qu
Hedyotis lindleyana
H
1.1. T n qu n v
NG
T NG QU N
Hedyotis
Chi Hedyotis có khoảng 150 loài, chủ yếu mọc ở những vùng có khí hậu nhiệt
đới và ấm áp. Chúng thường có thân thảo, hơi vuông, cao từ 30-85 cm. Lá nhỏ, phiến
lá hẹp, có gân giữa, gân phụ không nổi rõ. Hoa màu trắng hay vàng, mọc thành từng
cụm ở nách lá hay đỉnh nhánh. Các loài thuộc chi Hedyotis thường mọc ở sân vườn,
bình nguyên Việt Nam, chủ yếu là Hedyotis diffusa Willd, Hedyotis corymbosa (L.)
Lam, Hedyotis nigricans L...[1]
1.1.1 M t t
v t
Hedyotis lindleyana Hook ex H. Arn gọi là
n đi n lindley[2] thuộc chi
Hedyotis, họ Cà phê (Rubiaceae). Cỏ đa niên b , có ít r ở mắt; thân có 4 c nh tr n, có
lông theo 2 hàng. Lá có phiến oan, nhọn hay tà hai đ u, gân phụ 3 c p l i m t dưới,
cu n ngắn, là bẹ nhọn. Chụm dày ở nách, hoa ch 4, vành tai nhọn, ng có lông ở cổ.
ế quả tr n.
Cây mọc phân b rộng r i từ mi n ắc đến Huế, vùng đ ng b ng.
H n 1.1. Hình n đi n Lindley Hedyotis lindleyana Hook ex H. Arn
1
qu
Hedyotis lindleyana
Hedyotis biflora (L.)
Hedyotis corymbosa (L.) Lam
Hedyotis diffusa Willd
Hedyotis caerulea (L.) Hook
Hedyotis centranthoides
Hedyotis coriacea Sm.
Hedyotis crassifolia L.
Hedyotis dichotoma Koen.ex Roth
H n 1.2. Hình ảnh một s loài trong chi Hedyotis
2
qu
Hedyotis lindleyana
1.2. N
n
uv
tn
o dư c tính của cây
n đi n Hedyotis lindleyana Hook ex H. Arn chưa đư c
nghiên c u nên trong ph n này, dư c tính của một s loài trong chi Hedyotis s đư c
trình bày trong Bảng 1.1.
B ng 1.1. Ho t tính sinh học của một s cây thu c thuộc chi Hedyotis
Loà ây Hedyotis
H. auricularia L.[4]
D
tn
Thanh nhiệt, giải độc, làm
giảm đau, …
Ứn
ụn (đ u trị)
Cảm m o, phát s t, đau họng,
viêm ruột, viêm mủ da, mụn nhọt,
rắn rết cắn, ...
H. biflora (L.) Lam.[4],[17] Vị đắng, tính mát, thanh
nhiệt, giải độc, ...
Rắn cắn, đau bao tử, …
H. capitellata var. mollis
Pierre e Pit.[3]
Vị ngọt, thanh nhiệt, giải
độc, tiêu viêm, ...
Lở loét miệng lưỡi, loét d dày, tá
tràng, viêm họng, vết thương
nhanh lên da non, ...
H. corymbosa (L.)
Lam[5],[8]
Thanh nhiệt, tiêu viêm, l i
tiểu, tiêu sưng, ...
Rắn cắn, sởi, s t, th n kinh suy
như c, bệnh gan, giun, viêm phế
quản, đau nh c ương c t, thấp
khớp, mụn nhọt, ...
H. diffusa Willd[20],[21],[22] Kháng sinh, kháng ung
thư, kháng protease HIV-1
Viêm đường tiểu, đường ruột, d
dày, tá tràng, s t, sởi, thủy đậu, sỏi
thận, ung thư (gan, cổ tử cung,
phổi), …
H. hedyotidea ( C)
Hand. Marr.[4]
