Skip to main content
Log in

Four new pyrrole alkaloids from the rhizomes of Amomum koenigii

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

Abstract

Four new pyrrole alkaloids, named amokoens A–D (14), together with three known compounds (57) were isolated from the rhizomes of Amomum koenigii. Their structures and absolute configurations were established by spectroscopic data, including 1D and 2D NMR, and the optical rotation calculations. All the isolates were evaluated for their effects on nitric oxide (NO) production in lipopolysaccharide-induced RAW264.7 macrophages. Compounds 17 inhibited NO production ranging from 27.1 to 82.4% at a concentration of 100 μM, and compounds 5 and 6 showed efficacious inhibitory activities with IC50 values of 42.2 and 69.3 µM, respectively.

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

References

  1. Flora of China Editorial Committee (1981) Flora reipublicae popularis sinicae (Zhongguo Zhiwu Zhi). Sci Press Beijing 16(2):116

    Google Scholar 

  2. Qiao CF, Han QB, Song JZ, Yiu H, Xu HX (2007) Simultaneous HPLC-DAD analysis of four methylated flavonols in Amomum koenigii. Acta Chromatogr 19:217–226

    CAS  Google Scholar 

  3. Dong H, Gou YL, Cao SG, Chen SX, Sim KY, Goh SH, Kini RM (1999) Eicosenones and methylated flavonols from Amomum koenigii. Phytochemistry 50:899–902

    Article  CAS  Google Scholar 

  4. Yin H, Dan WJ, Fan BY, Guo C, Wu K, Li D, Xian KF, Pescitelli G, Gao JM (2019) Anti-inflammatory and α-glucosidase inhibitory activities of labdane and norlabdane diterpenoids from the rhizomes of Amomum villosum. J Nat Prod 82:2963–2971

    Article  CAS  Google Scholar 

  5. Yin H, Jiang N, Guo C, Gao JM (2019) A new bergamotane sesquiterpenoid from the rhizomes of Amomum villosum var. xanthioides. Nat Prod Res. https://doi.org/10.1080/14786419.2019.1633649

  6. Chin YW, Lim SW, Kim SH, Shin DY, Suh YG, Kim YB, Kim YC, Kim J (2003) Hepatoprotective pyrrole derivatives of Lycium chinense fruits. Bioorg Med Chem Lett 13:79–81

    Article  CAS  Google Scholar 

  7. Kim SB, Chang BY, Hwang BY, Kim SY, Lee MK (2014) Pyrrole alkaloids from the fruits of Morus alba. Bioorg Med Chem Lett 24:5656–5659

    Article  CAS  Google Scholar 

  8. Zhan ZJ, Wen YT, Ren FY, Rao GW, Shan WG, Li CP (2012) Diterpenoids and a diarylheptanoid from Hedychium coronarium with significant anti-angiogenic and cytotoxic activities. Chem Biodivers 9:2754–2760

    Article  CAS  Google Scholar 

  9. Luo JG, Yin H, Fan BY, Kong LY (2014) Labdane diterpenoids from the roots of Amomum maximum and their cytotoxic evaluation. Helv Chim Acta 97:1140–1145

    Article  CAS  Google Scholar 

  10. Kim MJ, Choi MY, Han MY, Choi YK, Lee JK, Park J (2002) Asymmetric transformations of acyloxyphenyl ketones by enzyme-metal multicatalysis. J Org Chem 67:9481–9483

    Article  CAS  Google Scholar 

  11. Colín-Lozano B, Estrada-Soto S, Chávez-Silva F, Gutiérrez-Hernández A, Cerón-Romero L, Giacoman-Martínez A, Almanza-Pérez JC, Hernández-Núñez E, Wang Z, Xie X, Cappiello M, Balestri F, Mura U, Navarrete-Vazquez G (2018) Design, synthesis and in combo antidiabetic bioevaluation of multitarget phenylpropanoic acids. Molecules 23:340–355

    Article  Google Scholar 

  12. Yin H, Luo JG, Kong LY (2013) Tetracyclic diterpenoids with isomerized isospongian skeleton and labdane diterpenoids from the fruits of Amomum kravanh. J Nat Prod 76:237–242

    Article  CAS  Google Scholar 

  13. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Jr. Montgomery JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian 16, Revision B.01, Gaussian Inc., Wallingford CT

Download references

Acknowledgements

We gratefully acknowledge Dr. Yun Deng in School of Pharmacy, Chengdu University of TCM, for the help in OR calculations. This work was supported by the National Natural Science Foundation of China [No. 31600275], the Key Project Plans of Synergetic Innovation in Yangling Demonstration [No. 2018CXY-03], and the Doctoral Starting Fund of Xinxiang Medical University [No. XYBSKYZZ201813].

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jin-Ming Gao.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

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 1587 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yin, H., Guo, C. & Gao, JM. Four new pyrrole alkaloids from the rhizomes of Amomum koenigii. J Nat Med 75, 173–177 (2021). https://doi.org/10.1007/s11418-020-01461-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-020-01461-2

Keywords

Navigation