Bioactive Compounds from Medicinal Plants in Myanmar
141
kinmoonosides A–C (1–3), and the new monoterpenoid 4-O-[(2E)-6-hydroxy2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose (4) were isolated
from a cytotoxic MeOH extract of the fruits of A. concinna, which showed cytotoxic effects against HT-1080 human fibrosarcoma cells [3] (Fig. 2). Kinmoonosides
A–C (1–3) have a conserved trisaccharide moiety at C-3 and the same tetrasaccharide at C-28 of the acacic acid moiety, and kinmoonosides A and B (1 and 2)
showed a diastereomeric relationship at C-6
. On the other hand, kinmoonoside C
(3) displayed structural differences compared with 1 and 2 at C-6
, since compound
3 lacks a quinovopyranosyl-monoterpenyl moiety. At present, only kinmoonosides
A–C (1–3) have been reported from A. concinna in Myanmar, suggesting that these
compounds may be utilized as chemical markers for this plant source.
In addition to these naturally occurring compounds, four monoterpenoids
(5–8) (menthiafolic acid (5) [4], a 1:1 mixture of (6S)- and (6R)-menthiafolic
acid 6-O-β-d-quinovopyranoside (6) [4], a 2:1 mixture of two diastereomers
of 3-hydroxy-2-(5-methyl-5-vinyltetrahydrofuran-2-yl) propanoic acid (7) [5],
a 1:1 mixture of (6S)- and (6R)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7octadienoic acid 6-O-β-d-quinovopyranoside (8)) (Fig. 3), five prosapogenins (9–13)
(acacic acid 3-O-α-l-arabinopyranosyl (1→6)-[β-d-glucopyranosyl(1→2)]-β-dglucopyranoside (9), acacic acid 3-O-α-l-arabinopyranosyl(1→6)-2-acetamido-2deoxy-β-d-glucopyranoside (10) [3], acacic acid 3-O-β-d-xylopyranosyl(1→2)-αl-fucopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranoside
(11)
[6], acacic acid 3-O-β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→6)-2acetamido-2-deoxy-β-d-glucopyranoside
xylo-pyranosyl(1→2)-α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]β-d-glucopyranoside (13, concinnoside F = albiziasaponin C) [4, 8])), and an acacic
acid lactone (14) [9] (Fig. 4) were obtained from the crude saponin fraction of A.
Fig. 3 Structures of
monoterpenoids 5–8
obtained from the crude
saponin fraction of A.
concinna by alkaline and
acid hydrolysis
COOH
O
6 ((6S)- and (6R)-menthiafolic acid
6-O-β-D-quinovopyranoside)
O
HOH 2 C
COOH
7 (3-hydroxy-2-(5-methyl-5-vinyltetrahydrofuran-2-yl)propanoic
acid)
HOH 2 C
COOH
O
Qui
8 ((2E)-6-hydroxy-2-hydroxymethyl6-methyl-2,7-octadienoic acid
6-O-β-D-quinovopyranoside)
Qui
O
OH
OH
OH
OH
Qui =
OH
COOH
5 (menthiafolic acid)
141
kinmoonosides A–C (1–3), and the new monoterpenoid 4-O-[(2E)-6-hydroxy2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose (4) were isolated
from a cytotoxic MeOH extract of the fruits of A. concinna, which showed cytotoxic effects against HT-1080 human fibrosarcoma cells [3] (Fig. 2). Kinmoonosides
A–C (1–3) have a conserved trisaccharide moiety at C-3 and the same tetrasaccharide at C-28 of the acacic acid moiety, and kinmoonosides A and B (1 and 2)
showed a diastereomeric relationship at C-6
. On the other hand, kinmoonoside C
(3) displayed structural differences compared with 1 and 2 at C-6
, since compound
3 lacks a quinovopyranosyl-monoterpenyl moiety. At present, only kinmoonosides
A–C (1–3) have been reported from A. concinna in Myanmar, suggesting that these
compounds may be utilized as chemical markers for this plant source.
In addition to these naturally occurring compounds, four monoterpenoids
(5–8) (menthiafolic acid (5) [4], a 1:1 mixture of (6S)- and (6R)-menthiafolic
acid 6-O-β-d-quinovopyranoside (6) [4], a 2:1 mixture of two diastereomers
of 3-hydroxy-2-(5-methyl-5-vinyltetrahydrofuran-2-yl) propanoic acid (7) [5],
a 1:1 mixture of (6S)- and (6R)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7octadienoic acid 6-O-β-d-quinovopyranoside (8)) (Fig. 3), five prosapogenins (9–13)
(acacic acid 3-O-α-l-arabinopyranosyl (1→6)-[β-d-glucopyranosyl(1→2)]-β-dglucopyranoside (9), acacic acid 3-O-α-l-arabinopyranosyl(1→6)-2-acetamido-2deoxy-β-d-glucopyranoside (10) [3], acacic acid 3-O-β-d-xylopyranosyl(1→2)-αl-fucopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranoside
(11)
[6], acacic acid 3-O-β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→6)-2acetamido-2-deoxy-β-d-glucopyranoside
xylo-pyranosyl(1→2)-α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]β-d-glucopyranoside (13, concinnoside F = albiziasaponin C) [4, 8])), and an acacic
acid lactone (14) [9] (Fig. 4) were obtained from the crude saponin fraction of A.
Fig. 3 Structures of
monoterpenoids 5–8
obtained from the crude
saponin fraction of A.
concinna by alkaline and
acid hydrolysis
COOH
O
6 ((6S)- and (6R)-menthiafolic acid
6-O-β-D-quinovopyranoside)
O
HOH 2 C
COOH
7 (3-hydroxy-2-(5-methyl-5-vinyltetrahydrofuran-2-yl)propanoic
acid)
HOH 2 C
COOH
O
Qui
8 ((2E)-6-hydroxy-2-hydroxymethyl6-methyl-2,7-octadienoic acid
6-O-β-D-quinovopyranoside)
Qui
O
OH
OH
OH
OH
Qui =
OH
COOH
5 (menthiafolic acid)