Kháng ung thư
Cảm l nh, viêm nhi m, …
H. herbacea L.[4]
Thanh nhiệt, tiêu viêm, …
Viêm ruột thừa, viêm gan, rắn cắn,
amidal, s t, s t rét, tê thấp, hen
suy n, lao phổi, …
H. heynii R. r.[11]
Thanh nhiệt, giải độc, …
Viêm gan, viêm đường tiết niệu,
rắn độc cắn, ung thư, ban, trái,
mẩn ng a, …
H. pinifolia Wall ex G.
Don.[6]
Tiêu sưng, giảm đau, …
Đau nh c, tổn thương da, …
H. scandens Roxb.[6]
Giảm đau, kháng viêm, …
Đau mắt, bong gân, r i lo n sau
khi sinh con, viêm khí quản, viêm
phổi, phổi kết h ch, viêm oang
miệng, …
3
qu
Hedyotis lindleyana
1.3. N
n
uv
tr n m t s
ây t u
Hedyotis
Tương tự, cho đến nay, hiện chưa có nghiên c u nào v thành ph n hóa học của
cây
n đi n Hedyotis lindleyana Hook ex H. Arn. Chính vì thế, thành ph n hóa học
của một s loài trong chi Hedyotis s đư c trình bày trong ảng 1.2. vì các loài cùng
chi thì có cùng đ c tính Hóa thực vật.
n 1.2. Thành ph n hóa học một s cây Hedyotis đ đư c công b .
Loà ây Hedyotis
H.
acutangula
[4]
Champ. e
enth.
H. affinni.[4]
H.
T àn p ần
Stigmasterol ( ), β-sitosterol (4), ursolic acid ( 4), oleanolic acid
(24), olean-12-en-3,28,29-triol (25), tara erol (40).
Serotonin ( 04).
auricularia
L.[3],[23]
, 4, Stigmasterol 3-O-β- -glucopyranoside (6), ( 4), (25),
naringenin (65), 3,7,2’,4’-tetrametho y-5-hydro yflavone (69),
auricularin ( 0), ethyl 1-O-β- -galactopyranoside ( 3), 6’-O1’-
(1-hydroxymethyl-2-hydroxy-1-methoxy)ethyl
desoxyglucopyranoside (116), 2-formyl-5-hydro ymethylfuran
( 23).
H. biflora (L.) Lam[7]
Stigmast-3,5,6-triol
glucopyranoside
(5),
(3),
(6),
(4),
-sitosterol
γ-sitosterol
(9),
3-O-- ( 4),
(24),
sumaresinolic acid (27), spergulacin (41), 1,5,6-trimethoxy-2hydroxyantraquinone (53), philonotisflavone 7-O-[4’’’’-O-β- galactopyranosyl]-β- -glucopyranoside (64), quercetin (68),
rutin (75), protopin (
), 1-ethoxy-2-L-arabinopyranosyl-3-
D-glucopyranosylpropan (118).
H.
capitellata
mollis
Pierre
var.
e
Hedyocapitin ( 05), capitellin ( 06), (–)-isocyclocapitellin ( 07),
(+)-cyclocapitellin ( 08), isochrisotricin ( 09).
Pit.[24]
H.
Asperulosidic acid (79), asperuloside (81), deacetylasperuloside
chrysotricha.[25],[26],[27]
(82), deacetylasperulosidic acid (85), asperulosidic acid ethyl
ester (87), acetylscandosic acid methyl ester (88), scandosic acid
methyl ester (89), hedyoside (99), 6’-acetylasperuloside (100),
4
qu
Hedyotis lindleyana
6’-acetyldeacetylasperuloside (101).
H. corymbosa (L.)
[6],[28],[29]
Lam.
(1), (9), (14), (24), (79), 6-Hydroxygeniposide (80), (81), (82),
10-O-benzoylasperulosidic
acid
methyl
ester
(84),
(85),
geniposide 86), (89), 10-O-benzoylscandosic acid methyl ester
(90), 10-O-p-hydroxybenzoylscandosic acid methyl ester (94),
10-O-p-coumaroylscandosic acid methyl ester (95).
H.
crassifolia
.
[9]
C.
(5),
3,13β- ihydro yurs-11-en-28-oic
acid
( 7),
3β-
hydro yurs-11-en-28(13)-lactone (20) and (27).
