Saponins and primary research within agriculture

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Erik Todd
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1 Saponins and primary research within agriculture Dave Preskett

2 Fruits of Common ivy (Hedera helix L.) - a biorefinery in action

3 Introduction 1. Principal fractions 2. Extraction equipment 3. Triterpenes 3.1 Applications 4. Summary 5. Discussion

4 4 principal fractions: Ivy fruits

5 4 principal fractions: Triterpenoid saponins having a single core aglycone present at ca. 15 % DM;

6 4 principal fractions: Triterpenoid saponins having a single core aglycone present at ca. 15 % DM; Triacylglycerols at ca. 35 % DM;

7 4 principal fractions: Triterpenoid saponins mostly having a single core aglycone present at ca. 15% DM; Triacylglycerols at ca. 30% DM; Protein at ca. 20% DM (uncharacterised);

8 4 principal fractions: Triterpenoid saponins having a single core aglycone present at ca. 15% DM; Triacylglycerols (fatty acids) at ca. 30% DM; Protein at ca. 20% DM (uncharacterised); Residual fraction at ca. 25% (uncharacterised, thought to contain sugars and minor bioactive components).

9 Kiln drying Extraction equipment

10 Kiln drying Hammermilling Extraction equipment

11 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels

12 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels 20L rotary evaporator

13 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels 20L rotary evaporator Accelerated solvent extraction 1,500 psi (11Bar) Ambient to 200 ºC

14 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels 20L rotary evaporator Accelerated solvent extraction 1,500 psi (11Bar) Ambient to 200 ºC CO 2 pilot scale extraction

$extraction 1,500 psi (11Bar) Ambient to 200 ºC CO 2 pilot scale extraction Wet fractionation Clarifier Decanter Cone mill$

15 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels 20L rotary evaporator Accelerated solvent extraction 1,500 psi (11Bar) Ambient to 200 ºC CO 2 pilot scale extraction Wet fractionation Clarifier Decanter Cone mill Reaction tanks

$solvent extraction 1,500 psi (11Bar) Ambient to 200 ºC CO 2 pilot scale extraction Wet fractionation$

16 Extraction equipment Kiln drying Hammermilling Two 50L extraction vessels 20L rotary evaporator Accelerated solvent extraction 1,500 psi (11Bar) Ambient to 200 ºC CO 2 pilot scale extraction Wet fractionation Ultrafiltration

17 Triterpenes

18 Triterpenes 15% DM OH O O OH HO HO Oleanolic acid, 10% Hederagenin, 90% HO Fruit monodesmosides (NB this is α- hederin, found in the leaf)

19 Triterpenes 15% DM 1 H-NMR of refined saponins

20 Triterpenes 15% DM 1 H-NMR of refined saponins

21 Triterpenes 15% DM 13 C-NMR of refined saponins

22 Triterpenes 15% DM C=O 13 C-NMR of refined saponins

23 Triterpenes 15% DM OH O O HO OH Oleanolic acid, 10% HO HO Hederagenin, 90% 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin

24 Triterpenes 15% DM Nature makes her molecules very efficiently OH O O HO OH Oleanolic acid, 10% HO HO Hederagenin, 90% 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin

25 Triterpenes 15% DM Example applications: Human health Cellulite Athlete's foot Candida albicans Dandruff Leishmaniasis Acanthamoeba

26 Triterpenes 15% DM Example applications: Human health Cellulite Athlete's foot Candida albicans Dandruff Leishmaniasis Acanthamoeba Plant protection Slugs efficacy at 0.01% Late potato blight efficacy at 0.01% Fungistatic activity on wood decay fungi (Heterobasidion annosum )

27 Fungicidal activity efficacy in field trials (0.08 ha) Phytophthora infestans

28 Fungicidal activity efficacy in field trials (0.08 ha) Phytophthora infestans

29 Fungicidal activity efficacy in field trials (0.08 ha)

30 Molluscicidal activity Limax maximus Arion rufus Arion ater

31 Molluscicidal activity Test arena layout

32 Molluscicidal activity Test arena results

33 Molluscicidal activity Effects of crude saponins and fruit base hydrolysis product on slug health

34 Summary Ivy fruits Four principal product streams Two well characterised, IP in place Exploitation routes in collaborative projects Cosmetics, biopesticides, animal/human health More applications being pursued within Beacon Work at multi-kg scale proven in Bangor Challenges Characterise remaining products Harvesting methodology, crop potential, i.d. cultivars

35 Not a biorefinery!!! Thanks for listening

Hedera helix folium. Efeublätter Ivy leaves

Hedera helix folium. Efeublätter Ivy leaves Hedera helix folium Efeublätter Ivy leaves General information Six European species of ivy belong to the genus Hedera in the ginseng family (Araliaceae). Common or English ivy, Hedera helix L. is a climbing,