Drobečková navigace

Ginsenosides / Panaxosides

Panaxosides are effective saponins typical of ginseng ( Panax ). Panaxosides are glycosides with triterpenoid (steroidal) aglycone and one or more sugar residues. With all its vagueness, the word saponin suggests that panaxosides are amphiphilic and thus able to penetrate the gastrointestinal tract into blood, brain, and all cells. Ginsenosides are a subset of panaxosides (often with all panaxosides incorrectly called ginsenosides ). Panaxosides have extensive modulation effects on physiological pathways ( Attele1999gpm , Christensen2009gcb ), are harmless and are the essence of the adaptogenic effect of ginseng.

Panaxosides act on membrane and nuclear receptors Panaxosides are amphiphilic glycosides Aglycons are divided into damars ( diol and triol ) and oleanic acids (neurosteroids and hormonal modulators) As well as steroid hormones, panaxosides penetrate into the bloodstream, brain and cells, Where they act mainly in the nucleus by changing gene expression, influencing the number of genes, such as regulators of inflammation and synthesis of nitric oxide (NO) - see, for example, glucocorticoid receptors and PPAR receptors , their cellular membrane stabilization ( Li1997eag , Choo2003aag )

Main ginseng panaxosides

In 2008, 182 different Panaxosides were isolated from the Panax family (see Christensen2009gcb for their review) and others are slowly growing. Of these, at least 50 are found in the right ginseng. We are interested in the root panaxoside head, which is remarkable by their high weight content: Panaxosides are formed by the age and quality of 2-20% of the dry weight of the root ( Zhu2004cst , Christensen2009gcb , Yuan2002gva ). Specific panaxoside profiles also include leaves, blooms and red ginseng berries. The main panaxosides are:

Main Panaxadiols:
Panaxosid effect
Ginsenoside Rb 1 Protects memory and brain, anti-stress, anti-inflammatory, antidiabetic, protects blood vessels from atherosclerosis, suppresses angiogenesis
Ginsenoside Rb 2 Anti-stress, anti-inflammatory, protects the brain, protects against radiation
Ginsenoside Rc Anti-stress, anti-inflammatory, strongly protects against radiation
Ginsenoside Rd Anti-stress, anti-inflammatory, protects the brain, protects blood vessels from atherosclerosis, protects against radiation
Ginsenoside Rg 3 Strongly releases blood vessels and reduces blood pressure, anti-stress, anti-inflammatory, inhibition of NMDA receptors in the hippocampus, neurosteroidal action on membrane receptors in the brain, inhibits fat cell growth, protects against arthritis
Ginsenoside Rh 2 Restores immunity after radiotherapy and chemotherapy, anti-inflammatory, anti-allergic, inhibition of NMDA receptors in the hippocampus
Main Panaxatriols:
Panaxosid effect
Ginsenoside Re Antioxidant, antihypertensive, protects memory and brain, strongly restores immunity after irradiation, protects 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 brain against ischemia, protects blood vessels from atherosclerosis, anti-stress, nootropic
Ginsenoside Rh 1 Anti-inflammatory, anti-allergic, affects estrogen receptors

How panaxosides work

Panaxosides are amphiphilic - soluble in both water and fat. The bearer of the nonpolar character is the triterpenoid (steroid) skeleton - aglycon. The carrier of the polar character is oxygen and sugar residues bound to the aglycon. Thus, panaxosides pass into the bloodstream and act - as well as steroid hormones that resemble their amphiphilic character - both in the nucleus of cells and as a result of neurosteroidal effects on membrane receptors, mainly in the brain.

As with steroid hormones, small differences in ligand triterpenoid nuclei have a great impact on the effect of the molecule, and in panaxosides small differences in sugar residues can be their functional diversity. Unlike steroid hormones, however, panaxosides undergo gradual deglycosylation, which begins in the digestive tract. By deglycosylation, more complex panaxosides become simpler. The simplest panaxosides are the aglycone alone: protopanaxadiol (PPD) , protopanaxatriol (PPT) and others. Even ginseng aglycone has extensive effects on the brain, central-vascular system, potency and other physiological parameters.

Structure of panaxosides

Triterpenoid saponins of ginseng - panaxosides - are divided by the type of aglycon into two groups: damaran and oleanic.

What does "triterpenoid"

The spooky word "triterpenoid" means literally "from six units of isoprene consisting of". The triterpenoid molecule is simply produced in a cell by combining six units of isoprene:

Isoprene molecule

Per squalene molecule:

The squalene molecule

After that, the ginseng cell is made up of either damarendiol:

Damarendiol

Or beta-amyrin:

Beta-amyrin

From damarendiol, damaran panaxosides, from β-amyrin oleanate, are also produced.

The synthesis of panaxosides is closely related to human steroid synthesis

The way ginseng produces panaxoside aglycones is very similar to the way our body produces steroid hormones. The difference occurs when rolling the squalene from which our body produces lanosterol:

Lanosterol

And in about ten steps (see the KEGG database ) cholesterol:

Cholesterol

Cholesterol is - the substance is superfluous - it serves as a basic raw material for the production of all steroid hormones.

