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Classification of Diverse Novel Meroterpenoids

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Novel Plant Natural Product Skeletons
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Abstract

Meroterpenoids are derived from the mixed biogenic pathway of terpenoids and other natural products.

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References

  1. Li YS, Matsunaga K, Ishibashi M, Ohizumi Y. Littoralisone, a novel neuritogenic iridolactone having an unprecedented heptacyclic skeleton including four- and nine-membered rings consisting of glucose from Verbena littoralis. J Org Chem. 2001;66:2165–7.

    Article  CAS  PubMed  Google Scholar 

  2. Liao HB, Lei C, Gao LX, Li JY, Li J, Hou AJ. Two enantiomeric pairs of meroterpenoids from Rhododendron capitatum. Org Lett. 2015;17:5040–3.

    Article  CAS  PubMed  Google Scholar 

  3. Liao HB, Huang GH, Yu MH, Lei C, Hou AJ. Five pairs of meroterpenoid enantiomers from Rhododendron capitatum. J Org Chem. 2017;82:1632–7.

    Article  CAS  PubMed  Google Scholar 

  4. Li C, Li CJ, Ma J, Chen FY, Li L, Wang XL, Ye F, Zhang DM. Magterpenoids A–C, three polycyclic meroterpenoids with ptp1b inhibitory activity from the bark of Magnolia officinalis var. biloba. Org Lett 2018;20:3682–86.

    Google Scholar 

  5. Xue GM, Zhao CG, Xue JF, Chen H, Zhao ZZ, Si YY, Du K, Zhi YL, Feng WS. Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum. Org Chem Front 2022;9:190–6.

    Google Scholar 

  6. Porzel A, Phuong Lien T, Schmidt J, Drosihn S, Wagner C, Merzweiler K, Van Sung T, Adam G. Fissistigmatins A-D: novel type natural products with flavonoid–sesquiterpene hybrid structure from Fissistigma bracteolatum. Tetrahedron. 2000;56:865–72.

    Article  CAS  Google Scholar 

  7. Tanaka N, Okasaka M, Ishimaru Y, Takaishi Y, Sato M, Okamoto M, Oshikawa T, Ahmed SU, Consentino LM, Lee KH. Biyouyanagin A, an anti-HIV agent from Hypericum chinense L. var. salicifolium. Org Lett 2005;7:2997–9.

    Google Scholar 

  8. Niwa K, Tanaka N, Kim SY, Kojoma M, Kashiwada Y. Hyperdioxane A, a conjugate of dibenzo-1,4-dioxane and sesquiterpene from Hypericum ascyron. Org Lett. 2018;20:5977–80.

    Article  CAS  PubMed  Google Scholar 

  9. Liu ML, Duan YH, Hou YL, Li C, Gao H, Dai Y, Yao XS. Nardoaristolones A and B, two terpenoids with unusual skeletons from Nardostachys chinensis batal. Org Lett. 2013;15:1000–3.

    Article  CAS  PubMed  Google Scholar 

  10. Liu HX, Chen K, Sun QY, Yang FM, Hu GW, Wang YH, Long CL. Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum. J Nat Prod. 2013;76:732–6.

    Article  CAS  PubMed  Google Scholar 

  11. Lin X, Ji S, Qiao X, Hu H, Chen N, Dong Y, Huang Y, Guo D, Tu P, Ye M. Density functional theory calculations in stereochemical determination of terpecurcumins J-W, cytotoxic terpene-conjugated curcuminoids from Curcuma longa L. J Org Chem. 2013;78:11835–48.

    Article  CAS  PubMed  Google Scholar 

  12. Qin DP, Pan DB, Xiao W, Li HB, Yang B, Yao XJ, Dai Y, Yu Y, Yao XS. Dimeric cadinane sesquiterpenoid derivatives from Artemisia annua. Org Lett. 2018;20:453–6.

    Article  CAS  PubMed  Google Scholar 

  13. Zhou M, Zhou J, Liu J, Liang JJ, Peng XG, Duan FF, Ruan HL. Parasubindoles A-G, seven eremophilanyl indoles from the whole plant of Parasenecio albus. J Org Chem. 2018;83:12122–8.

    Article  CAS  PubMed  Google Scholar 

  14. Cai YS, Wu Z, Zheng XQ, Wang C, Wang JR, Zhang XX, Qiu G, Zhu K, Cao S, Yu J. Spiroalanpyrroids A and B, sesquiterpene alkaloids with a unique spiro-eudesmanolide–pyrrolizidine skeleton from Inula helenium. Org Chem Front. 2020;7:303–9.

    Article  CAS  Google Scholar 

  15. Fu J, Wang YN, Ma SG, Li L, Wang XJ, Li Y, Liu YB, Qu J, Yu SS. Xanthanoltrimer A-C: three xanthanolide sesquiterpene trimers from the fruits of Xanthium italicum Moretti isolated by HPLC-MS-SPE-NMR. Org Chem Front. 2021;8:1288–93.

