第十八章 萜类和甾族化合物
Terpenes and Steroids
18.1 萜类
Terpenes
It has been known for centuries that
codistillation of many plant materials
with steam (called steam distillation)
produces a fragrant mixture of liquids
known as plant essential oils.
These compounds have had a
variety of uses,particularly in early
medicine and in the making of
perfumes.
Chemically,the essential oils of plants
consist largely of mixtures of lipids called
terpenes.
Terpenes are small organic molecules
that have an immense diversity of
structure,Thousands of different terpenes
are known; some are hydrocarbons,and
others contain oxygen; some are open-
chain molecules,and others contain rings.
Some terpenes isolated from essential oils
M y r c e n e ( o i l o f b a y )
- P i n e n e ( o i l o f t u r p e n t i n e )
O
C a r v o n e ( o i l o f s p e a r m i n t )
月 桂 烯
- 蒎 烯香 芹 酮
According to the isoprene rule proposed by
Ruzicka,terpenes can be considered to arise
from head-to-tail joining of simple five-carbon
isoprene units.
C H
2
C C H
C H
3
C H
2
1
2 3 4
I s o p r e n e
2 - M e t h y l - 1,3 - b u t a d i e n e
H e a d
T a i l
T a i l
H e a d M y r c e n e
T a i l
H e a d
- P i n e n e
Classification of Terpenes
Carbon atoms Isoprene units Classification
10 2 Monoterpenes
15 3 Sesquiterpenes
20 4 Diterpenes
25 5 Sesterterpenes
30 6 Triterpenes
40 8 Tetraterpenes
- P i n e n e C a m p h e n e L i m o n e n e
莰 烯 苧 烯? - 蒎 烯
- C a r y o p h y l l e n e
- 石 竹 烯
O H
C H
2
O H
C H
2
O H
C H
2
O H
L i n a l o o l N e r o l G e r a n i o l C i t r o n e l l o l
芳 樟 醇 橙 花 醇 香 叶 醇 香 茅 醇
O H
H O C H
2
M y c r e n o l L a v a n d u l o l
月 桂 烯 醇 薰 衣 草 醇
C H O
C H O
柠 檬 醛 a 柠 檬 醛 b
C i t r a l a C i t r a l b
O H
C a m p h o l ( B o r n e o l )
冰 片 ( 龙 脑 )
O
C a m p h o r
樟 脑
O H
O H
冰 片 异 冰 片
O H
O H O O
- 萜 品 醇 薄 荷 醇 薄 荷 酮 胡 薄 荷 酮
- T e r p i n e o l M e n t h o l M e n t h o n e P u l e g o n e
O
- I o n o n e? - 紫 罗 兰 酮
O
- I r o n e? - 鸢 尾 酮
C H
2
O H
- C a r o t e n e? - 胡 萝 卜 素
V i t a m i n e A
18.2 甾族化合物
Steroids
The lipid fractions obtained from plants
and animals contain another important
group of compounds known as steroids.
Steroids are derivatives of the following
perhydrocyclopentanophenanthrene ring
system.
The four rings are designated A,B,C,
and D,beginning at the lower left,and the
carbon atoms are numbered beginning in
the A ring.
H
3
C
H
3
C
R
A B
C D
1
2
3
4
5
6
7
8
9
1 0
1 1
1 2
1 3
1 4
1 5
1 6
1 7
A s t e r o i d
C H
3
C H
3
R
C H
3
C H
3
R
5? S e r i e s o f s t e r o i d s
( a l l r i n g j u n c t i o n s a r e t r a n s )
5? S e r i e s o f s t e r o i d s
( A,B r i n g j u n c t i o n i s c i s )
12
3 4
5
Cholesterol
H
3
C
H
3
C
H O
H
H
H
H
C H
3
H
H
5 - C h o l e s t e n - 3 -? - o l
Ergosterol and Vitamine D2
H
3
C
H
3
C
H O
H
H
H
H
C H
3
H
H
C H
3
h v
H
3
C
H O
H
H
H
C H
3
H
H
C H
3
V i t a m i n e D
2
E r g o s t e r o l
Sex Hormones
The sex hormones can be classified into
three groups:
The female sex hormones,or estrogens
The male sex hormones,or androgens
The pregnancy hormones,or
progestins
Female sex hormones H
3
C O
H O
H
H
H
H
3
C O H
H O
H
H
H
E s t r o n e E s t r a d i o l雌 酮 雌 二 醇
4 tones of sow ovaries
12 mg estradiol
Male sex hormones
H
3
C
H
3
C
H O
H
H
H
H
O
H
3
C
H
3
C
O
H
H
H
O H
A n d r o s t e r o n e T e s t o s t e r o n e雄 性 酮 睾 丸 素
Pregnancy hormone
H
3
C
H
3
C
O
H
H
H
C
C H
3
O
P r o g e s t e r o n e
黄 体 酮
Synthetic sex hormones
H
3
C
H
3
C
O
H
H
H
O H
C C H
H
3
C O H
H O
H
H
H
C C H
N o r e t h i n d r o n e 妊 娠 素 E t h y n y l e s t r a d i o l 炔 雌 醇
Adrenocortical Hormones
H
3
C
H
3
C
O
H
H
H
C
O H
C H
2
O H
O
O
H
3
C
H
3
C
O
H
H
H
C
O H
C H
2
O H
O
H O
C o r t i s o n e C o r t i s o l 氢 化 可 的 松可 的 松