77-52-1 |
| 时间：2023-07-15 来源：化工号 作者：C30H48O3 |
果蠟乌宋酸乌索酸乌苏酸熊果酸熊果酸(分析标准品)3-羟基-(3β)-乌索12-烯-28-酸
| 中文名 | 熊果酸
| | 英文名 | ursolic acid
| | 别名 | 果蠟
乌宋酸
乌索酸
乌苏酸
熊果酸
熊果酸(分析标准品)
3-羟基-(3β)-乌索12-烯-28-酸
| | 英文别名 | ursolic acid
Ursoliic acid
(3beta)-urs-12-en-28-oicaci
3B-HYDROXYURS-12-EN-28-OIC ACID
3BETA-HYDROXY-12-URSEN-28-IC ACID
(3beta)-3-hydroxyurs-12-en-28-oate
3BETA-HYDROXY-12-URSEN-28-OIC ACID
3beta-Hydroxyurs-12-en-28-oic acid
(3beta)-3-hydroxyurs-12-en-28-oic acid
3-hydroxy-,(3.beta.)-Urs-12-en-28-oicacid
(3beta,5xi,18alpha)-3-hydroxyurs-12-en-28-oic acid
Ursolic acid 3beta-Hydroxyurs-12-en-28-oic acid
(1S,2R,4aS,6aS,6bR,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
| | CAS | 77-52-1
| | EINECS | 201-034-0 | | 化学式 | C30H48O3
| | 分子量 | 456.71 | | InChI | InChI=1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/p-1/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 | | 密度 | 1.0261 (rough estimate) | | 熔点 | 292 °C (dec.) (lit.) | | 沸点 | 502.79°C (rough estimate) | | 比旋光度 | 59 º (c=0.3, pyridine) | | 闪点 | 304.6°C | | 水溶性 | insoluble | | 蒸汽压 | 1.01E-14mmHg at 25°C | | 溶解度 | Soluble in DMSO (up to 25 mg/ml with warming) | | 折射率 | 1.4940 (estimate) | | 酸度系数 | 4.68±0.70(Predicted) | | 存储条件 | 2-8°C | | 稳定性 | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. | | 外观 | Crystalline Powder or Needles | | 颜色 | White to off-white | | Merck | 14,9890 | | BRN | 2228563 | | 物化性质 | 易溶于甲醇，丙酮，吡啶，不溶于水和石油醚。 来源于木犀科植物女贞(Ligustrum lucidum Ait.)叶 | | MDL号 | MFCD00009621 | | 危险品标志 | Xi - 刺激性物品
| | 风险术语 | 36/37/38 - 刺激眼睛、呼吸系统和皮肤。
| | 安全术语 | S24/25 - 避免与皮肤和眼睛接触。
S36 - 穿戴适当的防护服。
S26 - 不慎与眼睛接触后，请立即用大量清水冲洗并征求医生意见。
| | WGK Germany | - | | RTECS | YU9520000 | | FLUKA BRAND F CODES | 10-23 | | 海关编号 | 29181990 | | 参考资料 展开查看 | 1. 钦富华 林杭娟 高建青. HPLC法测定熊果酸自微乳中熊果酸的含量[J]. 安徽医药 2012(09):45-46.
2. 覃晓娟 何忠 仇惠君 王灿琴 韦仕岩.不同产地仿野生态栽培灵芝主要活性成分比较[J].湖南农业科学 2016(07):73-74+78.
3. 林雨馨 宋建颖 李杭飞 等. 不同杀青工艺对枇杷花茶主要成分的影响[J]. 食品研究与开发 2020 v.41;No.383(10):87-93.
4. 马灵珍 葛珊.九蒸九制锁阳的炮制方法探讨与质量考察[J].辽宁中医药大学学报 2020 22(08):15-19.
5. 黄宗健 肖旺钏 郑可利.仙草总皂苷的超声波法提取工艺研究[J].三明学院学报 2016 33(06):72-77.
6. 李莹 陈新梅. 分光光度法测定大山楂丸中熊果酸含量[J]. 食品与药品 2013 15(003):200-201.
7. 邢占芬 成洪达 张平平 等. 分子印迹聚合物固相萃取黄毛耳草中熊果酸[J]. 食品工业 2019(7).
