Skip to main content
Log in

Chemical constituents from the roots of Lindera aggregata and their biological activities

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

Abstract

Three new benzylisoquinoline alkaloids, (1′S)-12′-hydroxyl-linderegatine (1), (1S)-5′-O-p-hydroxybenzoyl norreticuline (2), (1R, 1′R)-11,11′-biscoclaurine (3), along with 18 known compounds were isolated from the roots of Lindera aggregata (Sims) Kosterm. Their structures were determined on the basis of extensive spectroscopic analysis (IR, UV, HR-ESI–MS, 1D and 2D NMR). The absolute configurations of three new compounds were determined by comparing their experimental and calculated ECD for the first time. Compounds (4) and (9) showed cytotoxic activities against human colon carcinoma cell line (HCT-116), with IC50 values of 51.4 and 27.1 μM, respectively. Furthermore, compounds (10) and (11) showed inhibitory activities on nitric oxide production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells, with IC50 values of 37.8 and 38.7 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.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Wang C, Dai Y, Yang J (2007) Treatment with total alkaloids from Radix Linderae reduces inflammation and joint destruction in type II collagen-induced model for rheumatoid arthritis. J Ethnopharmacol 111:322–328

    Article  CAS  Google Scholar 

  2. Chou GX, Nakamura N, Ma CM (2005) Isoquinoline alkaloids from Lindera aggregata. Chin J Nat Med 3:272–275

    CAS  Google Scholar 

  3. Zhang C, Sun Q, Zhao Y (2001) Studies on flavonoids from leaves of Lindera aggregata (Sims) Kosterm. Chin J Med Chem 11:274–276

    CAS  Google Scholar 

  4. Gan LS, Zheng YL, Mo JX (2009) Sesquiterpene lactones from the root tubers of Lindera aggregata. J Nat Prod 72:1497–1501

    Article  CAS  Google Scholar 

  5. Luo Y, Liu M, Yao X (2009) Total alkaloids from Radix Linderae prevent the production of inflammatory mediators in lipopolysaccharide-stimulated RAW 264.7 cells by suppressing NF-κB and MAPKs activation. Cytokine 46:104–110

    Article  CAS  Google Scholar 

  6. Wangchuk P, Sastraruji T, Taweechotipatr M, Keller PA (2016) Anti-inflammatory, anti-bacterial and anti-acetylcholinesterase activities of two isoquinoline alkaloids-Scoulerine and Cheilanthifoline. Nat Prod Commun 11:1801–1804

    PubMed  Google Scholar 

  7. Jin TY, Li SQ, Jin CR et al (2018) Catecholic isoquinolines from Portulaca oleracea and their anti-inflammatory and β2-adrenergic receptor agonist activity. J Nat Prod 81:768–777

    Article  CAS  Google Scholar 

  8. Kupeli E, Koçar M, Yesilada E et al (2002) A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species. Life Sci 72:657

    Article  Google Scholar 

  9. Och A, Zalewski D, Komsta Ł et al (2019) Cytotoxic and proapoptotic activity of sanguinarine, Berberine, and Extracts of Chelidonium majus L. and Berberis thunbergii DC. toward Hematopoietic Cancer Cell Lines. Toxins 11:485

    Article  Google Scholar 

  10. Sun N, Han Y (2019) Cytotoxic isoquinoline alkaloids from the roots of Thalictrum foliolosum. J Asian Nat Prod Res. https://doi.org/10.1080/10286020.2019.1694515

    Article  PubMed  Google Scholar 

  11. Alexandrova R, Varadinova T, Velcheva M et al (2000) Cytotoxic effect of isoquinoline alkaloids on tumor cell lines. Exp Pathol Parasitol 4:8–14

    CAS  Google Scholar 

  12. Al-Khdhairawi AAQ, Krishnan P, Mai CW et al (2017) A Bis-benzopyrroloisoquinoline alkaloid incorporating a Cyclobutane Core and a Chlorophenanthroindolizidine alkaloid with cytotoxic activity from Ficus fistulosa var. tengerensis. J Nat Prod 80:2734–2740

