Citation: Panpan Zhang, Shang Xue, Pengfei Tang, Zhirong Cui, Zefan Wang, Jun Luo, Lingyi Kong. Aphamines A-C, dimeric acyclic diterpene enantiomers from Aphanamixis polystachya[J]. Chinese Chemical Letters, ;2021, 32(4): 1480-1484. doi: 10.1016/j.cclet.2020.09.028 shu

Aphamines A-C, dimeric acyclic diterpene enantiomers from Aphanamixis polystachya

State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, China

luojun@cpu.edu.cn

cpu_lykong@126.com,lykong@cpu.edu.cn

Received Date: 10 July 2020
Revised Date: 10 August 2020
Accepted Date: 18 September 2020
Available Online: 18 September 2020

Figures(5)

Aphamines A–C (1–3), three pairs of acyclic diterpene dimer enantiomers with an unprecedent ploymerization pattern, were discovered from Aphanamixis polystachya by NMR-guided isolation and chiral resolution. The elucidation of their novel carbon skeletons was achieved based on spectroscopic analysis, exciton chirality, and calculated electronic circular dichroism (ECD). Plausible Claisen rearrangement, 5-exo-trig cyclization, and reduction reactions may play important roles in the polymeric biosynthesis pathway. Compounds 1 and 3 showed inhibitory effects on nitric oxide (NO) production (IC₅₀: 6.71–15.36 μmol/L) and reduced the expression of iNOS in LPS-induced RAW 264.7 macrophages.
- Aphanamixis polystachya,
- Acyclic diterpene dimer,
- NMR-guided isolation,
- Chiral resolution,
- Anti-inflammatory activity
1. [1]
  H.J. Zhang, J. Luo, S.M. Shan, et al., Org. Lett. 15(2013) 5512-5515. doi: 10.1021/ol402516p
2. [2]
  H.J. Zhang, Y.M. Zhang, J.G. Luo, J. Luo, L.Y. Kong, Org. Biomol. Chem. 13(2015) 7452-7458. doi: 10.1039/C5OB00674K
3. [3]
  J. Liu, X.F. He, G.H. Wang, et al., J. Org. Chem. 79(2014) 599-607. doi: 10.1021/jo402340h
4. [4]
  H. Zhang, J. Liu, L.S. Gan, et al., Org. Biomol. Chem. 14(2016) 957-962. doi: 10.1039/C5OB02296G
5. [5]
  A. Astulla, Y. Hirasawa, A. Rahman, et al., Nat. Prod. Commun. 6(2011) 323-326.
6. [6]
  Y. Zhang, J.S. Wang, D.D. Wei, et al., J. Nat. Prod. 76(2013) 1191-1195. doi: 10.1021/np400126q
7. [7]
  H.F. Wu, X.P. Zhang, Y. Wang, et al., Fitoterapia 90(2013) 126-131. doi: 10.1016/j.fitote.2013.07.008
8. [8]
  R. Zhang, H.P. He, Y.T. Di, et al., Fitoterapia 92(2014) 100-104. doi: 10.1016/j.fitote.2013.10.014
9. [9]
  X.P. Zhang, Y.F. Tan, Y.B. Li, et al., Chem. Pharm. Bull. 62(2014) 494-498. doi: 10.1248/cpb.c14-00056
10. [10]
  H.Y. Zhang, C.M. Yuan, M.M. Cao, et al., Phytochem. Lett. 8(2014) 81-85. doi: 10.1016/j.phytol.2014.02.005
11. [11]
  F.H. Fang, W.J. Huang, S.Y. Zhou, et al., Eur. J. Org. Chem. 23(2017) 4429-4433.
12. [12]
  S. Xue, P.P. Zhang, P.F. Tang, et al., Fitoterapia 142(2020) 104518. doi: 10.1016/j.fitote.2020.104518
13. [13]
  J.P. Yin, M. Gu, Y. Li, F.J. Nan, J. Org. Chem. 79(2014) 6294-6301. doi: 10.1021/jo501117k
14. [14]
  J.X. Zhao, Y.Y. Yu, S.S. Wang, et al., J. Am. Chem. Soc. 140(2018) 2485-2492. doi: 10.1021/jacs.7b10135
15. [15]
  G.X. Yang, G.L. Ma, H. Li, et al., Chin. J. Nat. Med. 16(2018) 881-906.
16. [16]
  S.K. Chen, B.Y. Chen, H. Li, Flora Reipublicae Popularis Sinicae (Zhongguo Zhiwu Zhi), Science Press, Beijing, 1997.
17. [17]
  N. Berova, L.D. Bari, G. Pescitelli, Chem. Soc. Rev. 36(2007) 914-931. doi: 10.1039/b515476f
18. [18]
  J.H. Reed, P.A. Donets, S. Miaskiewicz, N. Cramer, Angew. Chem. Int. Ed. 58(2019) 8893-8897. doi: 10.1002/anie.201904411
19. [19]
  A.O. Olabisi, M.P.D. Mahindaratne, K. Wimalasena, J. Org. Chem. 70(2005) 6782-6789. doi: 10.1021/jo0508550
