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Ginsenosides / Panaxosides

Panaxosidy are effective saponins typical for the genus Ginseng (Panax). Panaxosidy are glycosides with triterpenoidním (steroid) aglycone and one or more sugar residues. Despite its vagueness word saponin indicates that panaxosidy are amphiphilic and thus able to penetrate from the digestive tract into the blood, the brain and in all cells. Ginsenosides are a subset panaxosidů (often incorrectly called all panaxosidům ginsenosides). Panaxosidy have extensive modulatory effects on physiological pathways ( Attele1999gpm , christensen2009gcb ) they are harmless and are the essence of adaptogenic effects of ginseng.

Main ginseng panaxosidy

The year 2008 has been isolated from the genus Panax 182 different panaxosidů (see the survey in christensen2009gcb ) and slowly gain more. Of these, at least 50 occurs in ginseng. They're interested head panaxosidy root, which are notable for their high weight content: Panaxosidy forms depending on the age and quality of 2-20% of the dry weight of the root ( Zhu2004cst , christensen2009gcb , Yuan2002gva ). Specific panaxosidové profiles also have leaves, flowers and berries red ginseng. Main panaxosidy are:

Main panaxadioly:
panaxosid effect
ginsenoside Rb 1 protects memory and brain, anti-stress, anti-inflammatory, anti-diabetic, protects vessels from atherosclerosis, angiogenesis suppresses
ginsenoside Rb 2 anti-stress, anti-inflammatory, protects the brain from radiation
ginsenoside Rc anti-stress, anti-inflammatory, strongly protects against radiation
ginsenoside Rd anti-stress, anti-inflammatory, protects the brain, protects vessels from atherosclerosis, protects against radiation
ginsenoside Rg 3 strongly relaxes blood vessels and reducing blood pressure, anti-stress, anti-inflammatory, inhibition of NMDA receptors in the hippocampus, neurosteroid effects on brain membrane receptors, inhibit the growth of fat cells, protects against arthritis
ginsenoside Rh 2 restores immunity after radiotherapy and chemotherapy, anti-inflammatory, anti-allergy, inhibition of NMDA receptors in the hippocampus
Main panaxatrioly:
panaxosid effect
ginsenoside Re antioxidant, antihypertensive, protects memory and brain, strongly restores immunity after exposure, protect the heart and blood vessels
ginsenoside Rf blocks N-type calcium channels in the brain, regulates fat metabolism by acting on PPAR receptors
ginsenoside Rg 1 anti-inflammatory, antihypertensive, protects the brain, strongly protects against radiation increases angiogenesis
ginsenoside Rg 2 protects neurons, protects the brain during ischemia protects vessels from atherosclerosis, anti-stress, nootropic
ginsenoside Rh 1 anti-inflammatory, antiallergic, acts on estrogen receptors

How panaxosidy work

Panaxosidy amphiphilic - soluble in water and fat. The bearer of a non-polar character in them triterpenoid (steroid) skeleton - aglycone. The bearer of the polar nature of the oxygen and sugar moieties attached to the aglycone. Panaxosidy thanks to pass into the bloodstream and acting - as steroid hormones which with its amphiphilic character similar - as in the nucleus of cells and neurosteroidním due to membrane receptors mainly in the brain.

As with the steroid hormone small differences in the ligand triterpenoidního cores have a large impact on the effect of the molecule, even small differences in panaxosidů sugar residues can for their functional diversity. Unlike steroids, however, are subject to gradual panaxozidy deglycosylation begins in the digestive tract. Deglycosylation is difficult panaxosidy changes easier. The simplest panaxosidy are very aglycones: protopanaxadiol (PPD) , protopanaxatriol (PPT) and others. Even ginseng aglycones have large effects on the brain, sredčně-vascular system, the potency and other physiological parameters.

The structure panaxosidů

Ginseng triterpenoid saponins - panaxosidy - are divided according to the type of aglycone into two groups: damaranové and oleananové.

What does "triterpenoid"

Scary word, "triterpenoid" literally means "six isoprene units consisting". Triterpenoid molecule is simply the cell produces the merger of six isoprene units:

isoprene molecule

per molecule of squalene:

squalene molecule

Squalene cell ginseng then rolls up on either damarendiol:

damarendiol

or β-amyrin:

beta-amyrin

Of damarendiolu also produced damaranové panaxosidy of β-amyrin oleananové.

The synthesis panaxosidů is close to the human synthesis of steroids

The manner in which ginseng produced aglycones panaxosidů very similar to the manner in which our body produces steroid hormones. The difference occurs when scrolling squalene, from which our body produces lanosterol:

lanosterol

and about ten steps (see database KEGG ) Cholesterol:

cholesterol

Cholesterol is - a substance very, very necessary - then serves as raw material for the production of steroid hormones.

aglycones panaxosidů

Panaxosidy is divided into two main groups according to the type of aglycone: Damaranové and oleananové. Damaranové panaxosidy further by place of attachment of sugar residues are divided into protopanaxadiolové (PPD) protopanaxatriolové (PPT) and okotilolové. Oleananové panaxosidy are derived from another aglycone - oleanolic acid. Other types are panaxosidů panaxatriolové and damarendiolové. Four malonylované derivatives panaxosidů Rb 1, Rb 2, Rc and Rd together with Panaxosidy Ro and other esterified panaxosidy called "sour panaxosidy" while the others are called "neutral panaxosidy" ( christensen2009gcb , Attele1999gpm ).

