Adekenov SM (2017) Sesquiterpene lactones with unusual structure their biogenesis and biological activity. Fitoterapia 121:16–30. https://doi.org/10.1016/j.fitote.2017.05.017

Article  CAS  PubMed  Google Scholar 

Arietta-García AG, Calzada F, Ramírez-Sánchez I, Bautista E, García-Hernandez N, Ordoñez-Razo RM (2023) Advances in the properties of incomptine A: cytotoxic activity and downregulation of hexokinase II in breast cancer cell lines. Int J Mol Sci 24:12406. https://doi.org/10.3390/ijms241512406

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bautista E, Calzada F, Yepez-Mulia L, Chavez-Soto M, Ortega A (2012) Incomptines C and D, two heliangolides from Decachaeta incompta and their antiprotozoal activity. Planta Med 78:1698–1701. https://doi.org/10.1055/s-0032-1315255

Article  CAS  PubMed  Google Scholar 

Bautista E, Calzada F, López-Huerta FA, Yépez-Mulia L, Ortega A (2014) Antiprotozoal activity of 8-acyl and 8-alkyl incomptine A analogs. Bioorg Med Chem Lett 24:3260–3262. https://doi.org/10.1016/j.bmcl.2014.06.017

Article  CAS  PubMed  Google Scholar 

Bautista E, Fragoso-Serrano M, Pereda-Miranda R (2015a) Jalapinoside, a macrocyclic bisdesmoside from the resin glycosides of Ipomea purga, as a modulator of multidrug resistance in human cancer cells. J Nat Prod 78:168–172. https://doi.org/10.1021/np500762w

Article  CAS  PubMed  Google Scholar 

Bautista E, Fragoso-Serrano M, Toscano RA, García-Peña MDR, Ortega A (2015b) Teotihuacanin, a diterpene with an unusual spiro-10/6 system from Salvia amarissima with potent modulatory activity of multidrug resistance in cancer cells. Org Lett 17:3280–3282. https://doi.org/10.1021/acs.orglett.5b01320

Article  CAS  PubMed  Google Scholar 

Bautista E, Lozano-Gamboa S, Fragoso-Serrano M, Rivera-Chávez J, Salazar-Olivo LA (2022) Jatrophenediol, a pseudoguaiane sesquiterpenoid from Jatropha dioica rhizomes. Tetrahedron Lett 104:154040. https://doi.org/10.1016/j.tetlet.2022.154040

Article  CAS  Google Scholar 

Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G (2013) SpecDis: Quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25:243–249. https://doi.org/10.1002/chir.22138

Article  CAS  PubMed  Google Scholar 

Bohlmann F, Borthakur N (1982) Sesquiterpenes and norsesquiterpenes from Pechuel-loeschea leibnitziae. Phytochemistry 21:1160–1162. https://doi.org/10.1016/S0031-9422(00)82441-3

Article  CAS  Google Scholar 

Calzada F, Bautista E, Hidalgo-Figueroa S, García-Hernández N, Barbosa E, Velázquez C, Ordoñez-Razo RM, Arietta-García AG (2021) Antilymphoma effect of incomptine A: in vivo, in silico, and toxicological studies. Molecules 26:6646. https://doi.org/10.3390/molecules26216646

Article  CAS  PubMed  PubMed Central  Google Scholar 

Calzada F, Bautista E, Hidalgo-Figueroa S, García-Hernández N, Velázquez C, Barbosa E, Valdes M, Solares-Pascasio JI (2022) Understanding the anti-diarrhoeal properties of incomptines A and B: antibacterial activity against Vibrio cholerae and its enterotoxin inhibition. Pharmaceuticals 15:196. https://doi.org/10.3390/ph15020196

Article  CAS  PubMed  PubMed Central  Google Scholar 

Capasso R, Izzo AA, Pinto L, Bifulco T, Vitobello C, Mascolo N (2000) Phytotherapy and quality of herbal medicines. Fitoterapia 71:S58–S65. https://doi.org/10.1016/S0367-326X(00)00173-8

Article  PubMed  Google Scholar 

Dupuy OA, Murillo R, Bonilla JA (2008) Sesquiterpene lactones of the plants Viguiera sylvatica and Decachaeta thieleana (Asteraceae) modulate nitric oxide production and phagocytosis of macrophages cell line RAW. Rev Biol Trop 56:1063–1073

PubMed  Google Scholar 

Fan YY, Zhang XR, Zheng CY, Li Y, Yue JM (2024) Eleven highly oxygenated and anti-inflammatory guaian-8,12-olides from Hedyosmum orientale. Tetrahedron 152:133841. https://doi.org/10.1016/j.tet.2024.133841

Article  CAS  Google Scholar 

Flack HD, Bernardinelli G (2008) The use of X-ray crystallography to determine absolute configuration. Chirality 20:681–690. https://doi.org/10.1002/chir.20473

