logo

OR SEARCH CITATIONS

My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2015, 17, 6, 1565-1568

COVID-19 Remote Access Support:

Learn More about expanded access to ACS Publications research.

RETURN TO ISSUEPREVLetterNEXT

(±)-Sinensilactam A, a Pair of Rare Hybrid Metabolites with Smad3 Phosphorylation Inhibition from Ganoderma sinensis

View Author Information
† State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China
‡ Henan College of Traditional Chinese Medicine, Zhengzhou 450008, P. R. China
§ University of Chinese Academy of Sciences, Beijing 100049, P. R. China
∥ Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Guangzhou 510650, P. R. China
Cite this: Org. Lett. 2015, 17, 6, 1565-1568
Publication Date (Web):March 6, 2015
https://doi.org/10.1021/acs.orglett.5b00448
Copyright © 2015 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
1845
Altmetric
-
Citations
48
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (917 KB)
Supporting Info (1)»
SUBJECTS:

Abstract

Abstract Image

(+)- and (−)-Sinensilactam A (1), novel hybrid metabolites possessing a unique 2H-pyrrolo[2,1-b][1,3]oxazin-6(7H)-one ring system, were isolated from the fruit bodies of Ganoderma sinensis. The structures of these substances and absolute configurations at their stereocenters were assigned using spectroscopic and computational methods along with X-ray crystallographic analysis. A plausible pathway for the biosynthesis of 1 is proposed. (−)-1 was found to be a Smad3 phosphorylation inhibitor in TGF-β1 induced human renal proximal tubular cells.

Supporting Information

ARTICLE SECTIONS
Jump To

1D, 2D NMR, and MS spectra, detailed isolation procedures, crystallographic data, computational and bioassay methods. This material is available free of charge via Internet at http://pubs.acs.org.

Terms & Conditions

Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 48 publications.

