You are on page 1of 17

GERANIUM

NIVEUM (GERANIACEAE)

Geranium niveum S. Watson (Geraniaceae) ,


-
, . ,
"makiki ,

,
.

Giardia lamblia Entamoeba histolytica


G niveum (Calzada et al.,
1998).
CHCl3-MeOH (1:1)

niveum

4.3),

.
CHCl3
EtOAc.
G lamblia
histolytica. , EtOAc
(IC50 6,6 18,7 g / ml E. histolytica G lamblia, ).


,
(Sephadex LH-20) HPLC (Spherisorb S5ODS2)
- ,

--(4 8,
2 7) - (6), --(4 8, 2 7)
(7) Geranins B
( 4.8), (Calzada et al., 1999).


, geranin (6) .
Geranin (6)
C30H24O10

HRFABMS. -

H-,

13

C-

(4.9) COSY NMR .


4.3l

MeOH-CHCl3 (1:1)

geranins (6) (B) G. niveum

6
7
*

IC50
Giardia lamblia
20.6 (20.720.5)
2.4 (2.62.1)
6.0 (7.05.9)
0.21

g/mL (CI)a
Entamoeba histolytica
8.7 (8.98.5)
184.7 (186.1183.4)
13.6 (14.013.0)
0.04

*
,

H-NMR

, (U) (T) 3- . U
AB 4,08 (d, 3,5 Hz, H-3U) 4.26 (H-4U, d, 3.5= Hz).

R1

R2

6a

Me

6b

Me

(S)-MTPA H

6c

Me

(R)-MTPA OH

H
4.8:

(OH)

Geranium niveum (Geraniaceae).


T A2XY 4.08 (d,
=8,0 Hz, H-2 ), 4.17 (ddd, =8,5, 8,0 5.5 Hz, H-3T), 2,93 (dd, =16,5,
5,5 Hz, H-4Ta) 2.58 (dd, =16,5, 8,5 Hz, H-4TB). J (8 Hz)
H-2T H-3T .
,
.
6.10 (H-6T), A2B2 B
- -
, .

4.9:

H (A, 500 MHz)

13

C (B, 125 MHz) NMR

geranin A (6) MeOH-d4.


,

. -,


- , (4 8,
2 7), (4 6, 2 5) (4 6, 2 7).
NOESY , ,
H-4U/H-2T, H-3U H-6U/H-2 , H-6 T (4 8,
2 7) . H-2T/H-3U H-4U ,
COSY 6.


CD

Mosher

4R-
200-220 nm, 4S-
(Barret et al., 1979). CD-
geranin (6)
220 nm ( [ ] =3.26 x 103), C-4U
R. C-2U R.
C-3U C-3T, S-(+)
R-(-)MTPA 6b 6c, ,
6, , , 6 .
R-S R-(+) S-(-)-MTPA 6c 6b
H-2, 6 U [R-S = 0.13] H-3 , 5U [R-S = 0.20]
H-6U [ 0,12]
C-3U R.
H-4Tax [ 0.13]
H-2T [ 0,10] H-2, 6 t [ 0,10]
C-3T .
C-2T ,
H-3T H-2T Geranins (6) (7)
,
, G lamblia histolytica ( 4.3).
, G lamblia .
geranins
(-7 , -29

, A-549 ) 7- MTT
(Calzada et al., 1999).

. ,

.

4.4
ANNONA
Annonaceus

ROLLINIA MUCOSA

PURPUREA
acetogenins

(ANONNACEAE)


Annonaceae.
TP
I NADH
.

, ,

- (Alali et al.,1999
). Annonaceae
, , ,

. ,
(BST), Annonaceous
acetogenins (, 1991), ,
Annonaceae
Los Tuxtlas, ,
Rollinia mucosa (Jacquin) Baillon Annona purpurea . & Sess
Dunal (Annonaceae) .

4.4.1
Rollinia

mucosa

Rollinia

Mucosa

. ,
"anonillo'' ,anonita del monte " "cherimoya",

. , ,
R mucosa
(Alali et al,
1999 ;. Cave et al, 1997
. ).

R mucosa,
, jimenezin (8) ( 4.10),
tryptamine, N-palmi-toyltryptamine (9), N-stearoyltryptamine (9), Narachidoyltryptamine

(9B),

tricosanoyltryptamine (9d),

N-behenoyltryptamine
N-lignoceroyltryptamine

(9c),
(9),

NN-

pentacosanoyltryptamine (9F) N-cerotoyltryptamine (9g), ( 4.11)


(Cavez et al., 1998, 1999).
R. Mucosa CH-Cl3-MeOH
(1:1). ,

(
4.4).

