Pharmaceutical and biological properties of <i>Stachys</i> species: A review

Kanjevac, Milica; Zlatić, Nenad; Bojović, Biljana; Stanković, Milan

doi:10.1590/s2175-97902022e20211

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e20211 copy

Pharmaceutical and biological properties of Stachys species: A review

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

The genus Stachys includes about 300 cosmopolitan species, making it one of the largest genera of the Lamiaceae family. The purpose of this paper is to present a review of Stachys species in the flora of Serbia among which some species are endemic to the Balkan Peninsula. This review comprises morphological, phytochemical, medicinal and food application of 17 taxa: S. аlopecuros, S. аlpina, S. аnisochila, S. аnnua, S. аtherocalyx, S. cretica subsp. cassia, S. germanica, S. leucoglossa, S. milanii, S. officinalis, S. palustris, S. plumose, S. recta, S. tymphaea, S. scardica, S. serbica, and S. sylvatica. The species of the genus Stachys are rich sources of biologically active substances and well known for their worldwide application. For most of the Stachys species, it has been shown that their extracts possess biological activities such as antibacterial, anti-inflammatory, antioxidant, and anticancer. The main goals of this review include the morphological description of species, representation of the major secondary metabolites, and presentation of traditional knowledge in food preparation.

Keywords:
Essential oils; Medicinal application; Morphology; Secondary metabolites

