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KIMIA ORGANIK BAHAN ALAM
Terpenoid
DEFINITIONS
DEFINITIONS
Myrcene Geraniol
Geranium flower (Geranium L.)
(constituent of bayberry oil) (constituent of geranium oil)
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In nature, terpenoids serve a variety of purposes
including defence, signaling and as key agents in
metabolic processes
2
PURPOSES
&
FUNCTIONS Terpenoids have been used in perfumery,
cosmetics , and medicine for thousands of years
and are still extracted from natural sources for
these uses.
3 Diterpenoids 4 20
Sesterterpenoids 5 25
CLASSIFICATION Triterpenoids 6 30
Tetraterpenoids 8 40
Polyisoprenoids
>8 >40
(Polyterpenoids)
Steroids 6 30
Caretenoids 8 40
4
ISOPRENE RULE
head-to-tail type to produce a monoterpenoids backbone
4
ISOPRENE RULE This link is called a head-to-head or 1-1 link
2. The head of one isoprene molecule could link with the tail
of another isoprene molecule.
4
This link is called a tail-to-tail or 4-4 link
ISOPRENE RULE
head-to-head, tail-to-tail, head-to-tail, by far the commonest
fusion is head-to-tail.
Limonene
Retinol
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β-carotene
4
After formation of the C5n skeleton, the chain may be folded
ISOPRENE RULE to produce rings and functionalized by the introduction of
oxygen or other heteroatom
6
3
TERPENOIDS
IN
NATURE
4
4. Chlorophyll-a is green pigment found, for example, in plant
leaves and is a key factor of photosynthesis through which
atmospheric carbon dioxide is converted to glucose
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Defence Terpenoids as terpenoid chemicals to protect
themselves via production of resins
6
Pheromones
TERPENOIDS
IN
NATURE Semiochemicals
Allelochemicals
TERPENOIDS
IN
NATURE
NATURE
Synomones
6
TERPENOIDS
IN
NATURE d-limonene in the latex exuded by trees of the species
Araucaria bidwilli. These tree are protected from termite
attack because the d-limonene they produce is an alarm
pheromone for termites that live in the area. Similarly,
antifeedants could be considered to be allomones since
the signal generator, the plant, receives the benefit of not
being eaten.
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Myrcene is a kairomones , in that it is produced by the
penderosa pine and its presence attracts the females of
the bark beetle, Dendroctonous brevicomis.
6
TERPENOIDS
IN
NATURE
6
TERPENOIDS
IN The major being the trans, trans-isomer (1.2) and the minor the
trans, cis-isomer (1.3). Neptalactone is the principal component
NATURE of the oil catnip or cat mint (Nepta cataria), constituting 70-90%
of the oil. It is an insect repellent, which is probably why the
plant produces it. However, it has a surprising effect on all
felines, from domestic cats to lions and tigers, in that it induces
grooming and rolling behaviour in them. This is probably purely
coincidental as it is hard to see what benefit this would be to the
plant.
UNIVERSITAS NEGERI SEMARANG
Many commercial uses of terpenoids reflect their natural
uses. Those that are produced in nature because of their
biological activity may well find commercial use as drugs or
pest control agents.