Tông quan cây an điền hedyotis linleyana hook , họ cà phê rubiaceae

MỞ ĐẦU Ngày nay, với tiến vượt bậc ngành khoa học kĩ thuật nói chung, ngành hóa học góp phần khơng nhỏ vào phát triển nhằm phục vụ đời sống người tốt Các nhà hóa học tổng hợp nhiều loại hợp chất chữa trị nhiều loài bệnh khác Tuy nhiên, loại thuốc thường đắt tiền số chúng có tác dụng phụ, u hướng quay với y học cổ truyền, sử dụng thảo mộc làm thuốc trị bệnh iệt am có nguồn thực vật đa dạng phong phú ưu lớn nhà nghiên cứu hóa học hợp chất thiên nhiên Hiện nay, nhân dân ta dùng số thuộc chi Hedyotis, họ Cà phê (Rubiaceae) làm thuốc chữa rắn cắn, suy nhược thần kinh, đau dày, ương cốt, bệnh viêm nhiễm, trị ung thư … Các nghiên cứu hóa học cho thấy thuộc chi thường chứa sterol, triterpen, anthraquinone, iridoid … hợp chất có iên quan đến dược tính trình bày Cây An điền Lindley Hedyotis lindleyana Hook ex H Arn lồi thuộc chi Hedyotis, nhiên, chưa có cơng trình cơng bố dược tính thành phần hóa học Chính thế, việc tìm hiểu nghiên cứu thành phần hóa học dược tính Hedyotis lindleyana s àm tăng giá trị ứng dụng vào thực tế sống góp phần àm phong phú hiểu biết hóa thực vật, dược tính thuộc chi Hedyotis qu Hedyotis lindleyana H 1.1 T n qu n v NG T NG QU N Hedyotis Chi Hedyotis có khoảng 150 lồi, chủ yếu mọc vùng có khí hậu nhiệt đới ấm áp Chúng thường có thân thảo, vng, cao từ 30-85 cm Lá nhỏ, phiến hẹp, có gân giữa, gân phụ không rõ Hoa màu trắng hay vàng, mọc thành cụm nách hay đỉnh nhánh Các loài thuộc chi Hedyotis thường mọc sân vườn, bình nguyên Việt Nam, chủ yếu 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 n n lindley[2] thuộc chi Hedyotis, họ Cà phê (Rubiaceae) Cỏ đa niên b , có r mắt; thân có c nh tr n, có lơng theo hàng Lá có phiến oan, nhọn hay tà hai đ u, gân phụ c p l i m t dưới, cu n ngắn, bẹ nhọn Chụm dày nách, hoa ch 4, vành tai nhọn, ng có lơng cổ ế 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 n Lindley Hedyotis lindleyana Hook ex H Arn 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 s lồi chi Hedyotis qu Hedyotis lindleyana 1.2 N n uv tn o dư c tính n n Hedyotis lindleyana Hook ex H Arn chưa đư c nghiên c u nên ph n này, dư c tính s lồi chi Hedyotis s đư c trình bày Bảng 1.1 B ng 1.1 Ho t tính sinh học s 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, nhiệt, giải độc, Rắn cắn, đau bao tử, … H capitellata var mollis Pierre e Pit.[3] Vị ngọt, 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 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 sinh con, viêm khí quản, viêm phổi, phổi kết h ch, viêm oang miệng, … qu Hedyotis lindleyana 1.3 N n uv tr n m t s ây t u Hedyotis Tương tự, nay, chưa có nghiên c u v thành ph n hóa học n n Hedyotis lindleyana Hook ex H Arn Chính thế, thành ph n hóa học s lồi chi Hedyotis s đư c trình bày ảng 1.2 lồi chi có đ c tính Hóa thực vật n 1.2 Thành ph n hóa học s Hedyotis đ đư c cơng b Lồ 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), 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- 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 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] qu