Skip to main content
Log in

Two new rearranged clerodane diterpenes from Thai Tinospora baenzigeri

  • Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

A new rearranged clerodane-type diterpene (1), tinobaenzigeride, and a new rearranged clerodane glucoside (2) were isolated from the stems of Tinospora baenzigeri, along with four known compounds (36). Their structures were elucidated by spectroscopic data analysis. In addition, the structure and configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 are a rare example of rearranged clerodanes, since it contains a fully oxygenated tetrahydrofuran moiety. The isolated compounds were evaluated for their cytotoxicity against Hep-G2 and MCF-7 cancer cells, none of them did show any significant activity at 25 μM.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

References

  1. Ahmad SM, Hoot SB, Qazi PH (2009) Phylogenetic and genetic diversity of Indian Tinospora species based on chloroplast sequence and cytochrome P450 polymorphism. Plant Syst Evol 281:87–96

    Article  CAS  Google Scholar 

  2. Liu YH, Luo XR, Wu RF, Zhang BN (1996) Flora of China (Zhongguo Zhiwu Zhi), vol. 30-1. Science Press, Beijing, pp 19–25

    Google Scholar 

  3. Ragasa CY, Cruz MC, Gula R, Rideout JA (2000) Clerodane diterpenes from Tinospora rumphii. J Nat Prod 63:509–511

    Article  CAS  Google Scholar 

  4. Choudhary MI, Ismail M, Shaari K, Abbaskhan A, Sattar SA, Lajis NH, Rahman A (2010) cis-Clerodane-type furanoditerpenoids from Tinospora crispa. J Nat Prod 73:541–547

    Article  CAS  Google Scholar 

  5. Lam SH, Ruan CT, Hsieh PH, Su MJ, Lee SS (2012) Hypoglycemic diterpenoids from Tinospora crispa. J Nat Prod 75:153–159

    Article  CAS  Google Scholar 

  6. Qin N, Wang A, Li D, Wang K, Lin B, Li Z, Hua H (2015) Cytotoxic clerodane furanoditerpenoids from the root of Tinospora sagittata. Phytochem Lett 12:173–176

    Article  CAS  Google Scholar 

  7. Guanhua L, Wenbing D, Fanghao W, Youzhi L (2016) Two new clerodane diterpenes from Tinospora sagittata. Molecules 15:1250

    Google Scholar 

  8. Zhang G, Ma H, Hu S, Xu H, Yang B, Yang Q, Xue Y, Chenga L, Jiang J, Zhang J, Wang F, Zhang Y (2016) Clerodane-type diterpenoids from tuberous roots of Tinospora sagittata (Oliv.) Gagnep. Fitoterapia 110:59–65

    Article  CAS  Google Scholar 

  9. Tuntiwachwuttikul P, Boonrasria N, Bremner JB, Taylor WC (1999) Rearranged clerodane diterpenes from Tinospora baenzigeri. Phytochemistry 52:1335–1340

    Article  CAS  Google Scholar 

  10. Tuntiwachwuttikul P, Taylor WC (2001) New rearranged clerodane diterpenes from Tinospora baenzigeri. Chem Pharm Bull 47:854–857

    Article  Google Scholar 

  11. Hanthanong S, Choodej S, Teerawatananond T, Pudhom K (2019) Rearranged clerodane diterpenoids from the stems of Tinospora baenzigeri. J Nat Prod 82:1405–1411

    Article  CAS  Google Scholar 

  12. Bruker (2014) SHELXTL. Bruker AXS Inc., Madison

    Google Scholar 

  13. Spek AL (2015) PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors. Acta Cryst C71:9–18

    Google Scholar 

  14. Chokpaiboon S, Sommit D, Teerawatananond T, Muangsin N, Bunyapaiboonsri T, Pudhom K (2010) Cytotoxic nor-chamigrane and chamigrane endoperoxides from a basidiomycetous fungus. J Nat Prod 73:1005–1007

    Article  CAS  Google Scholar 

  15. Mohamed AA, Alwahsh MK, Wong KC (2015) Chemical constituents and antioxidant activity of Teucrium barbeyanum Aschers. Rec Nat Prod 9:159–163

    Google Scholar 

  16. Jain R, Mittal M (2012) Naringenin, a flavonone from the stem of Nyctanthesarbor tristis Linn. IJBPAS 1:964–972

    Google Scholar 

  17. Encarnacion DR, Nogueiras CL, Salinas VHA, Anthoni U (1999) Isolation of eriodictyol identical with Huazhongilexone from Solanum hindsianum. Acta Chem Scand 53:375–377

    Article  CAS  Google Scholar 

  18. Zhenggang Y, Hui Q, Yuhua L, Yang S, Zhipeng W, Tiehong Y, Li L, Minchang W, Feng F, Qibing M (2013) Chemical constituents of the root of Jasminum giraldii. Molecules 18:4766–4775

    Article  Google Scholar 

  19. Noman MAA, Hossain T, Ahsan M, Jamshidi S, Hasan CM, Rahman KM (2018) Crispenes F and G, cis-clerodane furanoditerpenoids from Tinospora crispa, inhibit STAT3 dimerization. J Nat Prod 81:236–242

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the financial support provided by the 90th Anniversary of Chulalongkorn University Fund (Ratchadaphiseksomphot Endowment Fund). T.A. is grateful to the Ratchadapisek Sompoch Endowment Fund (CU-GR_62_53_23_19), Chulalongkorn University, for partial support of X-ray diffraction facility.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Khanitha Pudhom.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 559 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hanthanong, S., Choodej, S., Aree, T. et al. Two new rearranged clerodane diterpenes from Thai Tinospora baenzigeri. J Nat Med 75, 201–206 (2021). https://doi.org/10.1007/s11418-020-01450-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-020-01450-5

Keywords

Navigation