  1. Fu-Ying Qin, Hao-Xing Zhang, Qian-Qian Di, Yan Wang, Yong-Ming Yan, Wei-Lin Chen, Yong-Xian Cheng. Ganoderma cochlear Metabolites as Probes to Identify a COX-2 Active Site and as in Vitro and in Vivo Anti-Inflammatory Agents. Organic Letters 2020, 22 (7) , 2574-2578. DOI: 10.1021/acs.orglett.0c00452.
  2. Yong-Ming Yan, Hao-Xing Zhang, Huan Liu, Yan Wang, Jing-Bo Wu, Yan-Peng Li, Yong-Xian Cheng. (+/−)-Lucidumone, a COX-2 Inhibitory Caged Fungal Meroterpenoid from Ganoderma lucidum. Organic Letters 2019, 21 (21) , 8523-8527. DOI: 10.1021/acs.orglett.9b02840.
  3. Wenbin Shao, Jun Huang, Kai Guo, Jianxian Gong, Zhen Yang. Total Synthesis of Sinensilactam A. Organic Letters 2018, 20 (7) , 1857-1860. DOI: 10.1021/acs.orglett.8b00380.
  4. Lea-Marina Mehl and Martin E. Maier . A Radical-Based Synthesis of Lingzhiol. The Journal of Organic Chemistry 2017, 82 (18) , 9844-9850. DOI: 10.1021/acs.joc.7b01416.
  5. Qi Luo, Zhu-Liang Yang, Yong-Ming Yan, and Yong-Xian Cheng . Ganotheaecolin A, a Neurotrophic Conjugated Ergosterol with a Naphtho[1,8-ef]azulene Scaffold from Ganoderma theaecolum. Organic Letters 2017, 19 (3) , 718-721. DOI: 10.1021/acs.orglett.7b00012.
  6. Qi Luo, Xiao-Yi Wei, Jing Yang, Jin-Feng Luo, Rui Liang, Zheng-Chao Tu, and Yong-Xian Cheng . Spiro Meroterpenoids from Ganoderma applanatum. Journal of Natural Products 2017, 80 (1) , 61-70. DOI: 10.1021/acs.jnatprod.6b00431.
  7. Lei Li, Huan Li, Xing-Rong Peng, Bo Hou, Mu-Yuan Yu, Jin-Run Dong, Xiao-Nian Li, Lin Zhou, Jian Yang, and Ming-Hua Qiu . (±)-Ganoapplanin, a Pair of Polycyclic Meroterpenoid Enantiomers from Ganoderma applanatum. Organic Letters 2016, 18 (23) , 6078-6081. DOI: 10.1021/acs.orglett.6b03064.
  8. Andrei G. Kutateladze and Olga A. Mukhina . Minimalist Relativistic Force Field: Prediction of Proton–Proton Coupling Constants in 1H NMR Spectra Is Perfected with NBO Hybridization Parameters. The Journal of Organic Chemistry 2015, 80 (10) , 5218-5225. DOI: 10.1021/acs.joc.5b00619.
  9. Yi-Min Fan, Ping Yi, Yang Li, Chen Yan, Tao Huang, Wei Gu, Yuan Ma, Lie-Jun Huang, Jian-Xin Zhang, Chong-Lin Yang, Yan Li, Chun-Mao Yuan, and Xiao-Jiang Hao . Two Unusual Polycyclic Polyprenylated Acylphloroglucinols, Including a Pair of Enantiomers from Garcinia multiflora. Organic Letters 2015, 17 (9) , 2066-2069. DOI: 10.1021/acs.orglett.5b00588.
  10. Kazumi Naruse, Ryo Katsuta, Arata Yajima, Tomoo Nukada, Hidenori Watanabe, Ken Ishigami. Formal synthesis of cochlearol A, a meroterpenoid with renoprotective activity. Tetrahedron Letters 2020, 61 (19) , 151845. DOI: 10.1016/j.tetlet.2020.151845.
  11. Shuang-Yang Lu, Qiang-Qiang Shi, Xing-Rong Peng, Lin Zhou, Xiao-Nian Li, Ming-Hua Qiu. Isolation of benzolactones, Ganodumones A–F from Ganoderma lucidum and their antibacterial activities. Bioorganic Chemistry 2020, 98, 103723. DOI: 10.1016/j.bioorg.2020.103723.
  12. Wei-Feng Dai, Yan-Xia Zhu, Fu-Ying Qin, Jun-Lei Chang, Yue Zeng, Ji-Gang Wang, Yuan-Yuan Zhang, Yong-Xian Cheng. Skeletal meroterpenoids from Ganoderma petchii mushrooms that potentially stimulate umbilical cord mesenchymal stem cells. Bioorganic Chemistry 2020, , 103675. DOI: 10.1016/j.bioorg.2020.103675.
  13. Yan-Jiao Yin, Dan-Ling Huang, Bin Qiu, Dan Cai, Jiao-Jiao Zhang, Shao-Xiang Wang, Da-Peng Qin, Yong-Xian Cheng. Meroterpenoids from the Fungus Ganoderma sinensis and First Absolute Configuration Clarification of Zizhine H. Molecules 2020, 25 (1) , 158. DOI: 10.3390/molecules25010158.
  14. Ren-Qiang Mei, Feng-Jiao Zuo, Xiao-Yan Duan, Yi-Na Wang, Jun-Rong Li, Cheng-Zhen Qian, Ji-Ping Xiao. Ergosterols from Ganoderma sinense and their anti-inflammatory activities by inhibiting NO production. Phytochemistry Letters 2019, 32, 177-180. DOI: 10.1016/j.phytol.2019.06.006.
