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Triterpene Saponins from Polygalaceae

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Abstract

The aim of this review is to give updated results on the chemistry and biological activities of Polygalaceae saponins from literature data and from authors’ studies. During the last decade the improvement of isolation and structure elucidation techniques allowed the characterization of about 150 complex triterpene saponins from Polygalaceae having mainly preatroxigenin, medicagenic acid and presenegenin as aglycone. The sequence 3-O-(β-d-glucopyranosyl)-presenegenin 28-[O-α-L-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl] ester with additional acylations with p-methoxy-, di- or trimethoxycinnamoyl groups at the position 4 of the fucopyranosyl moiety often encountered in the genera Polygala, Muraltia, Carpolobia, and Securidaca may represent a chemotaxonomic marker for the Polygalaceae family. The biological and pharmacological properties of some Polygalaceae species such as in vitro activity on the central nervous system, the hypoglycemic, cytotoxic, immunomodulatory activities and in vivo immunoadjuvant properties are highlighted.

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References

  • IW Chung SR Kim EG Kim (1992) ArticleTitleDopamine-2 and serotonine-2 receptor bindings in antipsychotic medicines from natural products J. Korean Neuropsychiatr. Assoc. 31 856–867

    Google Scholar 

  • IW Chung NA Moore W-K Oh MF O’Neill JS Ahn JB Park UG Kang YS Kim (2002) ArticleTitleBehavioural pharmacology of polygalasaponins indicates potential antispychotic efficacy Pharmacol. Biochem. Behav. 71 191–195 Occurrence Handle10.1016/S0091-3057(01)00648-7 Occurrence Handle11812522 Occurrence Handle1:CAS:528:DC%2BD38Xms1Khtg%3D%3D

    Article  PubMed  CAS  Google Scholar 

  • MR Daros FJ Abreu Matos Particlede J Paz Parente (1996) ArticleTitleA new triterpenoid saponin, bredemeyeroside B from the roots of Bredemeyera floribunda Planta Med. 62 523–527

    Google Scholar 

  • C Delaude (1971) ArticleTitleEtude comparative des saponines extraites de deux Polygalacées africaines le ≪ Securidaca longepedunculata ≫ Rees. Var. parvifolia et le Polygala acicularis OLIV Bull. Soc. Roy. Sc. Liège 40 397–400 Occurrence Handle1:CAS:528:DyaE38XntVSnsQ%3D%3D

    CAS  Google Scholar 

  • C Delaude (1990) ArticleTitleContribution a l’étude chimique des Polygalaceae.. Examen de Muraltia ononidifolia Bull. Soc. Roy. Sc. Liège 59 455–456 Occurrence Handle1:CAS:528:DyaK38XhvVersw%3D%3D

    CAS  Google Scholar 

  • C Delaude (1991) ArticleTitleContribution à l’étude chimique des Polygalaceae.. Examen d’espèces de Muraltia Bull. Soc. Roy. Sc. Liège 60 385–386 Occurrence Handle1:CAS:528:DyaK38Xkt1egsb8%3D

    CAS  Google Scholar 

  • C Delaude (1992) ArticleTitleLes Polygalaceae et leurs saponines. Bull. Soc. Roy. Sc. Liège 61 245–288 Occurrence Handle1:CAS:528:DyaK3sXjvVWh

    CAS  Google Scholar 

  • S Desbène B Hanquet Y Shoyama H Wagner MA. Lacaille-Dubois (1999) ArticleTitleBiologically active triterpene saponins from callus tissue of Polygala amarella J. Nat. Prod. 62 923–926 Occurrence Handle10395523

    PubMed  Google Scholar 

  • MA Dubois A Neszmelyi G Heubl M Fiebig H Wagner (1989) ArticleTitleAmarelloside, a bitter tri-O-acetyl-tri-O-benzoyl tetrasaccharide from Polygala amarella Phytochemistry 28 3355–3359 Occurrence Handle1:CAS:528:DyaK3cXhsFGiu70%3D Occurrence Handle10.1016/0031-9422(89)80346-2

    Article  CAS  Google Scholar 

  • M Elbandy T Miyamoto C Delaude MA Lacaille-Dubois (2002a) ArticleTitleFive new medicagenic acid saponins from Muraltia ononidifolia Helv. Chim. Acta 85 2721–2728 Occurrence Handle10.1002/1522-2675(200209)85:9<2721::AID-HLCA2721>3.0.CO;2-A Occurrence Handle1:CAS:528:DC%2BD38XotVGlsLk%3D

    Article  CAS  Google Scholar 

  • M Elbandy T Miyamoto B Chauffert C Delaude MA Lacaille-Dubois (2002b) ArticleTitleNovel acylated triterpene glycosides from Muraltia heisteria J. Nat. Prod. 65 193–197 Occurrence Handle10.1021/np010381+ Occurrence Handle1:CAS:528:DC%2BD38XhtVWksrY%3D

