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

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

European Pharmaceutical Journal

Volume 68 (2021): Issue 1 (January 2021)

By: E. Háznagy-Radnai, Sz. Czigle and I. Máthé

Open Access

|Jul 2021

Figures & Tables

Isolated compounds.

1H and 13C NMR spectral data for isolated iridoids_

Aucubin (methanol):
C/H	DEPT	δ_C	δ_H	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	δ_C	δ_H	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]	λ_max [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)

DOI: https://doi.org/10.2478/afpuc-2020-0024 | Journal eISSN: 2453-6725

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Language: English

Page range: 54 - 58

Submitted on: Mar 16, 2021

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Accepted on: May 6, 2021

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Published on: Jul 25, 2021

Published by: Comenius University in Bratislava, Faculty of Pharmacy

In partnership with: Paradigm Publishing Services

Publication frequency: 2 issues per year

Keywords:

Stachys germanica,

Stachys byzantina,

Related subjects:

Pharmacy, other

© 2021 E. Háznagy-Radnai, Sz. Czigle, I. Máthé, published by Comenius University in Bratislava, Faculty of Pharmacy
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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