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Natural Product Research
Formerly Natural Product Letters
Volume 33, 2019 - Issue 15
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Research Articles

Senecipyrrolidine, an unusual pyrrolidine alkaloid isolated from Jacobaea gigantea (Desf.) Pelser (Asteraceae)

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Pages 2182-2191 | Received 20 Mar 2018, Accepted 23 Jun 2018, Published online: 30 Oct 2018

References

  • Abbott TP, Kleiman R. 1991. Solvent selection guide for counter-current chromatography. J Chromatogr A. 538:109–118.
  • Abdellaoui SE, Destandau E, Krolikiewicz-Renimel I, Cancellieri P, Toribio A, Jeronimo-Monteiro V, Landemarre L, André P, Elfakir C. 2014. Centrifugal partition chromatography for antibacterial bio-guided fractionation of Clidemia hirta roots. Sep Purif Technol. 123:221–228.
  • Ahmed S, Ahmad MS, Yousaf M, Nur‐e‐Alam M, Al‐Rehaily AJ. 2017. Two new sesquiterpene alcohols isolated from Senecio hadiensis Forssk. Grown in Saudi Arabia. Chem Biodivers. 14:e1700144.
  • Bai S-M, Ren H-M, Zheng G-J, Chen G. 2017. Senobtusin, a novel alkaloid with amidine moiety from Senecio obtusatus Wall. ex DC. Nat Prod Res. 31:2450–2453.
  • Bisson J, Poupard P, Pawlus AD, Pons A, Darriet P, Mérillon J-M, Waffo-Téguo P. 2011. Development of hybrid elution systems for efficient purification of stilbenoids using centrifugal partition chromatography coupled to mass spectrometry. J Chromatogr A. 1218:6079–6084.
  • Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ. 2000. Role of quinones in toxicology. Chem Res Toxicol. 13:135–160.
  • Case RJ, Wang Y, Franzblau SG, Soejarto DD, Matainaho L, Piskaut P, Pauli GF. 2007. Advanced applications of counter-current chromatography in the isolation of anti-tuberculosis constituents from Dracaena angustifolia. J Chromatogr A. 1151:169–174.
  • Dewick PM. 2009. Medicinal natural products: a biosynthetic approach. 3rd ed. Chichester: John Wiley & Sons Ltd.
  • Ge F, Ke C, Tang W, Yang X, Tang C, Qin G, Xu R, Li T, Chen X, Zuo J, et al. 2007. Isolation of chlorogenic acids and their derivatives from Stemona japonica by preparative HPLC and evaluation of their anti-AIV (H5N1) activity in vitro. Phytochem Anal. 18:213–218.
  • Guo X, Wang D, Duan W, Du J, Wang X. 2010. Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography. Phytochem Anal. 21:268–272.
  • Hase T, Kawamoto Y, Ohtani K, Kasai R, Yamasaki K, Picheansoonthon C. 1995. Cyclohexylethanoids and related glucosides from Millingtonia hortensis. Phytochemistry. 39:235–241.
  • Huang S, Zhou XL, Wang HY, Wang CJ, Zhou XL, Xiao F, Weng J. 2013. Eremophilane derivatives from Senecio dianthus. J Nat Med. 67:711–718.
  • Ito Y, Weinstein M, Aoki I, Harada R, Kimura E, Nunogaki K. 1966. The coil planet centrifuge. Nature. 212:985–987.
  • Jerga C, Merfort I, Willuhn G. 1990. Flavonoid glycosides and other hydrophilic compounds from flowers of Heterotheca inuloides. Planta Med. 56:413–415.
  • Lee E, Moon B-H, Park Y, Hong S, Lee S, Lee Y, Lim Y. 2008. Effects of hydroxy and methoxy substituents on NMR data in flavonols. Bull Korean Chem Soc. 29:507–510.
  • Loizzo MR, Tundis R, Statti GA, Menichini F. 2007. Jacaranone: a cytotoxic constituent from Senecio ambiguus subsp. ambiguus (Biv.) DC. against renal adenocarcinoma ACHN and prostate carcinoma LNCaP cells. Arch Pharm Res. 30:701–707.
  • Ma HY, Yang L, Zhang M, Wang CH, Wang ZT. 2008. A new compound from Senecio cannabifolius var integrilifolius. Yao Xue Xue Bao. 43:626–629.
  • Mansour RMA, Saleh NAM. 1981. Flavonoids of three local Senecio species. Phytochemistry. 20:1180–1181.
  • Marston A, Hostettmann K. 2006. Developments in the application of counter-current chromatography to plant analysis. J Chromatogr A. 1112:181–194.
  • Massanet GM, Rodriguez-Luis F, Chozas CV, Guerra FM, Dorado JM. 1993. Guaianolides and an ethylcyclohexane lactone from Andriala integrifolia. Phytochemistry. 34:1565–1567.
  • Merfort I, Wendisch D. 1988. Flavonoid glucuronides from the flowers of Arnica montana1. Planta Med. 54:247–250.
  • Mezache N, Derbré S, Akkal S, Laouer H, Séraphin D, Richomme P. 2009. Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae). Nat Prod Commun. 4:1357–1362.
  • Ndom JC, Mbafor JT, Azebaze AGB, Vardamides JC, Kakam Z, Kamdem AFW, Deville A, Ngando TM, Fomum ZT. 2006. Secondary metabolites from Senecio burtonii (Compositae). Phytochemistry. 67:838–842.
  • Paredes A, Palacios J, Quispe C, Nwokocha CR, Morales G, Kuzmicic J, Cifuentes F. 2016. Hydroalcoholic extract and pure compounds from Senecio nutans Sch. Bip (Compositae) induce vasodilation in rat aorta through endothelium-dependent and independent mechanisms. J Ethnopharmacol. 192:99–107.