H. dichotoma Koen.
(22E)-5-Stigmasta-7,22-dien-3β-ol
(2),
(22E)-5α-stigmasta-
E Roth.[10],[30]
7,22-dien-3-O-β- -glucopyranoside
7,
(22E)-5α-poriferasta-
7,22-dien-3-O-β- -glucopyranoside
3-O-[-L-
(8),
rhamnopyranosyl-(1→4)-- -glucopyranosyl-(1→3)--Larabinopyranosyl]-30-norolean-12,20(29)-dien-28-oic acid (38),
1,4-dihydro y-2,3-dimetho yanthraquinone (47), 9-hydro y-2,3dimetho y-1,4-anthraquinone
benzoquinone (56),
(55),
2,5-dimetho y-1,4-
-(+)-pinitol ( 5), (6R,9S)-roseoside ( 9),
4-hydro y-3-metho ybenzoic acid ( 27).
( ),
H. diffusa Willd.[4]
(4),
(5),
(9),
methylanthraquinone
( 4),
(24),
(45),
metho yanthraquinone
2,3- imetho y-6-
3-hydro y-2-methyl-1-
(46),
kaempferol
3-O-[β- -
galactopyranosyl-(1→6)-β- -glucopyranoside] (74), quercetin 3O-[β- -galactopyranosyl-(1→6)-β- -glucopyranoside]
(76),
quercetin 3-O-[(6-O-E-feruloyl)-β- -glucopyranosyl-(1→6)]-β-glucopyranoside 77, quercetin 3-O-[(6-O-E-feruloyl)-β- galactopyranosyl-(1→6)]-β- -glucopyranoside (78), (82), 6-O-pcoumaroylscandosic
acid
methyl
ester
(9 ),
6-O-(p-
meto ycinamoyl)scandosic acid methyl ester (92), 6-O-Eferuloylscadosic acid methyl ester (93).
H. hedyotidea ( C.)
Hand. Marr.[31]
H. herbacea L.[32]
(79), (80), (8 ), (82), Hedyotoside (98).
α- myrin
( 2),
( 4),
hydro ymethylanthraquinone
(24),
(47),
(48),
1,4-dihydro y-210-hydro y-2-
5
qu
Hedyotis lindleyana
hydro ymethyl-1,4-anthraquinone (54), (55).
H. heynii R. r.[4],[11]
( ), (4), (5), ( 4), (24).
H. lawsoniae Wight
3β,24- ihydro yurs-12-en-28-oic
and Arn.[4],[32]
trihydro yurs-12-en-28-oic acid ( 8), 3β,23-dihydro yurs-12-en-
acid
( 5),
2α,3β,24-
28-oic acid ( 9).
H. lineata Ro b.[12]
(1), (6), 3β-Hydroxyurs-12-en-28-al (13), (14), 3β-acetoxy-19hydroxyurs-12-en-28-oic acid (16), (24), 3,5,6-trimethyl-2-(3hydroxy-3’,7’,11’,14’-tetramethyl)pentadecylbenzoquinone (57),
4-hydroxy-3,5-dimethoxybenzaldehyde (124),
4-hydroxybenzaldehyde (125).
H. merguensis Hook.
( ), (4), (5), (14), 3-O-[-L-rhamnopyranosyl-(1→3)--D-
f.[13]
glucopyranosyl]oleanolic acid (32), 3-O-{[-D-glucopyranosyl(1→2)]-[-D-glucopyranosyl-(1→3)]--Dacid
glucopyranosyl}oleanolic
(33),
3-O-{[-L-
rhamnopyranosyl-(1→2)--D-glucopyranosyl-(1→4)]-[-Dglucopyranosyl-(1→2)]--D-glucopyranosyl}oleanolic acid (34),
-D-glucopyranosyl 3-O--D-glucopyranosyloleanoate (35), D-xylopyranosyl-(1→2)--D-glucopyranosyl
3-O-[-L-
rhamnopyranosyl-(1→3)--D-glucopyranosyl]oleanoate (38).
H.
microcephala
(1), (4), (5), (14), 3-O-β-D-glucopyranosyloleanolic acid (30),
Pierre e Pit.[14]
(31), (123), ethyl 1’-O-β-D-glucopyranoside (114).
H. nigricans L.[4]
( ), ( 2), ( 4), β- myrin (23), (24), primuletin (58), chrysin (59),
luteolin (60), biochanin
H. nudicaulis[33]
- -Glucopyranosyl
(66), arbutin ( 2).
3-O-[- -galactopyranosyl-(1→3)--L-
arabinopyranosyl]oleanoate (35), - -glucopyranosyl 3-O-{[L-rhamnopyranosyl-(1→2)]-[- -glucopyranosyl-(1→3)]--Larabinopyranosyl}oleanoate (36), - -glucopyranosyl 3-O-[- galactopyranosyl-(1→3)--L-arabinopyranosyl]-30-norolean12,20(29)-dien-28-oate (39).
