丁香属次生代谢产物及其与系统演化和地理环境的关联

doi:10.11983/CBB20178

植物学报 ›› 2021, Vol. 56 ›› Issue (4): 470-479.DOI: 10.11983/CBB20178

丁香属次生代谢产物及其与系统演化和地理环境的关联

张照宇¹^,²^,³, 王清芸⁴, 石雷³, 余文刚⁴, 张永清¹^,²^,^*(), 崔洪霞³^,^*()

¹山东中医药大学, 济南 250300
²山东省高等学校中药资源学重点实验室, 济南 250355
³中国科学院植物研究所, 北方资源植物重点实验室/北京植物园, 北京 100093

收稿日期:2020-11-11 接受日期:2021-04-19 出版日期:2021-07-01 发布日期:2021-06-30
通讯作者: 张永清,崔洪霞
作者简介:cuihongxia@ibcas.ac.cn
*E-mail: zyq622003@126.com;
基金资助:
国家自然科学基金(31370361);国家自然科学基金(31870516)

Secondary Metabolites of Syringa and the Linking with Phylogenetic Evolution and Geographical Distributions

Zhaoyu Zhang¹^,²^,³, Qingyun Wang⁴, Lei Shi³, Wengang Yu⁴, Yongqing Zhang¹^,²^,^*(), Hongxia Cui³^,^*()

¹Shandong University of Traditional Chinese Medicine, Jinan 250300, China
²Key Laboratory of Chinese Medicine Resources in Colleges and Universities of Shandong Province, Jinan 250355, China
³Key Laboratory of Plant Resources and Beijing Botanical Garden, Institute of Botany, Chinese Academy of Sciences, Beijing 100093, China 4Horticulture College, Hainan University, Haikou 570228, China

Received:2020-11-11 Accepted:2021-04-19 Online:2021-07-01 Published:2021-06-30
Contact: Yongqing Zhang,Hongxia Cui

1. 附表1 丁香属已发表的次生代谢产物信息汇总.pdf(919KB)

摘要/Abstract

摘要： 环境塑造的植物次生代谢产物富于变化, 也可能带有系统演化的信息。由于完整或具有系统学代表性的专属植物收集存在较大困难, 使得次生代谢产物与系统学的关联研究尚不多见。通过文献汇总获得了存在于丁香属(Syringa)植物根、茎、叶和花中的10类377个次生代谢产物, 主要涉及甲戊二羟酸途径、脱氧木酮糖磷酸酯途径以及莽草酸途径。在叠加丁香属的系统演化背景后发现: 在先分化的组系中特定类型次生代谢产物的优势度较高, 后继分化的组系成分优势度降低, 化学多样性呈增加趋势, 各类次生代谢产物的相对占比趋于均衡; 苯丙素类和环/裂环烯醚萜类化合物的表达具有明显的系统保守性。在叠加了地理分布跨度后发现: 部分后继分化的局域种比在先分化的广布种具有更为多样的次生代谢成分; 木脂素类成分的占比优势与环境胁迫相关。该文为化学多样性与进化的关联研究及次生代谢调控的系统性研究提供了新的启示。

关键词: 丁香属, 次生代谢产物, 系统学, 进化, 环境胁迫

Abstract: Secondary metabolites of plants induced by environmental factors are highly variable, but the given metabolic pathways may have some phylogenetic implications. Due to the difficulty in complete and systematic collections in certain plant groups, the research on the correlation between secondary metabolites and phylogeny is limited. Based on the published papers, 377 secondary metabolites in the roots, stems, leaves and flowers of Syringa were collected, which mainly derived from the mevalonic acid pathway, deoxyxylulose-5-P pathway and shikimic acid pathway. After superimposing phylogenetic background, we found that dominance of a given type of secondary metabolites was high for the firstly diverged series, and the dominance declined for subsequently diverged series with the increase of chemical diversity. Phenylpropanoids and iridoids/secoiridoids were phylogenetically conserved. After superimposing geographical distributions, we found that some local species which were lately diverged had more diverse secondary metabolites compared with widespread species firstly diverged. The high proportion of lignans was highly related to the environmental pressure. This review provided a new clue for the systematic study on the variation pattern of chemical diversity in the taxa within genus in the light of evolution.

Key words: Syringa, secondary metabolites, phylogeny, evolution, environmental stress

张照宇, 王清芸, 石雷, 余文刚, 张永清, 崔洪霞. 丁香属次生代谢产物及其与系统演化和地理环境的关联. 植物学报, 2021, 56(4): 470-479.

