Chemistry Reference
In-Depth Information
OH
N
N
H
H
N
N
H
H
MeOOC
MeOOC
OH
OH
MeO
MeO
N
OAc
COOMe
N
OAc
COOMe
H
H
Me
R
A1
Vinblastine (Velban) R
=
CH
3
A3
Vinorelbine (Navelbine)
A2
Vincristine (Oncovin) R
=
CHO
OH
H
N
N
F
F
H
H
N
N
H
H
MeOOC
MeOOC
OH
OH
MeO
MeO
N
OH
CONHR
N
OAc
COOMe
H
H
CH
3
A4
Vindesine (Eldisine) R
Me
A6
Vinflunine
H
=
H
2
N
NH
HN
CO
2
H
HO
2
C
O
O
O
N
N
N
O
S
H
O
S
HO
2
C
H
HO
2
C
H
HO
2
C
N
H
A5
EC145 R
=
O
O
O
O
N
H
NH
N
N
NH
2
Spacer
Folic Acid
Figure 14.1
Structures of natural and synthetic
Catharanthus
alkaloids.
of current
important antineoplastic compounds will be organized by plant
species.
14.1.1 Catharanthus species
Catharanthus alkaloids, particularly vinblastine (
A1
) and vincristine (
A2
), are well
known anticancer drugs, which are used clinically to treat Hodgkin's lymphoma
and acute childhood lymphoblastic leukemia, respectively. These alkaloids inter-
act with tubulin, a protein necessary for cell division, and are inhibitors of mitosis
(the process of cell division).
Originally, these compounds were isolated from
Catharanthus roseus
(L.) G.
Don [formerly known as
Vinca rosea
(Apocynaceae family)], which is used as
folk medicine in Madagascar to inhibit milk secretion and as a hypotensive agent,
astringent, and emetic. Moreover, native people in England and the West Indies
have used this species to lower blood sugar.