H. pinifolia Wall e
G. on.
[6]
(1), (4), (5), Phytol (10), (14), (24), 2,3,23-trihydroxyolean12-en
(29),
1,6-dihydroxy-7-methoxy-2-methylanthraquinone
6
qu
Hedyotis lindleyana
(49), 3,6-dihydroxy-2-methylanthraquinone (50), 1,6-dihydroxy2-methylanthraquinone
methylanthraquinone
(51),
(52),
1,3,6-trihydroxy-24-O-[3-hydroxy-2-
(dihydroxymethylmethyloxy)]propyl--L-rhamnopyranose
(117).
H. pressa Pierre e .[3]
mentoflavone (63), kaempferol (67), kaempferol 3-O-- glucopyranoside (70).
H.
retrorsa
(4), (5), Hederagenin (26).
oiss.[13],[33]
H.
rudis
Pierre
Pit.[15]
e
(4), (14), 3β-O-Acetylursolic acid (22), 3β-O-acetylbetulinic acid
(42),
(1S,4S,4aR,5R,7aR)-5-ethoxy-1-β-D-glucopyranosyl-4-
hydroxy-7-
hydroxymethyl-1,3,4,4a,5,7a-
hexahydrocyclopenta[c]pyran (102),
(1S,4S,4aR,7aR)-1-β-D-
glucopyranosyl-4-hydroxy-7-hydroxymethyl-1,3,4,4a,5,7ahexahydrocyclopenta[c]pyran
(103),
1-O-ethyl-3,6-di-O-(2-
hydroxy-1-hydroxymethylethyl)--D-glucopyranose (120).
H. symplociformis (Pit.) (1), (4), (5), (14), (17), (24), Kaempferol 3,7-O-di(-LPhamhoang).[16]
rhamnopyranoside) (73), (114), ethyl (19Z,22Z)-heptacosa-19,22dienoate (121), triacontanol (122), vanilin (126).
H.
lume.[17]
tenelliflora (5), Squalene (11), (14), 6-hydroxygeniposide (83), (89),
corosolic acid (21), maslinic acid (28), daphylloside (87),
tenellioside A (96), tenellioside B (97), 6-Omethyldeacetylasperulosidic acid methyl ester (128), 6-Omethylscandosic acid methyl ester (129), 6α-methoxygeniposidic
acid (130), mollugosic acid methyl ester (131).
H.
umbellata lizarin-1-methyl ether (43), 1,2,3-trimetho yanthraquinone (44).
Lamk.[3],[17]
Hedyotis vestita R. Br. Isorhamnetin 3-O-rutinoside (132), vomifoliol 9-O- β-Dex
glucopyranoside (133), 6-methoxygeniposide (134).
G. Don.[20]
7
qu
Hedyotis lindleyana
Cấu trúc những h p chất đ cô lập đư c trong các cây Hedyotis:
21
STEROID
20
12
19
11
5
3
9
6
24
25
16
14
10
29
23
17
13
1
2
28
22
18
26
27
15
8
7
4
1
: Stigmasterol
2
3β-OH; ∆7,22E; 24S
: (22E)-5α-Stigmasta-7,22-dien-3β-ol
3
3β,5α,6β-OH; ∆22E; 24S
: Stigmast-3,5α,6-triol
4
3β-OH; ∆5; 24R
: β-Sitosterol
5
3β-O-Glc; ∆5; 24R
: -Sitosterol 3-O-- -glucopyranoside
6
3β-O-Glc; ∆5,22E; 24S
: Stigmasterol 3-O-β- -glucopyranoside
7
3β-O-Glc; ∆7,22E; 24S
: (22E)-5α-Stigmasta-7,22-dien 3-O-β- -glucopyranoside
8
3β-O-Glc; ∆7,22E; 24R
