011
9	甲基鞣花酸六碳糖		A	CH₃, hexose, H, H										-			-			种仁			Robbins et al., 2014
10	甲基鞣花酸五碳糖		A	CH₃, pentose, H, H										-			-			种仁			Robbins et al., 2014
11	二甲基鞣花酸		A	CH₃, CH₃, H, H										-			-			种仁, 叶			Gad et al., 2007
12	二甲基鞣花酸六碳糖		A	CH₃, CH₃, hexose, H										-			-			种仁			Robbins et al., 2014
13	二甲基鞣花酸五碳糖		A	CH₃, CH₃, pentose, H										-			-			种仁			Robbins et al., 2014
编号	名称	母核				取代基															部位			参考文献
编号	名称	母核				R1		R2		R3			R4			R5		R6			部位			参考文献
14	鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					H			H		-			种仁			Robbins et al., 2014
15	橡椀酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-valoneoyl					H			H		-			种仁			Jia et al., 2018
16	二鞣花酰基葡萄糖	B				OH		R2-R3=(S)-HHDP					R4-R5=(S)-HHDP					-			-			Jia et al., 2018
17	鞣花酰基橡椀酰基葡萄糖	B				OH		R2-R3=(S)-HHDP/(S)-valoneoyl					R4-R5=(S)-valoneoyl/(S)-HHDP					-			-			Jia et al., 2018
单宁-水解单宁-棓单宁
18	没食子酸	C				OH		OH		OH			-			-		-			种仁, 叶			Malik et al., 2009
19	没食子酸六碳糖	C				Ohexose, OH, OH							-			-		-			种仁			de la Rosa et al., 2011
20	甲基没食子酸	C				OCH₃, OH, OH							-			-		-			种仁, 叶			Jia et al., 2018
21	乙基没食子酸	C				OCH₃CH₂, OH, OH							-			-		-			种仁			Robbins et al., 2014
22	2, 3-双没食子酰基葡萄糖	B				OH		G		G			H			H		-			种仁, 叶			Gong and Pegg, 2017
单宁-水解单宁-鞣花单宁和棓单宁混合结构
23	双没食子酰基鞣花酸	A				G, G, H, H										-		-			种仁			Robbins et al., 2014
24	没食子酰基鞣花酸五碳糖	A				G, pentose, H, H										-		-			种仁			Robbins et al., 2015
25	没食子酰基甲基鞣花酸五碳糖	A				G, pentose, CH₃, H										-		-			种仁			Robbins et al., 2014
26	没食子酰基鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					G, H					-			种仁			Gong and Pegg, 2017
27	双没食子酰基鞣花酰基葡萄糖	B				OH		R2-R3/R4-R5=(S)-HHDP					G			G		-			种仁			Gong and Pegg, 2017
28	戊烯酸双内酯	-				-		-		-			-			-		-			种仁			Robbins et al., 2015
29	戊烯酸双内酯水合物	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
单宁-缩合单宁-单体黄烷及其衍生物
30	(表)儿茶素	D				H		H		H			H			H		H			种仁			Robbins et al., 2014
31	儿茶素六碳糖	D				hexose, H, H, H, H												H			种仁			Gong and Pegg, 2017
32	(表)儿茶素没食子酸酯	D				G		H		H			H			H		H			种仁			Robbins et al., 2014
33	(表)没食子儿茶素	D				H		H		H			H			H		OH			种仁			de la Rosa et al., 2011
34	(表)没食子酸儿茶素没食子酸酯	D				G		H		H			H			H		OH			种仁, 叶			Gad et al., 2007
单宁-缩合单宁-原花青素