8. 张新新 李进伟 刘元法 等. 分子蒸馏精制灵芝孢子油的工艺研究[J]. 中国油脂 2013(07):12-15.
9. 张俊 李进 吕海英 等. 响应面法优化扁桃果皮熊果酸的纯化工艺[J]. 食品与发酵工业 2017(10):175-181.
10. 马延 王瑾 席鹏洲 等. 响应面法优化陆英中熊果酸的提取工艺[J]. 西北农业学报 2012 21(6):156-161.
11. 余丹妮, 伍薇, 祁玮玮,等. 女贞子三萜-胡椒碱共无定型复合物的表征和体外溶出度评价[J]. 中草药, 2018, 049(003):561-568.
12. 孟楠楠, 弓志青, 杨正友,等. 山东省灵芝子实体及孢子粉中营养成分比较[J]. 食品工业, 2019, v.40;No.277(10):326-329.
13. 张俊, 李进, 吕海英,等. 扁桃果皮熊果酸提取工艺优化及体外抗氧化活性研究[J]. 食品与机械, 2018, 34(002):154-158.
14. 德丽达·木拉提别克, 古丽美克热依·吐尼亚孜, 阿来·海拉希,等. 新疆多花蔷薇根中熊果酸的提取及分离纯化工艺研究[J]. 云南大学学报:自然科学版, 2019(3).
15. 孙千鸿. 油茶蒲中总三萜提取工艺研究[J]. 中国油脂, 2017, 42(011):121-123.
16. 李龙龙, 刘琪, 张光强,等. 熊果酸对乳腺癌MCF-7细胞生长抑制作用机制探讨[J]. 中华肿瘤防治杂志, 2020, v.27(09):26-31.
17. 王文静, 吴韶飞, 郭飘婷,等. 熊果酸对卵巢癌干细胞荷瘤裸鼠耐药的逆转作用[J]. 上海中医药杂志, 2016, v.50;No.556(05):76-82.
18. 林杭娟, 钦富华, 高建青. 熊果酸平衡溶解度和油水分配系数的测定[J]. 中国现代应用药学, 2012, 029(007):635-637.
19. 邱琳, 赵修华, 祖元刚,等. 熊果酸纳米粒的乳化溶剂蒸发制备工艺、表征及溶出特征[J]. 中草药, 2018, 049(010):2387-2393.
20. 张婕,齐聪.熊果酸联合顺铂对卵巢癌干细胞的增殖、凋亡、侵袭和迁移的影响[J].现代肿瘤医学,2019,27(10):1655-1661.
21. 钦富华, 林杭娟, 高建青. 熊果酸自微乳的制备及其大鼠在体肠吸收动力学研究[J]. 中药材, 2012, 35(012):2000-2003.
22. 钦富华, 林杭娟, 高建青. 熊果酸自微乳给药系统的制备及质量评价[J]. 中成药, 2012(11):2261-2264.
23. 张家敏, 张骋, 王鹏,等. 白藤梨根体外抗肿瘤作用部位筛选及总三萜含量测定[J]. 中国现代应用药学, 2019, 036(010):1232-1235.
24. 姜敏. 秦巴山区秦艽中熊果酸的提取及性质研究[J]. 时珍国医国药, 2016, v.27;No.248(04):839-843.
25. 丁田华, 孟雪飞. 药酒中熊果酸微乳含量测定方法研究[J]. 酿酒, 2017(2).
26. 王为兰, 陈开旭, 刘军,等. 阿魏菇醇提物抗肿瘤功效及三萜类成分的提取[J]. 生物技术通报, 2016, 32(007):206-216.
27. 孙丽萍, 伊作林, 金晓露,等. 新疆红花蜜成分分析[J]. 食品工业科技, 2017(21):281-285.
28. 谭传波, 田华, 赖琼玮,等. 不同工艺山茶油中生物活性物质含量的比较[J]. 中国油脂, 2018, 43(12):48-51+56.
29. 杨妮娜 杨春勇 王元忠 等. FTIR结合有效成分定量分析在傣药灯台叶质量控制中的应用[J]. 光谱学与光谱分析 2017 37(001):58-64.
