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Planta Med 2016; 82(09/10): 882-887
DOI: 10.1055/s-0042-106168
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Unusual Cytotoxic Steroidal Saponins from the Gorgonian Astrogorgia dumbea

Ya-Nan Lu
1   Key Laboratory of East China Sea & Oceanic Fishery Resources Exploitation and Utilization, Ministry of Agriculture, East China Sea Fisheries Research Institute, Chinese Academy of Fishery Sciences, Shanghai, P. R. China
,
Ping Cui
2   Changchun University of Chinese Medicine, Changchun, P. R. China
,
Xiao-Qing Tian
1   Key Laboratory of East China Sea & Oceanic Fishery Resources Exploitation and Utilization, Ministry of Agriculture, East China Sea Fisheries Research Institute, Chinese Academy of Fishery Sciences, Shanghai, P. R. China
,
Li-Guang Lou
3   Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
,
Cheng-Qi Fan
1   Key Laboratory of East China Sea & Oceanic Fishery Resources Exploitation and Utilization, Ministry of Agriculture, East China Sea Fisheries Research Institute, Chinese Academy of Fishery Sciences, Shanghai, P. R. China
› Author Affiliations
Further Information

Publication History

received 09 September 2015
revised 11 March 2016

accepted 22 March 2016

Publication Date:
28 June 2016 (online)

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Abstract

Three steroidal saponins, including astrogorgiosides A (1) and B (2) bearing acetamido-glucose moieties, and astrogorgioside C (3) with a 19-nor and bearing an aromatized B ring steroid aglycone, together with a known major saponin dimorphoside A (4), were obtained from the gorgonian Astrogorgia dumbea collected near Dongshan Island in East China Sea. Structures of these compounds were elucidated by in-depth spectral and chemical methods, including 2D-NMR, HR-ESI-MS spectra, and acidic hydrolysis. For the first time, acetamido-glucose moiety is being reported from a gorgonian. The B-ring aromatized steroid aglycone of compound 3 is also rare in marine natural products. Compounds 1–3 exhibited moderate cytotoxic activity with IC50 values of 26.8–45.6 µM against human tumor cells Bel-7402 and K562.

Key words

Astrogorgia dumbea - Plexauridae - steroidal saponin - astrogorgiosides A–C - cytotoxic activity

Supporting Information

 

  • References

  • 1 Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR. Marine natural products. Nat Prod Rep 2013; 30: 237-323
    CrossrefPubMedSearch in Google Scholar
  • 2 Cui P, Fan CQ, Lu YN, Shao SN. [Chemical constituents and their activities from gorgonian in China Sea]. Jilin J Trad Chin Med 2011; 31: 571-575
    PubMedSearch in Google Scholar
  • 3 Berrue F, Kerr RG. Diterpenes from gorgonian corals. Nat Prod Rep 2009; 26: 681-710
    CrossrefPubMedSearch in Google Scholar
  • 4 Zhang W, Guo YW. A pharmaceutical perspective on gorgonian: chemistry and bioactivity. Chin J Nat Med 2003; 1: 69-75
    PubMedSearch in Google Scholar
  • 5 Li XB, Huang H, Lian JS, Yang JH, Huang LM. Diversity and spatial distribution of gorgonian coral in Dongshan coastal waters in Fujian, China. J Oceanogr Taiwan 2011; 30: 92-96
    PubMedSearch in Google Scholar
  • 6 Fusetani N, Nagata H, Hirota H, Tsuyuki T. Astrogorgiadiol and astrogorgin, inhibitors of cell division in fertilized starfish eggs, from a gorgonian Astrogorgia sp. Tetrahedron Lett 1989; 30: 7079-7082
    CrossrefPubMedSearch in Google Scholar
  • 7 Taber DF, Farach-Carson MC, Malcolm SC, Xu Y. Treatment of osteoporosis and autoimmune disease with astrogorgiadiol. US Patent US7345035 B2, 2008
    PubMedSearch in Google Scholar
  • 8 Lai DW, Yu SJ, Ofwegen LV, Totzke F, Proksch P, Lin WH. 9,10-Secosteroids, protein kinase inhibitors from the Chinese gorgonian Astrogorgia sp. Bioorg Med Chem 2011; 19: 6873-6880
    CrossrefPubMedSearch in Google Scholar
  • 9 Fusetani N, Yasukawa K, Matsunage S, Hashimoto K. Dimorphosides A and B, novel steroid glycosides from the gorgonian Anthoplexaura dimorpha . Tetrahedron Lett 1987; 28: 1187-1190
    CrossrefPubMedSearch in Google Scholar
  • 10 Horo I, Bedir E, Perrone A, Ozgökçe F, Piacente S, Alankuş-Calişkan O. Triterpene glycosides from Astragalus icmadophilus . Phytochemistry 2010; 71: 956-963
    CrossrefPubMedSearch in Google Scholar
  • 11 Antonov SA, Afiyatullov SS, Kalinovsky IA, Ponomarenko PL, Dmitrenok SP, Aminin LD, Agafonova GI, Stonik AV. Mycalosides B–I, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima . J Nat Prod 2003; 66: 1082-1088
    CrossrefPubMedSearch in Google Scholar
  • 12 Barrero FA, Oltra JE, Poyatos AJ, Jiménez D, Oliver E. Phycomysterols and other sterols from the fungus Phycomyces blakesleeanus . J Nat Prod 1998; 61: 1491-1496
    CrossrefPubMedSearch in Google Scholar
  • 13 Luo X, Li F, Shinde BP, Hong J, Lee CO, Im KS, Jung JH. 26,27-Cyclosterols and other polyoxygenated sterols from a marine sponge Topsentia sp. J Nat Prod 2006; 69: 1760-1768
    CrossrefPubMedSearch in Google Scholar
  • 14 Ni G, Zhang QJ, Zheng ZF, Chen RY, Yu DQ. 2-Arylbenzofuran derivatives from Morus cathayana . J Nat Prod 2009; 72: 966-968
    CrossrefPubMedSearch in Google Scholar