The genus Cinnamomum

108 U.M. Senanayake and R.O.B. Wijesekera
A group of compounds known as cinncassiols have been isolated from cinnamon and
cassia barks (Nohara et al., 1980a, 1980b, 1980c, 1981, 1982, 1985; Yagi et al., 1980).
They are diterpenoids, designated as: Cinncassiol A, Cinncassiol B, Cinncassiol C1,
Cinncassiol C2, Cinncassiol C3, Cinncassiol D1, Cinncassiol D2, Cinncassiol D3,
Cinncassiol D4, Cinncassiol E and their glucosides (Fig. 3A.2). These compounds
exhibit various biological activities. Cinncassiol C1 and D4 and their glucosides exhibit
antiallergic activity. Cinncassiol B and its glucoside show anti-complement activity
(Fig. 2–9).
Gellert and Summons (1970) identified the important alkaloids present in cinnamon
bark as benzylisoqinolines: (1) ()-1-(4-hydroxybenzyl)-6,7-methylenedioxy-1,2,3,4tetrahydroisoquinoline
(norcinnamolaurine); (2) ()-cinnamolaurine; (3) ()-reticuline;
(4) aporphine, and, (5) ()-corydine. Norcinnamolaurine is unique to the cinnamon bark
(Fig. 10–12). The alkaloid’s reticuline and laurolitsine were isolated by Tomita and
Kozuka (1964) from C. camphora. ()-corydine was isolated by Craig and Roy (1965).
Cinnamolaurine and norcinnamolaurine have optical rotations of opposite sign at the
sodium D-line. However, they both possess the same absolute configuration and that
N-methylation of ()-norcinnamolaurine gives (–)-cinnamolaurine. Both belong to the
D-series of benzyl iso-quinoline alkaloids.
19 Me
HO
20
Me
18
HO
2
19
17
M
e OH
12
13
14
H
O
7
8
11
9
10
Cinncassiol A
20
HO
18
HO
1
O
6
5
13
14
M
16
e
11
17
OH
12
10
7
8
6
OH O 5
9
OH
16
Cinnzeylanine 1 R = Ac
Cinnzeylanine 2 R = H
OH
1
OH
4
HO
2
3
15
M
e
OR
1 2
4
3
15
OH
HO OH O OH
HO
3
Cinncassiol B
Figure 3A.1 Secondary metabolites from cinnamon and cassia barks (see text for explanation).
OH