Zhaoyu Zhang, Qingyun Wang, Lei Shi, Wengang Yu, Yongqing Zhang, Hongxia Cui. Secondary Metabolites of Syringa and the Linking with Phylogenetic Evolution and Geographical Distributions. Chinese Bulletin of Botany, 2021, 56(4): 470-479.

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https://www.chinbullbotany.com/CN/Y2021/V56/I4/470

图/表 5

表1 已报道次生代谢成分的丁香属种质地理分布

Table 1 Geographical distributions of Syringa with secondary metabolites reported

组系	物种	自然分布	海拔(m)	经度(E)	纬度(N)	生态幅
欧丁香系 (Ser. Syringa)	欧洲丁香(S. vulgaris)	东南欧(阿尔卑斯山和喀尔巴阡山)	1000-1200	5°36'-66°10'	36°00'-67°46'	广布种
	紫丁香(S. oblata)	中国东北、华北、西北、华东和川西北	300-2400	96°23'-135°02'	34°19'-55°33'	广布种
	朝阳丁香(S. oblata var. dilatata)	中国华北-东北-朝鲜半岛	300-2400	40°51'-129°40'	33°56'-53°19'	广布种
	阿富汗丁香(S. afghanica)	中国青海-阿富汗		60°29'-74°53'	29°21'-38°27'	局域种
羽叶丁香系 (Ser. Pinnatifoliae)	羽叶丁香(S. pinnatifolia)	贺兰山、陕西南部、甘肃、青海东部和四川南部	1700-3100	105°13'-112°32'	26°03'-37°09'	局域种
短花冠管组 (Sect. Ligustrina)	暴马丁香(S. amurensis)	中国东北和西北, 俄罗斯远东地区, 朝鲜	100-1200	103°04'-163°19'	31°09'-72°33'	广布种
	日本丁香(S. reticulata)	日本北部(北海道地区)		139°20'-148°53'	40°33'-45°33'	局域种
巧玲花系 (Ser. Pubescentes)	巧玲花(S. pubescens)	河北、陕西东部、山西东部和河南	900-2100	109°29'-119°53'	31°23'-42°37'	局域种
	关东丁香(S. velutina)	辽宁和吉林长白山区	300-1200	118°53'-135°05'	38°43'-53°33'	局域种
红丁香系 (Ser. Villosae)	西蜀丁香(S. komarowii)	甘肃南部、陕西南部、四川和云南北部		105°31'-114°11'	24°20'-35°28'	局域种
	辽东丁香(S. wolfii)	中国东北, 朝鲜	500-1600	118°53'-128°28'	37°35'-72°33'	局域种

表2 丁香属组系水平的次生代谢产物类别及各类成分计数(单位: 个)

Table 2 The classification and count of secondary metabolites in Syringa at the level of series (section) (unit: number of components)

代谢产物类别	欧丁香系 (Ser. Syringa)	羽叶丁香系 (Ser. Pinnatifoliae)	短花冠管组 (Sect. Ligustrina)	巧玲花系 (Ser. Pubescentes)	红丁香系 (Ser. Villosae)
环/裂环烯醚萜	96	6	17	9	2
倍半萜	8	46	6	10	-
苯丙素	30	5	11	8	8
木脂素	5	58	8	1	5
黄酮	8	-	-	5	-
三萜	15	8	2	2	12
单萜	3	-	-	-	-
脂肪酸	3	-	-	-	-
醌类	-	2	-	-	-
生物碱	-	-	-	1	3
合计	168	125	44	36	30

表3 丁香属物种水平的次生代谢产物类别及成分计数(单位: 个)

Table 3 The classification and count of secondary metabolites in Syringa at the level of species (unit: number of compound)

