Table 12.
Iridoids from Stachys spp.
| Species | Plant Parts | Compound | Ref |
|---|---|---|---|
| Subgenus Stachys | |||
| Section Ambleia | |||
| S. inflata Benth. | Ajugol (146), Ajugoside (147), | [121] | |
| Section Aucheriana | |||
| S. glutinosa L. | Aerial parts | Harpagide (148), Acetylharpagide (150), Monomelittoside (165), Melittoside (166), Allobetonicoside (161), 5-Allosyloxy-aucubin (167) |
[122] |
| Section Campanistrum | |||
| S. ocymastrum (L.) Briq. (=S. hirta L.) | Leaves | 6β-Acetoxyipolamiide (172), 6β-Hydroxyipolamiide (173), Ipolamiide (174), Ipolamiidoside (175), Lamiide (176) | [123] |
| Section Candida | |||
| S. iva Griseb. | Flowering Aerial parts | Harpagide (148), 8-Acetylharpagide (150), 8-Epi-loganic acid (157), Gardoside (160), 8-Epi-loganin (159), Monomelittoside (165), Melittoside (166) |
[56] |
| Section Corsica | |||
| S. corsica Pers. | Harpagide (148), Acetylharpagide (150) |
[79] | |
| Section Eriostomum | |||
| S. alpina L. | Stems, Leaves # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Aucubin (164), Catalpol (163) |
[124] |
| S. balansae Boiss. & Kotschy | Ajugol (146), Ajugoside (147) | [125] | |
| S. germanica L. | Harpagide (148) | [125] | |
| Leaf, Inflorescence # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Aucubin (164), Catalpol (163) |
[124] | |
| S. spectabilis Choisy ex DC. | Ajugol (146), Ajugoside (147), Harpagide (148) | [125] | |
| S. byzantina Κ. Koch. | Aerial parts # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] |
| S. germanica L. subsp. salviifolia (Zen.) Gams | Flowering Aerial parts | Harpagide (148) | [86] |
| Aerial parts | Ajugol (146), Harpagide (148), 7-Hydroxyharpagide (149), 5-Allosyloxy-aucubin (167) |
[109] | |
| S. lanata Crantz. (=S. germanica L. subsp. germanica) | Roots | Stachysosides E (168), G (170), H (171) | [82] |
| Aerial parts | Stachysosides E (168), F (169) | [82] | |
| S. tymphaea Hausskn. (=S. germanica subsp. tymphaea (Hausskn.) R. Bhattacharjee) | Aerial parts | Harpagide (148) | [86] |
| Section Olisia | |||
| S. angustifolia M. Bieb. | Ajugoside (147), Acetylharpagide (150), Harpagide (148), Melittoside (166) |
[92] | |
| S. annua (L.) L. | Ajugoside (147), Acetylharpagide (150), Melittoside (166) |
[92] | |
| S. atherocalyx C. Koch. | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) |
[92,125] | |
| S. beckeana Dörfl. & Hayek | Harpagide (148), Ajugol (146), Acetylharpagide (150), Melittoside (166) |
[92] | |
| S. iberica M. Bieb. | Ajugol (146), Ajugoside (147), Harpagide (148), Acetylharpagide (150) | [121] | |
| S. recta L. | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| Leaves | 8-Acetylharpagide (150), Melittoside# (166) | [14] | |
| Aerial parts # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] | |
| S. baldaccii (Maly) Hand-Mazz (=S. recta L. subsp. baldaccii (K. Maly) Hayek) | Ajugol (146), Ajugoside (147), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| S. subcrenata Vis. (=S. recta subsp. subcrenata) | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| S. labiosa Bertol. | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| S. leucoglossa Griseb. | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| S. spinosa L. | Aerial parts | Ajugol (146), Harpagide (148), 7-O-Acetyl-8-epi-loganic acid (158) | [98] |
| S. tetragona Boiss. & Heldr. | Ajugol (146), Ajugoside (147), Harpagide (148), Acetylharpagide (150), Melittoside (166) | [92] | |
| Aerial parts | 8-Acetyl-harpagide (150), 5-O-Allopyranosyl-monomelittoside (167) | [100] | |
| Section Stachys | |||
| S. affinis Bunge (= S. sieboldii Miq.) | Tubers | Harpagide (148), Acetylharpagide (150), Melittoside (166), 5-Allosyloxy-aucubin (167) | [27] |
| S. palustris L. | Aerial parts # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] |
| S. sylvatica L. | Aerial parts # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] |
| Section Swainsoniana | |||
| S. anisochila Vis. & Pancic | Acetylharpagide (150), Melittoside (166) |
[92] | |
| S. ionica Halácsy | 8-epi-loganic acid (157), Gardoside (160) |
[20] | |
| S. menthifolia Vis. (= S. grandiflora Host.) | Ajugol (146), Harpagide (148), Acetylharpagide (150), Melittoside (166) |
[92] | |
| Aerial parts # | Ajugoside (147) Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] | |
| Section Zietenia | |||
| S. lavandulifolia Vahl. | Ajugol (146), Ajugoside (147) | [125] | |
| Aerial parts | Melittoside (166), Monomelittoside (165), 5-O-Allopyranosyl-monomelittoside (167) | [12] | |
| Subgenus Betonica | |||
| Section Betonica | |||
| S. alopecuros (L.) Benth subsp. divulsa (Ten.) Grande | Flowering aerial parts | Harpagide (148), Acetylharpagide (150), 4′-O-β-D-galactopyranosyl-teuhircoside (162) |
[119] |
| S. foliosa Rupr. (=S. betoniciflora Rupr.; Betonica foliosa Rupr.) | Harpagide (148), Acetylharpagide (150) | [126] | |
| S. betonicaeflora Rupr. | Harpagide (148), Acetylharpagide (150) | [126] | |
| S. macrantha (C. Koch.) Stearn (=Betonica grandiflora Steph. ex Willd.) | Aerial parts | Ajugol (146), Ajugoside (147), Harpagide (148), 8-O-Acetyl-harpagide (150), Reptoside (153), Macranthoside [=8-O- (3, 4-dimethoxy-cinnamoyl-harpagide)] (156), Allobetonicoside (161) |
[117] |
| S. officinalis (L.) Trevis. (=Betonica officinalis L.) | Aerial parts | Acetylharpagide (150), Reptoside (153), 6-O-Acetylmioporoside (155), Allobetonicoside (161) |
[127] |
| Harpagide (148), Acetylharpagide (150) | [128] | ||
| Aerial parts # | Ajugoside (147), Harpagide (148), Acetylharpagide (150), Harpagoside (154), Catalpol (163), Aucubin (164) |
[124] | |
| Unknown Section | |||
| S. grandidentata Lindl. ** | Aerial parts | Ajugol (146), Harpagide (148), Acetylharpagide (150), 5-Desoxy-harpagide (151), 5-Desoxy-8-acetyl-harpagide (152), Monomelittoside (165), Melittoside (166) |
[129] |
# identified compounds#identified compounds by means of HPLC, LC-MS, etc; ** endemic species of Chile.