30. 李俊 张燕 李凤华 等. HPLC法测定金叶女贞果实中有效成分的含量[J]. 食品与药品 2013(02):123-126.
31. 杨妮娜 赵应红. 不同干燥方法对傣药灯台叶HPLC指纹图谱研究[J]. 中国民族医药杂志 2016 22(7):41-44.
32. 杨妮娜 徐安顺 赵应红 等. 傣药"摆埋丁别"生药学鉴别研究[J]. 中国民族医药杂志 2018 024(001):24-28.
33. 周广志 鲁敏 安华明. 刺梨果实发育过程中主要活性物质含量及其抗氧化性分析[J]. 食品科学 2018 39(22):27-32.
34. 罗小芳 郭乙颖 胡柳 等. 响应面法优化云南宣木瓜齐墩果酸和熊果酸的提取工艺研究[J]. 食品研究与开发 2018 v.39；No.342(17):38-43.
35. 李平媛,汪鋆植,柳杰,冯天艳,王宇,贺海波,付宜和,苏香萍,邓张双.土家药木瓜产地趁鲜切制及炮制规范研究[J].中国民族医药杂志,2020,26(05):46-51.
36. 张婕,梁程程,杨爱仲,齐聪.增免抑瘤方及有效组分对卵巢癌干细胞裸鼠移植瘤Notch/Jagged1信号通路的影响[J].中国实验方剂学杂志,2020,26(15):46-53.
37. 金珊珊, 柯斌榕, 吴小平,等. 适于菌草代料栽培的杂交灵芝菌株选育[J]. 亚热带资源与环境学报, 2014, 000(004):56-62.
38. 杨妮娜, 徐安顺, 杨春勇,等. 道路绿化灯台叶质量评价[J]. 中国实验方剂学杂志, 2017, 023(015):76-84.
39. 李维霞, 魏佳, 苏玉红,等. 高效液相色谱法测定巴旦木青皮提取物中齐墩果酸和熊果酸[J]. 食品科学, 2016, 37(010):151-157.
40. 李高燕 孙昭倩 郭庆梅 周凤琴.4种大枣的营养成分分析[J].山东科学 2017 30(03):33-39.
41. 李俊, 徐凌川, 李凤华. 女贞属三种植物成熟果实中有效成分含量的比较[J]. 江西中医药, 2012(01):54-56.
42. 佚名. 石榴花中多酚、黄酮及萜类物质同步提取工艺优化[J]. 湖北农业科学, 2017(15).
43. 哈及尼沙, 李改茹, 马桂芝. 榅桲委陵菜酸,熊果酸和齐墩果酸等三萜酸类薄层色谱分离鉴别[J]. 食品安全质量检测学报, 2020, v.11(07):88-93.
44. 周广志 鲁敏 安华明. 刺梨及其近缘种质叶片主要活性物质含量及抗氧化性分析[J]. 核农学报 2019 v.33(08):214-221.
45. 蔡丹凤, 陈丹红. 松蔸栽培茯苓主要营养成分的累积特性[J]. 中华中医药杂志, 2018, 033(001):373-375.
46. 谭传波. 鲜榨山茶油中生物活性物质研究[J]. 粮食与油脂, 年度湖南省科技重大专项(2018NK1030).
47. 韩根利 刘宏胜 王树森 等. RP-HPLC法同时测定山茱萸萜类制剂中莫诺苷 马钱苷 山茱萸新苷 齐墩果酸及熊果酸[J]. 中草药 2017 48(024):5168-5173.
48. 张巧,顾欣哲,吴永进,屠康.枇杷果皮热风干燥前后功能性成分含量变化与挥发性成分分析[J].食品科学,2016,37(16):117-122.
49. 陶玉菡,许惠琴,李莉,农伟虎,李伟.生地、山茱萸抑制和清除糖基化产物的效应成分研究[J].中药药理与临床,2013,29(04):30-33.
50. 梁亚丽, 秦礼康, 王何柱,等. 红托竹荪及竹荪蛋各部位主要营养功能成分分析[J]. 食品与机械, 2020, v.36;No.222(04):78-82+120.
