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каштан -эсцин PDF
каштан -эсцин PDF
каштан -эсцин PDF
Introduction
In recent years, the cosmetic industry has become increasingly interested in using plantderived natural products in cosmetic formulations. This is not merely a marketing tool, but
* To whom correspondence should be addressed: (T) 144 181 362 6425; (F) 144 181 805 0702. E-mail:
J.Wilkinson@mdx.ac.uk
01425463 1999 International Journal of Cosmetic Science
438
a result of the plant material itself having biological activity that is beneficial to skin [1].
The use of horse chestnut preparations as herbal medicines has been adequately described
elsewhere, so this paper therefore focuses on the biological potential of extracts from this
species as cosmoceuticals and for skin-care products.
escin Ia
escin Ib
desacylescin I
escin IIa
escin IIb
desacylescin II
R1
Tig
Ang
H
Tig
Ang
H
R2
Ac
Ac
H
Ac
Ac
H
439
R3
CH2OH
CH2OH
CH2OH
H
H
H
R 5 Rutinoside: Rutin
R 5 Rhamnoside: Quercitrin
R 5 Glucose: Isoquercitrin
R 5 Arabinoside: Quercetin 3-arabinoside
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Other constituents
Seeds of A. hippocastanum have also been described as containing starch (4050% weight)
[6], sugars, proteins (specifically the globulin, hippocastanine, containing L-(1)lysine and
L-(1)-tryptophan), a fatty oil (containing oleic, linoleic, linolenic, stearic and palmitic
acids) and purines (adenosine, adenine and guanine). [5]
Bark
The bark of Aesculus hippocastanum, in common with the seeds, has been described as
containing the saponin mixture escin [3]. Coumarin glycosides, including esculin,
scopolin and fraxin, and their respective aglycones, esculetin, scopoletin and fraxetin, are
also present in the bark of A. hippocastanum (Figure 4), in contrast to seed tissues, in
which these compounds have not been detected. The flavonoid glycoside quercitrin (Figure
2), and its corresponding aglycone have also been detected in bark tissues. Additional
compounds, including allantoin, sterols, leucocyanidin, leucodelphinidin, catechol tannins
and alkanes have also been described as occurring in bark tissues. [3]
Figure 4. Coumarins and coumarin glycosides present in the leaves and bark of Aesculus
hippocastanum.
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Leaves
In common with the bark of A. hippocastanum, leaf tissues contain the coumarin
glycosides scopolin, fraxin and esculin (Figure 4) [3]. A range of flavonoid glycosides
of quercetin (e.g. quercitrin, rutin, isoquercitrin and quercetin 3-arabinoside) and the
corresponding glycosides of kaemperfol have also been detected in leaf tissues (Figure 2).
In addition to these glycosides, escin has been detected (but only in trace amounts), as well
as leucanthocyans, cis,trans-polyprenols, amino acids, fatty acids and sterols (sitosterol,
stigmasterol and campesterol).
442
1
Ground tissue consists of proteoglycans and glucosaminoglycans, including hyaluronic acid.
Cellular components (fibroblasts, macrophages, plasma cells, adipocytes and mast cells) and tissues
(collagen, elastic and reticular fibres) omitted for clarity.
2
Fluid leakage due to capillary permeability and density of surrounding ground substance. Increased
capillary permeability can result in oedema typical of diseases resulting from venous insufficiency.
Flavonoids
As a class of phytochemicals, flavonoids are widely accepted as possessing a range of
biological activities [12] which may be of relevance in the context of topical application of
flavonoid-containing preparations. Some of these activities are listed in Table I.
In the specific case of horse chestnut flavonoids, rutin has been described as possessing
radical scavenging, anti-bacterial and anti-viral activities, and is also used medicinally in
the treatment of varicosis and capillary fragility [13]. Quercitrin and isoquercitrin are also
antibacterial (e.g. against Pseudomonas maltophilia), and the former additionally possesses
anti-haemorrhagic activity [13].
Proanthocyanidin A2 has been demonstrated to possess a range of biological activities,
similar to those of escin, which would be beneficial in cosmetic applications [5, and refs.