  • Parra C, Soto E, León G, Salas CO, Heinrich M, Echiburú-Chau C. 2018. Nutritional composition, antioxidant activity and isolation of scopoletin from Senecio nutans: support of ancestral and new uses. Nat Prod Res. 32:719–722.
  • Pelser PB, Gravendeel B, Meijden R. 2002. Tackling speciose genera: species composition and phylogenetic position of Senecio sect. Jacobaea (Asteraceae) based onplastid and nrDNA sequences. Am J Bot. 89:929–939.
  • Pelser PB, Veldkamp J-F, Van der Meijden R. 2006. New combinations in Jacobaea Mill. (Asteraceae - Senecioneae). Comp Newsl. 44:1–11.
  • Pérez C, Agnese AM, Cabrera JL. 1999. The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests. J Ethnopharmacol. 66:91–96.
  • Pinel B, Audo G, Mallet S, Lavault M, De La Poype F, Séraphin D, Richomme P. 2007. Multi-grams scale purification of xanthanolides from Xanthium macrocarpum: centrifugal partition chromatography versus silica gel chromatography. J Chrom A. 1151:14–19.
  • Podeschwa M, Plettenburg O, vom Brocke J, Block O, Adelt S, Altenbach H-J. 2003. Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone. Eur J Org Chem. 2003:1958–1972.
  • Prakash AS, Pereira TN, Reilly PEB, Seawright AA. 1999. Pyrrolizidine alkaloids in human diet. Mutat Res. 443:53–67.
  • Quézel P, Santa S. 1962–1963. Nouvelle flore de l’Algérie et des régions désertiques méridionales. Paris: Éditions du Centre national de la Recherche scientifique.
  • Rayyan S, Fossen T, Nateland HS, Andersen ØM. 2005. Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi folium cum flore' (Hawthorn). Phytochem Anal. 16:334–341.
  • Read MA. 1995. Flavonoids: naturally occurring anti-inflammatory agents. Am J Pathol. 147:235–237.
  • Schinkovitz A, Pro SM, Main M, Chen S-N, Jaki BU, Lankin DC, Pauli GF. 2008. Dynamic nature of the ligustilide complex. J Nat Prod. 71:1604–1611.
  • Shen S, Shen L, Lei Q, Zhang J, Li G, Si J. 2012. A new cyclohexylacetic acid derivative from the aerial parts of Emilia sonchifolia. Nat Prod Res. 27:1330–1334.
  • Shen S, Shen L, Zhang J, Li G, Li Z, Pan R, Si J. 2013. Emiline, a new alkaloid from the aerial parts of Emilia sonchifolia. Phytochemistry Lett. 6:467–470.
  • Siasos G, Tousoulis D, Tsigkou V, Kokkou E, Oikonomou E, Vavuranakis M, Basdra EK, Papavassiliou AG, Stefanadis C. 2013. Flavonoids in atherosclerosis: an overview of their mechanisms of action. Curr Med Chem. 20:2641–2660.
  • Tan D-P, Chou G-X, Wang Z-T. 2010. Phenolic compounds from Senecio scandens. Biochem Syst Ecol. 38:122–124.
  • Tatsis EC, Boeren S, Exarchou V, Troganis AN, Vervoort J, Gerothanassis IP. 2007. Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry. 68:383–393.
  • The Plant List. 2013. The Plant List: A working list on all plant species. Jacobaea gigantea (Desf.) Pelser [accessed 2018 May 9]. http://www.theplantlist.org/tpl1.1/record/gcc-23164.
  • Thuong PT, Su ND, Ngoc TM, Hung TM, Dang NH, Thuan ND, Bae K, Oh WK. 2009. Antioxidant activity and principles of Vietnam bitter tea Ilex kudingcha. Food Chem. 113:139–145.
  • Tian G, Zhang U, Zhang T, Yang F, Ito Y. 2004. Separation of flavonoids from the seeds of Vernonia anthelmintica Willd by high-speed counter-current chromatography. J Chromatogr A. 1049:219–222.
  • Toma W, Trigo JR, Paula ACBd, Brito ARMS. 2004. Preventive activity of pyrrolizidine alkaloids from Senecio brasiliensis (Asteraceae) on gastric and duodenal induced ulcer on mice and rats. J Ethnopharmacol. 95:345–351.
  • Torres P, Grande C, Anaya J, Grande M. 2000. Secondary metabolites from Senecio minutus and Senecio boissieri: a new jacaranone derivative. Fitoterapia. 71:91–93.
  • Tundis R, Loizzo MR, Bonesi M, Menichini F, Dodaro D, Passalacqua NG, Statti G, Menichini F. 2009. In vitro cytotoxic effects of Senecio stabianus Lacaita (Asteraceae) on human cancer cell lines. Nat Prod Res. 23:1707–1718.
  • Tundis R, Loizzo MR, Statti GA, Deguin B, Amissah R, Houghton PJ, Menichini F. 2005. Chemical composition of and inhibition of angiotensin-converting enzyme by Senecio samnitum huet. Pharm Biol. 43:605–608.
  • Yang Y, Gu D, Yili A, Zhao Y, He D, Aisa HA. 2010. One-step separation and purification of rupestonic acid and chrysosptertin B from Artemisia rupestris L. by high-speed counter-current chromatography. Phytochem Anal. 21:205–209.
  • Zhai D-D, Zhong J-J. 2010. Simultaneous analysis of three bioactive compounds in Artemisia annua hairy root cultures by reversed-phase high-performance liquid chromatography-diode array detector. Phytochem Anal. 21:524–530.
  • Zhang C-f, Jin J, Zhang M. 2008. Studies on chemical constituents of Senecio laetus Edgew. Chin Pharm J. 16:1214–1217.

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