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 9–12.
Graphical Abstract
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References
Zhao QL, Wang MJ, Zhao M, Zheng BJ (2018) Research progress on Atractylodes japonica. Chin Tradit Herbal Drugs. 49:3797–3803
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
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
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
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
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
Rui M, Chou G (2022) Three new polyacetylenes from Atractylodes japonica Koidz.ez Kitam. Nat Prod Res 36:2063–2070
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
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
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
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
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
Wang F, Yang K, Ren FC, Liu JK (2009) Sesquiterpene lactones from Carpesium abrotanoides. Fitoterapia 80:21–24
Liu C, Dou DQ (2014) Chemical constituents of Atractylodes Macrocephala from Yuqian. Chin Arch Tradit Chin Med 32:1615–1616
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
Wang BD, Yu YH, ** NN, Jiang SH, Zhu DY (1999) Structural elucidation of biepiasterolid. Acta Chim Sinica 57:1022–1025
Li Y, Yang XW (2014) New eudesmane-type sesquiterpenoids from the processed rhizomes of Atractylodes macrocephala. J Asian Nat Prod Res 16:123–128
**a GP, Feng X, Chen Y, Wang M, Dong YF (2010) Chemical Constituents of Salicornia bigelovii Torr. Nat Prod Res Dev 22:1012–1014
Wang HX, Liu CM, Liu Q, Gao K (2008) Three types of sesquiterpenes from rhizomes of Atractylodes lancea. Phytochemistry 69:2088–2094
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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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.
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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