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Two new sesterterpenoids from Atractylodes japonica Koidz. ex Kitam

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Abstract

Two new sesterterpenoids, atractylodes japonica terpenoid acid I (1) and atractylodes japonica terpenoid aldehyde I (2), were isolated from the rhizomes of Atractylodes japonica Koidz. ex Kitam together with ten known compounds (3–12). Their structures were elucidated on the basis of comprehensive spectroscopic analysis (1D/2D NMR, HRESIMS and IR). In addition, all of these isolated compounds were evaluated for their cytotoxic activities against human gastric cancer cell MGC-803 and human hepatocellular cancer cell HepG-2. Most of them exhibited moderate to weak inhibitory effects with IC50 values in the range of 25.15–88.85 μM except for 912.

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References

  1. Zhao QL, Wang MJ, Zhao M, Zheng BJ (2018) Research progress on Atractylodes japonica. Chin Tradit Herbal Drugs. 49:3797–3803

    Google Scholar 

  2. Choi KH, Jeong SI, Lee JH, Hwang BS, Kim SJ, Lee S, Choi BK, Jung KY (2011) Pharmacological mechanism responsible for the Atractylodes japonica-induced distal colonic contraction in rats. Phytomedicine 18:408–413

    Article  CAS  PubMed  Google Scholar 

  3. Kimura Y, Sumiyoshi M (2012) Effects of an Atractylodes lancea rhizome extract and a volatile component β-eudesmol on gastrointestinal motility in mice. J Ethnopharmacol 141:530–536

    Article  CAS  PubMed  Google Scholar 

  4. Park JJ, Chon NR, Lee YJ, Park H (2015) The effects of an extract of Atractylodes Japonica Rhizome, SKI3246 on Gastrointestinal Motility in Guinea Pigs. J Neurogastroenterol Motil 21:352–360

    Article  PubMed  PubMed Central  Google Scholar 

  5. Son HJ, Jung K, Park YH, Jeon HJ, Kang M, Ryu KH, Pyo SS, Eutamene H, Bueno L, Sun WS (2015) Inhibitory effects of SKI3246, the rhizome extract of Atractylodes japonica, on visceral hypersensitivity in experimental irritable bowel syndrome rat models. Arch Pharm Res 38:642–649

    Article  CAS  PubMed  Google Scholar 

  6. Choi KH, Jeong SI, Lee JH, Hwang BS, Lee S, Choi BK, Jung KY (2011) Acetylene compound isolated from Atractylodes japonica stimulates the contractility of rat distal colon via inhibiting the nitrergic-purinergic relaxation. J Ethnopharmacol 134:104–110

    Article  CAS  PubMed  Google Scholar 

  7. Rui M, Chou G (2022) Three new polyacetylenes from Atractylodes japonica Koidz.ez Kitam. Nat Prod Res 36:2063–2070

    Article  CAS  PubMed  Google Scholar 

  8. Kitajima J, Kamoshita A, Ishikawa T, Takano A, Fukuda T, Isoda S, Ida Y (2003) Glycosides of Atractylodes japonica. Chem Pharm Bull (Tokyo) 51:152–157

    Article  CAS  PubMed  Google Scholar 

  9. Lim H, Lee JH, Kim J, Kim YS, Kim HP (2012) Effects of the rhizomes of Atractylodes japonica and atractylenolide I on allergic response and experimental atopic dermatitis. Arch Pharm Res 35:2007–2012

    Article  CAS  PubMed  Google Scholar 

  10. Han SB, Lee CW, Yoon YD, Lee JH, Kang JS, Lee KH, Yoon WK, Lee K, Park SK, Kim HM (2005) Prevention of arthritic inflammation using an oriental herbal combination BDX-1 isolated from Achyranthes bidentata and Atractylodes japonica. Arch Pharm Res 28:902–908

    Article  CAS  PubMed  Google Scholar 

  11. Choi EM, Kim GH, Lee YS (2009) Atractylodes japonica root extract protects osteoblastic MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation. Phytother Res 23:1537–1542

    Article  CAS  PubMed  Google Scholar 

  12. Chen LG, Jan YS, Tsai PW, Norimoto H, Michihara S, Murayama C, Wang CC (2016) Anti-inflammatory and Antinociceptive Constituents of Atractylodes japonica Koidzumi. J Agric Food Chem 64:2254–2262

    Article  CAS  PubMed  Google Scholar 

  13. Wang F, Yang K, Ren FC, Liu JK (2009) Sesquiterpene lactones from Carpesium abrotanoides. Fitoterapia 80:21–24

    Article  CAS  PubMed  Google Scholar 

  14. Liu C, Dou DQ (2014) Chemical constituents of Atractylodes Macrocephala from Yuqian. Chin Arch Tradit Chin Med 32:1615–1616

    CAS  Google Scholar 

  15. Bagal SK, Adlington RM, Baldwin JE, Marquez R (2004) Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (+/-)-biatractylolide and (+/-)-biepiasterolide. J Org Chem 69:9100–9108

    Article  CAS  PubMed  Google Scholar 

  16. Wang BD, Yu YH, ** NN, Jiang SH, Zhu DY (1999) Structural elucidation of biepiasterolid. Acta Chim Sinica 57:1022–1025

    CAS  Google Scholar 

  17. Li Y, Yang XW (2014) New eudesmane-type sesquiterpenoids from the processed rhizomes of Atractylodes macrocephala. J Asian Nat Prod Res 16:123–128

    Article  CAS  PubMed  Google Scholar 

  18. **a GP, Feng X, Chen Y, Wang M, Dong YF (2010) Chemical Constituents of Salicornia bigelovii Torr. Nat Prod Res Dev 22:1012–1014

    CAS  Google Scholar 

  19. Wang HX, Liu CM, Liu Q, Gao K (2008) Three types of sesquiterpenes from rhizomes of Atractylodes lancea. Phytochemistry 69:2088–2094

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

Thanks for the support of New Drug Research Foundation of Heilongjiang University of Chinese Medicine (2018xy02) and Heilongjiang Touyan Innovation Team Program.

Funding

This work was financially sponsored partly by grants from Natural Science Foundation of Heilongjiang Province of China (grant number LH2019H048), China Postdoctoral Science Foundation funded project (grant number 2013M530164 and 2014T70374), New Drug Research Foundation of Heilongjiang University of Chinese Medicine (grant number 2018xy02), Heilongjiang Touyan Innovation Team Program (grant number 2019–5-39).

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Authors and Affiliations

Authors

Contributions

Yuan-Yuan Zhou: Conceptualization, Methodology, Writing-Review & Editing. Zhao Sun: Data Curation, Visualization, Writing-Original Draft. Yan Liu: Investigation, Validation, Resources. Zhen-**ng Fang: Investigation, Validation. Hui-Rui Gao: Data Curation, Visualization. Ning-Yu Liu: Data Curation, Visualization. **ao-Juan Zhang: Formal analysis, Writing—Review & Editing. Bing-You Yang: Supervision, Project administration. Hai-Xue Kuang: Supervision, Project administration.

Corresponding authors

Correspondence to Bing-You Yang or Hai-Xue Kuang.

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Conflict of interest

The method of extraction and separation of the new compounds described in the paper has already been patented by us under Patent No. CN113214214A. And there are no conflicts of interest with the authors.

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Zhou, YY., Sun, Z., Liu, Y. et al. Two new sesterterpenoids from Atractylodes japonica Koidz. ex Kitam. J Nat Med 78, 702–708 (2024). https://doi.org/10.1007/s11418-024-01793-3

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  • DOI: https://doi.org/10.1007/s11418-024-01793-3

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