35	原花青素的A型二聚体	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
36	原花青素的B型二聚体	-				-		-		-			-			-		-			种仁			Robbins et al., 2014
类黄酮
37	杜鹃黄素	E				OH		OCH₃		OH			OH			OH		-			树皮			Abdallah et al., 2011
38	杜鹃黄素-3-葡萄糖苷	E				OGlu		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
39	杜鹃黄素-3-鼠李糖苷	E				ORha		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
40	杜鹃黄素-3-阿拉伯糖苷	E				OAra		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
41	杜鹃黄素-3-双葡萄糖苷	E				OGluGlu		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
42	杜鹃黄素-3-芸香糖苷	E				ORut		OCH₃		OH			OH			OH		-			树枝			Ishak et al., 1980
43	槲皮素	E				OH		OH		OH			OH			OH		-			叶, 树皮			Abdallah et al., 2011
44	槲皮素-3-葡萄糖苷(异槲皮苷)	E				OGlu		OH		OH			OH			OH		-			叶			Gad et al., 2007
编号	名称	母核			取代基																	部位			参考文献
编号	名称	母核			R1				R2		R3		R4		R5				R6			部位			参考文献
45	槲皮素-3-鼠李糖苷	E			ORha				OH		OH		OH		OH				-			叶			Gad et al., 2007
46	槲皮素-3-阿拉伯糖苷	E			OAra				OH		OH		OH		OH				-			叶			Ishak et al., 1980
47	槲皮素-3-半乳糖苷	E			OGal				OH		OH		OH		OH				-			叶			Ishak et al., 1980
48	槲皮素-3-(6''-没食子酰基)半乳糖苷	E			OGal-6''-G				OH		OH		OH		OH				-			叶			Gad et al., 2007
49	山核桃黄素	E			OCH₃				OCH₃		OH		OH		OH				-			树皮			Abdallah et al., 2011
50	山核桃黄素-3'-/4'-葡萄糖苷	E			OCH3				OCH3		OH		OGlu/OH		OH/OGlu				-			树皮			Abdallah et al., 2011
51	山核桃黄素-3'-/4'-鼠李糖苷	E			OCH₃				OCH₃		OH		ORha/OH		OH/ORha				-			树枝			Ishak et al., 1980
52	山核桃黄素-3'-硫酸盐	E			OCH₃				OCH₃		OH		OSO₃H		OH				-			树皮			Abdallah et al., 2011
53	3'-甲氧基山核桃黄素	E			OCH₃				OCH₃		OH		OCH₃		OH				-			树皮			Abdallah et al., 2011
54	3'-甲氧基山核桃黄素- 7-葡萄糖苷	E			OCH₃				OCH₃		OGlu		OCH₃		OH				-			树皮			Abdallah et al., 2011
55	山奈酚	E			OH				OH		OH		H		OH				-			叶			Gad et al., 2007
56	3-甲氧基山奈酚	E			OCH₃				OH		OH		H		OH				-			叶			Ishak et al., 1980
57	山奈酚-3-半乳糖苷(三叶豆苷)	E			OGal				OH		OH		H		OH				-			叶			Gad et al., 2007
58	山奈酚-3-(6''-没食子酰基)半乳糖苷	E			OGal-6''-G				OH		OH		H		OH				-			叶			Gad et al., 2007
酚酸类
59	对香豆酸	F			H				OH		-		-		-				-			种仁			Senter et al., 1980
60	咖啡酸	F			OH				OH		-		-		-				-			种仁			Malik et al., 2009
61	咖啡酸六碳糖	F			OH/Ohexose				Ohexose/ OH		-		-		-				-			种仁			Malik et al., 2009
62	原儿茶酸六碳糖	C			OH/Ohexose				Ohexose/ OH		H		-		-				-			种仁, 树皮			Gong and Pegg, 2017
63	对羟基苯甲酸	C			H				OH		H		-		-				-			种仁, 叶			Gad et al., 2007