代谢产物类别	欧丁香系 (Ser. Syringa)				羽叶丁香系 (Ser. Pinna tifoliae)	短花冠管组 (Sect. Ligustrina)		巧玲花系 (Ser. Pubescentes)		红丁香系 (Ser. Villosae)
	欧洲丁香 (S. vulgaris)	紫丁香 (S. ob- lata)	朝阳丁香 (S. oblata var. dilatata)	阿富汗丁香 (S. afghanica)	羽叶丁香 (S. pinnatifolia)	暴马丁香 (S. amu- rensis)	日本丁香 (S. reticulata)	关东丁香 (S. velutina)	巧玲花 (S. pubescens)	辽东丁香 (S.wolfii)	西蜀丁香 (S. komarowii)
环/裂环烯醚萜	60	16	10	20	6	13	5	7	3	-	2
倍半萜	-	6	2	-	46	6	-	-	10	-	-
苯丙素	28	3	-	-	5	6	5	7	1	-	8
木脂素	5	-	-	-	58	1	7	1	-	-	5
黄酮	5	5	-	-	-	-	-	5	-	-	-
三萜	-	14	2	-	8	2	-	2	-	2	10
单萜	-	3	-	-	-	-	-	-	-	-	-
脂肪酸	1	2	-	-	-	-	-	-	-	-	-
醌类	-	-	-	-	2	-	-	-	-	-	-
生物碱	-	-	-	-	-	-	-	1	-	-	3
合计	99	49	14	20	125	28	17	23	14	2	28

图1 丁香属组系水平的次生代谢成分相对占比色块内颜色从深到浅表示各类产物的相对数量占比从高到低的连续变化(组系内特定类别产物的相对数量占比=特定类别产物的成分计数/该组系内所有类别产物计数总和), 同一类别产物包含具有相同母核但取代基团、基团数量、基团位置和空间构象不同的化合物。热图下方的不同颜色条表示不同类别产物。为保证成分计数占比分析的客观性, 图中每个物种收入的成分信息需至少来自3篇文献。欧丁香系的阿富汗丁香及红丁香系的辽东丁香和西蜀丁香因各仅有1篇文献而暂未收入。

Figure 1 Proportion of secondary metabolites in Syringa at the level of series (section) The color in the block progressively varying from dark to light represents the continuous change in the percentage of components in the series (section) from high to low (the percentage of specific type of components in a series (section) = the number of specific type of components in a series (section)/the total number of components in this series (section)). The products of the same type include different components with the same parent nucleus but different in substituent groups, group numbers, group positions and conformations. The different color-stipes below the heatmap represent different types of products. In order to ensure the objective counting of the components, at least three reference were required for the metabolite information of each species. Therefore, the S. afghanica in Ser. Syringa as well as the S. wolfii and S. komarowii in Ser. Villosae has not been included because only one related reference was found.

图2 丁香属内组系的系统演化关系和组系中各类产物的占比及其主要代谢途径 (A) 丁香属组系的系统演化关系(Li et al., 2012)及各类产物在各组系中的占比; (B) 甲戊二羟酸途径(MVA)和脱氧木酮糖磷酸酯途径(DXP) (Mint Evolutionary Genomics Consortium, 2018); (C) 莽草酸途径(刘津等, 2016; 张旭等, 2019)。图(A)组系下方的色条表示各类产物(颜色含义同图1), 色条内的百分数指特定类别产物计数在该组系内成分计数总和中所占的百分比(详见图1图注)。图(B)和图(C)中化合物色框颜色含义与图(A)相同。图(B)和图(C)中虚线表示由多步反应完成。

Figure 2 The phylogenetic relationship of Syringa, and the percentage of metabolites and their main metabolic pathways at the level of series (section) (A) The phylogenetic relationship (Li et al., 2012) and percentage of metabolites of Syringa at the level of series (section); (B) Mevalonic acid pathway (MVA) and Deoxyxylulose-5-P pathway (DXP) (Mint Evolutionary Genomics Consortium, 2018); (C) Shikimic acid pathway (Liu et al., 2016; Zhang et al., 2019, in Chinese). The color-stripes below the series (section) indicate different types of metabolites in (A), and the percentage in the color-stripe represents the percentage of a given type of compounds within the series (section) (please see Figure 1 for details). The meanings of the color frames indicating the compound in (B) and (C) are the same as those of (A). The dotted lines in (B) and (C) represent the process of multi-step reactions.