Aglycans of panaxosides

Panaxosides are divided into two main groups according to the type of aglycon: Damaran and oleanic. Damaran panaxosides are further subdivided into protopanaxadiol (PPD), protopanaxatriol (PPT) and octylol, depending on the location of the sugar residue. Oleanan panaxosides are derived from another aglycon-oleanolic acid. Other panaxoside types are panaxatriol and damarndiol. The four malonyl derivatives of panaxosides Rb 1 , Rb 2 , Rc and Rd together with panaxoside Ro and other esterified panaxosides are called "acid panaxosides", while others are called "neutral panaxosides" ( Christensen2009gcb , Attele1999gpm ).

Note: The word "damaran" comes from the white damaron ( Agathis dammara , bee- eyed , see the stock of the plants ), from which a damar resin is obtained for the production of varnishes. The word "oleanic" comes from the name of the olives ( Olea ). The origin of the word "okotilol" is unknown.

Panaxadioly - general structure and examples of representatives:

Panaxadiol

Structure of the main panaxadiols:
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 the main panaxatriols:
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 notice that the differences between the panaxosides described above are minimal in terms of human observer. Less typical panaxosides are:

Panaxosid Rh3:

Panaxosid Rh3

General Structure of Oleic Acid Esters:

Structure of oleic acid esters

Eg panaxoside Ro: R1 = -glcUA (2-1); R2 = -glc

General properties of panaxosides

The panaxoside structure is characterized by their typical chemical properties:

  • Panaxosides are chemically stable. In addition to one unsaturated C = C linkage, the steroidal panaxoside skeleton contains only aliphatic linkages whose stability is generally known. I was surprised, however, by the recent reading that the glycosidic bond (through oxygen) that the sugars are bound to is also amazingly stable - under standard conditions, its hydrolysis half life is incredible 20 million years, about 100 times more stable than phosphodiester DNA binding and 100,000 times more stable Than the peptide bond of proteins ( Wolfenden 19988g ).
  • Panaxosides are amphiphilic . The steroidal skeleton is hydrophobic with affinity for fatty substances, while sugar residues in panaxosides confer water solubility. This is also associated with their next feature:
  • Panaxosides are highly mobile. The ability of ginsenosides to move in both the aqueous and fatty environment helps them to easily enter the human body, including the blood-brain barrier.

Which panaxosides are most abundant in ginseng?

In terms of quantity, more than 90% of the total panaxoside content of ginseng root consists of the following 10 panaxosides ( Christensen2009gcb ):

  • PPD ginsenosides Rb 1 , Rb 2 , Rc and Rd
  • PPT ginsenosides Re and Rg 1
  • Acidic ginsenosides malonyl-Rb1, malonyl-Rb2, malonyl-Rc and malonyl-Rd

The amount and content of panaxosides varies greatly according to age and conditions in which ginseng grew. However, there are panaxoside profile specifics that distinguish between genuine ginseng, American ginseng , notoginsenge and other Panax species .

What are the differences in panaxoside profile of ginseng right and American?

Ginsenoside Rf is characteristic of genuine ginseng and is not present in American ginseng or other species of the genus Panax . Octylol panaxoside 24 (R) -pseudoginsenoside F11 is again characteristic of American ginseng, while in ginseng right almost does not occur. These panaxosides can be used to distinguish these two species of ginseng ( Christensen2009gcb ). Another difference is in the ratio of ginsenosides Rb 1 / Rg 1 . The ratio of Rb 1 / Rg 1 is greater than 10 for ginseng in the United States, but for ginseng it is between 1 and 3. Ginseng American generally contains more PPDs than PPT panaxosides, whereas ginseng is the opposite. The ratio of malonyl-Rc and malonyl- Rb2 ginsenosides to malonyl-Rb 1 ginsenoside is lower for ginseng than for ginseng.

What are the specifics of panoxoside profile notoginsengu?

The specificity of notoginseng ginseng is the ratio of malonyl-ginsenoside content. The most abundant malonyl-ginsenoside is notoginsengu ginsenosid malonyl-Rb 1 .

Panaxosides, apart from the Panax family, are not found anywhere else

The rule for plants is that the secondary metabolites contained in them occur in many different plant species. The ginseng is different - panaxosides are unique and characteristic of the genus Panax . I know only one other known plant known as panaxosides: Gynostem five-leaf squash contains triterpenoids, nine of which are identical to known panaxosides ( Christensen2009gcb , page 29, Table 1.1). The Gynostema Five-lobster, also called Jiuogulan , misspelled "5-Ginseng Ginseng" contains these panaxosides in leaves, and its cultivation represents a cheap source of these saponins for those seniors who are deep in their pockets. The content of panaxosides in gynostema leaves is about 1.5% dry weight, that is, as in a weak young ginseng.

Changes in panaxoside profile during processing on red ginseng

To increase the shelf life and improve some pharmacological properties, ginseng root (so-called white ginseng, ginseng radix album ) is processed by soaking red ginseng, ginseng radix rubra . Ginseng drying results in the partial cleavage of panaxoside acid residues and partial deglycosylation. In the subsequent grying of ginseng, which takes place at ~ 100 ° C and takes several hours, the Maillard reaction (caramelization) proceeds and deglycosylation of panaxosides proceeds. Thus, red ginseng has a higher ratio of simpler panaxosides (e.g., ginsenoside Rg 3 and compound K ) and also contains more free aglycone (mainly PPD and PPT). Further hydrolysis and deglycosylation of panaxosides occurs in the digestive system.

List of Panaxosides:

Related articles