    Article  CAS  Google Scholar 

  • M Elbandy T Miyamoto C Delaude MA Lacaille-Dubois (2003a) ArticleTitleNew acylated preatroxigenin saponins from Atroxima congolana Helv. Chim. Acta 86 522–531 Occurrence Handle10.1002/hlca.200390052 Occurrence Handle1:CAS:528:DC%2BD3sXisVaqtLc%3D

    Article  CAS  Google Scholar 

  • M Elbandy T Miyamoto C Delaude MA Lacaille-Dubois (2003b) ArticleTitleAcylated preatroxigenin glycosides from Atroxima congolana J. Nat. Prod. 66 1154–1158 Occurrence Handle1:CAS:528:DC%2BD3sXmtlOksbs%3D

    CAS  Google Scholar 

  • M Elbandy T Miyamoto C Delaude MA Lacaille-Dubois (2004) ArticleTitleNew acylated presenegenin saponins from two Species of Muraltia Helv. Chim. Acta 87 340–348 Occurrence Handle10.1002/hlca.200490031 Occurrence Handle1:CAS:528:DC%2BD2cXis1ehsb8%3D

    Article  CAS  Google Scholar 

  • A Estrada GS Katselis B Laarveld B Barl (2000) ArticleTitleIsolation and evaluation of immunological adjuvant activities of saponins from Polygala senega L Comp. Immunol. Microbiol. Infect. Dis. 23 27–43 Occurrence Handle10660256 Occurrence Handle1:STN:280:DC%2BD3c7itlKmsA%3D%3D

    PubMed  CAS  Google Scholar 

  • G Gaidi T Miyamoto V Laurens MA Lacaille-Dubois (2002) ArticleTitleNew acylated triterpene saponins from Silene fortunei that modulate lymphocyte proliferation J. Nat. Prod. 65 1568–1572 Occurrence Handle10.1021/np020105a Occurrence Handle12444678 Occurrence Handle1:CAS:528:DC%2BD38XntV2rsLo%3D

    Article  PubMed  CAS  Google Scholar 

  • M Haddad T Miyamoto C Delaude MA Lacaille-Dubois (2003) ArticleTitleNew acylated saponins from Polygala myrtifolia Helv. Chim. Acta 86 3055–3065 Occurrence Handle10.1002/hlca.200390247 Occurrence Handle1:CAS:528:DC%2BD3sXotVWisrY%3D

    Article  CAS  Google Scholar 

  • M Kako T Miura Y Nishiyama M Ichimaru M Moriyasu A Kato (1997) ArticleTitleHypoglycemic activity of some triterpenoid glycosides J. Nat. Prod. 60 604–605 Occurrence Handle10.1021/np9605403 Occurrence Handle9214731 Occurrence Handle1:CAS:528:DyaK2sXjsFeruro%3D

    Article  PubMed  CAS  Google Scholar 

  • CR Kensil U Patel M Lennick D Marciani (1991) ArticleTitleSeparation and characterisation of saponins with adjuvant activity from Quillaja saponaria Molina cortex J. Immunol. 146 431–437 Occurrence Handle1987271 Occurrence Handle1:CAS:528:DyaK3MXit1Sqt78%3D

    PubMed  CAS  Google Scholar 

  • M Kuroda Y Mimaki Y Sashida M Kitahara M Yamazaki S. Yui (2001) ArticleTitleSecuriosides A and B, novel acylated triterpene bisdesmosides with selective cytotoxic activity against M-CSF-stimulated macrophages Bioorg. Med. Chem. Lett. 11 371–374 Occurrence Handle10.1016/S0960-894X(00)00674-0 Occurrence Handle11212113 Occurrence Handle1:CAS:528:DC%2BD3MXhtFylsL0%3D

    Article  PubMed  CAS  Google Scholar 

  • MA Lacaille-Dubois H Wagner (1996) ArticleTitleA review of the biological and pharmacological activities of saponins Phytomedicine 2 363–386 Occurrence Handle1:CAS:528:DyaK28XjsFWntbg%3D

    CAS  Google Scholar 

  • MA Lacaille-Dubois H Wagner (2000) Bioactive saponins from plants: an update Atta-Ur-Rahman (Eds) Studies in Natural Products Chemistry NumberInSeriesVol. 21 Elsevier Amsterdam 633–687

    Google Scholar 

  • MA Lacaille-Dubois (2000) Biologically and pharmacologically active saponins from plants: recent advances A Marston W Oleszek (Eds) Saponins in Food, Feedstuffs and Medicinal Plants Kluwer Academic Publisher Dordrecht 205–218