NB. The word "damaranový" comes from the white kauri (Agathis dammar, araucariaceae see database gymnosperms ), from which is obtained dammar resins to produce coatings. The word "oleananový" comes from the name of olive (Olea). The origin of the word "okotilolový" I do not know.

Panaxadioly - general structure and examples of Representatives:

Panaxadiol

Structure of major panaxadiolů:
panaxosid R1 R2
Rb1 -Glc (2-1) Glc -Glc (6-1) Glc
Rb2 -Glc (2-1) Glc Glc (6-1) Arap
rc -Glc (2-1) Glc Glc (6-1) Araf
Rd -Glc (2-1) Glc Glc
RG3 -Glc (2-1) Glc -H
Rh2 Glc -H

Panaxatrioly - general structure and examples of Representatives:


Panaxatriol

Structure of major panaxatriolů:
panaxosid R1 R2
Re Glc (2-1) Rha Glc
Rf -Glc (2-1) Glc -H
Rg1 Glc Glc
RG2 Glc (2-1) Rha -H
RH1 Glc -H

We can see that the differences between the above-described panaxosidy in terms of minimum human observer. Less typical panaxosidy are:

Panaxosid Rh3:

panaxosid Rh3

General structure of oleanolic acid esters:

structure esters oleanolic

e.g. panaxosid Ro: R1 = -glcUA (2-1); R2 = -Glc

General properties panaxosidů

From the structure panaxosidů derive their typical chemical properties:

  • Panaxosidy are chemically stable. Besides one unsaturated C = C bond comprises a steroidal skeleton panaxosidů only aliphatic bonds, whose stability is generally known. It surprised me, but when I recently read that the glycosidic linkage (via oxygen) which are linked sugars is also amazingly stable - under standard conditions, its half-life of hydrolysis incredible 20 million years, about 100 times more stable than the phosphodiester bond DNA strands and 100,000 times more stable than the peptide binding protein ( Wolfenden1998shg ).
  • Panaxosidy are amphiphilic. Steroid skeleton is hydrophobic, with an affinity for fatty substances, while the sugar residues panaxosidům impart water solubility. This is also linked to their other property:
  • Panaxosidy are highly mobile. Ginsenosides ability to move both in water and in a lipid environment helps them to easily entering the human body, including the blood brain barrier.

Panaxosidy which is the most widely occurring ginseng?

In terms of amount, more than 90% of the total content panaxosidového ginseng root consists of 10 panaxosidů ( christensen2009gcb )

  • PPD ginsenosides Rb 1, Rb 2, Rc and Rd
  • PPT ginsenosides Re and Rg 1
  • acid malonyl-ginsenosides Rb 1, Rb 2-malonyl, malonyl-Rc and malonyl-Rd

The quantity and content panaxosidů varies greatly according to age and the conditions in which ginseng growing. However, there are specifics panaxosidového profile that helps differentiate between ginseng right , ginseng, American , Notoginseng and other species of the genus Panax .

What are the differences in panaxosidovém profile ginseng and American?

Ginsenoside Rf is characteristic of true ginseng and is not present in ginseng American or other species of the genus Panax. Okotilolový panaxosid 24 (R) F11 -pseudoginsenosid turn is characteristic of American ginseng, while Ginseng is almost completely absent. These panaxosidy can be used to distinguish these two types of ginseng ( christensen2009gcb ). Another difference is the ratio of ginsenosides Rb 1 / Rg first 1 ratio Rb / Rg 1 is the American ginseng greater than 10, but ginseng is between 1 to 3 American Ginseng generally contains more than PPD PPT panaxosidů, while ginseng is the other way round. Ginsenosides ratio malonyl-Rc and malonyl-Rb 2 to ginsenosides malonyl-Rb 1 is ginseng American lower than that of ginseng.

What are the specifics panaxosidového profile Notoginseng?

The uniqueness of ginseng notoginseng is the ratio of the content of malonyl-ginesnosidů. The most abundant malonyl-ginsenosides is at notoginseng ginsenoside malonyl-Rb 1 .

Panaxosidy addition to the genus Panax occur almost anywhere else

The rule in plants the situation is that the secondary metabolites contained in them occur in many different plant species. For ginseng is different - panaxosidy are unique and characteristic for the genus Panax. I only know of one other known plant science containing panaxosidy: cucurbits creeper Jiaogulan contains triterpenoids, nine of which are identical to known panaxosidy ( christensen2009gcb , p. 29, Table 1.1). Jiaogulan, also known as Tiao-to-lan (pinyin jiaogulan) incorrectly "ginseng five-bladed," contains these panaxosidy paper and its cultivation is a cheap source of saponins for those of our seniors who have deep pockets. Panaxosidů content in leaves gynostemy is about 1.5% of dry weight, about as vulnerable young ginseng.

Panaxosidového profile changes during processing red ginseng

To increase durability and improve some of the pharmacological properties of the ginseng root (ie. White ginseng, ginseng radix alba) handles the so-called steaming. Red ginseng, radix ginseng rubra . Already during drying ginseng is a partial cleavage of acidic residues panaxosidů and partial deglycosylation. During subsequent steaming ginseng, which takes place at a temperature of ~ 100 ° C and lasts for several hours takes place Maillard reaction (caramelisation), and continues deglycosylation panaxosidů. The red ginseng has therefore higher ratio simpler panaxosidů (e.g. ginsenoside Rg 3 and Compound K ) and also contains large amounts of free aglycones (especially PPD and PPT). To further hydrolysis and deglycosylation panaxosidů occurs in the digestive system.

List panaxosidů:

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