Citation: Ding Gang, Wang Jing, Fei Jiao-Dong, Li Rong-Tao, Jia Hong-Mei, Zhang Tao, Yu Chang-Yuan, Zou Zhong-Mei. Fimbrialtols K-M, highly functionalized ent-kaurane diterpenoids from traditional Chinese plant Flickingeria fimbriata (B1.) Hawkes[J]. Chinese Chemical Letters, ;2017, 28(3): 593-596. doi: 10.1016/j.cclet.2016.10.033 shu

Fimbrialtols K-M, highly functionalized ent-kaurane diterpenoids from traditional Chinese plant Flickingeria fimbriata (B1.) Hawkes

Ding Gang ^a ,
Wang Jing ^a,b ,
Fei Jiao-Dong ^a,b ,
Li Rong-Tao ^c ,
Jia Hong-Mei ^a ,
Zhang Tao ^a ,
Yu Chang-Yuan ^b,, ,
Zou Zhong-Mei ^a,,

a.
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China
b.
Beijing University of Chemical Technology, Beijing 100029, China
c.
Hainan Branch of Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, China

Corresponding author: Yu Chang-Yuan, yucy@mail.buct.edu.cn Zou Zhong-Mei, zmzou@implad.ac.cn
Received Date: 17 August 2016
Revised Date: 13 October 2016
Accepted Date: 19 October 2016
Available Online: 2 March 2016

Figures(2)