: (22E)-5α-Poriferasta-7,22-dien 3-O-β- -glucopyranoside
9
DITERPENE
3β-OH; ∆5,22E; 24S
3β-OH; ∆5,22E; 24S
: γ-Sitosterol
3
7
11
15
20
HO
19
18
16
17
1
Phytol
0
27
TRITERPENE
1
3
2
7
6
10
14
30
29
26
25
11
15
18
19
22
23
24
28
Squalene
12
3β-OH; ∆12
: α- myrin
13
3β-OH; 28-CHO; ∆12
: 3β-Hydroxyurs-12-en-28-al
14
3β-OH; 28-COOH; ∆12
: Ursolic acid
8
qu
Hedyotis lindleyana
15
3β,24-OH; 28-COOH; ∆12
: 3β,24- ihydro yurs-12-en-28-oic acid
16
3β-OAc; 19α-OH; 28-COOH; ∆12
: 3β-Acetoxy-19-hydroxyurs-12-en-28-oic acid
17
3β,13β-OH; 28-COOH; ∆11
: 3β,13β- ihydro yurs-11-en-28-oic acid
18
2α,3β,24-OH; 28-COOH; ∆12
: 2α,3β,24-Trihydro yurs-12-en-28-oic acid
19
3β,23-OH; 28-COOH; ∆12
: 3β,23- ihydro yurs-12-en-28-oic acid
11
20
3β-OH; 28→13 lacton; ∆
: 3β-Hydro yurs-11-en-28(13)-lactone
21
2α,3β-OH; 28-COOH; ∆12
: Corosolic acid
22
3β-OAc; 28-COOH; ∆12
: 3β-O-Acetylursolic acid
23
3β-OH; ∆12
: β- myrin
24
3β-OH; 28-COOH; ∆12
: Oleanolic acid
25
3β,28,29-OH; ∆12
: Olean-12-en-3,28,29-triol
26
3β,23-OH; 28-COOH; ∆12
: Hederagenin
27
3β,6β-OH; 28-COOH; ∆12
: Sumaresinolic acid
28
2α,3β-OH; 28-COOH; ∆12
: Maslinic acid
29
2α,3β,23-OH; ∆12
: 2,3,23-Trihydroxyolean-12-ene
30
3β-O-Glc; 28-COOH; ∆12
: 3-O-β-D-Glucopyranosyloleanolic acid
31
3β-O-Rha(1→3)Glc;
: 3-O-[-L-Rhamnopyranosyl-(1→3)-
28-COOH; ∆
32
12
-D-glucopyranosyl]oleanolic acid
3β-O-Glc(1→2)[Glc(1→3)]Glc;
28-COOH; ∆
12
: 3-O-{-D-Glucopyranosyl-(1→2)[-D-glucopyranosyl-(1→3)]--Dglucopyranosyl}oleanolic acid
33
: 3-O-{-L-Rhamnopyranosyl-(1→2)-
3β-O-Rha(1→2)Glc(1→4)[Glc(1→2)]Glc; 28-COOH; ∆
12
-D-glucopyranosyl-(1→4)-[-D-glucopyranosyl(1→2)]--D-glucopyranosyl}oleanolic acid
34
3β-O-Glc; 28-COO-Glc; ∆12
: -D-Glucopyranosyl 3-O--Dglucopyranosyloleanoate
9
qu
Hedyotis lindleyana
3β-O-Gal(1→3) ra;
35
28-COO-Glc; ∆
:
12
28-COO-Glc; ∆
3-O-[- -galactopyranosyl-
(1→3)--L-arabinopyranosyl]oleanoate
: - -Glucopyranosyl 3-O-{-L-rhamnopyranosyl-
3β-O-Rha(1→2)[Glc(1→3)] ra;
36
- -Glucopyranosyl
12
(1→2)-[- -glucopyranosyl-(1→3)]--Larabinopyranosyl}oleanoate
: -D-Xylopyranosyl-(1→2)--D-glucopyranosyl
3β-O-Rha(1→3)Glc;
37
28-COO-Xyl(1→2)Glc; ∆
12
3-O-[-L-rhamnopyranosyl-(1→3)--Dglucopyranosyl]oleanoate
: 3-O-[-L-Rhamnopyranosyl-(1→4)-
3β-O-Rha(1→4)Glc(1→3) ra;
38
28-COOH; 30-nor; ∆
12,20(29)
