Figure 1
Isolated compounds.
Table 1
Physical and UV spectroscopic data on iridoids from S. byzantina and S. germanica.
| Iridoids | M. P. [oC] | λmax [nm] |
|---|---|---|
| Ajugoside | amorph. powder | 206 |
| Aucubin | 179 – 183 | 210 |
| Harpagide | amorph. powder | 210 |
| Harpagoside | amorph. powder | 216 |
[i] M. P., melting point.
Table 2
1H and 13C NMR spectral data for isolated iridoids.
| Aucubin (methanol): | |||||
| C/H | DEPT | δC | δH | J(Hz) | HMBC(C→H) |
| 1 | CH | 96.1 | 4.94 d | (7.1) | H-1′, H-3′, H-9 |
| 3 | CH | 140.1 | 6.3 dd | (6.3, 1.8) | H-1, H-4 |
| 4 | CH | 104.1 | 5.08 dd | (6.3, 4.0) | H-3, H-5 |
| 5 | CH | 44.8 | 2.65 m | H-3, H-4, H-7, H-9 | |
| 6 | CH | 81.3 | 4.43 m | H-4, H-5, H-7, H-9 | |
| 7 | CH | 128.9 | 5.76 s | H-9, H-10 | |
| 8 | C | 81.2 | H-7, H-9 | ||
| 9 | CH | 46.5 | 2.89 t | (7.3) | H-1, H-7 |
| 10 | CH2 | 60.0 | 4.16 d | (15.4) | H-7 |
| 4.34 d | (15.4) | ||||
| 1′ | CH | 98.5 | 4.67 d | (7.8) | H-1, H-2′ |
| 2′ | CH | 73.5 | 3.22* | H-1′ | |
| 3′ | CH | 76.6 | 3.37* | H-1′, H-2′, H-4′ | |
| 4′ | CH | 70.2 | 3.28* | H-3′, H-5′, H-6′ | |
| 5′ | CH | 76.9 | 3.26* | H-1′, H-4′, H-6′ | |
| 6′ | CH2 | 61.2 | 3.64 dd | (12.2, 5.2) | H-5′ |
| 3.85 d | (12.2) | ||||
| Harpagide (methanol): | |||||
| C/H | DEPT | δC | δH | J(Hz) | HMBC(C→H) |
| 1 | CH | 92.0 | 5.74 s | H-1′, H-3, H-9 | |
| 3 | CH | 141.3 | 6.31 d | (6.5) | H-1, H-4 |
| 4 | CH | 107.2 | 4.95 dd | (6.5, 1.5) | H-3, H-6, H-9 |
| 5 | C | 70.4 | H-1, H-3, H-7, H-9 | ||
| 6 | CH | 77.0 | 3.70* | H-4, H-7, H-9 | |
| 7 | CH2 | 45.8 | 1.80 dd | (13.8, 3.8) | H-10 |
| 1.91 dd | (13.8, 4.8) | ||||
| 8 | C | 81.2 | H-7, H-9 | ||
| 9 | CH | 58.5 | 2.55 s | H-4, H-7, H-10 | |
| 10 | CH2 | 23.6 | 1.25 s | H-7, H-9 | |
| 1′ | CH | 98.1 | 4.58 d | (8.0) | H-1, H-2′ |
| 2′ | CH | 73.1 | 3.21 dd | (9.1, 8.0) | H-1′ |
| 3′ | CH | 76.4 | 3.38* | H-1′, H-2′ | |
| 4′ | CH | 70.4 | 3.29* | H-3′ | |
| 5′ | CH | 77.0 | 3.30* | H-4′, H-6′ | |
| 6′ | CH2 | 61.4 | 3.66 dd | (11.8, 5.5) | H-5′ |
| 3.90 d | (11.8) | ||||
Table 3
The isolated iridoid components of Stachys species.
| Species | Iridoids |
|---|---|
| S. alpina | harpagide, 8-O-acetylharpagide (Háznagy-Radnai, 2006, 2007) |
| S. annua | melittoside (Lenherr, 1984) |
| S. byzantina | harpagide, 8-O-acetylharpagide (Háznagy-Radnai, 2006, 2007) |
| S. germanica | harpagide, 8-O-acetylharpagide (Háznagy-Radnai, 2006, 2007) |
| S. grandiflora | harpagide, 8-O-acetylharpagide, melittoside (Háznagy-Radnai, 2006, 2007) |
| S. macrantha | harpagide, 8-O-acetylharpagide, ajugol, ajugoside, reptoside, allobetonicosid, macrathoside (Calis, 1991; Háznagy-Radnai, 2006, 2007) |
| S. officinalis | harpagide, 8-O-acetylharpagide, ajugol, ajugoside, reptoside, allobetonicosid, 6-O-acetylmioporoside (Kobzar, 1986; Derkach, 1987; Jeker, 1989; Háznagy-Radnai, 2006, 2007) |
| S. palustris | harpagide, 8-O-acetylharpagide, aucubin (Adema, 1968; Háznagy-Radnai, 2006, 2007) |
| S. recta | harpagide, 8-O-acetylharpagide, aucubin, ajugol, ajugoside, melittoside (Lenherr, 1984; Háznagy-Radnai, 2006, 2007) |
| S. sylvatica | harpagide, 8-O-acetylharpagide (Kukic, 2006; Háznagy-Radnai, 2006, 2007) |