Three new ent-kaurane diterpenoids fimbrialtols K-M (3-5) with highly substituted functionalities were isolated from the extract of Flickingeria fimbriata (B1.) Hawkes. The structures of these new compounds were determined by NMR and HR-ESIMS. The relative configurations of these compounds were determined by analysis of NOESY correlations. The absolute configurations of these new compounds were established by CD methods together with considering the biosynthetic pathway. Compounds 3 and 4 contain a cinnamic carboxyl group, whereas compound 5 possesses a benzoic carboxyl group representing the first report in more than known 600 ent-kaurane diterpenoids.
- Flickingeria fimbriata (B1.) Hawkes,
- ent-Kaurane diterpenoids,
- Fimbrialtols,
- NMR,
- CD
1. [1]
  Zou G., Ding G., Su Z.H.. Lactonecembranoids from Croton laevigatus[J]. J. Nat. Prod., 2010,73:792-795. doi: 10.1021/np100044t
2. [2]
  Yu Y.M., Yang J.S., Peng C.Z.. Lactones from Angiopteris caudatiformis[J]. J. Nat. Prod., 2009,72:921-924. doi: 10.1021/np900027m
3. [3]
  Yu L.L., Hu W.C., Ding G.. Gusanlungionosides A-D, potential tyrosinase inhibitors from Arcangelisia gusanlung[J]. J. Nat. Prod., 2011,74:1009-1014. doi: 10.1021/np100900k
4. [4]
  X.H. Tian, L. Li, Y.B. Hu, et al., Dichrocephones A and B, two cytotoxic sesquiterpenoids with the unique[3.3.3] propellane nucleus skeleton from Dichrocephala benthamii, RSC Adv. 3(2013) 7880-7883.
5. [5]
  G. Ding, J.D. Fei, J. Wang, et al., Fimbriatols A-J, highly oxidized ent-kaurane diterpenoids from traditional Chinese plant Flickingeria fimbriata (B1.) Hawkes, Sci. Rep. 6(2016) 30560.
6. [6]
  Tinto W.F., Blyden G., Reynolds W.F., McLean S.. Diterpene and anthraquinone constituents of Glycydendron amazonicum[J]. J. Nat. Prod., 1991,54:1127-1130. doi: 10.1021/np50076a037
7. [7]
  Sun H.D., Huang S.X., Han Q.B.. Diterpenoids from Isodon species and their biological activities[J]. Nat. Prod. Rep., 2006,23:673-698. doi: 10.1039/b604174d
8. [8]
  (a) I. Kubo, M. Taniguchi, Y. Satomura, T. Kubota, Antibacterial activity and chemical structure of diterpenoids, Agric. Biol. Chem. 38(1974) 1261-1262
  (b) E. Fujita, Y. Nagao, M. Node, et al., Antitumor activity of the Isodon diterpenoids:structural requirements for the activity, Experientia 32(1976) 203-206.
9. [9]
  (a) Y.L. Yang, F.R. Chang, C.C. Wu, W.Y. Wang, Y.C. Wu, New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa, J. Nat. Prod. 65(2002) 1462-1467;
  (b) L. Han, X.S. Huang, I. Sattler, et al., New diterpenoids from the marine mangrove Bruguiera gymnorrhiza, J. Nat. Prod. 67(2004) 1620-1623;
  (c) X. Ge, G. Ye, P. Li, et al., Cytotoxic diterpenoids and sesquiterpenoids from Pteris multifida, J. Nat. Prod. 71(2008) 227-231;
  (d) H.H. Ko, W.L. Chang, T.M. Lu, Antityrosinase and antioxidant effects of entkaurane diterpenes from leaves of Broussonetia papyrifera, J. Nat. Prod. 71(2008) 1930-1933;
  (e) T.T. Dao, K.Y. Lee, H.M. Jeong, et al., ent-Kaurane diterpenoids from Croton tonkinensis stimulate osteoblast differentiation, J. Nat. Prod. 74(2011) 2526-2531;
  (f) P.C. Kuo, M.L. Yang, T.L. Hwang, et al., Anti-inflammatory diterpenoids from Croton tonkinensis, J. Nat. Prod. 76(2013) 230-236.
10. [10]
  Zou J., Du X., Pang G.. Ternifolide A, a new diterpenoid possessing a rare macrolide motif from Isodon ternifolius[J]. Org. Lett., 2012,14:3210-3213. doi: 10.1021/ol3013205
1. [1]
  Zhike Yang , Jinfan Xu , Junhao Chen , Zheng Yang , Fei Ding , Neil Qiang Su . AI NMR Assistant: A DP5-Based Intelligent System for NMR Spectral Interpretation. University Chemistry, 2026, 41(1): 20-28. doi: 10.12461/PKU.DXHX202506013
2. [2]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
3. [3]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
4. [4]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
5. [5]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
6. [6]
  Ke Gong , Jinghan Liao , Jiangtao Lin , Quan Wang , Zhihua Wu , Liting Wang , Jiali Zhang , Yi Dong , Yourong Duan , Jianhua Chen . Mitochondria-targeted nanoparticles overcome chemoresistance via downregulating BACH1/CD47 axis in ovarian carcinoma. Chinese Chemical Letters, 2024, 35(5): 108888-. doi: 10.1016/j.cclet.2023.108888
7. [7]
  Xinzhi Ding , Chong Liu , Jing Niu , Nan Chen , Shutao Xu , Yingxu Wei , Zhongmin Liu . Solid-state NMR study of the stability of MOR framework aluminum. Chinese Journal of Structural Chemistry, 2024, 43(4): 100247-100247. doi: 10.1016/j.cjsc.2024.100247
8. [8]
  Hanqi Zhang , Biao Gao , Yuanyuan Feng , Guijuan Zheng , Zhijun Liu , Lichun Kong , Junjun Liu , Haji Akber Aisa , Guangmin Yao . DFT calculations and dynamic NMR revealed the coalescent NMR phenomena of the 6/6/6/9 tetracyclic merosesquiterpenoids with an unprecedented 9,15-dioxatetracyclo[8.5.3.0^4,17.0^14,18]octadecane core skeleton. Chinese Chemical Letters, 2025, 36(9): 111234-. doi: 10.1016/j.cclet.2025.111234
9. [9]
  Honglin Gao , Chunlin Yuan , Hongyu Chen , Aiyi Dong , Pan Gao , Guangjin Hou . Surface gallium hydride on Ga2O3 polymorphs: A comparative solid-state NMR study. Chinese Journal of Structural Chemistry, 2025, 44(4): 100561-100561. doi: 10.1016/j.cjsc.2025.100561
10. [10]
  Xiaonan LI , Hui HAN , Yihan ZHANG , Jing XIONG , Tingting GUO , Juanzhi YAN . A viologen‐based Cd(Ⅱ) coordination polymer: Self‐assembly, thermochromism, and electrochemical property. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1439-1444. doi: 10.11862/CJIC.20240376
11. [11]
  Wenwen Zhang , Peichao Zhang , Conghao Gai , Xiaoyun Chai , Yan Zou , Qingjie Zhao . Unveiling Kinetics at Natural Abundance: ¹³C NMR Isotope Effect Experiments. University Chemistry, 2025, 40(10): 203-207. doi: 10.12461/PKU.DXHX202411076
12. [12]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
13. [13]
  Wei GUO , Zhuoyi GUO , Xiaoxin LI , Wei ZHANG , Juanzhi YAN , Tingting GUO . Electrochemical sensor based on a Co(Ⅱ)-based metal-organic framework for the detection of Cd²⁺ and Pb²⁺. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1889-1902. doi: 10.11862/CJIC.20250097
14. [14]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
15. [15]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
16. [16]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
17. [17]
  Pengyu Chen , Beibei Chen , Man He , Yuxi Zhou , Lei Lei , Jian Han , Bingsheng Zhou , Ligang Hu , Bin Hu . Nanoplastics and nano-ZnO facilitate Cd accumulation in zebrafish larvae via a distinct pathway: Revelation by LA-ICP-MS imaging. Chinese Chemical Letters, 2025, 36(2): 109908-. doi: 10.1016/j.cclet.2024.109908
18. [18]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
19. [19]
  Jingzhuo Tian , Chaohong Guan , Haobin Hu , Enzhou Liu , Dongyuan Yang . Waste plastics promoted photocatalytic H₂ evolution over S-scheme NiCr₂O₄/twinned-Cd_0.5Zn_0.5S homo-heterojunction. Acta Physico-Chimica Sinica, 2025, 41(6): 100068-0. doi: 10.1016/j.actphy.2025.100068
20. [20]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1339)
HTML views(62)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142