参考文献 43

[1]	崔洪霞, 蒋高明, 臧淑英 (2004). 丁香属植物的地理分布及其起源演化. 植物研究 (02), 141-145.
[2]	董娟娥, 张康健, 梁宗锁 (2009). 植物次生代谢与调控. 杨凌: 西北农林科技大学出版社. pp. 102-119.
[3]	杜玮炜, 黄宏文 (2008). 雷公藤次生代谢产物雷公藤红素含量与环境因子相关性分析. 植物学通报 25, 707-713.
[4]	高坤, 常金科, 黎家 (2018). 植物根向水性反应研究进展. 植物学报 53, 154-163.
[5]	高艳, 崔洪霞, 石雷, 曲延英 (2008). 丁香属植物叶片表皮形态特征与环境适应及系统学关联. 西北植物学报 28, 475-484.
[6]	刘津, 于思礼, 马雅婷, 张铁军, 赵广荣 (2016). 天然木脂素的代谢工程和合成生物学研究进展. 中草药 47, 2556-2562.
[7]	刘盟盟, 贾丽, 程路芸, 张洪芹, 臧晓琳, 宝音陶格涛, 张汝民, 高岩 (2017). 冷蒿酚酸及其抗氧化防御酶活性对机械损伤的响应. 植物生态学报 41, 219-230. DOI
[8]	刘晓侠, 刘吉利, 吴娜, 相宗杰, 刘根红, 康建宏 (2015). 不同地域枸杞主要次生代谢物含量与初生代谢物含量的关系研究. 北方园艺 (23), 163-169.
[9]	苏国柱, 陈洁, 曹愿, 白睿峰, 陈苏依勒, 屠鹏飞, 柴兴云 (2015). 蒙药山沉香的化学成分和药理活性研究进展. 中国中药杂志 40, 4333-4338.
[10]	王宇希 (2013). 丁香叶总黄酮的提取工艺及抑菌效果评价. 硕士论文. 哈尔滨: 东北农业大学. pp. 8-23.
[11]	魏华, 王岩, 刘宝辉, 王雷 (2018). 植物生物钟及其调控生长发育的研究进展. 植物学报 53, 456-467.
[12]	杨然, 方磊, 李佳, 张永清 (2018). 环烯醚萜苷类生物合成途径及相关酶的研究进展. 中草药 49, 2482-2488.
[13]	藏淑英, 李容辉 (1992). 论丁香属植物引种的现状与前景. 植物学通报 (2), 30-33.
[14]	张美珍, 缪柏茂, 陆瑞林, 邱莲卿, 韦直, 李秉滔 (1992). 中国植物志, 第61卷. 北京: 科学出版社. pp. 155-156.
[15]	张旭, 王小佳, 黎思辰, 董甜甜, 汪志辉 (2019). 柑橘果实粒化过程中木质素生物合成与调控研究进展. 浙江农业学报 31, 2131-2140.
[16]	张永增 (2018). 次生代谢产物在种子植物生命之树中的分布规律. 博士论文. 昆明: 云南大学. pp. 20-44.
[17]	祝志欣, 鲁迎青 (2016). 花青素代谢途径与植物颜色变异. 植物学报 51, 107-119.
[18]	Allevato DM, Groppo M, Kiyota E, Mazzafera P, Nixon KC (2019). Evolution of phytochemical diversity in Pilocarpus (Rutaceae). Phytochemistry 163, 132-146. DOI URL
[19]	Chadwick M, Trewin H, Gawthrop F, Wagstaff C (2013). Sesquiterpenoids lactones: benefits to plants and people. Int J Mol Sci 14, 12780-12805. DOI PMID
[20]	Chen F, Tholl D, Bohlmann J, Pichersky E (2011). The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J 66, 212-229. DOI URL
[21]	Chen YG, Mulder PPJ, Schaap O, Memelink J, Klinkhamer PGL, Vrieling K (2020). The evolution of pyrrolizidine alkaloid diversity among and within Jacobaea species. J Syst Evol doi: 10.1111/jse.12671.
[22]	Cui HX, Cong SH, Wang XZ, Hao HP, Shi L, Zhang HJ, Li ZG, Hu TH, Qin YS (2016). Mechanistic examination of causes for narrow distribution in an endangered shrub: a comparison of its responses to drought stress with a widespread congeneric species. Trees 30, 2227-2236. DOI URL
[23]	Ernst M, Saslis-Lagoudakis CH, Grace OH, Nilsson N, Simonsen HT, Horn JW, Rønsted N (2016). Evolutionary prediction of medicinal properties in the genus Euphorbia L. Sci Rep 6, 30531. DOI URL
[24]	Fiala JL (2008). Lilacs. Portland, London: Timber Press. pp. 1-508.
[25]	Filipek A, Wyszomierska J, Michalak B, Kiss AK (2019). Syringa vulgaris bark as a source of compounds affecting the release of inflammatory mediators from human neutrophils and monocytes/macrophages. Phytochem Lett 30, 309-313. DOI URL
[26]	Gaylord ML, Kolb TE, Pockman WT, Plaut JA, Yepez EA, Macalady AK, Pangle RE, McDowell NG (2013). Drought predisposes piñon-juniper woodlands to insect attacks and mortality. New Phytol 198, 567-578. DOI PMID
[27]	Guitton Y, Nicolè F, Jullien F, Caissard JC, Saint-Marcoux D, Legendre L, Pasquier B, Moja S (2018). A comparative study of terpene composition in different clades of the genus Lavandula. Bot Lett 165, 494-505.
[28]	Kim KJ, Jansen RK (1998). A chloroplast DNA phylogeny of lilacs (Syringa, Oleaceae): plastome groups show a strong correlation with crossing groups. Am J Bot 85, 1338-1351. PMID