    Article  CAS  Google Scholar 

  13. Jin Q, Yang D, Dai Z et al (2018) Antitumor aporphine alkaloids from Thalictrum wangii. Fitoterapia 128:204–212

    Article  CAS  Google Scholar 

  14. Gan L, Zhao X, Yao W (2008) A novel bisbenzylisoquinoline alkaloid from Lindera aggregata. J Chem Res 2008:285–286

    Article  Google Scholar 

  15. Bick IC, Sevenet T, Sinchai W (1981) Alkaloids of Cryptocarya longifolia: X-ray crystal structure of thalifoline and longifolonine. Aust J Chem 34:195–207

    Article  CAS  Google Scholar 

  16. Böhlke M, Guinaudeau H, Angerhofer CK (1996) Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark. J Nat prod 59:576–580

    Article  Google Scholar 

  17. Frydman B, Bendisch R, Deulofeu V (1958) A synthesis of laudanine and (±)-pseudocodamine: resolution into the optical isomers. Tetrahedron 4:342–350

    Article  CAS  Google Scholar 

  18. Faria TJ, Cafêu MC, Akiyoshi G (2007) Alkaloids from flowers and leaves of Erythrina speciosa Andrews. Química Nova 30:525–527

    Article  CAS  Google Scholar 

  19. Chang FR, Wei JL, Teng CM (1998) Two new 7-dehydroaporphine alkaloids and antiplatelet action aporphines from the leaves of Annona purpurea. Phytochemistry 49:2015–2018

    Article  CAS  Google Scholar 

  20. Babcock PA, Segelman AB (1974) Alkaloids of Lindera benzoin (L.) Blume (Lauraceae) I: Isolation and identification of laurotetanine. J Pharm Sci 63:1495–1496

    Article  CAS  Google Scholar 

  21. Guinaudenu H, Leboeuf M, Cave A (1979) Aporphine alkaloids. J Nat Prod 42:325–360

    Article  Google Scholar 

  22. Leslie Gunatilaka A, Sotheeswaran S, Sriyani B (1981) Isoboldine and lupenone from Neolitsea fuscata. Planta Med 43:309–310

    Article  CAS  Google Scholar 

  23. Sun C, Li J, Wang D (2015) Preparative separation of alkaloids from Litsea cubeba using combined applications of pH-zone-refining and high-speed counter-current chromatography. RSC Adv 5:75831–75837

    Article  CAS  Google Scholar 

  24. Chen JJ, Chang YL, Teng CM (2001) A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi. Planta Med 67:423–427

    Article  CAS  Google Scholar 

  25. Chen CK, Chen CH, Lee SS (2007) Isoquinoline alkaloids from the leaves of Dehaasia hainanensis. Nat Prod Commun 2:75–78

    CAS  Google Scholar 

  26. Lu ST, Wu YC, Leou SP (1987) The Oxidation of Isoquinoline Alkaloids with m-Chloroperbenzoic Acid. J Chin Chem Soc 34:33–42

    Article  CAS  Google Scholar 

  27. Sanyar G, Gülgeze HB, Gözler B (1992) Salutaridine N-Oxide from the capsules of Papaverbracteatum. Planta Med 58:368–369

    Article  CAS  Google Scholar 

  28. Lu ST, Chen IS (1976) Structure of a new bisbenzylisoquinoline alkaloid, lindoldhamine. Heterocycles 4:1073–1076

    Article  CAS  Google Scholar 

  29. Chou J (2013) The analysis of total alkaloids from different sources of linderae radix: quality control and identification of anti-inflammation compounds. Thesis (M.Phil.)-Hong Kong University of Science and Technology. http://hdl.handle.net/1783.1/62353

  30. Wang J, Zhang H, Yang X (2008) HS071, a new furan-type cytotoxic metabolite from Streptomyces sp. HS-HY-071. J Antibiot 40:623–626

    Article  Google Scholar 

  31. Feng X, Wang M, Cheng J (2017) Two new secolignans with in vitro anti-inflammatory activities from Urtica fissa rhizomes. J Nat Med 71:553–557

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Gui-Xin Chou.

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 (DOCX 48826 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yang, JJ., Chen, Y., Guo, ML. et al. Chemical constituents from the roots of Lindera aggregata and their biological activities. J Nat Med 74, 441–447 (2020). https://doi.org/10.1007/s11418-019-01385-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-019-01385-6

Keywords

Navigation