(LC50

0,41

g/ml)

10% H2O MeOH.



( ) LC50 6 10 2 g / ml).

8b

(S)-MTPA

8c

(R)-MTPA

4.10; (8)

14

9d

21

9a

16

9e

22

9b

18

9f

23

9c

20

9g

24

4.11 Rollinia Mucosa

T 4.4

purpurea R. mucosa

A-549

MCF-7c HT-29d A-498e

PC-3f

A. purpurea extract 1.1

<102

1,53

1,47

3,53

1,16

<10-2

R. mucosa extract

>10

>10

1.69

<10-3

<10-3

6,95

<10-7

1,36

[]

0.41

purpurediolin (10) 7.0x10-2 4,43x10-1 9,16x10-1


purpurenin (11)

2.9x10-2 1,29

purpuracenin (12)

3.0

annoglaucin (13)

2.2x10-2

jimenezin (8)

5.47x10-3 1,64x10-2

adriamycin

1,67

3,16x10-1 1,25

4.8x10-2

>10

>10

1,08

1,56

<10-7

>10-1

4,27x10-3

3,53x10-1

PACA-2g

1,44

1,07

1,98

<10-3

<10-3

>10

1,01

3,56x10-1

1,45

4,94x10-2 2,77x10-4 1,69x10-4

4,47x10-3 8,97x10-2 1,62x10-2 1,10x10-3 2,13x10-2 2,88x10-3


14
(F1-F14). HPLC [ , -iPrOH-MeOH, (92:4:5)]
F6 (

LC50 7 10 3 g / ml ) (8) (Chvez et al., 1998). HPLC


F4 (
LC50 41,9 g / ml) 9-9g. , HPLC
F5 F7 (BST LC50 2,2 g
/ ml 4.5 10 1 g / ml, )
(membranacin, desacetyluvaricin, rolliniastatin 1, bullatacin, squamocin,
motrilin)( Chvez et al., 1999).

Jimenezin (8), ,
a (THP).

( Chvez et al., 1998).


C37H66O7 HRFABMS. IR
(3418 1)
(1715 1).
H2O FABMS -TMSi

. jimenezin (8) ,- -
C-4 1 NMR
( 4.12) 7.18 (H-35), 5,06 (H-36), 3.85 (H-4), 2.53 (H3), 2.40 (H-3), 1,43 (H-37) 13C NMR (
4.13)

174,6

(C-1),

151,7

( -35),

131,2 (-35), 78,0 (-36), 70,0 (C-4), 33.3 (C-3) 19.1 (C-37).
H-4 1H NMR
H 3,0-4,0.
3.75 (H-15), 3.90 (H-16) 3,94 (H-19) THF
. 3,00 (H-24), 3.24 (H20) 3,28 (H-23) THP
. COSY NMR H-16/H-15,
H-20/H-19, H-24/H-23, H-23/H-22, H-22/H-21 H-21 / 20,
THP , ,
THF
.

4.12; 1H NMR(500 MHz) (8) CDCl3

4.13; 13C NMR(125 MHz) (8) CDCl3

THF-THP ,

-TMSi 8 ( 4.14).
m / z 455 ( C15/C-16) / z 525 ( C-19/20)
THF C-15 C-19
THP C-20 C-24.

4.17 EIMS TMSi 8

C-15/C-16 threo
C-15 (73,9)
H-15 (3.35) ( et al., 1990). ,
THF
, NMR
. THP
NOESY ( 4.15),
H-20 (3.24) H-24 (3,00).

, - H-23 H-24
NMR ( 4.16). ,
1.42 (H-25)
H-24 ( 9.2 Hz).

-23 H-24 , ,

C-23.


Mosher .
SR ( 4.5) per-(S)- per (R)-MTPA
Mosher

8C

C-15, -23 C- 4 R, R R,
. , C-16, -19, -20 C-24
R, R, S S, . ,
S C-36

Mosher Hoyes

(Hoye et al., 1994). , SR -35


H-36 0,25 0,06, ,

S-4/S-36. C-4 R , C-36


S. 238 nm
CD jimenezin
S C-36.

4.15 NOESY (500 MHz, CDCl3 )


(8) H-20/H-24.


,
(Chvez et al., 1999).

Annonaceae,