ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2010, 12, 6, 1196-1199
RETURN TO ISSUEPREVLetterNEXT

Two New Quinochalcones from the Florets of Carthamus tinctorius

View Author Information
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College (Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education), Beijing 100050, People’s Republic of China
* To whom correspondence should be addressed. Phone: 86-10-63165231. Fax: 86-10-63017757. [email protected]
Cite this: Org. Lett. 2010, 12, 6, 1196–1199
Publication Date (Web):February 19, 2010
https://doi.org/10.1021/ol902971w
Copyright © 2010 American Chemical Society
RIGHTS & PERMISSIONS

Article Views

1574

Altmetric

-

Citations

42
LEARN ABOUT THESE METRICS
Read OnlinePDF (181 KB)
Get e-Alerts
Supporting Info (1)»
SUBJECTS:

Abstract

Abstract Image

Two new quinochalcone compounds, named saffloquinoside A (1) and saffloquinoside B (2), were isolated from the florets of Carthamus tinctorius. Their unusual structures including their absolute stereochemistry were elucidated based on UV, IR, HRESIMS, 1D and 2D NMR data, and CD spectrum. Saffloquinoside A has an uncommon six−five member dioxaspirocycle and saffloquinoside B has a cyclohexatrione skeleton with a benzyl group and two C-glycosyl units. Saffloquinoside A exhibited middling anti-inflammatory activity.

Supporting Information

ARTICLE SECTIONS
Jump To

MS, HRMS, IR, UV, 1D and 2D NMR, and CD spectra of compounds 1 and 2. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 42 publications.

