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FAIR-CT96-1781
Terpenes as Natural Chiral Starting Materials For the Synthesis of Flavours, Fragrances, Pharmaceuticals and Biocontrol Agents
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Contacts
Further Information
To find similar Items, click on a keyword below:
FAIR Area 1.2 - Green Chemicals and Polymers Chain
:
Fine Chemicals
:
Flavours/Fragrances
:
Integrated Crop Protection & Biological Control
:
Pharmaceuticals/Cosmetics
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Type of Project |
Shared Cost |
| Contract No |
FAIR-CT96-1781 |
| Total Cost |
2,085,207 ECU |
| EC Contribution |
1,700,000 ECU |
| Start Date |
01/12/1996 |
| Duration |
48 Months |
Terpenes as natural chiral starting materials for the synthesis of flavours,
fragrances, pharmaceuticals and biocontrol agents
Objectives
Technical Approach
Research on abundantly available natural terpenes; agriculturally produced, collected from nature or
isolated from industrial waste streams.
- The screening of agro-industrial crop plants and agro-industrial waste products for abundantly
available terpenes that can serve as starting material for the production of useful compounds for flavours,
fragrances, pharmaceutical intermediates and biocontrol agents.
- The investigation of useful, industrial applicable, isolation methods for selected natural products.
- Target oriented synthesis of industrially important compounds from terpenes.
- Explorative research towards the utility of abundantly available chiral natural terpenes as starting
material for the synthesis of chiral intermediates and other useful compounds.
- The investigation of the biosynthesis of terpenes and the possibility for their biotechnological
production.
- Phytochemical research towards new bioactive terpenes.
- Publication of the results of this research in international well known chemical journals, which will
focus the attention to these chiral terpenes and thus stimulate their use and application.
- The type of research will be explorative, innovative and pre-competitive.
Expected Results
I. Direct Results
This project will contribute and extend these possibilities of industrial use of sesqui- and di-terpenes
significantly because it is focuses on:
- The development of industrially feasible isolation procedures for higher terpenes from their natural
biological matrices.
- Target oriented synthesis towards industrially important products starting from terpenes.
- Explorative synthesis starting from terpenes, aiming at other chiral intermediates and products.
- The investigation of natural sources by phytochemical methods to discover new terpenes with
interesting biological activities.
II. Indirect Results
- Agricultural producers, industrial producers of (collected) natural products, academic researchers
from several EU countries and potential industrial users of the isolated or produced natural products will
co-operate closely together in a joint project.
- The "green" agricultural product is a renewable source of starting material for the production of
useful products for the industry (flavours, fragrances, pharmaceuticals and biocontrol agents such as
pheromones).
- The academic research laboratories involved all possess extensive specialist know-how on isolation,
synthetic conversion and physiological activities of terpenoid natural products. This know-how will be
mobilised for the cooperating industries.
The terpenes that will be investigated as chiral starting material are carvone, aromadendrane, guaiol,
santonine, lactaranes, uvidins, labdanolic acid and related labdanes, ingenol and taxanes, and eventually
other terpenes when they will be discovered during the project. The sesquiterpenes that will be
investigated belong to the classes of the germacranes, the eudesmanes, the guaianes, the lactaranes, the
drimanes, and the aromadendranes; the diterpenes that will be investigated are members of the classes of
the labdanes, clerodanes, ingenanes and taxanes.
Applications
New products will be developed for the pharmaceutical industry and for the flavour and fragrance
industries. New opportunities for agricultural production of specialised crops will be developed.
Valorisation of waste products may be expected.
Results To Date
- Isolation and conversion of aromadendrene, alpha-santonin, labdanes, taxanes, isovelleral and
drimanes.
- Aromadendrene, obtained from the leaves of Eucalyptus globulus has been converted into
good flavouring compounds and into the colouring substance guaiazulene, a good industrially applicable
procedure for these transformations is not yet available.
- The synthesis of two furanoeudesmanes starting from alpha-santonin has been achieved. Both these
compounds show ichtiotoxicity towards a killi-fish Orizias latipes and the 15-acetoxyderivative
shows cytotoxicity against B-16 melanoma cells in vitro.
- Novel derivatives and analogues from chamazulene and alpha-santonin with diverse lipophilicity
have been prepared and biological activity was tested.
- Labdanolic acid has been isolated from the acidic fraction of the gum of the easily to collect species
of Cistus ladaniferus. The conversion of labdanolic acid and larixyl acetate into Ambrox€
and its derivatives is investigated.
- Large amounts (approximately 50 kg) of Lactarius vellereus, were collected and extracted,
from which the sesquiterpene isovelleral was isolated and used for chemical investigations.
- The fruiting bodies of few species of Lactarius, e.g. L. uvidus and L. luridus,
contain a large amount of drimane sesquiterpenes: drimenol, uvidins A and B and the corresponding
fatty acid esters, which can be extracted and isolated in good yield. Both drimenol and uvidin A have
already been used for the semisynthesis of biologically active compounds like cinnamodial,
cinnamosmolide and pereniporin A.
- The fruit bodies of Russula delica have been investigated and this has yielded many new
sesquiterpenes, the major component found in intact fruit bodies is stearoyldelicone.
- Compositae
of agricultural relevance, such as Artemisia nitida Bertol., were
investigated with respect to the content of sesquiterpene lactones, this species is endemic to the
Northern Apennines and is used for the production of liqueurs.
- To make maximum use of compounds from cultivated aromatic plants, the potential of discarded
distillation wastes was evaluated for the production of antioxidants and antifeedant diterpenoids.
- Two related species, Achillea erba-rotta All. and A. moschata Wulf, grow in the
Western Alps and are employed in the production of bitter liqueurs. Very little was known about their
constituents, besides highly methoxylated
flavonoids, a series of related sesquiterpene lactones was isolated and identified.
- Crude taxine B, isolated from dried needles of the Taxus baccata, contains two
compounds that miss the 1-hydroxy functionality present in Paclitaxel (Taxol€), and these compounds
were chosen as starting compounds to synthesise new analogues.
- Due to the low availability of the starting compound that is present in only 2%, quick new analytical
methods were developed to screen Taxus cultivars for their taxine content, in order to find
cultivars that can provide better starting material.
- Isolation and characterisation of new compounds from the fruiting bodies of inedible European
mushrooms Lactarius violascens (Otto) Fr. and L. rubrocinctus Fr. afforded two new
protoilludane and four new marasmane sesquiterpenes
- A three-step isolation procedure to obtain ingenol from the seeds of Euphorbia lathyris L.,
an agricultural commodity, was developed. An investigation for new sources of ingenol on spurges
endemic to Europe was started, looking for species lacking cocarcinogenic compounds
Bitterprinciples from chicory roots
Use of terpenes in biological control products
Taxus spp.
Contacts
Coordinator
EC Scientific Officer
Participant