[29]	Konno K, Hirayama C, Yasui H, Nakamura M (1999). Enzymatic activation of oleuropein: a protein crosslinker used as a chemical defense in the privet tree. Proc Natl Acad Sci USA 96, 9159-9164. DOI URL
[30]	Lendvay B, Kadereit JW, Westberg E, Cornejo C, Pedryc A, Höhn M (2016). Phylogeography of Syringa josikaea (Oleaceae): Early Pleistocene divergence from East Asian relatives and survival in small populations in the Carpathians. Biol J Linn Soc 119, 689-703. DOI URL
[31]	Li JH, Goldman-Huertas B, DeYoung J, Alexander J (2012). Phylogenetics and diversification of Syringa inferred from nuclear and plastid DNA sequences. Castanea 77, 82-88. DOI URL
[32]	McKelvey SD (1928). The Lilac. New York, Boston, Chicago, Dallas, Atlanta, San Francisco: The Macmillan Company. pp.1-121.
[33]	Mint Evolutionary Genomics Consortium (2018). Phylogenomic mining of the mints reveals multiple mechanisms contributing to the evolution of chemical diversity in Lamiaceae. Mol Plant 11, 1084-1096. DOI URL
[34]	Rehder A (1940). Manual of Cultivated Trees and Shrubs. New York:Macmillan. pp. 777-783.
[35]	Rønsted N, Savolainen V, Mølgaard P, Jäger AK (2008). Phylogenetic selection of Narcissus species for drug discovery. Biochem Syst Ecol 36, 417-422. DOI URL
[36]	Sedio BE (2017). Recent breakthroughs in metabolomics promise to reveal the cryptic chemical traits that mediate plant community composition, character evolution and lineage diversification. New Phytol 214, 952-958. DOI URL
[37]	Sharma A, Shahzad B, Rehman A, Bhardwaj R, Landi M, Zheng BS (2019). Response of phenylpropanoid pathway and the role of polyphenols in plants under abiotic stress. Molecules 24, 2452. DOI URL
[38]	Thakur M, Bhattacharya S, Khosla PK, Puri S (2019). Improving production of plant secondary metabolites through biotic and abiotic elicitation. J Appl Res Med Aroma Plants 12, 1-12.
[39]	Varga E, Barabás C, Tóth A, Boldizsár I, Noszál B, Tóth G (2019). Phenolic composition, antioxidant and antinociceptive activities of Syringa vulgaris L. bark and leaf extracts. Nat Prod Res 33, 1664-1669. DOI URL
[40]	Vleminckx J, Salazar D, Fortunel C, Mesones I, Davila N, Lokvam J, Beckley K, Baraloto C, Fine PVA (2018). Divergent secondary metabolites and habitat filtering both contribute to tree species coexistence in the Peruvian Amazon. Front Plant Sci 9, 836. DOI PMID
[41]	Wang SC, Alseekh S, Fernie AR, Luo J (2019). The structure and function of major plant metabolite modifications. Mol Plant 12, 899-919. DOI URL
[42]	Xu SQ, Yao SC, Huang RS, Tan Y, Huang D (2020). Transcriptome-wide analysis of the AP2/ERF transcription factor gene family involved in the regulation of gypenoside biosynthesis in Gynostemma pentaphyllum. Plant Physiol Biochem 154, 238-247. DOI URL
[43]	Zhang RF, Feng X, Su GZ, Mu ZJ, Zhang HX, Zhao YN, Jiao SG, Cao L, Chen SYL, Tu PF, Chai XF (2018). Bioactive sesquiterpenoids from the peeled stems of Syringa pinnatifolia. J Nat Prod 81, 1711-1720. DOI URL

丁香属次生代谢产物及其与系统演化和地理环境的关联

Secondary Metabolites of Syringa and the Linking with Phylogenetic Evolution and Geographical Distributions

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