Planta Med 2017; 83(01/02): 111-116
DOI: 10.1055/s-0042-107252
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Diterpenoid Alkaloids from Delphinium ajacis and Their Anti-RSV Activities

Li Yang
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Yu-Bo Zhang
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Ling Zhuang
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Tao Li
2   School of Biomedical Sciences, The University of Hong Kong, Central and Western District, Hong Kong
,
Neng-Hua Chen
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Zhong-Nan Wu
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Pan Li
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Yao-Lan Li
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
,
Guo-Cai Wang
1   Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, P. R. China
› Author Affiliations
Further Information

Publication History

received 30 November 2015
revised 06 April 2016

accepted 15 April 2016

Publication Date:
12 July 2016 (online)

Abstract

Five new diterpenoid alkaloids, ajacisines A–E (15), were isolated from Delphinium ajacis, along with seven known alkaloids (612). On the basis of their spectral data (IR, UV, HR-ESI-MS, 1D and 2D NMR) and chemical properties, the structures of compounds 112 were identified. All isolated compounds were evaluated for their in vitro antiviral activities against respiratory syncytial virus, and compounds 35 and 8 exhibited moderate to weak effects with IC50 values of 75.2 ± 1.1, 35.1 ± 0.6, 10.1 ± 0.3, and 50.2 ± 0.5 µM, respectively.

Supporting Information

 
  • References

  • 1 Liang XH, Ross SA, Sohni YR, Sayed HM, Desai HK, Joshi BS, Pelletier SW. Norditerpenoid alkaloids from the stems and leaves of Delphinium ajacis . J Nat Prod 1991; 54: 1283-1287
  • 2 Ran XD. Zhong Hua Yao Hai. Harbin: Harbin Publishing House; 1993: 219
  • 3 Chen QY, Chen M, Liu H, Du M, Zhang H, Feng F, Gong J, Ni SF. [Overview of pharmaceutical research on Consolida (DC.) Opiz]. J Anhui Agric Sci 2013; 41: 8143-8144
  • 4 Mericli AH, Yazici S, Eroglu-Ozkan E, Sen B, Kurtoglu S, Ozcelik H, Zapp J, Kiemer AK, Mericli F. Norditerpenoid alkaloids from Consolida thirkeana and Consolida sulphurea . Chem Nat Compd 2012; 48: 525-526
  • 5 Marín C, Boutaleb-Charki S, Díaz JG, Huertas O, Rosales MJ, Pérez-Cordon G, Guitierrez-Sánchez R, Sánchez-Moreno M. Antileishmaniasis activity of flavonoids from Consolida oliveriana . J Nat Prod 2009; 72: 1069-1074
  • 6 Kokoska L, Urbanova K, Kloucek P, Nedorostova L, Polesna L, Malik J, Jiros P, Havlik J, Vadlejch J, Valterova I. Essential oils in the Ranunculaceae family: chemical composition of hydrodistilled oils from Consolida regalis, Delphinium elatum, Nigella hispanica, and N. nigellastrum seeds. Chem Biodivers 2012; 9: 151-161
  • 7 He YQ, Ma ZY, Wei XM, Liu DJ, Du BZ, Yao BH, Gao LM. Honatisine, a novel diterpenoid alkaloid, and six known alkaloids from Delphinium honanense and their cytotoxic activity. Chem Biodivers 2011; 8: 2104-2109
  • 8 Lin CZ, Zhao ZX, Xie SM, Mao JH, Zhu CC, Li XH, Zeren-dawa B, Suolang-qimei K, Zhu D, Xiong TQ, Wu AZ. Diterpenoid alkaloids and flavonoids from Delphinium trichophorum . Phytochemistry 2014; 97: 88-95
  • 9 Atta-ur-Rahman. Nasreen A, Akhtar F, Shekani MS, Clardy J, Parvez M, Choudhary MI. Antifungal diterpenoid alkaloids from Delphinium denudatum . J Nat Prod 1997; 60: 472-474
  • 10 Lu J, Desai HK, Ross SA, Sayed HM, Pelletier SW. New norditerpenoid alkaloids from the leaves of Delphinium ajacis . J Nat Prod 1993; 56: 2098-2103
  • 11 Mericli F, Mericli AH, Becker H, Ulubelen A, Özden S, Dürüst N, Tanker M. Norditerpenoid alkaloids from Delphinium formosum . Phytochemistry 1996; 42: 1249-1251
  • 12 Desai HK, El-Sofany RH, Pelletier SW. Isodelectine: a new norditerpenoid alkaloid from Delphinium vestitum . J Nat Prod 1990; 53: 1606-1608
  • 13 Zhou XL, Chen QH, Wang FP. Three new lycoctonine-type C19-diterpenoid alkaloids from Delphinium giraldii . Heterocycles 2004; 63: 123-128
  • 14 Yue J, Xu J, Zhao Q, Sun H. Diterpenoid alkaloids from Aconitum leucostomum . J Nat Prod 1996; 59: 277-279
  • 15 Huang Z, Tang J, Gao H, Li Y, Hong K, Li J, Yao X. [Studies on the cytotoxic constituents from marine actinomycete Micromonospora sp. (M2DG17)]. Chin J Mar Drugs 2011; 30: 29-33
  • 16 Al-Sehemi AGM. [Synthesis characterization and stereostructures of the pyridazino[6,1-b]quinazolinones]. J King Abdulaziz Univ Sci 2006; 18: 47-62
  • 17 Xu JJ, Wu X, Li MM, Li GQ, Yang YT, Luo HJ, Huang WH, Chung HY, Ye WC, Wang GC, Li YL. Antiviral activity of polymethoxylated flavones from “Guangchenpi”, the edible and medicinal pericarps of Citrus reticulata ‘Chachi’. J Agric Food Chem 2014; 62: 2182-2189
  • 18 Wang GC, Li JG, Li GQ, Xu JJ, Wu X, Ye WC, Li YL. Clerodane diterpenoids from Croton crassifolius . J Nat Prod 2012; 75: 2188-2192
  • 19 Zhang XL, Guo YS, Wang CH, Li GQ, Xu JJ, Chung HY, Ye WC, Li YL, Wang GC. Phenolic compounds from Origanum vulgare and their antioxidant and antiviral activities. Food Chem 2014; 152: 300-306
  • 20 Zhang YB, Wu P, Zhang XL, Xia C, Li GQ, Ye WC, Wang GC, Li YL. Phenolic compounds from the flowers of Bombax malabaricum and their antioxidant and antiviral activities. Molecules 2015; 20: 19947-19957