- -glucopyranosyl-(1→3)--L-arabinopyranosyl]30-norolean-12,20(29)-dien-28-oic acid
: - -Glucopyranosyl 3-O-[- -galactopyranosyl-
3β-O-Gal(1→3) ra;
39
28-COO-Glc; 30-nor; ∆
12,20(29)
(1→3)--L-arabinopyranosyl]-30-norolean-12,20(29)dien-28-oate
3β-OH; 13-Me; 27-nor; ∆14
40
: Tara erol
29
20
30
OH
19
20
12
21
12
1
8
10
25
C
14
16
Rha(13)Glc-O
O
OH
2
3
2'
1'
O
24
4
Spergulacin
11
26
1
4
10
5
9
6
21
22
13
14
O
3
4
19
18
15
17
16
COOH
28
8
7
27
23
42 3β-O-Acetylbetulinic acid
O
QUINONE
8
7
1
12
11
6
9
10
5
2
13
14
3
4
O
43
1-OMe; 2-OH
: lizarin-1-methyl ether
44
1,2,3-OMe
: 1,2,3-Trimetho y-9,10-anthraquinone
45
2,3-OMe; 6-Me
: 2,3- imetho y-6-methyl-9,10-anthraquinone
46
1-OMe; 2-Me; 3-OH
: 3-Hydro y-2-methyl-1-metho y-9,10-anthraquinone
47
1,4-OH; 2,3-OMe
: 1,4- ihydro y-2,3-dimetho y-9,10-anthraquinone
48
1,4-OH; 2-CH2OH
: 1,4- ihydro y-2-hydro ymethyl-9,10-anthraquinone
49
1,6-OH; 2-Me
: 1,6-Dihydroxy-2-methyl-9,10-anthraquinone
50
2-Me; 3,6-OH
: 3,6-Dihydroxy-2-methyl-9,10-anthraquinone
10
qu
Hedyotis lindleyana
51
1,6-OH; 2-Me; 7-OMe
: 1,6-Dihydroxy-7-methoxy-2-methyl-9,10-anthraquinone
52
1,3,6-OH; 2-Me
: 1,3,6-Trihydroxy-2-methyl-9,10-anthraquinone
53
1,5,6-OMe; 2-OH
: 1,5,6-Trimethoxy-2-hydroxy-9,10-anthraquinone
O
5
10
6
11
12
7
4
14
13
8
3
2
1
9
O
54
2-CH2OH; 10-OH
: 10-Hydro y-2-hydro ymethyl-1,4-anthraquinone
55
2,3-OMe; 9-OH
: 9-Hydro y-2,3-dimetho y-1,4-anthraquinone
O
OMe
1
2
5 4
MeO
O
2,5- imetho y-1,4-benzoquinone
56
O
OH
1'
1
6
15'
3'
2
7'
11'
14'
5 4 3
O
3,5,6-Trimethyl-2-(3-hydroxy-3’,7’,11’,14’-tetramethyl)pentadecylbenzoquinone
57
FL VONE
3'
4'
2'
8
O
1
7
1'
6
4
5'
2
6'
3
5
O
58
5-OH
: Primuletin
59
5,7-OH
: Chrysin
60
5,7,3’,4’-OH
: Luteolin
61
5,6,7,8,3’,4’-OMe
: 5,6,7,8,3’,4’-He ametho yflavone
62
5,6,7,3’,5’-OMe; 4’-OH
: 4’-Hydro y-5,6,7,3’,5’-pentametho yflavone
OH
OH
5'
HO
6'
O
Gal(1 4)Glc-O
O
5"
1"
HO
2"
7 8
6 5
OH
63
mentoflavone
OH
OH
O
1'
7
6
8
5
1
4
4'
1 2
3
4
OH
1'
O
OH
4'
OH
3'
2'
2
OH
3
O
HO
O
OH
O
O
64
64 Philonotisflavone 7-O-[4’’’’-O-β- galactopyranosyl]-β- -glucopyranoside
11
qu
Hedyotis lindleyana
OH
FL V NONE
4'
HO
1
5
2
4
OH
O
Naringenin
65
ISOFL VONE
1'
O
7
HO
O
1
7
5
4
3
1'
OH
4'
O
OH
iochanin
66
FL VONOL
3'
4'
2'
8
O
1
7
6
1'
4
5
2
5'
6'
3
OR
O
67
3,5,7,4’-OH
: Kaempferol
68
3,5,7,3’,4’-OH
: Quercetin
69
3,7,2’,4’-OMe; 5-OH
: 3,7,2’,4’-Tetrametho y-5-hydro yflavone