64	儿茶酚	-			-				-		-		-		-				-			种仁			Malik et al., 2009
65	原儿茶醛	-			-				-		-		-		-				-			种仁			de la Rosa et al., 2011
66	绿原酸	-			-				-		-		-		-				-			种仁			Malik et al., 2009
67	短叶苏木酚酸	-			-				-		-		-		-				-			种仁			Robbins et al., 2015

名称	结构类型	部位	参考文献
(表)没食子儿茶素	黄烷醇	种仁, 壳	da la Rosa et al., 2011; Hilbig et al., 2018a
(表)儿茶素	黄烷醇	壳	Hilbig et al., 2018a
表儿茶素没食子酸酯	缩合单宁	壳	Hilbig et al., 2018a
黄颜木素	黄烷酮	壳	Hilbig et al., 2018a
紫杉叶素	黄烷酮	壳	Hilbig et al., 2018a
槲皮素	黄酮醇	壳	Hilbig et al., 2018a
杨梅黄酮	黄酮醇	壳	Hilbig et al., 2018a
香树素	黄酮醇	壳	Hilbig et al., 2018a
圣草酚	黄烷酮	壳	Hilbig et al., 2018a
柚皮素	黄烷酮	壳	Hilbig et al., 2018a
芹菜素	黄酮	壳	Hilbig et al., 2018a
高良姜素	黄酮醇	壳	Hilbig et al., 2018a
羟甲香豆素	香豆素	壳	Hilbig et al., 2018a
没食子酸	酚酸	种仁, 壳	Senter et al., 1980; da la Rosa et al., 2011; Hilbig et al., 2018a
龙胆酸	酚酸	种仁	Senter et al., 1980
香草酸	酚酸	种仁	Senter et al., 1980
原儿茶酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
原儿茶醛	酚酸	种仁	Senter et al., 1980; da la Rosa et al., 2011
对羟基苯甲酸	酚酸	种仁	Senter et al., 1980; da la Rosa et al., 2011
对羟基苯乙酸	酚酸	种仁	Senter et al., 1980
香豆酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
丁香酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
苦杏仁酸	酚酸	壳	Hilbig et al., 2018a
绿原酸	酚酸	壳	Hilbig et al., 2018a
香兰素	酚酸	壳	Hilbig et al., 2018a
阿魏酸	酚酸	壳	Hilbig et al., 2018a
迷迭香酸	酚酸	壳	Hilbig et al., 2018a
水杨酸	酚酸	壳	Hilbig et al., 2018a
白藜芦醇	酚酸	壳	Hilbig et al., 2018a
对茴香酸	酚酸	壳	Hilbig et al., 2018a
芥子醛	酚酸	壳	Hilbig et al., 2018a
鞣花酸	酚酸	壳	da la Rosa et al., 2011; Hilbig et al., 2018a
甲基鞣花酸	酚酸	种仁	da la Rosa et al., 2011
戊烯酸双内酯	酚酸	种仁	da la Rosa et al., 2011

名称	结构类型	部位	参考文献
(表)没食子儿茶素	黄烷醇	种仁, 壳	da la Rosa et al., 2011; Hilbig et al., 2018a
(表)儿茶素	黄烷醇	壳	Hilbig et al., 2018a
表儿茶素没食子酸酯	缩合单宁	壳	Hilbig et al., 2018a
黄颜木素	黄烷酮	壳	Hilbig et al., 2018a
紫杉叶素	黄烷酮	壳	Hilbig et al., 2018a
槲皮素	黄酮醇	壳	Hilbig et al., 2018a
杨梅黄酮	黄酮醇	壳	Hilbig et al., 2018a
香树素	黄酮醇	壳	Hilbig et al., 2018a
圣草酚	黄烷酮	壳	Hilbig et al., 2018a
柚皮素	黄烷酮	壳	Hilbig et al., 2018a
芹菜素	黄酮	壳	Hilbig et al., 2018a
高良姜素	黄酮醇	壳	Hilbig et al., 2018a
羟甲香豆素	香豆素	壳	Hilbig et al., 2018a
没食子酸	酚酸	种仁, 壳	Senter et al., 1980; da la Rosa et al., 2011; Hilbig et al., 2018a
龙胆酸	酚酸	种仁	Senter et al., 1980
香草酸	酚酸	种仁	Senter et al., 1980