    Google Scholar 

  • MA Lacaille-Dubois (1999) Saponins as immunoadjuvants and immunostimulants H Wagner (Eds) Immunomodulatory Agents from Plants Birkhäuser Verlag Basel 243–272

    Google Scholar 

  • AC Mitaine-Offer T Miyamoto IA Khan C Delaude MA Lacaille-Dubois (2002) ArticleTitleThree new triterpene saponins from two species of Carpolobia J. Nat. Prod. 65 553–557 Occurrence Handle10.1021/np010546e Occurrence Handle11975499 Occurrence Handle1:CAS:528:DC%2BD38XitFahsbk%3D

    Article  PubMed  CAS  Google Scholar 

  • AC Mitaine-Offer T Miyamoto V Laurens C Delaude MA Lacaille-Dubois (2003) ArticleTitleNew acylated triterpene saponins from Polygala arenaria Helv. Chim. Acta 86 2404–2413 Occurrence Handle10.1002/hlca.200390193 Occurrence Handle1:CAS:528:DC%2BD3sXms1Wnsrw%3D

    Article  CAS  Google Scholar 

  • T Miyase H Saitoh KI Shiokawa A Ueno (1995) ArticleTitleSix new presenegenin glycosides A-F, from Polygala reinii root Chem. Pharm. Bull. 43 466–472 Occurrence Handle7774030 Occurrence Handle1:CAS:528:DyaK2MXnsVWmurw%3D

    PubMed  CAS  Google Scholar 

  • T Nagai Y Suzuki H Kiyohara E Susa T Kato T Nagamine Y Hagiwara S.I Tamura T Yabe C Aizawa H Yamada (2001) ArticleTitleOnjisaponins, from the Root of Polygala tenuifolia WILLDENOW, as effective adjuvants for nasal influenza and diphtheria-pertussis-tetanus vaccines Vaccine 19 4824–4834 Occurrence Handle11535335 Occurrence Handle1:CAS:528:DC%2BD3MXmsFWrtb4%3D

    PubMed  CAS  Google Scholar 

  • K Oda H Matsuda T Murakami S Katayama T Ohgitani M Yoshikawa (2003) ArticleTitleRelationship between adjuvant activity and amphipathic structure of soyasaponins Vaccine 21 2145–2151 Occurrence Handle10.1016/S0264-410X(02)00739-9 Occurrence Handle12706705 Occurrence Handle1:CAS:528:DC%2BD3sXjtFWlsrg%3D

    Article  PubMed  CAS  Google Scholar 

  • SW Pelletier S Nakamura R Soman (1971) ArticleTitleConstituents of Polygala species. The structure of tenuifolin, a prosapogenin from P. senega and P. tenuifolia Tetrahedron 27 4417–4427 Occurrence Handle10.1016/S0040-4020(01)98155-4 Occurrence Handle1:CAS:528:DyaE38XhslKg

    Article  CAS  Google Scholar 

  • S Sakuma J Shoji (1981a) ArticleTitleStudies on the constituents of the root of Polygala tenuifolia WILLDENOW. I.1) Isolation of saponins and the structures of onjisaponins G and F Chem. Pharm. Bull. 29 2431–2441 Occurrence Handle1:CAS:528:DyaL38XitVSjsL4%3D

    CAS  Google Scholar 

  • S Sakuma J. Shoji (1981b) ArticleTitleStudies on the constituents of the root of Polygala tenuifolia WILLDENOW. II.1) On the structures of onjisaponins A, B and E Chem. Pharm. Bull. 30 810–821

    Google Scholar 

  • R Teng Z Wu Y He D Wang C Yang (2002) ArticleTitleRevised structures of arillatanosides A-C from Polygala arillata Magn. Reson. Chem. 40 424–429 Occurrence Handle1:CAS:528:DC%2BD38XktFyksbw%3D

    CAS  Google Scholar 

  • Y Tsukitani S Kawanishi J Shoji (1973a) ArticleTitleStudies of the constituents of Senegae radix. II.1) The structure of senegin II, a saponin from Polygala senega Linne var. latifolia Torey et Gray Chem. Pharm. Bull. 21 791–799 Occurrence Handle1:CAS:528:DyaE3sXksFSksbo%3D

    CAS  Google Scholar 

  • Y Tsukitani J Shoji (1973b) ArticleTitleStudies on the constituents of Senegae radix. III.1) The structures of Senegin III and IV, saponins from Polygala senega Linne var. latifolia Torey et Gray Chem. Pharm. Bull. 21 1564–1574 Occurrence Handle1:CAS:528:DyaE3sXltFGrsbk%3D

    CAS  Google Scholar 

  • T Yabe H Tuchida H Kiyohara T Takeda H Yamada (2003) ArticleTitleInduction of NGF synthesis in astrocytes by onjisaponins of Polygala tenuifolia, constituents of Kampo (Japanese herbal) medicine, Ninjin-Yoei-To Phytomedicine 10 106–114 Occurrence Handle10.1078/094471103321659799 Occurrence Handle12725562 Occurrence Handle1:CAS:528:DC%2BD3sXksFGkt7k%3D

    Article  PubMed  CAS  Google Scholar 

  • M Yoshikawa T Murakami T Ueno M Kadoya H Matsuda J Yamahara N. Murakami (1995a) ArticleTitle E-senegasaponins A and B, Z-senegasaponins A and B, Z-senegins II and III, new type inhibitors of ethanol absorption in rats from Senegae Radix, the roots of Polygala senega L. var latifolia TORREY et GRAY Chem. Pharm. Bull. 43 350–352 Occurrence Handle1:CAS:528:DyaK2MXksVShu78%3D

    CAS  Google Scholar 

  • M Yoshikawa T Murakami T Ueno M Kadoya H Matsuda J Yamahara N. Murakami (1995b) ArticleTitleBioactive saponins and glycosides. I. Senegae Radix. (1): E-senegasaponins a and b and Z-senegasaponins a and b, their inhibitory effect on alcohol absorption and hypoglycemic activity Chem. Pharm. Bull. 43 2115–2122 Occurrence Handle1:STN:280:BymC3s3hsF0%3D

    CAS  Google Scholar 

  • S Yui K Ubukata K Hodono M Kitahara M Mimaki Y Kuroda Y Sashida M Yamazaki (2001) ArticleTitleMacrophage-oriented cytotoxic activity of novel triterpene saponins extracted from Roots of Securidaca inappendiculata Int. Immunopharmacol. 1 1989–2000 Occurrence Handle10.1016/S1567-5769(01)00126-6 Occurrence Handle11606030 Occurrence Handle1:CAS:528:DC%2BD3MXns1Gmtrw%3D

    Article  PubMed  CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara A Ueno (1995a) ArticleTitleStudies on the constituents of Polygala japonica HOUTT. I. Structures of polygalasaponins I-X Chem. Pharm. Bull. 43 115–120 Occurrence Handle1:CAS:528:DyaK2MXksVSqtL0%3D

    CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara A Ueno (1995b) ArticleTitleStudies on the constituents of Polygala Japonica HOUTT. II.1) Structures of polygalasaponins XI-XIX Chem. Pharm. Bull. 43 966–970 Occurrence Handle1:CAS:528:DyaK2MXntlWitrY%3D

    CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara H. Noguchi (1996a) ArticleTitleNine new triterpene saponins, polygalasaponins XXXIII-XLI from the roots of Polygala fallax HEMSL Chem. Pharm. Bull. 44 2092–2099 Occurrence Handle1:CAS:528:DyaK28Xnt1yjtrY%3D

    CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara A Ueno (1996b) ArticleTitleStudies on the constituents of Polygala japonica HOUTT. III. Structures of polygalasaponins XX-XXVII Chem. Pharm. Bull. 44 173–179 Occurrence Handle1:CAS:528:DyaK28XotVeqtw%3D%3D

    CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara A Ueno (1996c) ArticleTitleFive new triterpene saponins, polygalasaponins XXVIII-XXXII from the root of Polygala japonica HOUTT Chem. Pharm. Bull. 44 810–815 Occurrence Handle1:CAS:528:DyaK28XisVektb0%3D

    CAS  Google Scholar 

  • D Zhang T Miyase M Kuroyanagi K Umehara H Noguchi (1998) ArticleTitlePolygalasaponins XLII-XLVI from roots of Polygala glomerata Phytochemistry 47 459–466 Occurrence Handle10.1016/S0031-9422(97)00490-1 Occurrence Handle9433820 Occurrence Handle1:CAS:528:DyaK1cXjvFGlsg%3D%3D

    Article  PubMed  CAS  Google Scholar 

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  1. Laboratoire de Pharmacognosie, Unité de Molécules d’Intérêt Biologique, UPRES-EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7 Bd Jeanne d’Arc, 21079, DIJON, Cedex, France

    Marie-Aleth Lacaille-Dubois & Anne-Claire Mitaine-Offer

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  1. Marie-Aleth Lacaille-Dubois
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Correspondence to Marie-Aleth Lacaille-Dubois.

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Lacaille-Dubois, MA., Mitaine-Offer, AC. Triterpene Saponins from Polygalaceae. Phytochem Rev 4, 139–149 (2005). https://doi.org/10.1007/s11101-005-2606-6

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