70
3-O-Glc; 5,7,4’-OH
: Kaempferol 3-O-- -glucopyranoside
71
3-O- ra; 5,7,4’-OH
: Kaempferol 3-O--L-arabinopyranoside
72
3-O-Rha(1→6)Glc; 5,7,4’-OH
: Kaempferol 3-O-rutinoside
73
3,7-O-Rha; 5,4’-OH
: Kaempferol 3,7-O-di(-L-rhamnopyranoside)
74
3-O-Gal(1→6)Glc; 5,7,4’-OH
: Kaempferol 3-O-[β- -galactopyranosyl-(1→6)β- -glucopyranoside]
75
3-O-Rha(1→6)Glc; 5,7,3’,4’-OH
: Rutin
76
3-O-Gal(1→6)Glc; 5,7,3’,4’-OH
: Quercetin 3-O-[β- -galactopyranosyl-(1→6)β- -glucopyranoside]
77
3-O-[6-O-E-Fer-Glc(1→6)Glc];
5,7,3’,4’-OH
78
3-O-[6-O-E-Fer-Gal(1→6)Glc];
5,7,3’,4’-OH
: Quercetin 3-O-[(6-O-E-feruloyl)β- -glucopyranosyl-(1→6)]-β- -glucopyranoside
: Quercetin 3-O-[(6-O-E-feruloyl)β- -galactopyranosyl-(1→6)]-β- -glucopyranoside
12
qu
Hedyotis lindleyana
132 Isorhamnetin 3-O-rutinoside
11
IRIDOID
6
H
5
7
9
8
4
1
3
2
O
H
10
O
Glc
79
6α-OH; 10-OAc; 11-COOH
: Asperulosidic acid
80
6α,10-OH; 11-COOEt
: 6-Hydroxygeniposide
81
10-O c; 11→6α lactone
: Asperuloside
82
10-OH; 11→6α lactone
: Deacetylasperuloside
83
6α,10-OH; 11-COOMe
: 6-Hydroxygeniposide
84
6α-OH; 10-OBz; 11-COOMe
: 10-O-Benzoylasperulosidic acid methyl ester
85
6α,10-OH; 11-COOH
: Deacetylasperulosidic acid
86
10-OH; 11-COOH
: Geniposide
87
6α-OH; 10-OAc; 11-COOMe
: Asperulosidic acid ethyl ester
88
6β-OH; 10-OAc; 11-COOMe
: Acetylscandosic acid methyl ester
89
6β,10-OH; 11-COOMe
: Scandosic acid methyl ester
90
6β-OH; 10-OBz; 11-COOMe
: 10-O-Benzoylscandosic acid methyl ester
91
6β-O-p-Cmr; 10-OH; 11-COOMe
: 6-O-p-Coumaroylscandosic acid methyl ester
92
6β-O-p-Mcn; 10-OH; 11-COOMe
: 6-O-(p-Metho ycinnamoyl)scandosic acid
methyl ester
93
6β-O-p-Fer; 10-OH; 11-COOMe
: 6-O-Feruloylscandosic acid methyl ester
94
6β-OH; 10-OCO-C6H4-OH(p); 11-COOMe
: 10-O-p-Hydroxybenzoylscandosic acid
methyl ester
95
6β-OH; 10-O-p-Cmr; 11-COOMe
: 10-O-p-Coumaroylscandosic acid methyl ester
13
qu
Hedyotis lindleyana
O
O
C
O
C
O
H
OMe
O
O
H
Glc
O
AcO
Tenellioside A
96
O
H
O
HO
COOMe
H
OMe
97
Glc
O
HO
Tenellioside B
Glc
Hedyotoside
98
O
O
C
O
O
C
O
COOMe
AcO
OAc
HO
HO
O
O
O
O
O
O
O
HO
OAc
OH
HO
HO
Glc
O
OH
99 Hedyoside
100 6’-Acetylasperuloside
EtO
H
5
6
7
HOH2 C
O
4a
7a
101 6’-Acetyldeacetylasperuloside
OH
4
1
H
5
3
2
6
7
O
H
HOH2C
OGlc
4a
7a
OH
4
1
3
2
O
H
OGlc
102 (1S,4S,4aR,5R,7aR)-5-Ethoxy-1-β-D-
103 (1S,4S,4aR,7aR)-1-β-D-Glucopyranosyl-4-