Table I. General biological activities of flavonoids
Activity
Reduction of capillary fragility and permeability
Anti-inflammatory
Anti-allergenic
Anti-bacterial
Anti-viral
Enzyme inhibitory
Activities as described in Bruneton (1995) [6]
443
therein]. These activities are primarily venotonic and vasoprotective, such as depermeabilisation of capillaries, but also include wound healing, powerful antioxidant, antiinflammatory, and anti-enzymatic properties. In a similar manner to escin, proanthocyanidin
A2 has been shown to be able to inhibit lipid peroxidation, which is indicative of cellularprotective effects of this compound. Similarly, proteolytic enzymes in the extravascular
matrix are inhibited by proanthocyanidin A2, with -glucuronidase, elastase and collagenase all being more strongly inhibited than hyaluronidase. Compounds such as proanthocyanidin A2 may well be at least partly responsible for the differences between the
venotonic effects of escin (which inhibits hyaluronidase [11]), and the more powerful
effects of crude A. hippocastanum extracts.
444
Table II. Superoxide-anion, hydroxyl radical and singlet oxygen scavenging activities of Aesculus
hippocastanum and antioxidants
IC50 mg (dry material) ml21
Treatment
Superoxide anions
Hydroxyl radicals
Singlet oxygens
Aesculus hippocastanum
L-Ascorbic acid
dl-a-Tocopherol
DMSO
Sodium azide
0.24 6 0.01
4.10 6 0.39
576.20 6 38.70
7.79 6 0.26
3.30 6 0.03
253.70 6 38.70
(2.55 6 0.1) 3 105
72.98 6 6.20
21.18 6 0.39
43.75 6 8.99
445
290
295
300
305
310
315
320
SPFa
0.091
0.079
0.065
0.053
0.045
0.038
0.034
0
0.528
0.569
0.598
0.625
0.651
0.625
0.553
6b
and post-thrombotic syndrome have all been treated using gels containing escin [5, and
refs. therein], suggesting that the topical administration of extracts, as would be the case
in the application of cosmetics, is potentially an equally valid delivery system.
The positive effects of A. hippocastanum extracts on circulation are due to a range of
complex interactions with veins, the lymphatic system, capillaries and connective tissue.
Extracts of A. hippocastanum have been demonstrated to possess venotonic effects in vitro
and in vivo, in both animal and human systems [5, and refs. therein]. For example, A.
hippocastanum extract led to an increase in pressure of flow through both normal and
constricted isolated veins, and an increased effect of noradrenaline on increasing the blood
pressure (and consequently flow) through such vessels [18]. Similarly, capillaries have
been shown to be strengthened by administration of A. hippocastanum extract.
In addition to the direct effects of A. hippocastanum extract on blood vessels, benefit
may also be gained from the protective effects of the extract on connective tissues which
surround the capillary vessels. In chronic venous insufficiency, the capillaries become
highly permeable, resulting in water and proteins leaving the vascular system, which in
turn cause swelling; this may be as a result of the degradation of the extracellular matrix
surrounding the microvasculature (Figure 5). The main component of this extracellular
matrix is hyaluronic acid, a simple glucosaminoglycan consisting of up to several thousand
sugar residues; levels of this compound are usually regulated by the enzyme hyaluronidase,
which promotes the degradation of hyaluronic acid. Recently, escin and its aglycone,
escinol, have been demonstrated to possess non-competitive antihyaluronidase activity
(Table IV), even at concentrations well below that expected as a result of topical
application of these compounds [11].
This inhibition of hyaluronidase should lead to the recovery of the integrity of
hyaluronic acid, and consequently the extracellular matrix surrounding the microvasculature, and may therefore be responsible for some of the beneficial effects of A.
hippocastanum extracts.
446
Triterpene sapogenin
Steroidal sapogenin
c
Obtained from leaf tissues
Modified from Facino et al., 1995 [11].
280.4 6 2.7 mM
300.2 6 3.1 mM
. 5 mM
1.65 6 0.03 mM
. 5 mM
. 5 mM
149.9 6 2.6 mM
Conclusions
In addition to the existing uses of extracts of horse chestnut as treatments for venous
insufficiency, preparations containing phytochemicals from horse chestnut have considerable potential for inclusion in a range of cosmetic formulations. Inclusion of horse chestnut
extracts (especially those from the seeds of the plant, rather than the more poorlycharacterised extracts from leaf and bark tissue) could result in a number of beneficial
actions on the skin after topical administration. Such effects would include potent antioxidative activity, which could help decrease the visible signs of skin ageing, anti-bacterial
and anti-viral properties (largely due to flavonoids), reduction in skin reddening and
cutaneous swelling as a result of effects on capillary vessels and their surrounding connective tissues (due to saponins and the epicatechin dimer proanthocyanidin A2) and also
the potential synergistic enhancement of the efficacy (SPF) of sun screens.
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447
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Note added in proof: Extracts of Aesculus Hippocastanum referred to in Tables II and III were
prepared in 50% ethanol [16] and ethanol [17] respectively.