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Sesquiterpenes. Farnesane 2,6,10-Trimethyldodecane or farnesane, the parent compound of about 10 000 sesquiterpenes known to date.

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Presentation on theme: "Sesquiterpenes. Farnesane 2,6,10-Trimethyldodecane or farnesane, the parent compound of about 10 000 sesquiterpenes known to date."— Presentation transcript:

1 Sesquiterpenes

2 Farnesane 2,6,10-Trimethyldodecane or farnesane, the parent compound of about 10 000 sesquiterpenes known to date.

3 The (E,E)-isomer of  -farnesene is a component of the flavors and natural coatings of apples, pears and other fruits. Associated with (E)-  -farnesene, it also occurs in several ethereal oils, for example those of camomile, citrus, and hops.

4 Chamomile

5 Aldehydes such as  - and  - sinensal derived from  - and  -farnesene contribute to the flavor of the oil of orange expressed from the fresh peel of ripe fruits of Citrus sinensis (Rutaceae); mandarin peel oil from Citrus reticulata and C. aurantium (Rutaceae) contains 0.2% of  -sinensal with the smell of oranges.

6 ( S)-(+)-Nerolidol in the oil of neroli ( زهر البرتقال ) obtained from orange flowers and found in many other flowers is used in perfumery, similar to farnesol from Acacia farnensiana (Mimosaceae) and the oils of bergamot, hibiscus, jasmine and rose, and pleasantly smelling blossoms such as lily of the valley.

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8 Actinodaphne longifolia

9 السنط Acacia farnensiana

10 Lily of the valley المضعف او زنبق الوادي

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12 Monocyclic Farnesane Sesquiterpenes

13 Cyclofarnesanes and Bisabolanes Cyclofarnesanes formally arise when carbon atoms C-6 and C-7 of farnesane close a ring. Abscisic acid, occurring in the leaves of cabbage, potatoes, roses, and young fruits of cotton. Abscisic acid acts as an antagonist of plant growth hormones and controls flowering, falling of fruits and shedding of leaves.

14 (+)-dihydroxy-  -ionylidene acetic acid are produced by the fungus Cercospora cruenta which is antibacterially active

15 Formally, C-1 and C-6 of farnesane close a cyclohexane ring in the bisabolanes, which represent a more prominent class of monocyclic sesquiterpenes. Additional cyclizations increase the diversity. More than 100 bisabolane derivatives of plant origin are known to date Oil of ginger obtained from the rhizome of Zingiber officinalis (Zingiberaceae) consists predominantly of (-)-zingiberene (20- 40%),  -sesquiphellandrene and (+)-  bisabolene

16 Ginger rhizome

17  -bisabolene also occurs in Chamaecyparis nootkatensis (Cupressaceae) and in the Sibirian pine tree Pinus sibirica (Pinaceae)

18 (+)-  - and (+)-  -bisabolol are fragrant sesquiterpenes found in the essential oils of various plants; they also contribute to the odors of camomile and of bergamot oil from unripe fruits of Citrus aurantium var. bergamia (Rutaceae) growing in southern Italy.

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20 Schisandra chinensis

21 Germacranes and Elemanes Germacranes formally result from ring closure of C-1 and C-10 of farnesane. 1(10),4-Germacradienes such as 1(10),4-germacradien-6-ol present as a glycoside in Pittosporum tobira may ungergo COPE rearrangements to elemadienes, exemplified by shyobunol from the oils of galbanum and kalmus, so that some isolated elemane derivatives are supposed to be artifacts arising from germacranes.

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23 Pittosporum tobira

24 galbanum

25 kalmus

26 About 50 elemanes known to date comprise  -elemenone from the oil of myrrh, representing the COPE rearrangement product of germacrone, (-)-bicycloelemene from peppermint oils of various provenance (e.g. Mentha piperita or Mentha arvensis), and  -elemol which is not only a minor component of Javanese( ( من جزيرة جاوة oil of citronella but is also found in the elemi oil with an odor like pepper and lemon, expressed from the Manila elemi resin of the tree Canarum luzonicum (Burseraceae).

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28 Humulanes Ring closure of C-1 and C-11 of farnesane, not only formally but also in biogenesis via farnesyldiphosphate, produces the sesquiterpene skeleton of more than 30 naturally occurring humulanes. Regioisomeric  - and  -humulene occur in the leaves of Lindera strychnifolia (Lauraceae).

29 Lindera strychnifolia

30 tree Canarum luzonicum (Burseraceae).

31 Mentha arvensis نعناع حقلي

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