20. [20]
  K. Wimalasena, M.P.D. Mahindaratne, J. Org. Chem. 59(1994) 3427-3432. doi: 10.1021/jo00091a036
21. [21]
  Y. Shi, X.L. Jiang, W.S. Tian, J. Org. Chem. 82(2017) 269-275. doi: 10.1021/acs.joc.6b02391
22. [22]
  D. François, M.C. Lallemand, M. Selkti, et al., Angew. Chem. Int. Ed. 37(1998) 104-105. doi: 10.1002/(SICI)1521-3773(19980202)37:1/2<104::AID-ANIE104>3.0.CO;2-K
23. [23]
  T.G. LaCour, C.X. Guo, S. Bhandaru, M.R. Boyd, P.L. Fuchs, J. Am. Chem. Soc. 120(1998) 692-707. doi: 10.1021/ja972160p
24. [24]
  R. Bigler, K.A. Mack, J. Shen, et al., Angew. Chem. Int. Ed. 132(2020) 2866-2871. doi: 10.1002/ange.201912640
25. [25]
  S. Kraft, K. Ryan, R.B. Kargbo, J. Am. Chem. Soc. 139(2017) 11630-11641. doi: 10.1021/jacs.7b07188
26. [26]
  M. Biosca, E. Salomo', P. de la Cruz-Sa'nchez, et al., Org. Lett. 21(2019) 807-811. doi: 10.1021/acs.orglett.8b04084
27. [27]
  C.N. Serhan, N.A. Petasis, Chem. Rev. 111(2011) 5922-5943. doi: 10.1021/cr100396c
28. [28]
  F.R. Greten, S.I. Grivennikov, Immunity 51(2019) 27-41. doi: 10.1016/j.immuni.2019.06.025
29. [29]
  S.S. Wei, J. Chi, M.M. Zhou, et al., Ind. Crop. Prod. 137(2019) 367-376. doi: 10.1016/j.indcrop.2019.05.041
1. [1]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
2. [2]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
3. [3]
  Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
4. [4]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
5. [5]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
6. [6]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
7. [7]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
8. [8]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
9. [9]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
10. [10]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
11. [11]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
12. [12]
  Wenying Cui , Zhetong Jin , Wentao Fu , Chengshuo Shen . Flag-hinge-like highly luminescent chiral nanographenes with twist geometry. Chinese Chemical Letters, 2024, 35(11): 109667-. doi: 10.1016/j.cclet.2024.109667
13. [13]
  Genlin Sun , Yachun Luo , Zhihong Yan , Hongdeng Qiu , Weiyang Tang . Chiral metal-organic frameworks-based materials for chromatographic enantioseparation. Chinese Chemical Letters, 2024, 35(12): 109787-. doi: 10.1016/j.cclet.2024.109787
14. [14]
  Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
15. [15]
  Chuang LIU , Lichao SUN , Qingfeng ZHANG . Chiral inorganic nanocatalysts for electrochemical and enzyme-mimicked biosensing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 59-78. doi: 10.11862/CJIC.20240406
16. [16]
  Yan-Bo Li , Yi Li , Liang Yin . Copper(Ⅰ)-catalyzed diastereodivergent construction of vicinal P-chiral and C-chiral centers facilitated by dual "soft-soft" interaction. Chinese Chemical Letters, 2024, 35(7): 109294-. doi: 10.1016/j.cclet.2023.109294
17. [17]
  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
18. [18]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
19. [19]
  Feng Wu , Xuemin Kong , Yixuan Liu , Shuli Wang , Zhong Chen , Xu Hou . Microfluidic-based isolation of circulating tumor cells with high-efficiency and high-purity. Chinese Chemical Letters, 2024, 35(8): 109754-. doi: 10.1016/j.cclet.2024.109754
20. [20]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(512)
HTML views(55)

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