Article  CAS  PubMed  Google Scholar 

García-Nava X, Fragoso-Serrano M, Bautista E, de Loera D, Cortezano-Arellano O, Calzada F, Bedolla-García BY (2022) Amarisolide H and 15-epi-Amarisolide H, two diterpenoid glucosides from Salvia circinnata. Rev Bras Farmacogn 32:993–999. https://doi.org/10.1007/s43450-022-00332-z

Article  CAS  Google Scholar 

Ge ZP, Gao Y, Zhang Y, Liu HC, Zhao JX, Yue JM (2023) Highly modified sesquiterpene lactones with cytotoxic activities from Strobocalyx chunii. J Org Chem 88:11122–11129. https://doi.org/10.1021/acs.joc.3c01104

Article  CAS  PubMed  Google Scholar 

Gómez CD, Rivera AV, Rodulfo de Gil E, Vogler de Valeri B, Triana J (1987) X-ray structure of 6-deoxymikanokryptin, a new guaianolide from Vernonia scorpioides Pers: 3-oxo-1α,7α,8β,10β(H)-guaia-4(5),11(13)-dien-8,12-olide. Acta Cryst Section c: Crystal Structure Communications 43:2216–2218. https://doi.org/10.1107/S0108270187088395

Article  Google Scholar 

Han Z, Liu FY, Lin SQ, Zhang CY, Ma JH, Guo C, Jia FJ, Zhang Q, Xie WD, Li X (2019) Ivalin induces mitochondria-mediated apoptosis associated with the NF-κB activation in human hepatocellular carcinoma SMMC-7721 cells. Molecules 24:3809. https://doi.org/10.3390/molecules24203809

Article  CAS  PubMed  PubMed Central  Google Scholar 

Herz W, Högenauer G (1962) Ivalin, a new sesquiterpene lactone. J Org Chem 27:905–910. https://doi.org/10.1021/jo01050a052

Article  CAS  Google Scholar 

Holub M, Buděšínský M, Samek Z, Drożdż B, Grabarczyk H, Ulubelen A, Öksüz S, Rychlewska U (1982) Absolute configuration of xerantholide, a sesquiterpene lactone from Anthemis austriaca Jacq. Collect Czech Chem Commun 47:670–675. https://doi.org/10.1135/cccc19820670

Article  CAS  Google Scholar 

King RM, Robinson H (1969) Studies in the eupatorieae (Compositae). XVI a monograph of the genus Decachaeta DC. Brittonia 21:275–284. https://doi.org/10.2307/2805579

Article  Google Scholar 

Klein-Junior LC, de Souza MR, Viaene J, Bresolin TMB, de Gasper AL, Henriques AT, Vander-Heyden Y (2021) Quality control of herbal medicines: from traditional techniques to state-of-the-art approaches. Planta Med 87:964–988. https://doi.org/10.1055/a-1529-8339

Article  CAS  PubMed  Google Scholar 

Länger R, Stöger E, Kubelka W, Helliwell K (2018) Quality standards for herbal drugs and herbal drug preparations-appropriate or improvements necessary? Planta Med 84:350–360. https://doi.org/10.1055/s-0043-118534

Article  CAS  PubMed  Google Scholar 

Li C, Jones AX, Lei X (2016) Synthesis and mode of action of oligomeric sesquiterpene lactones. Nat Prod Rep 33:602–611. https://doi.org/10.1039/C5NP00089K

Article  CAS  PubMed  Google Scholar 

Martínez-Aldino IY, Villaseca-Murillo M, Morales-Jiménez J, Rivera-Chávez J (2021) Absolute configuration and protein tyrosine phosphatase 1B inhibitory activity of xanthoepocin, a dimeric naphtopyrone from Penicillium sp. IQ-429. Bioorg Chem 115:105166. https://doi.org/10.1016/j.bioorg.2021.105166

Article  CAS  PubMed  Google Scholar 

Ortega A, Pastor-Palacios G, Ortiz-Pastrana N, Ávila-Cabezas E, Toscano RA, Joseph-Nathan P, Morales-Jiménez J, Bautista E (2020) Further galphimines from a new population of Galphimia glauca. Phytochemistry 169:112180. https://doi.org/10.1016/j.phytochem.2019.112180

Article  CAS  PubMed  Google Scholar 

Pereda-Miranda R, Bautista E, Martínez-Fructuoso L, Fragoso-Serrano M (2023) From relative to absolute stereochemistry of secondary metabolites: applications in plant chemistry. Rev Bras Farmacogn 33:1–48. https://doi.org/10.1007/s43450-022-00333-y

Article  CAS  Google Scholar 

Pina-Jiménez E, Calzada F, Bautista E, Ordoñez-Razo RM, Velázquez C, Barbosa E, García-Hernández N (2021) Incomptine A induces apoptosis, ROS production and a differential protein expression on non-Hodgkin’s lymphoma cells. Int J Mol Sci 22:10516. https://doi.org/10.3390/ijms221910516

Article  CAS  PubMed