  1. Dawei Chen, Shuai Fan, Ridao Chen, Kebo Xie, Sen Yin, Lili Sun, Jimei Liu, Lin Yang, Jianqiang Kong, Zhaoyong Yang, Jungui Dai. Probing and Engineering Key Residues for Bis-C-glycosylation and Promiscuity of a C-Glycosyltransferase. ACS Catalysis 2018, 8 (6) , 4917-4927. https://doi.org/10.1021/acscatal.8b00376
  2. Shi-Jun Yue, Cheng Qu, Peng-Xuan Zhang, Yu-Ping Tang, Yi Jin, Jian-Shuang Jiang, Ya-Nan Yang, Pei-Cheng Zhang, and Jin-Ao Duan . Carthorquinosides A and B, Quinochalcone C-Glycosides with Diverse Dimeric Skeletons from Carthamus tinctorius. Journal of Natural Products 2016, 79 (10) , 2644-2651. https://doi.org/10.1021/acs.jnatprod.6b00561
  3. Vinod Khatri, Amit Kumar, Balram Singh, Shashwat Malhotra, and Ashok K. Prasad . Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols. The Journal of Organic Chemistry 2015, 80 (21) , 11169-11174. https://doi.org/10.1021/acs.joc.5b01933
  4. Jun He, Ya-Nan Yang, Jian-shuang Jiang, Zi-Ming Feng, and Pei-Cheng Zhang . Saffloflavonesides A and B, Two Rearranged Derivatives of Flavonoid C-glycosides with a Furan–Tetrahydrofuran Ring from Carthamus tinctorius. Organic Letters 2014, 16 (21) , 5714-5717. https://doi.org/10.1021/ol502789x
  5. Kebo Xie, Ridao Chen, Jianhua Li, Ruishan Wang, Dawei Chen, Xiaoxiang Dou, and Jungui Dai . Exploring the Catalytic Promiscuity of a New Glycosyltransferase from Carthamus tinctorius. Organic Letters 2014, 16 (18) , 4874-4877. https://doi.org/10.1021/ol502380p
  6. Wei-Zhong Liu, Li-Ying Ma, De-Sheng Liu, Yu-Ling Huang, Chun-Hua Wang, Shou-Sen Shi, Xiao-Hong Pan, Xiao-Dong Song, and Rong-Xiu Zhu . Peniciketals A–C, New Spiroketals from Saline Soil Derived Penicillium raistrichii. Organic Letters 2014, 16 (1) , 90-93. https://doi.org/10.1021/ol403076s
  7. Zi-Ming Feng, Jun He, Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, and Pei-Cheng Zhang . NMR Solution Structure Study of the Representative Component Hydroxysafflor Yellow A and Other Quinochalcone C-Glycosides from Carthamus tinctorius. Journal of Natural Products 2013, 76 (2) , 270-274. https://doi.org/10.1021/np300814k
  8. Ya-Qun Zhang, Meng Zhang, Zi-Long Wang, Xue Qiao, Min Ye. Advances in plant-derived C-glycosides: Phytochemistry, bioactivities, and biotechnological production. Biotechnology Advances 2022, 60 , 108030. https://doi.org/10.1016/j.biotechadv.2022.108030
  9. Bin Xian, Rui Wang, Huajuan Jiang, Yongfeng Zhou, Jie Yan, Xulong Huang, Jiang Chen, Qinghua Wu, Chao Chen, Ziqing Xi, Chaoxiang Ren, Jin Pei. Comprehensive review of two groups of flavonoids in Carthamus tinctorius L.. Biomedicine & Pharmacotherapy 2022, 153 , 113462. https://doi.org/10.1016/j.biopha.2022.113462
  10. Hong Yingqi, Yanxi Lv, Jianyi Zhang, Naveed Ahmad, Youbao Li, Nan Wang, Liu Xiuming, Yao Na, Xiaokun Li. Identification and functional characterization of safflower cysteine protease 1 as negative regulator in response to low-temperature stress in transgenic Arabidopsis. Planta 2022, 255 (5) https://doi.org/10.1007/s00425-022-03875-6
  11. Temitope Isaac Adelusi, Lei Du, Apu Chowdhury, Gu Xiaoke, Qian Lu, Xiaoxing Yin. Signaling pathways and proteins targeted by antidiabetic chalcones. Life Sciences 2021, 284 , 118982. https://doi.org/10.1016/j.lfs.2020.118982
  12. Hao Zhang, Chen-Ping Duan, Xia Luo, Zi-Ming Feng, Ya-Nan Yang, Xu Zhang, Jian-Shuang Jiang, Pei-Cheng Zhang. Two new quinochalcone glycosides from the safflower yellow pigments. Journal of Asian Natural Products Research 2020, 22 (12) , 1130-1137. https://doi.org/10.1080/10286020.2020.1846530
  13. Lu Yu, Zhili Liu, Wendi He, Huifen Chen, Zelin Lai, Yanhong Duan, Xiaohua Cao, Jie Tao, Chuan Xu, Qiujuan Zhang, Zheng Zhao, Jun Zhang. Hydroxysafflor Yellow A Confers Neuroprotection from Focal Cerebral Ischemia by Modulating the Crosstalk Between JAK2/STAT3 and SOCS3 Signaling Pathways. Cellular and Molecular Neurobiology 2020, 40 (8) , 1271-1281. https://doi.org/10.1007/s10571-020-00812-7