glucopyranosyl-4-hydroxy-7-hydroxymethyl-
hydroxy-7-hydroxymetyl-1,3,4,4a,5,7a-
1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran
hexahydrocyclopenta[c]pyran
128 6-O-Methyldeacetylasperulosidic acid
methyl ester
130 6α-Methoxygeniposidic acid
129 6-O-methylscandosic acid
methyl ester
131 Mollugoside methyl ester
14
qu
Hedyotis lindleyana
134 6-Metoxygeniposide
LK LOID
OH
OH
NH2
NH2
N
H
N
H
04 Serotonin
05 Hedyocapitin
N
N
N
N
H
NH
N
H
OH
HO
OH
OH
Capitellin
106
O
O
107 (–)- Isocyclocapitellin
(+)-Cyclocapitellin
108
N
O
H
N
H
N
O
O
H
N
H
Isochrisotricin
109
GLY OSIDE
HO
HO
110
O
H
O
uricularin
Protopin
111
OH
OH
4'
N
H
6'
OH
6
O
5'
2'
3'
1
4
O
1'
4
OH
HO
5
O
2
3
OH
O
113
2'
1'
OH
rbutin
112
1
Ethyl 1-O-β- -galactopyranoside
OH
OH
4
HO
HO
6
5
3
O
2
1
OH
114
OH
3
O
2'
MeO
4
HO
1
6
HO
1'
Ethyl 1’-O-β-D-glucopyranoside
2
5
OH
115
-(+)-Pinitol
15
qu
Hedyotis lindleyana
6
3'
4
CH 2OH
CH 2OH
HO
6
4
HC
O
2
3
OH
CH
3''
H 2C
3'
HO
6’-O-(1-Hydroxymethyl-2-hydroxy-
1
2
3
2'
O
CH2
1
OH
116
O
HO
H 2C
2''
5
O
1'
1''
CH2
O
HO
HO
OH
5
2'
1'
H 3CO
H 3C
OH
4-O-[3-Hydroxy-2(dihydroxymethylmethyl-oxy)]
117
1-methoxy)ethyl 1’-desoxyglucopyranoside
propyl--L-rhamnopyranose
OH
4'
5'
O
2'
3'
HO
4
1'
OH
4''
OH
6''
HO
HO
1
O
5''
HO
HO
2
O
O
2''
3''
4'
1''
6'
O
OH
5
5'
HO
O
2'
3'
O
1'
9
8
7
OH
3
H 3C
OH
3
6
2
1
H
10
O
1-Ethoxy-2β-L-arabinopyranosyl-
118
119
(6R,9S)-Roseoside
3-D-glucopyranosylpropane
2'''
HO CH2
6
1'''
CH2
CH
3'''
O
HO CH2
HO
2''
HO CH2
4
O
O
5
2
3
1''
CH
3''
1
2'
O
1'
CH2
OH
CH3
HO CH2
133 Vomifoliol 9-O-β-D-glucopyranoside
120 1-O-Ethyl-3,6-di-O-(2-hydroxy-1-hydroxymethylethyl)--D-glucopyranose
HỢP HẤT ÉO
1'
CH3
27
1
CH2
O
C
CH2
(CH2 )15
CH2
CH 2
C
C
C
H
121
CH 2
CH2
CH 3
22
19
O
CH2
H
H
C
H
Ethyl (19Z,22Z)-heptacosa-19,22-dienoate
CH3-(CH2)29-OH
122
Triacontanol
HỢP HẤT DỊ
HO
VÒNG
CH2
CH=O
O
123
2-Formyl-5-hydro ymethylfuran
CH=O
HỢP HẤT TH M
MeO
CH=O
OMe
OH
124 4-Hydroxy-3,5-dimethoxybenzaldehyde
OMe
OH
125 Vanillin
16
qu
Hedyotis lindleyana
CH=O
COOH
OH
OH
OMe
M t s ký
27 4-Hydro y-3-metho ybenzoic acid
4-Hydroxybenzaldehyde
126
ệu v ết tắt
H
OH
OH
O
HO
HO
OH
MeO
O
H
OH
O
Gl
HO
O
Me
MeO
Bz
OH
O
C
HO
C
H
C
HO
O
E-Fer
O
R
H
OH
HO
O
C
O
C
HO
H
OH
C
O
p-M n
H
C
G l
C
O
HO
r
OH
C
C
O
p- mr
17
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