  15. Fu-Ying Qin, Yong-Ming Yan, Zheng-Chao Tu, Yong-Xian Cheng. (±) Cochlearoids N–P: three pairs of phenolic meroterpenoids from the fungus Ganoderma cochlear and their bioactivities. Journal of Asian Natural Products Research 2019, 21 (6) , 542-550. DOI: 10.1080/10286020.2018.1481052.
  16. Qi Luo, Wen-Wen Cao, Ze-Hong Wu, Shu-Mei Wang, Yong-Xian Cheng. Zizhines G–O, AchE inhibitory meroterpenoids from Ganoderma sinensis. Fitoterapia 2019, 134, 411-416. DOI: 10.1016/j.fitote.2019.03.016.
  17. Ting Gong, Renyi Yan, Jie Kang, Ruoyun Chen. Chemical Components of Ganoderma. 2019,,, 59-106. DOI: 10.1007/978-981-13-9867-4_3.
  18. Guo-Xun YANG, Guang-Lei MA, Hao LI, Ting HUANG, Juan XIONG, Jin-Feng HU. Advanced natural products chemistry research in China between 2015 and 2017. Chinese Journal of Natural Medicines 2018, 16 (12) , 881-906. DOI: 10.1016/S1875-5364(18)30131-6.
  19. Fu-Ying Qin, Yong-Ming Yan, Zheng-Chao Tu, Yong-Xian Cheng. Meroterpenoid dimers from Ganoderma cochlear and their cytotoxic and COX-2 inhibitory activities. Fitoterapia 2018, 129, 167-172. DOI: 10.1016/j.fitote.2018.06.019.
  20. Li-Zhi Cheng, Fu-Ying Qin, Xiao-Chi Ma, Shu-Mei Wang, Yong-Ming Yan, Yong-Xian Cheng. Cytotoxic and N-Acetyltransferase Inhibitory Meroterpenoids from Ganoderma cochlear. Molecules 2018, 23 (7) , 1797. DOI: 10.3390/molecules23071797.
  21. Xingrong Peng, Minghua Qiu. Meroterpenoids from Ganoderma Species: A Review of Last Five Years. Natural Products and Bioprospecting 2018, 8 (3) , 137-149. DOI: 10.1007/s13659-018-0164-z.
  22. Xingrong Peng, Xia Wang, Long Chen, Han Yang, Lei Li, Shuangyang Lu, Lin Zhou, Minghua Qiu. Racemic meroterpenoids from Ganoderma cochlear. Fitoterapia 2018, 127, 286-292. DOI: 10.1016/j.fitote.2018.03.005.
  23. Lin Chen, Tian Yang, De-Wen Lu, Hui Zhao, Ya-Long Feng, Hua Chen, Dan-Qian Chen, Nosratola D. Vaziri, Ying-Yong Zhao. Central role of dysregulation of TGF-β/Smad in CKD progression and potential targets of its treatment. Biomedicine & Pharmacotherapy 2018, 101, 670-681. DOI: 10.1016/j.biopha.2018.02.090.
  24. Haishan Liu, Guoliang Zhu, Yaqin Fan, Yuqi Du, Mengmeng Lan, Yibo Xu, Weiming Zhu. Natural Products Research in China From 2015 to 2016. Frontiers in Chemistry 2018, 6 DOI: 10.3389/fchem.2018.00045.
  25. Qi Luo, Zheng-Chao Tu, Zhu-Liang Yang, Yong-Xian Cheng. Meroterpenoids from the fruiting bodies of Ganoderma theaecolum. Fitoterapia 2018, 125, 273-280. DOI: 10.1016/j.fitote.2018.01.015.
  26. Fu-Ying Qin, Yong-Ming Yan, Zheng-Chao Tu, Yong-Xian Cheng. Cochlearoids L and M: Two New Meroterpenoids from the Fungus Ganoderma cochlear. Natural Product Communications 2018, 13 (3) , 1934578X1801300. DOI: 10.1177/1934578X1801300310.
  27. Clovis Peter, Philippe Geoffroy, Michel Miesch. Highly diastereoselective access to polyfunctionalized 1,3-oxazines promoted by Brønsted/Lewis acids. Organic Chemistry Frontiers 2018, 5 (4) , 566-570. DOI: 10.1039/C7QO00891K.
  28. Chunmei Sai, Dahong Li, Shengge Li, Tong Han, Yongzhi Guo, Zhanlin Li, Huiming Hua. LC-MS guided isolation of three pairs of enantiomeric alkaloids from Macleaya cordata and their enantioseparations, antiproliferative activity, apoptosis-inducing property. Scientific Reports 2017, 7 (1) DOI: 10.1038/s41598-017-15423-4.
  29. Rathikrishnan Rengarasu, Martin E. Maier. Total Synthesis of Lingzhiol and its Analogues through the Wittig Reaction of an Oxocyclopentane Carboxylate. Asian Journal of Organic Chemistry 2017, 6 (1) , 108-117. DOI: 10.1002/ajoc.201600455.
  30. He-Ping Chen, Ji-Kai Liu. Secondary Metabolites from Higher Fungi. 2017,,, 1-201. DOI: 10.1007/978-3-319-59542-9_1.
  31. Yan-Long Yang, Qiao-Qiao Tao, Jun-Jie Han, Li Bao, Hong-Wei Liu. Recent Advance on Bioactive Compounds from the Edible and Medicinal Fungi in China. 2017,,, 253-312. DOI: 10.1007/978-981-10-5978-0_9.
  32. Xin-Long Wang, Man Dou, Qi Luo, Li-Zhi Cheng, Yong-Ming Yan, Rong-Tao Li, Yong-Xian Cheng. Racemic alkaloids from the fungus Ganoderma cochlear. Fitoterapia 2017, 116, 93-98. DOI: 10.1016/j.fitote.2016.11.011.