原儿茶酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
原儿茶醛	酚酸	种仁	Senter et al., 1980; da la Rosa et al., 2011
对羟基苯甲酸	酚酸	种仁	Senter et al., 1980; da la Rosa et al., 2011
对羟基苯乙酸	酚酸	种仁	Senter et al., 1980
香豆酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
丁香酸	酚酸	种仁, 壳	Senter et al., 1980; Hilbig et al., 2018a
苦杏仁酸	酚酸	壳	Hilbig et al., 2018a
绿原酸	酚酸	壳	Hilbig et al., 2018a
香兰素	酚酸	壳	Hilbig et al., 2018a
阿魏酸	酚酸	壳	Hilbig et al., 2018a
迷迭香酸	酚酸	壳	Hilbig et al., 2018a
水杨酸	酚酸	壳	Hilbig et al., 2018a
白藜芦醇	酚酸	壳	Hilbig et al., 2018a
对茴香酸	酚酸	壳	Hilbig et al., 2018a
芥子醛	酚酸	壳	Hilbig et al., 2018a
鞣花酸	酚酸	壳	da la Rosa et al., 2011; Hilbig et al., 2018a
甲基鞣花酸	酚酸	种仁	da la Rosa et al., 2011
戊烯酸双内酯	酚酸	种仁	da la Rosa et al., 2011

部位	溶剂	提取方法	检测方法	组分	参考文献
种仁	含0.1% HCl的甲醇	冷浸3小时	纸层析显色	初步认为含无色花色素	Senter et al., 1978
种仁	含0.1% HCl的甲醇	回流提取2小时2次, 合并浓缩后用1 mol·L^-1 HCl回流水解2小时, 乙酸乙酯萃取, 甲酯化	GC-MS	8个酚酸	Senter et al., 1980
树枝, 叶	70%乙醇	回流提取, 浓缩后聚酰胺柱反复柱层析分离	H¹-NMR, C¹³- NMR	从树枝中分离出4个类黄酮; 从叶中分离出5个类黄酮、	Ishak et al., 1980
叶	水	回流提取, 烘干, 再用乙醇提取, Sephadex LH-20柱反复柱层析分离	H¹-NMR, C¹³- NMR	1个酚酸、8个类黄酮和6个单宁	Gad et al., 2007
种仁	70%丙酮	正己烷脱脂, 匀浆, 5°C摇床振摇过夜。分别用6 mol·L^-1 HCl和8 mol·L^-1NaOH进行酸和碱水解	HPLC-DAD	4个酚类代谢物	Villarreal-Lozoya et al., 2007
种仁	80%甲醇	正己烷脱脂, 匀浆机提取30秒, 2次, 再用Sephadex LH-20小柱除杂	HPLC-DAD	8个酚酸	Malik et al., 2009
种仁	80%丙酮	正己烷脱脂, 50°C匀浆提取30分钟, 2次	HPLC-DAD, HPLC-ESI-MS	5个酚酸、2个类黄酮、5个鞣花单宁和1个棓单宁	de la Rosa et al., 2011
树皮	70%乙醇	70°C回流提取, 硅胶柱及Sephadex LH-20柱反复柱层析	H¹-NMR, C¹³- NMR	6个类黄酮和1个酚酸	Abdallah et al., 2011
种仁	丙酮:水:乙酸(70:29.5:0.5) (v/v/v)	正己烷脱脂, 50°C摇床提取30分钟, 3次, 减压回收有机溶剂, 冻干, Sephadex LH-20柱分段	HPLC-DAD, HPLC-ESI-MS/MS	27个酚类代谢物, 其中包含2个鞣花单宁、2个棓单宁和2个缩合单宁	Robbins et al., 2014
种仁	丙酮:水:乙酸(70:29.5:0.5) (v/v/v)	正己烷脱脂, 50°C摇床提取30分钟, 3次, 减压回收有机溶剂, 冻干。分别用 6 mol·L^-1 HCl和2 mol·L^-1NaOH进行酸和碱水解	HPLC-DAD, HPLC-ESI-MS/MS	水解前13个酚类代谢物, 碱水解后8个, 酸水解后9个	Robbins et al., 2015
种仁	丙酮:水:乙酸(70:29.5:0.5) (v/v/v)	正己烷脱脂, 50°C摇床提取30分钟, 3次, 减压回收有机溶剂, 冻干, Sephadex LH-20柱分段	HPLC-DAD, HPLC-ESI-Q/TOF-MS	38个酚类代谢物, 其中包含15个鞣花单宁、3个棓单宁和13个原花青素	Gong et al., 2017
种仁	80%丙酮	正己烷脱脂, 提取液冷浸过夜, 室温超声提取2小时, 2次, 50°C氮吹仪吹干, 冻干	HPLC-DAD, UPLC-ESI-Q/TOF-MS	35个酚类代谢物, 其中包含18个鞣花单宁、2个棓单宁和2个原花青素	Jia et al., 2017
壳	20%乙醇	80°C超声提取1小时, 减压回收溶剂	HPLC-ESI-MS/MS	29个酚酸苷元, 其中包含12个类黄酮和1个香豆素	Hilbig et al., 2018a