Hedyotis lindleyana Cấu trúc h p chất đ cô lập đư c Hedyotis: 21 STEROID 20 12 19 11 24 25 16 14 10 29 23 17 13 28 22 18 26 27 15 DITERPENE 3β-OH; ∆5,22E; 24S : Stigmasterol 3β-OH; ∆7,22E; 24S : (22E)-5α-Stigmasta-7,22-dien-3β-ol 3β,5α,6β-OH; ∆22E; 24S : Stigmast-3,5α,6-triol 3β-OH; ∆5; 24R : β-Sitosterol 3β-O-Glc; ∆5; 24R : -Sitosterol 3-O-- -glucopyranoside 3β-O-Glc; ∆5,22E; 24S : Stigmasterol 3-O-β- -glucopyranoside 3β-O-Glc; ∆7,22E; 24S : (22E)-5α-Stigmasta-7,22-dien 3-O-β- -glucopyranoside 3β-O-Glc; ∆7,22E; 24R : (22E)-5α-Poriferasta-7,22-dien 3-O-β- -glucopyranoside 3β-OH; ∆5,22E; 24S : γ-Sitosterol HO 11 15 20 19 18 17 16 Phytol 27 TRITERPENE 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 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 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 10 25 C 14 16 Rha(13)Glc-O O OH 2' 1' O 24 Spergulacin 11 26 10 21 22 13 14 O 19 18 15 17 16 COOH 28 27 23 42 3β-O-Acetylbetulinic acid O QUINONE 12 11 10 13 14 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 10 11 14 12 13 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 MeO O 2,5- imetho y-1,4-benzoquinone 56 O OH 1' 15' 3' 7' 11' 14' O 3,5,6-Trimethyl-2-(3-hydroxy-3’,7’,11’,14’-tetramethyl)pentadecylbenzoquinone 57 FL VONE 3' 4' 2' O 1' 5' 6' 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" OH 63 mentoflavone OH OH O 1' 4' OH 1' O OH 4' OH 3' 2' OH 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 OH O Naringenin 65 ISOFL VONE 1' O HO O 1' OH 4' O OH iochanin 66 FL VONOL 3' 4' 2' O 1' 5' 6' 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 H 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 HOH2 C O 4a 7a 101 6’-Acetyldeacetylasperuloside OH H O H HOH2C OGlc 4a 7a OH 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 O 5' 2' 3' O 1' OH HO O OH O 113 2' 1' OH rbutin 112 Ethyl 1-O-β- -galactopyranoside OH OH HO HO O OH 114 OH O 2' MeO HO HO 1' Ethyl 1’-O-β-D-glucopyranoside OH 115 -(+)-Pinitol 15 qu Hedyotis lindleyana 3' CH 2OH CH 2OH HO HC O OH CH 3'' H 2C 3' HO 6’-O-(1-Hydroxymethyl-2-hydroxy- 2' O CH2 OH 116 O HO H 2C 2'' O 1' 1'' CH2 O HO HO OH 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 1' OH 4'' OH 6'' HO HO O 5'' HO HO O O 2'' 3'' 4' 1'' 6' O OH 5' HO O 2' 3' O 1' OH H 3C OH H 10 O 1-Ethoxy-2β-L-arabinopyranosyl- 118 119 (6R,9S)-Roseoside 3-D-glucopyranosylpropane 2''' HO CH2 1''' CH2 CH 3''' O HO CH2 HO 2'' HO CH2 O O 1'' CH 3'' 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 CH2 O C CH2 (CH2 )15 CH2 CH C C C H 121 CH CH2 CH 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 ... 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... Lam[5 ],[ 8] Thanh nhiệt, tiêu viêm, l i tiểu, tiêu sưng, Rắn cắn, sởi, s t, th n kinh suy c, bệnh gan, giun, viêm phế quản, đau nh c ương c t, thấp khớp, mụn nhọt, H diffusa Willd[20 ],[ 21 ],[ 22]... hydroxymethyl- 1,3 , 4,4 a, 5,7 a- hexahydrocyclopenta[c]pyran (102 ), (1S,4S,4aR,7aR)-1-β-D- glucopyranosyl-4-hydroxy-7-hydroxymethyl- 1,3 , 4,4 a, 5,7 ahexahydrocyclopenta[c]pyran (103 ), 1-O-ethyl- 3,6 -di-O-(2-