  33. Qi Luo, Zheng-Chao Tu, Yong-Xian Cheng. Two rare meroterpenoidal rotamers from Ganoderma applanatum. RSC Advances 2017, 7 (6) , 3413-3418. DOI: 10.1039/C6RA26572C.
  34. Qi Luo, Zhen Wang, Jin-Feng Luo, Zheng-Chao Tu, Yong-Xian Cheng. (±)-Applanatumines B–D: novel dimeric meroterpenoids from Ganoderma applanatum as inhibitors of JAK3. RSC Advances 2017, 7 (60) , 38037-38043. DOI: 10.1039/C7RA04862A.
  35. Shi-Xing Ma, You-Quan Shang, Huan-Qiao Zhang, Wei Su, . Action Mechanisms and Therapeutic Targets of Renal Fibrosis. Journal of Nephrology Advances 2016, 1 (2) , 4-14. DOI: 10.14302/issn.2574-4488.jna-18-2443.
  36. Qi Luo, Xiao-Hua Yang, Zhu-Liang Yang, Zheng-Chao Tu, Yong-Xian Cheng. Miscellaneous meroterpenoids from Ganoderma applanatum. Tetrahedron 2016, 72 (30) , 4564-4574. DOI: 10.1016/j.tet.2016.06.019.
  37. Yan-Long Yang, Hui Zhou, Gang Du, Ke-Na Feng, Tao Feng, Xiao-Li Fu, Ji-Kai Liu, Ying Zeng. A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway. Angewandte Chemie 2016, 128 (18) , 5553-5556. DOI: 10.1002/ange.201510928.
  38. Yan-Long Yang, Hui Zhou, Gang Du, Ke-Na Feng, Tao Feng, Xiao-Li Fu, Ji-Kai Liu, Ying Zeng. A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway. Angewandte Chemie International Edition 2016, 55 (18) , 5463-5466. DOI: 10.1002/anie.201510928.
  39. Wen-Wen Cao, Qi Luo, Yong-Xian Cheng, Shu-Mei Wang. Meroterpenoid enantiomers from Ganoderma sinensis. Fitoterapia 2016, 110, 110-115. DOI: 10.1016/j.fitote.2016.03.003.
  40. Yao Liu, Chu-Jun Zhou, Qingjiang Li, Honggen Wang. Total synthesis of (±)-ganocins B and C. Organic & Biomolecular Chemistry 2016, 14 (44) , 10362-10365. DOI: 10.1039/C6OB02049F.
  41. Qi Luo, Lei Di, Xiao-Hua Yang, Yong-Xian Cheng. Applanatumols A and B, meroterpenoids with unprecedented skeletons from Ganoderma applanatum. RSC Advances 2016, 6 (51) , 45963-45967. DOI: 10.1039/C6RA05148K.
  42. He-Ping Chen, Zhen-Zhu Zhao, Yu Zhang, Xue Bai, Ling Zhang, Ji-Kai Liu. (+)- and (−)-ganodilactone, a pair of meroterpenoid dimers with pancreatic lipase inhibitory activities from the macromycete Ganoderma leucocontextum. RSC Advances 2016, 6 (69) , 64469-64473. DOI: 10.1039/C6RA10638B.
  43. Wei-Yi Ding, Jun Ai, Xin-Long Wang, Fayang G. Qiu, Qing Lv, Ping Fang, Fan-Fan Hou, Yong-Ming Yan, Yong-Xian Cheng. Isolation of lingzhifuran A and lingzhilactones D–F from Ganoderma lucidum as specific Smad3 phosphorylation inhibitors and total synthesis of lingzhifuran A. RSC Advances 2016, 6 (81) , 77887-77897. DOI: 10.1039/C6RA17900B.
  44. Zhen-Zhu Zhao, He-Ping Chen, Tao Feng, Zheng-Hui Li, Ze-Jun Dong, Ji-Kai Liu. Lucidimine A-D, four new alkaloids from the fruiting bodies of Ganoderma lucidum. Journal of Asian Natural Products Research 2015, 17 (12) , 1160-1165. DOI: 10.1080/10286020.2015.1119128.
  45. Qin-Lei Gao, Ping-Xia Guo, Qi Luo, Hui Yan, Yong-Xian Cheng. Petchienes A–E, Meroterpenoids from Ganoderma petchii. Natural Product Communications 2015, 10 (12) , 1934578X1501001. DOI: 10.1177/1934578X1501001201.
  46. Wei-Feng Dai, Ping-Xia Guo, Zheng-Chao Tu, Rong-Tao Li, Yong-Xian Cheng. Five new compounds from the fungus Ganoderma petchii. Fitoterapia 2015, 106, 68-71. DOI: 10.1016/j.fitote.2015.08.002.
  47. Qi Luo, Lei Tian, Lei Di, Yong-Ming Yan, Xiao-Yi Wei, Xin-Fang Wang, Yong-Xian Cheng. ChemInform Abstract: (.+-.)-Sinensilactam A (I), a Pair of Rare Hybrid Metabolites with Smad3 Phosphorylation Inhibition from Ganoderma sinensis.. ChemInform 2015, 46 (31) , no-no. DOI: 10.1002/chin.201531247.
  48. Robert A. Hill, Andrew Sutherland. Hot off the press. Natural Product Reports 2015, 32 (6) , 760-764. DOI: 10.1039/C5NP90021B.

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.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE