Saponins as immunoadjuvants and immunostimulants

Lacaille‐Dubois, Marie‐Aleth

doi:10.1007/978-3-0348-8763-2_10

Cited by 15 publications

(15 citation statements)

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“…Saponins have been reported to present immunostimulating activities [18], and structureÀactivity relationships were deduced underlining the importance of the acylation of the sugars, especially by hydroxycinnamic acids for saponins× cytotoxicity [9]. Thus, a MPLC fraction of the crude saponin extract containing a mixture of 1/2 and 3/4 was tested in an in vitro lymphocyte proliferation assay.…”

mentioning

confidence: 99%

New Acylated Triterpene Saponins from Polygala arenaria

Mitaine-Offer¹,

Miyamoto²,

Laurens³

et al. 2003

Helvetica Chimica Acta

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Eight new acylated triterpene saponins 1–8 were isolated from the roots of Polygala arenaria as four inseparable (E)/(Z) mixtures of the 4‐methoxycinnamoyl and 3,4‐dimethoxycinnamoyl derivatives by repeated MPLC over silica gel. Their structures were established mainly by 600‐MHz 2D‐NMR techniques (1H,1H‐COSY, TOCSY, NOESY, HSQC, HMBC) as 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐(O‐β‐D‐galactopyranosyl‐(1→4)‐O‐[β‐D‐glucopyranosyl‐(1→3)]‐O‐β‐D‐xylopyranosyl‐(1→4)‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐4‐methoxycinnamoyl]}‐β‐D‐fucopyranosyl) ester and its (Z)‐isomer (1/2), 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐(O‐β‐D‐galactopyranosyl‐(1→4)‐O‐[β‐D‐glucopyranosyl‐(1→3)]‐O‐β‐D‐xylopyranosyl‐(1→4)‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]}‐β‐D‐fucopyranosyl) ester and its (Z)‐isomer (3/4), 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐(O‐β‐D‐glucopyranosyl‐(1→3)‐O‐α‐L‐arabinopyranosyl‐(1→4)‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐4‐methoxycinnamoyl]}‐β‐D‐fucopyranosyl) ester and its (Z)‐isomer (5/6), and 3‐O‐(β‐D‐glucopyranosyl)presenegenin 28‐(O‐β‐D‐glucopyranosyl‐(1→3)‐O‐α‐L‐arabinopyranosyl‐(1→4)‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐{4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]}‐β‐D‐fucopyranosyl) ester and its (Z)‐isomer (7/8) (presenegenin=(2β,3β)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid). In our in vitro lymphocyte proliferation assay (Jurkat T‐leukemia cells), a fraction containing 1–4 showed a concentration‐dependent immunomodulatory effect. This effect was not found for the prosapogenin (tenuifolin=3‐O‐(β‐D‐glucopyranosyl)presenegenin), underlining the importance of the acyloligosaccharidic moiety.

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mentioning

confidence: 99%

New Acylated Triterpene Saponins from Polygala arenaria

Mitaine-Offer¹,

Miyamoto²,

Laurens³

et al. 2003

Helvetica Chimica Acta

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“…In the in vitro lymphocyte proliferation assay, a good number of saponins were able to stimulate human lymphocyte proliferation at very low concentration ranging from 0.01 IlglmL to 1 pglmL, depending on the nature of the saponin [24]. Some compounds, such as squarroside A from Acanthophyllum squarrosum, showed at higher concentrations (100 or 200 IlglmL) inhibition of thymidine incorporation seen as an immunosupressive effect [26].…”

Section: Saponins As Immunostimulantsmentioning

confidence: 97%

“…Saponins were also shown to induce the production of cytokines in vitro [24]. Ginsenosides Rg) from Panax ginseng [30] and saikosaponins d, a, and a 23-O-acetyl saikosaponin from Bupleurum kaoi [31] induced the production of interleukin I from macrophages and virgaureasaponin E from Solidago virgaurea induced the production ofTNF and GM-CSF from macrophages [15].…”

Section: Saponins As Immunostimulantsmentioning

confidence: 98%

“…Saponins are considered to act on the immune system. In the group of immunomodulators, we can distinguish the specific immunomodulators which include the adjuvants in vaccines while the non specific immunostimulants are administered on their own in order to elicit a generalized state of resistance to pathogens or tumors [4,24].…”

Section: Chemopreventive Activity Of Saponinsmentioning

confidence: 99%

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Biologically and Pharmacologically Active Saponins from Plants: Recent Advances

Lacaille-Dubois

2000

Saponins in Food, Feedstuffs and Medicinal Plants

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“…Formulation of effective vaccines generally requires an appropriate adjuvant to optimize protective humoral and cell mediated immune responses (Lacaille- Dubois, 1999). If the saponins from Quillaja saponaria (Rosaceae) which are quillaic acid derivatives acylated by a dimeric fatty acid and their analogs have been extensively studied (Kensil et al, 1991) and used as immunoadjuvants in veterinary vaccines, few saponins from other sources have been reported to possess this property except some families including the Polygalaceae.…”

Section: Biological and Pharmacological Activities Of Polygalaceae Samentioning

confidence: 98%

Triterpene Saponins from Polygalaceae

Lacaille‐Dubois

Mitaine-Offer

2005

Phytochem Rev

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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-(b-D-glucopyranosyl)-presenegenin 28-[O-a-L-rhamnopyranosyl-(1 fi 2)-b-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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Saponins as immunoadjuvants and immunostimulants

Cited by 15 publications

References 58 publications

New Acylated Triterpene Saponins from Polygala arenaria

New Acylated Triterpene Saponins from Polygala arenaria

Biologically and Pharmacologically Active Saponins from Plants: Recent Advances

Triterpene Saponins from Polygalaceae

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