51. 霍宇航, 李檐堂, 刘丽丽,等. 基于主要功能成分的6 个品种枇杷叶分析评价[J]. 食品科学, 2019, 40(24).
52. 赵志国, 井凤, 张敏敏,等. 西藏木瓜HPLC指纹图谱研究及多成分测定[J]. 中草药, 2018, 49(10):239-244.
53. 刘淼琴,郭庆,许东亚,周青明.九制锁阳质量标准研究[J].海峡药学,2020,32(11):92-94.
54. 王庆卫,刘启玲,崔胜文.不同干燥方式对红枣营养品质及抗氧化活性的影响[J].食品工业,2020,41(12):218-222.
55. 宗彦红,霍丽静,常胜.熊果酸对人肝癌HepG_2细胞凋亡及PI_3K/Akt信号通路的影响[J].医学研究杂志,2020,49(09):107-111+115.
56. 张艳慧,丁玉,李淑荣.熊果酸磷脂复合物纳米结构脂质载体的制备及其体内药动学研究[J].中成药,2021,43(02):302-307.
57. 李媛,朱建勇,顾伟鹰,时扣荣,刘娟,张春燕,罗兰.瓜蒌当归降脂颗粒质量标准研究[J].中国药业,2021,30(06):50-54.
58. 徐芳芳,张秀莉,侯滔,曲腊腊,王纪霞,刘艳芳,梁鑫淼.天然产物中FFA1受体新激动剂的发现与研究[J].上海中医药大学学报,2021,35(01):12-19.[4]宫梦琪,孙倩,李振.天麻中天麻素提取工艺优化及抑制α-葡萄糖苷酶活性研究[J].中国果菜,2020,40(09):14-17+23.
59. 李栋,薛瑞婷.高温高湿气体冲击处理对中短波红外干制红枣品质的影响[J].食品研究与开发,2020,41(22):107-112.
60. 李诗卉,梁诗瑶,伊美瑾,夏伯候,黄胜,颜冬兰,林丽美.夏枯草茎叶复合菌发酵工艺、成分及活性变化研究[J].时珍国医国药,2020,31(11):2629-2633.
61. Luo J, Hu YL and Wang H: Ursolic acid inhibits breast cancer growth by inhibiting proliferation, inducing autophagy and apoptosis, and suppressing inflammatory responses via the PI3K/AKT and NF‑κB signaling pathways in vitro. Exp Ther Med 14: 3623-3631, 20
62. Zhang, W, Cai, Y, Chen, X, Ji, T, Sun, L. Optimized extraction based on the terpenoids of Heterotrigona itama propolis and their antioxidative and anti-inflammatory activities. J Food Biochem. 2020; 44:e13296. https://doi.org/10.1111/jfbc.13296
63. Wang, Xutong, et al. "Molecular cloning, characterisation, and heterologous expression of farnesyl diphosphate synthase from Sanghuangporus baumii." Molecular biotechnology 62.2 (2020): 132-141.https://doi.org/10.1007/s12033-019-00231-0
64. iao, S, Li, Y, Wang, Z, et al. Optimization of enzyme-assisted extraction of bioactive-rich juice from Chaenomeles sinensis (Thouin) Koehne by response surface methodology. J Food Process Preserv. 2020; 44:e14638. https://doi.org/10.1111/jfpp.14638
65. Zhao, Wenjia, et al. "Inducement and cultivation of novel red Cyclocarya paliurus callus and its unique morphological and metabolic characteristics." Industrial Crops and Products 147 (2020): 112266.https://doi.org/10.1016/j.indcrop.2020.112266
66. Liao, Xiaoyan, Fangli Hu, and Zilin Chen. "Identification and quantitation of the bioactive components in Osmanthus fragrans fruits by HPLC-ESI-MS/MS." Journal of agricultural and food chemistry 66.1 (2018): 359-367.https://doi.org/10.1021/acs.jafc.7b05560
67. Liu, Huan, et al. "Antimicrobial activity and virulence attenuation of citral against the fish pathogen Vibrio alginolyticus." Aquaculture 515 (2020): 734578.https://doi.org/10.1016/j.aquaculture.2019.734578
68. Zhu, Hao, et al. "Anti-inflammatory effects of p-coumaric acid, a natural compound of Oldenlandia diffusa, on arthritis model rats." Evidence-Based Complementary and Alternative Medicine 2018 (2018).https://doi.org/10.1155/2018/5198594
69. Zhang, Minmin, et al. "Chemical characterization and evaluation of the antioxidants in Chaenomeles fruits by an improved HPLC-TOF/MS coupled to an on-line DPPH-HPLC method." Journal of Environmental Science and Health, Part C 36.1 (2018): 43-62.https://doi
70. [IF=5.279] Xiaoyan Liao et al."Identification and Quantitation of the Bioactive Components in Osmanthus fragrans Fruits by HPLC-ESI-MS/MS."J Agr Food Chem. 2018;66(1):359–367
