Nutraceuticals Derived from Lipidcontaining n3 and n6 Polyunsaturated Fatty Acids

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Nutraceuticals Derived from Lipid-containing n-3
and n-6 Polyunsaturated Fatty Acids

• Keith Coupland
• Lipid Research Centre
• The University of Hull

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Disease patterns for Greenland natives compared
to Danes
these are the two most prevalent diseases found
in Eskimo
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Disease management with lipids

• psoriasis and atopic eczema
• hypertriglyceridemia and hypercholesteremia
• cyclical mastalgia
• cancer
• adrenoleukodystrophy and multiple sclerosis
• schizophrenia and alcoholism
• dyslexia
• autism

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Desaturation-elongation Pathways for Synthesis of
PUFA
n-9 n-6 n-3 181 182 183 182 183 18
4 202 203 204 203 204 205 223 2
24 225 245 226 246
??6 desaturase elongase ??5 desaturase elongase
??4 desaturase
??6 desaturase
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Factors which reduce ???- desaturase activity

• dietary factors such as a high intake of
  saturated fat
• excessive alcohol consumption
• stressful lifestyle
• age
• disease conditions eg, atopic eczema, diabetes,
  viral infection and cancer

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Stearidonic Acid (6,9,12,15 -184)
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Where is it Found

• some vegetable oils as a trigylceride - usually
  with ?-linolenic acid (GLA)
• micro-organisms particularly extremophiles -
  Antarctic phytoplankton
• seaweed and shellfish
• most fish oils at low concentrations

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Polyunsaturated Fatty Acids in Fish Oils
Source William E.M.Lands Fish and Human Health
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Stearidonic Acid Content of Plant Seed Oils
1 Crossential SA6 2 Crossential SA 14
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An Overview of the Actions of Stearidonic Acid
Lipids 1988 - 1991

• 1988 J. Brod et al improves dry skin
  condition - moisturisation
• 1989 G. Crozier-Willi inhibits cell
  adhesion - antithrombotic
• 1989 V. Kockmann et al inhibits platelet
  aggregation - antithrombotic
• 1991 D. F. Horrobin et al inhibits phospholipase
  A2 - anti-inflammatory
• 1991 M. Berger et al alters HDL/LDL
  balance - anti-inflammatory

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An Overview of the Actions of Stearidonic Acid
Lipids 1992-1997

• 1992 T. Liang et al inhibits 5
  ?-reductase - treatment for acne, prostate
  cancer
• 1993 M. Guichardant et al inhibits
  5-lipoxygenase - anti-inflammatory
• 1993 R.C. Cantrill inhibits NIH-3T3 tumour
  cell growth - anticancer
• 1996 K. Coupland et al inhibits prostaglandin E2
  synthesis - anti-inflammatory
• 1997 K. Coupland et al inhibits TNF? ?-
  anti-inflammatory

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LTB
4
synthesis is reduced by
Stearidonic acid
)
20,000
Control
10 µmol
20 µmol
15,000
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10,000
5,000
0
LTB4
LTB4 (A isomer)
LTB4 (B isomer)
Guichardant 1993
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Effect of UVB on skin
UVB
skin model
AA release
PGE2 inflammatory response
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Anti-inflammatory properties of lipids
ZK1301 skin model - prostaglandin release
tissue alone
marine oil
borage oil
blackcurrant seed oil
trichodesma oil
echium oil
0
5
10
15
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Prostaglandin E2 release
(pg/g tissue) x 1000
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Tumour necrosis factor alpha (TNF?) release from
irradiated skin treated with lipids
TNFa (pg/tissue)
Not detectable
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Effect of Echium Oil on Skin Rugosity - 28 days
treatment
Before treatment
After treatment
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Topical Application of Echium Oil Creams Reduces
Skin Wrinkling
8.6
30.6
Mean wrinkle depth mm
Days of treatment
Note Ten subjects per group
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Echium Oil a Valuable Source of n-3 / n-6 PUFA

• Some PUFA are essential (EFA) to health
• Defective delta 6 desaturase may render
  gamma-linolenic acid and stearidonic acid
  essential
• Seed oils of some boraginacea contain both GLA
  and SA
• Echium plantageneum seed oil has been
  domesticated to the 700 Ha scale
• Echium seed oil has anti-inflammatory activity in
  both in-vivo and in-vitro models and shows
  anti-aging properties in skin

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Acknowledgements
David Coupland Paul Speight Colin
Douglas Jenny Hutty Ron Stobart Clare
Packer Andrew Fieldsend Julie Nichol Andrew
Hebard John Sargent Clifford Spencer Richard
Hanson
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