    Article  CAS  Google Scholar 

  16. Wang P, Li RJ, Liu RH, Jian KL, Yang MH, Yang L, Kong LY, Luo J. Sarglaperoxides A and B, sesquiterpene–normonoterpene conjugates with a peroxide bridge from the seeds of Sarcandra glabra. Org Lett. 2016;18:832–5.

    Article  CAS  PubMed  Google Scholar 

  17. Feng T, Li XM, He J, Ai HL, Chen HP, Li XN, Li ZH, Liu JK. Nicotabin A, a sesquiterpenoid derivative from Nicotiana tabacum. Org Lett. 2017;19:5201–3.

    Article  CAS  PubMed  Google Scholar 

  18. Xu G, Hou AJ, Wang RR, Liang GY, Zheng YT, Liu ZY, Li XL, Zhao Y, Huang SX, Peng LY, Zhao QS. Przewalskin A: a new c23 terpenoid with a 6/6/7 carbon ring skeleton from Salvia przewalskii Maxim. Org Lett. 2006;8:4453–6.

    Article  CAS  PubMed  Google Scholar 

  19. Zhou M, Zhang HB, Wang WG, Gong NB, Zhan R, Li XN, Du X, Li LM, Li Y, Lu Y, Pu JX, Sun HD. Scopariusic acid, a new meroditerpenoid with a unique cyclobutane ring isolated from Isodon scoparius. Org Lett. 2013;15:4446–9.

    Article  CAS  PubMed  Google Scholar 

  20. Tanaka N, Niwa K, Kajihara S, Tsuji D, Itoh K, Mamadalieva NZ, Kashiwada Y. C28 terpenoids from lamiaceous plant Perovskia scrophulariifolia: their structures and anti-neuroinflammatory activity. Org Lett. 2020;22:7667–70.

    Article  CAS  PubMed  Google Scholar 

  21. Hayes PY, Chow S, Somerville MJ, De Voss JJ, Fletcher MT. Pimelotides A and B, diterpenoid ketal-lactone orthoesters with an unprecedented skeleton from Pimelea elongata. J Nat Prod. 2009;72:2081–3.

    Article  CAS  PubMed  Google Scholar 

  22. Zhao JX, Liu CP, Zhang MM, Li J, Yue JM. Dysohonin A, a meroditerpenoid incorporating a 6,15,6-fused heterotricyclic ring system from Dysoxylum hongkongense. Org Chem Front. 2018;5:2202–7.

    Article  CAS  Google Scholar 

  23. Zhang J, He J, Cheng YC, Zhang PC, Yan Y, Zhang HJ, Zhang WK, Xu JK. Fischernolides A-D, four novel diterpene-based meroterpenoid scaffolds with antitumor activities from Euphorbia fischeriana. Org Chem Front. 2019;6:2312–8.

    Article  CAS  Google Scholar 

  24. Fort DM, Ubillas RP, Mendez CD, Jolad SD, Inman WD, Carney JR, Chen JL, Ianiro TT, Hasbun C, Bruening RC, Luo J, Reed MJ, Iwu M, Carlson TJ, King SR, Bierer DE, Cooper R. Novel antihyperglycemic terpenoid-quinones from Pycnanthus angolensis. J Org Chem. 2000;65:6534–9.

    Article  CAS  PubMed  Google Scholar 

  25. Qin JJ, Fu YF, Chen X, Liu YT, Zhao JH, Zuo JP, Li YM, Zhu WL, Zhao WM. Celamonols A-D, four triterpenoid and catechin conjugates with immunosuppressive activities from the stems of Celastrus monospermus. Org Chem Front. 2019;6:3786–92.

    Article  CAS  Google Scholar 

  26. Farimani MM, Taheri S, Ebrahimi SN, Bahadori MB, Khavasi HR, Zimmermann S, Brun R, Hamburger M. Hydrangenone, a new isoprenoid with an unprecedented skeleton from Salvia hydrangea. Org Lett. 2012;14:166–9.

    Article  CAS  PubMed  Google Scholar 

  27. Chen CC, Wu JH, Yang NS, Chang JY, Kuo CC, Wang SY, Kuo YH. Cytotoxic C35 terpenoid cryptotrione from the bark of Cryptomeria japonica. Org Lett. 2010;12:2786–9.

    Article  CAS  PubMed  Google Scholar 

  28. Torres A, Molinillo JMG, Varela RM, Casas L, Mantell C, Martínez de la Ossa EJ, Macías FA. Helikaurolides A–D with a diterpene-sesquiterpene skeleton from supercritical fluid extracts of Helianthus annuus L. var. Arianna. Org Lett 2015;17:4730–3.

    Google Scholar 

  29. Kim SY, Nagashima H, Tanaka N, Kashiwada Y, Kobayashi J, Kojoma M. Hitorins A and B, hexacyclic C25 terpenoids from Chloranthus japonicus. Org Lett. 2016;18:5420–3.

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Yongxian Cheng .

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Cheng, Y., Qin, D. (2024). Classification of Diverse Novel Meroterpenoids. In: Novel Plant Natural Product Skeletons. Springer, Singapore. https://doi.org/10.1007/978-981-99-7329-3_8

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