  14. Shahid Akbar. Carthamus tinctorius L. (Asteraceae/Compositae). 2020, 515-527. https://doi.org/10.1007/978-3-030-16807-0_55
  15. Evgeny Chupakhin, Olga Babich, Alexander Prosekov, Lyudmila Asyakina, Mikhail Krasavin. Spirocyclic Motifs in Natural Products. Molecules 2019, 24 (22) , 4165. https://doi.org/10.3390/molecules24224165
  16. Wan Gao, Zhong Chen, Yanan Yang, Jianshuang Jiang, Ziming Feng, Xu Zhang, Xiang Yuan, Peicheng Zhang. Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives. Carbohydrate Research 2019, 484 , 107756. https://doi.org/10.1016/j.carres.2019.107756
  17. Wan Gao, Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, Zi-Ming Feng, Xu Zhang, Xiang Yuan, Pei-Cheng Zhang. Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside. Organic Chemistry Frontiers 2019, 6 (11) , 1858-1862. https://doi.org/10.1039/C9QO00279K
  18. Yujiao Zhang, Kebo Xie, Aijing Liu, Ridao Chen, Dawei Chen, Lin Yang, Jungui Dai. Enzymatic biosynthesis of benzylisoquinoline alkaloid glycosides via promiscuous glycosyltransferases from Carthamus tinctorius. Chinese Chemical Letters 2019, 30 (2) , 443-446. https://doi.org/10.1016/j.cclet.2018.05.010
  19. Doha A. Mohamed, Sherein S. Abdelga, Rasha S. Mohamed, Hend A. Essa. Impact of Safflower Petals and Moringa Leaves Extracts in Experimental Hyper and Hypothyroidism in Rats. International Journal of Pharmacology 2019, 15 (2) , 219-228. https://doi.org/10.3923/ijp.2019.219.228
  20. Lu Yu, Yanhong Duan, Zheng Zhao, Wendi He, Ming Xia, Qiujuan Zhang, Xiaohua Cao. Hydroxysafflor Yellow A (HSYA) Improves Learning and Memory in Cerebral Ischemia Reperfusion-Injured Rats via Recovering Synaptic Plasticity in the Hippocampus. Frontiers in Cellular Neuroscience 2018, 12 https://doi.org/10.3389/fncel.2018.00371
  21. Li Sun, Yan-Wei Xu, Jing Han, Chen Xiao, Shan-Shan Cao, Hao Liang, Yan Cheng. Hydroxysafflor Yellow A Shows Protection against PPAR γ Inactivation in Nitrosative Neurons. Oxidative Medicine and Cellular Longevity 2018, 2018 , 1-13. https://doi.org/10.1155/2018/9101740
  22. Jing Pan, Xiaomin Yi, Shujuan Zhang, Jun Cheng, Yihai Wang, Chunyu Liu, Xiangjiu He. Bioactive phenolics from mango leaves (Mangifera indica L.). Industrial Crops and Products 2018, 111 , 400-406. https://doi.org/10.1016/j.indcrop.2017.10.057
  23. Toshiyuki Suzuki, Mitsuo Ishida, Toshihiro Kumazawa, Shingo Sato. Oxidation of 3,5-di-C-(per-O-acetylglucopyranosyl)phloroacetophenone in the synthesis of hydroxysafflor yellow A. Carbohydrate Research 2017, 448 , 52-56. https://doi.org/10.1016/j.carres.2017.05.009
  24. Feng Li, Zhisheng He, Yang Ye. Isocartormin, a novel quinochalcone C -glycoside from Carthamus tinctorius. Acta Pharmaceutica Sinica B 2017, 7 (4) , 527-531. https://doi.org/10.1016/j.apsb.2017.04.005
  25. Dan-Dan Guo, Fei Liu, Yan-Hua Tu, Bei-Xuan He, Yue Gao, Mei-Li Guo, . Expression Patterns of Three UGT Genes in Different Chemotype Safflower Lines and under MeJA Stimulus Revealed Their Potential Role in Flavonoid Biosynthesis. PLOS ONE 2016, 11 (7) , e0158159. https://doi.org/10.1371/journal.pone.0158159
  26. Zsuzsanna Rozmer, Pál Perjési. Naturally occurring chalcones and their biological activities. Phytochemistry Reviews 2016, 15 (1) , 87-120. https://doi.org/10.1007/s11101-014-9387-8
  27. Xue Xie, Jianming Zhou, Lin Sun, Hongda Zhang, Yiwu Zhao, Yaling Song, Xuejing Wang, Fuyong Ni, Wenzhe Huang, Zhenzhong Wang, Wei Xiao. A new flavonol glycoside from the florets of Carthamus tinctorius L.. Natural Product Research 2016, 30 (2) , 150-156. https://doi.org/10.1080/14786419.2015.1045905
  28. Le-Le Zhang, Ke Tian, Zheng-Hai Tang, Xiao-Jia Chen, Zhao-Xiang Bian, Yi-Tao Wang, Jin-Jian Lu. Phytochemistry and Pharmacology of Carthamus tinctorius L.. The American Journal of Chinese Medicine 2016, 44 (02) , 197-226. https://doi.org/10.1142/S0192415X16500130