71. [IF=4.759] Lu Wang et al."A strategy for identification and structural characterization of compounds from Gardenia jasminoides by integrating macroporous resin column chromatography and liquid chromatography-tandem mass spectrometry combined with ion-mobility spectr
72. [IF=3.935] Li Li et al."Rapid identification of urokinase plasminogen activator inhibitors from Traditional Chinese Medicines based on ultrafiltration, LC–MS and in silico docking."J Pharmaceut Biomed. 2019 Feb;164:241
73. [IF=3.503] Chang-Geng Xu et al."Ursolic acid inhibits epithelial-mesenchymal transition in vitro and in vivo."Pharm Biol. 2019;57(1):169-175
74. [IF=2.494] Xifeng Zhang et al."Deep eutectic solvents aqueous two-phase system based ultrasonically assisted extraction of ursolic acid (UA) from Cynomorium songaricum Rupr.."Chem Eng Commun. 2019;206(4):419-431
75. [IF=1.984] Zhu Hao et al."Anti-Inflammatory Effects of the Bioactive Compound Ferulic Acid Contained in Oldenlandia diffusa on Collagen-Induced Arthritis in Rats."Evid-Based Compl Alt. 2014;2014:573801
76. [IF=1.984] Zhu Hao et al."Anti-Inflammatory Effects of p-Coumaric Acid, a Natural Compound of Oldenlandia diffusa, on Arthritis Model Rats."Evid-Based Compl Alt. 2018;2018:5198594
77. [IF=1.785] Juan Luo et al."Ursolic acid inhibits breast cancer growth by inhibiting proliferation, inducing autophagy and apoptosis, and suppressing inflammatory responses via the PI3K/AKT and NF‑κB signaling pathways in vitro."Exp Ther Med. 2017 Oct;14(4):3623-363
78. [IF=7.46] Yuqiu Zi et al."Aggregation-enhanced emission of metal nanoclusters triggered by peptide self-assembly and application in chymotrypsin inhibitor screening."Sensor Actuat B-Chem. 2021 Oct;345:130243
79. [IF=6.583] Kaiyong Yang et al."Ursolic Acid promotes apoptosis and mediates transcriptional suppression of CT45A2 gene expression in NSCLCs harboring EGFR T790M."Brit J Pharmacol. 2019 Dec;176(24):4609-4624
80. [IF=5.645] Wenjia Zhao et al."Inducement and cultivation of novel red Cyclocarya paliurus callus and its unique morphological and metabolic characteristics."Ind Crop Prod. 2020 May;147:112266
81. [IF=4.759] Keyu Feng et al."Configuration of the ion exchange chromatography, hydrophilic interaction chromatography, and reversed-phase chromatography as off-line three-dimensional chromatography coupled with high-resolution quadrupole-Orbitrap mass spectrometry fo
82. [IF=4.759] Yi Zhang et al."Screening of inhibitors against histone demethylation jumonji domain-containing protein 3 by capillary electrophoresis."J Chromatogr A. 2020 Feb;1613:460625
83. [IF=4.616] Xiaoyan Liao et al."A HPLC-MS method for profiling triterpenoid acids and triterpenoid esters in Osmanthus fragrans fruits."Analyst. 2019 Nov;144(23):6981-6988
84. [IF=4.411] Mengyuan Gao et al."Correlation between Quality and Geographical Origins of Cortex Periplocae, Based on the Qualitative and Quantitative Determination of Chemical Markers Combined with Chemical Pattern Recognition."Molecules. 2019 Jan;24(19):3621
85. [IF=4.36] Li Lin et al."Study on the alleviation of Fengshi Gutong capsule on rheumatoid arthritis through integrating network pharmacology and experimental exploration."J Ethnopharmacol. 2021 Nov;280:114471
