Table 1. Novel Chromones and Chromanones Isolated from Natural Sources.
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| Aquisinenone A (1) | Aquilaria sinensis | Inhibition of NO production | (24) |
| (−)-4′-Methoxyaquisinenone A (2) | |||
| Aquisinenone B (3) | |||
| (−)-6″-Hydroxyaquisinenone B (4) | |||
| (+)-6″-Hydroxy-4′,4‴-dimethoxyaquisinenone B (5) | |||
| Aquisinenone C (6) | |||
| (−)-Aquisinenone D (7) | |||
| 4′-Demethoxyaquisinenone D (8) | |||
| (+)-Aquisinenone E (9) | |||
| (−)-Aquisinenone F (10) | |||
| (−)-Aquisinenone G (11) | |||
| (+)-4′-Methoxyaquisinenone G (12) | |||
| (5R,6S,7S,8R)-2-[2-(3′-Hydroxy-4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (14) | Aquilaria sp. | PDE 3A inhibitory activity | (25) |
| (5R,6S,7S,8R)-2-[2-(4′-Methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (15) | |||
| (5R,6S,7S,8R)-2-[2-(4′-Hydroxyl-3′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (16) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| 6-Hydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone (17) | Aquilaria sp. | Tyrosinase inhibitory activity | (26) |
| 6-Methoxy-7-hydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (18) | |||
| 6-Hydroxy-7-methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl] chromone (19) | |||
| 6,8-Dihydroxy-2-[2-(4-methoxyphenyl)ethyl]chromone (20) | |||
| 8-Chloro-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydrochromone (21) | |||
| 8-Chloro-2–(2-(4-methoxyphenyl)ethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydrochromone (22) | |||
| Aquichromone A (23) | Aquilaria sinensis | Inhibition of NO production | (27) |
| Aquichromone B (24) | |||
| Aquichromone C (25) | |||
| Aquichromone D (26) | |||
| Aquichromone E (27) | |||
| 8-Epi-aquichromone C (28) | |||
| Aquifilarone A (29) | Aquilaria filaria | Inhibition of NO production | (28) |
| Aquifilarone B (30) | |||
| Aquifilarone C (31) | |||
| Aquifilarone D (32) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| Aquilasinenone L (33) | Aquilaria sinensis | —a | (29) |
| Aquilasinenone N (34) | |||
| 5S, 6R, 7S, 8R-Tetrahydroxy-[2-(3-methoxy-4-hydroxyphenyl)ethyl]- 5,6,7,8-tetrahydrochromone (35) | |||
| (6S,7S,8R)-6,7-Dihydroxy-8-chloro-5,6,7,8-tetrahydro-2-(2-(3-hydroxy-4-methoxyphenyl)ethyl)chromone (36) | Aquilaria crassna Pierre ex Lecomte | Weak cytotoxicity toward HeLa cell line | (30) |
| (5R,6S,7S,8R)-5,6,7-Trihydroxy-8-methoxy-5,6,7,8-tetrahydro-2-(2-(4-methoxyphenyl)ethyl)chromone (37) | |||
| 6,7-cis-Dihydroxy-5,6,7,8-tetrahydro-2-(2-(4-methoxyphenyl)ethyl)chromone (38) | |||
| 3′-Hydroxyaquisinenone D (39) | |||
| Wallone B (40) | Aquilaria walla | Cytotoxicity against human cancer cell lines (K562, BEL-7402, SGC-7901, A549, HeLa) | (31) |
| Wallone C (41) | |||
| Wallone D (42) | |||
| 6″-Hydroxy-4′′′-methoxy-crassin B (43) | |||
| 3′′′-Hydroxy-crassin G (44) | |||
| 4′-Demethoxyl-3′′′-hydroxy-crassin G (45) | |||
| 3′-Methoxyl-4′,7″-dihydroxyl-6″-demethoxy-crassin H (46) | |||
| Undulatoside A 6′-O-gallate (47) | Myrtus communis | —a | (33) |
| 5,7-Dihydroxy-2-isopropyl-6,8-dimethyl-4H-chromen-4-one (48) | Syzygium cerasiforme (Blume) Merr. and L.M. Perry | Inhibition of NO production | (35) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| 9,11-Dihydroxy-10-methylcoumarinochromone (boeravinone Y, 49) | Abronia nana | Inhibition of LPS release HMGB1; reduction of hyperpermeability, leukocyte adhesion and migration, and cell adhesion molecule expression; increase of the phagocytic activity of macrophages; and bacterial clearance effects | (36) |
| 6′-O-Coumaroylaloesin (50) | Aloe vera | Anti-LPS activity | (38) |
| Aloeveraside A (51) | |||
| Aloeveraside B (52) | |||
| 7-O-Methyl-6′-O-coumaroylaloesin (54) | Aloe monticola Reynolds | Antibacterial and antifungal activity | (39) |
| 5,7-Dihydroxychromone-3α-D-C-glucoside (macrolobin, 55) | Macrolobium Latifolium Vogel | AChE inhibitory activity; antibacterial activity against P. aeruginosa and S. enterica | (42) |
| 6-(Hydroxymethyl)-2,2-dimethyl-8-(2-oxopropyl)chroman-4-one (56) | Cassia pumila | Anti-MRSA activity | (44) |
| 2,2,6-Trimethyl-8-(2-oxopropyl)chroman-4-one (57) | |||
| 6-(2,2-Dimethyl-2H-chromene)-2-isopropyl-8-hydroxy-4H-chromen-4-one (58) | Cassia auriculata | Anti-MRSA activity; anti-TMV activity; and antirotavirus activity | (45 and 46) |
| 6-(2,2-Dimethyl-2H-chromene)-2,8-dimethyl-4H-chromen-4-one (59) | |||
| 2-(2-(Furan-2-yl)-2-oxoethyl)-6-methoxy-8-(2-oxopropyl)-chromone (60) | |||
| 2-(2-(Furan-2-yl)-2-oxoethyl)-5-methoxy-8-(2-oxopropyl)-chromone (61) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| Alatachromone A (62) | Cassia alata | Anti-TMV activity; antirotavirus activity | (47) |
| Alataindolein D (63) | |||
| 2-Acetyl-5-isopropyl-7-methyl-4H-chromen-4-one (64) | cassia rotundifolia | Anti-MRSA activity | (48) |
| 2-Acetyl-7-(hydroxymethyl)-5-isopropyl-4H-chromen-4-one (65) | |||
| Caloinophyllin A (67) | Calophyllum inophyllum | Antibacterial activity against S. aureus and E. coli | (52−55) |
| Calophinophyllin A (68) | |||
| Calophinophyllin B (69) | |||
| Inocalophylline C (70) | |||
| Calophylloidic acid B (71) | |||
| Isocaloteysmannic acid (72) | Calophyllum tacamahaca Willd | Moderate cytotoxicity against HepG2 and HT29 cell lines | (56) |
| Calopeekelioic acid A (73) | Calophyllum peekelii Lauterb | Antiplasmodial activity | (57) |
| Calopeekelioic acid B (74) | |||
| 2-{2-[(3′-O-β-d-Glucopyranosyl)phenyl]ethyl}chromone (75) | Limacia scandens | Senolytic activity | (58) |
| 3-Methoxy-2-{2-[(3′-O-β-d-glucopyranosyl)phenyl]ethyl}chromone (76) | |||
| Cnidimol G (77) | Cnidium monnieri (L.) Cusson | Inhibition of NO production | (60) |
| Cnidimol H (78) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Plants | |||
| Sadivamone A (79) | Saposhnikovia divaricata | Inhibition of NO production; inhibition of phosphorylation of ERK and the activation of ERK and JNK signaling | (61) |
| Sadivamone B (80) | |||
| Sadivamone C (81) | |||
| Sadivamone D (82) | |||
| Sadivamone E (83) | |||
| Cimifugin monoacetate (84) | |||
| Sadivamone F (85) | |||
| Sadivamone G (86) | |||
| Sadivamone H (87) | |||
| Sadivamone I (88) | |||
| Sadivamone J (89) | |||
| Sadivamone K (90) | |||
| Sadivamone L (91) | |||
| Sadivamone M (92) | |||
| Sadivamone N (93) | |||
| (S)-(+)-5,7-Dihydroxy-2-(1-methylpropyl) chromone-6-β-d-glucoside (94) | Hypericum elodeoides | Moderate α-glycosidase inhibitory activity | (62) |
| (2′R)-7-Hydroxy-5-methyl acetate-2-(2′-hydroxypropyl) chromone (95) | Rumex dentatus | —a | (63) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Fungi | |||
| (S)-5-Hydroxyl-2-(1-hydroxyethyl)-7-methylchromone (96) | Bipolaris eleusines | Weak antibacterial activity against S. aureus | (65) |
| (2′S)-2-(2-Acetoxypropyl)-7-hydroxy-5-methylchromone (98) | Alternaria brassicae (JS959) | Inhibition of cupric cation-induced LDL and HDL oxidation | (66) |
| 7-Hydroxy-2,5-dimethyl-4H-chromen-4-one (99) | |||
| 2-(2′R-Hydroxypropyl)-5-methyl-7-hydroxychromone (lawsozaheer, 100) | Paecilomyces variotii | Antibacterial activity against S. aureus | (67) |
| Phomochromenone D (101) | Phomopsis asparagi (DHS-48) | —a | (69) |
| Phomochromenone E (102) | |||
| Phomochromenone F (103) | |||
| Phomochromenone G (104) | |||
| 2,6-Dimethyl-5-methoxyl-7-hydroxylchromone (105) | Xylomelasma sp. (Samif07) | Antibacterial activity against E. carotovora | (70) |
| Mangrovamide H (106) | Penicillium sp. (SCSIO041218) | —a | (71) |
| Mangrovamide I (107) | |||
| Mangrovamide J (108) | |||
| Mangrovamide K (109) | |||
| Paecilin F (110) | Penicillium oxalicum | —a | (72) |
| Paecilin G (111) | |||
| Paecilin H (112) | |||
| 4-(5,7-Dimethoxy-4-oxo-4H-chromen-2-yl)butanoic acid methyl ester (113) | Penicillium sclerotiorum | Antibacterial activity against carbapenems-resistant P. aeruginosa | (73) |
| Aspergilluone A (114) | Aspergillus sp. | Antibacterial activity | (74) |
| 5-Hydroxy-2,3-dimethyl-4-oxo-7-(2-oxopropyl)-4H-chromene-8-carboxylic acid (115) | Aspergillus sp. | Inhibition of NO production | (75) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Fungi | |||
| 8-Methyl-2-(2-oxopropyl)-4H-pyrano[3,2-h]isoquinolin-4-one (116) | Aspergillus lentulus | Anti-TMV activity | (76) |
| 8-(Hydroxymethyl)-2-(2-oxopropyl)-4H-pyrano[3,2-h]isoquinolin-4-one (117) | |||
| 8-(3-Hydroxypropyl)-2-(3-hydroxy-1-oxopropyl)-6-methoxy-4H-chromen-4-one (118) | Aspergillus versicolor | Anti-TMV activity | (77) |
| 2-Acetyl-8-(3-hydroxypropyl)-6-methoxy-4H-chromen-4-one (119) | |||
| Botryochromone (120) | BCC 54265 | Weak cytotoxicity against KB and NCI-H187 cell-lines | (78) |
| Mycochromone A (121) | Mycosphaerella sp. | —a | (79) |
| Mycochromone B (122) | |||
| Paecilin Q (123) | Pseudofusicoccum stromaticum | Moderate antifungal activity against P. citricarpa | (80) |
| Paecilin R (124) | |||
| Arthone A (125) | Arthrinium sp. | Antioxidant activity | (82) |
| Arthone B (126) | |||
| Arthone C (127) | |||
| Arthone D (128) | |||
| Arthone E (129) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Fungi | |||
| Pyanochromone (130) | Penicillium erubescens | —a | (83) |
| Spirofuranochromone (131) | |||
| 7-Hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (132) | |||
| Erubescenschromone B (133) | |||
| Penithochromone M (134) | Penicillium thomii | α-glycosidase inhibition; weak antioxidant activity | (84) |
| Penithochromone N (135) | |||
| Penithochromone O (136) | |||
| Penithochromone P (137) | |||
| Penithochromone Q (138) | |||
| Penithochromone R (139) | |||
| Penithochromone S (140) | |||
| Penithochromone T (141) | |||
| Penithochromone U (142) | Penicillium thomii | —a | (85) |
| Penithochromone V (143) | |||
| Penithochromone W (144) | |||
| Pseudopestalone (145) | Pseudopestalotiopsis sp. | —a | (86) |
| 2,3-Dihydro-5,8-dihydroxy-2,2-dimethylchromen-4-one (146) |
| Compound | Natural source | Biological activity | Ref |
|---|---|---|---|
| Fungi | |||
| Phaseolorin A (147) | Diaporthe phaseolorum | —a | (87) |
| Phaseolorin B (148) | |||
| Phaseolorin C (149) | |||
| Phaseolorin D (150) | |||
| Phaseolorin E (151) | |||
| Diaporspchromanone A (152) | Diaporthe sp. | Inhibition of NO production | (88) |
| Diaporspchromanone B (153) | |||
| Diaporspchromanone C (154) | |||
| Diaporspchromanone H (155) | |||
| 9-Hydroxyeugenetin 9-O-β-D-(4-O-methyl) glucopyranoside (156) | Akanthomyces sp | —a | (89) |
| Ascherlactone A (157) | Aschersonia confluens | —a | (90) |
| Ascherlactone B (158) | |||
| Ascherchromanone A (159) | |||
| (5R,7R)-5,7-Dihydroxy-2-methyl-5,6,7,8-tetrahydro-4H-chromen-4-one (160) | Daldinia sp. | Anti-influenza A virus | (92) |
| (5R,7R)-5,7-Dihydroxy-2-propyl-5,6,7,8-tetrahydro-4H-chromen-4-one (161) |
a
No biological activity reported.