  29. Yanhua Tu, Yingru Xue, Dandan Guo, Lianna Sun, Meili Guo. Carthami flos: a review of its ethnopharmacology, pharmacology and clinical applications. Revista Brasileira de Farmacognosia 2015, 25 (5) , 553-566. https://doi.org/10.1016/j.bjp.2015.06.001
  30. F. S. Pashkovsky, J. S. Dontsu, D. B. Rubinov, F. A. Lakhvich. Reaction of Nitromethane with Cinnamoyl Derivatives of Cyclic β-dicarbonyl Compounds. Application to the Synthesis of 2(3)-(4-aryl-pyrrolidin-2-ylidene)-1,3(2,4)-diones*. Chemistry of Heterocyclic Compounds 2015, 50 (10) , 1421-1431. https://doi.org/10.1007/s10593-014-1606-0
  31. Siyu Zhao, Xinmiao Lu, Cheng Xiao, Zhangchi Ning, Honglian Zeng, Xinzhe Ding, Yinhuan Zhang, Cheng Lu, Yuanyan Liu. Diversified bioactivities of four types of naturally occurring quinochalcones. Fitoterapia 2014, 99 , 7-20. https://doi.org/10.1016/j.fitote.2014.08.017
  32. Xidan Zhou, Liying Tang, Yilong Xu, Guohong Zhou, Zhuju Wang. Towards a better understanding of medicinal uses of Carthamus tinctorius L. in traditional Chinese medicine: A phytochemical and pharmacological review. Journal of Ethnopharmacology 2014, 151 (1) , 27-43. https://doi.org/10.1016/j.jep.2013.10.050
  33. Zhong-Liang Tang, Lian Yin, Fang Wu, Xu Zhang. Investigation of a novel method for quality control of Chinese herbal compound prescription: HPLC fingerprint and multi-index components combining blending technology control for quality stability of Zhou's prescription extract. Analytical Methods 2014, 6 (12) , 4158. https://doi.org/10.1039/c3ay41884g
  34. Shijun Yue, Yuping Tang, Shujiao Li, Jin-Ao Duan. Chemical and Biological Properties of Quinochalcone C-Glycosides from the Florets of Carthamus tinctorius. Molecules 2013, 18 (12) , 15220-15254. https://doi.org/10.3390/molecules181215220
  35. Li Sun, Li Yang, Ying Fu, Jing Han, Yanwei Xu, Hao Liang, Yan Cheng. Capacity of HSYA to inhibit nitrotyrosine formation induced by focal ischemic brain injury. Nitric Oxide 2013, 35 , 144-151. https://doi.org/10.1016/j.niox.2013.10.002
  36. Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, Zi-Ming Feng, Pei-Cheng Zhang. Two new glycosides from the florets of Carthamus tinctorius. Journal of Asian Natural Products Research 2013, 15 (5) , 427-432. https://doi.org/10.1080/10286020.2013.780046
  37. Lingnan Li, Yi Yang, Xueling Hou, Dongyu Gu, Hang Ba, Rahima Abdulla, Guirong Wu, Xuelei Xin, Haji Akber Aisa. Bioassay-guided separation and purification of water-soluble antioxidants from Carthamus tinctorius L. by combination of chromatographic techniques. Separation and Purification Technology 2013, 104 , 200-207. https://doi.org/10.1016/j.seppur.2012.11.027
  38. Yang YE, Xi-Qiang LI, Chun-Ping TANG, Sheng YAO. Natural products chemistry research 2010's progress in China. Chinese Journal of Natural Medicines 2012, 10 (1) , 1-12. https://doi.org/10.1016/S1875-5364(12)60001-6
  39. Xian-Fu Wu, Ya-Dan Wang, Shi-Shan Yu, Nan Jiang, Jing Ma, Ren-Xiang Tan, You-Cai Hu, Jing Qu. Antioxidative acylphloroglucinols from the roots of Lysidice rhodostegia. Tetrahedron 2011, 67 (42) , 8155-8159. https://doi.org/10.1016/j.tet.2011.08.034
  40. Jun He, Yi Shen, Jian-Shuang Jiang, Ya-Nan Yang, Zi-Ming Feng, Pei-Cheng Zhang, Shao-Peng Yuan, Qi Hou. New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities. Carbohydrate Research 2011, 346 (13) , 1903-1908. https://doi.org/10.1016/j.carres.2011.06.015
  41. Shino Manabe, Yoshiyuki Aihara, Yukishige Ito. Radical C-glycosylation reaction of pyranosides with the 2,3-trans carbamate group. Chemical Communications 2011, 47 (34) , 9720. https://doi.org/10.1039/c1cc13172a
  42. Jian-Shuang Jiang, Jun He, Zi-Ming Feng, Pei-Cheng Zhang. ChemInform Abstract: Two New Quinochalcones from the Florets of Carthamus tinctorius.. ChemInform 2010, 41 (30) , no-no. https://doi.org/10.1002/chin.201030211

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect