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Iridoids from Stachys byzantina K. Koch (Lamb's Ears) and Stachys germanica L. (Downy Woundwort)

E. Háznagy-Radnai
E. Háznagy-Radnai
, 
Sz. Czigle
Sz. Czigle
 and 
I. Máthé
I. Máthé
   | Jul 25, 2021
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Article Category: Original Paper
Published Online: Jul 25, 2021
Page range: 54 - 58
Received: Mar 16, 2021
Accepted: May 06, 2021
DOI: https://doi.org/10.2478/afpuc-2020-0024
Keywords
© 2021 E. Háznagy-Radnai et al., published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Figure 1

Isolated compounds.
Isolated compounds.

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)

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

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)
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