86. [IF=4.098] Bin Li et al."Characteristics of the interaction mechanisms of procyanidin B1 and procyanidin B2 with protein tyrosine phosphatase-1B: Analysis by kinetics, spectroscopy methods and molecular docking."Spectrochim Acta A. 2021 Oct;259:119910
87. [IF=3.963] Lin Cai et al."Plant-derived compounds: A potential source of drugs against Tobacco mosaic virus."Pestic Biochem Phys. 2020 Oct;169:104589
88. [IF=3.69] Yuyun Li et al."Prediction of the mechanisms of Xiaoai Jiedu Recipe in the treatment of breast cancer: A comprehensive approach study with experimental validation."J Ethnopharmacol. 2020 Apr;252:112603
89. [IF=3.645] Jie Lu et al."Identification and determination of chemical constituents from Yinchen Qingjin granules by ultra high-performance liquid chromatography coupled with linear ion trap-Orbitrap mass spectrometry."J Sep Sci. 2021 Apr;44(7):1324-1344
90. [IF=3.205] Jie Tang et al."Metabolite profiling of Shuganzhi tablets in rats and pharmacokinetics study of four bioactive compounds with liquid chromatography combined with electrospray ionization tandem mass spectrometry."J Chromatogr B. 2021 Aug;1179:122827
91. [IF=2.72] Wenwen Zhang et al."Optimized extraction based on the terpenoids of Heterotrigona itama propolis and their antioxidative and anti-inflammatory activities."J Food Biochem. 2020 Aug;44(8):e13296
92. [IF=2.711] Sun H. D. et al."Optimization of the culture medium of adventitious root culture to produce the flavonoids and the triterpenoids of Actinidia arguta by using an orthogonal design process."Plant Cell Tiss Org. 2021 Mar;144(3):545-554
93. [IF=2.695] Wang Xutong et al."Molecular Cloning, Characterisation, and Heterologous Expression of Farnesyl Diphosphate Synthase from Sanghuangporus baumii."Mol Biotechnol. 2020 Feb;62(2):132-141
94. [IF=2.629] Su Xing et al."Synergistic Effect of Network-Based Multicomponent Drugs: An Investigation on the Treatment of Non-Small-Cell Lung Cancer with Compound Liuju Formula."Evid-Based Compl Alt. 2019;2019:9854047
95. [IF=2.19] Shenglong Jiao et al."Optimization of enzyme-assisted extraction of bioactive-rich juice from Chaenomeles sinensis (Thouin) Koehne by response surface methodology."J Food Process Pres. 2020 Sep;44(9):e14638
96. [IF=1.65] Xutong Wang et al."Molecular cloning, characterization, and heterologous expression of an acetyl-CoA acetyl transferase gene from Sanghuangporus baumii."Protein Expres Purif. 2020 Jun;170:105592
97. [IF=6.475] Tao-Tao Xue et al."Evaluation of antioxidant, enzyme inhibition, nitric oxide production inhibitory activities and chemical profiles of the active extracts from the medicinal and edible plant: Althaea officinalis."Food Res Int. 2022 Jun;156:111166
98. [IF=1.175] Wang Meng et al."Mechanism of molecules crosstalk and the critical role of jasmonic acid on triterpenoid synthesis in Cyclocarya Paliurus cells under Aspergillus niger elicitor."J Plant Biochem Biot. 2022 Jan;:1-16
99. [IF=3.196] Bo Xue et al."Mechanism underlying the interaction of malvidin-3-O-galactoside with protein tyrosine phosphatase-1B and α-glucosidase."J Mol Struct. 2022 Apr;1253:132249
100. [IF=5.753] Jianghong Gao et al."Molecular Cloning and Functional Characterization of a Sterol 3-O-Glucosyltransferase Involved in Biosynthesis of Steroidal Saponins in Trigonella foenum-graecum.."Front Plant Sci. 2021 Dec;12:809579-809579 |
|
|
|
|