Species	Secondary metabolites	Compound	References
S. alopecuros	Flavonoid heterozoids	Isoscutellarein 7-O-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
S. alopecuros	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside
S. alpine	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Bilušić Vundać et al., 2005Bilušić Vundać V, Maleš Ž, Plazibat M, Golja P, Cetina-Čižmek B. HPTLC determination of flavonoides and phenolic acids in some Croatian Stachys taxa. J Plan Chromatogr - Mod TLC. 2005;18(4):269-273.; Buchwald, Czapska, 1995*Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202..
S. anisochila	Flavonoid heterozoids	Isoscutellarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methyl hypo ethanol 7-O-[6 '' '- acetyl-β-D-allopyranosyl; (1-2)]-β-D-glucopyranoside; Hypolaetin 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	*Marin et al., 2004Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253.; Lenherr, Meier, Sticher, 1984aLenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.; Lenherr, Mabry, 1987*Lenherr A, Mabry TJ. Acetylated allose-containing flavonoid glucosides from Stachys anisochila. Phytochemistry. 1987;26(4):1185-1188..
S. anisochila	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
S. annua	Flavonoid aglycones	Baicalin; 4′-O-methyl skutelarine	Sheremet, Komissarenko, 1971Sheremet IP, Komissarenko NF. Stachyflaside - a flavone glycoside of Stachys annua. Chem Nat Comp . 1971;7:700-701..
	Flavonoid heterozoids	Scutellarein 7-O-[β-D-man pyranosyl- (1-2)]-β-D-glucopyranoside (stachyflazide); 4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methyl hypo ethanol 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	Lenherr, Meier, Sticher, 1984aLenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.; Sheremet, Komissarenko, 1971Sheremet IP, Komissarenko NF. Stachyflaside - a flavone glycoside of Stachys annua. Chem Nat Comp . 1971;7:700-701..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Czigle et al., 2007Czigle S, Háznagy-Radnai E, Tóth J, Máthé I, Grančai D. Rosmarinic acid in the genus Stachys L. Rev Med Farm. 2007;53:343-346.; Buchwald, Czapska, 1995*Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202..
	Diterpenes	Clerodane	Orgiyan, Popa, 1969Orgiyan TM, Popa DP. Diterpenoids from Stachys annua. Chem Nat Comp . 1969;5(1):7-10..
S. atherocalyh	Flavonoid heterozoids	Isoscutellarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; Scutellarein 7-O-[β-D-mannopyranosyl-(1-2)]-β-D-glucopyranoside (stachyflazide)); 4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methyl hypo ethanol 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	Lenherr, Meier, Sticher, 1984aLenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.; *Komissarenko et al., 1976Komissarenko NF, Sheremet IP, Derkach AI, Pakaln DA. Stachyflaside from Stachys inflata and S. atherocalyh. Chem Nat Comp . 1976;12(1):88.; Kostyuchenko et al., 1982Kostyuchenko OI, Komissarenko NF, Kovalev IP, Derkach AI, Gordienko VG. Acetylspectabiflaside from Stachys atherocalyh. Chem Nat Comp . 1982;18(2):170-172.; Lenherr, Meier, Sticher, 1984a*Lenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.;
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; p-Coumaric acid	Kostyuchenko, 1982Kostyuchenko OI, Komissarenko NF, Kovalev IP, Derkach AI, Gordienko VG. Acetylspectabiflaside from Stachys atherocalyh. Chem Nat Comp . 1982;18(2):170-172..
	Diterpenes	Clerodane	Piozzi, Bruno, 2011Piozzi F, Bruno M. Diterpenoids from roots and aerial parts of the genus Stachys. Rec Nat Prod . 2011;5(1):1-11..
S. germanica	Flavonoid heterozoids	4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
	Phenylethane heteroids	Acteoside; Martinoside	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202..
S. leucoglossa	Flavonoid heterozoids	Isoscutellarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)] - β-D-glucopyranoside; 4'-O-Methyl hypo ethanol 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	Lenherr, Meier, Sticher,1984aLenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.;
S. officinalis	Flavonoid aglycones	Apigenin; 7-O-Methyltricin	*El-Ansari et al., 1991El-Ansari MA, Barron D, Abdalla MF, Saleh NAM, Le Quere JL. Flavonoid constituents of Stachys aegyptiaca. Phytochemistry. 1991;30(4):1169-1173.. Kobzar, Nikonov, 1986*Kobzar AY, Nikonov GK. Flavonoids from the epigeal part of Betonica officinalis. Chem Nat Comp . 1986;22(5):600-601..
	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
	Phenylethane heteroids	Acteoside; Martinoside; Betonioside F; Forsythoside B; Leucosceptoside B	Miyase, Yamamoto, Ueno, 1996Miyase T, Yamamoto R, Ueno A. Phenylethanoid glycosides from Stachys officinalis. Phytochemistry . 1996;43(2):475-479.a; *Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Isochlorogenic acid; Rosmarinic acid; p-Coumaric acid; Protocatechuic acid; Sinapic acid	Kobzar, 1986Kobzar AY. Phytochemical study of Betonica officinalis. II. Acids from the epigeal part of Betonica. Chem Nat Comp . 1986;22(2):224-225.; Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Bilušić Vundać et al., 2005Bilušić Vundać V, Maleš Ž, Plazibat M, Golja P, Cetina-Čižmek B. HPTLC determination of flavonoides and phenolic acids in some Croatian Stachys taxa. J Plan Chromatogr - Mod TLC. 2005;18(4):269-273.; Czigle et al., 2007*Czigle S, Háznagy-Radnai E, Tóth J, Máthé I, Grančai D. Rosmarinic acid in the genus Stachys L. Rev Med Farm. 2007;53:343-346..
	Iridoidi	6-O-acetylmioporoside; Alobetonicoside	*Jeker et al., 1989*Jeker M, Sticher O, Calis I, Rüedi P. Allobetonicoside and 6-O-acetylmioporoside: Two new iridoid glycosides from Betonica officinalis L. Helv Chim Acta. 1989;72(8):1787-1791..
	Diterpenes	Clerodan	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
S. palustris	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Czigle et al., 2007*Czigle S, Háznagy-Radnai E, Tóth J, Máthé I, Grančai D. Rosmarinic acid in the genus Stachys L. Rev Med Farm. 2007;53:343-346..
	Diterpenes	Clerodan	Piozzi, Bruno, 2011Piozzi F, Bruno M. Diterpenoids from roots and aerial parts of the genus Stachys. Rec Nat Prod . 2011;5(1):1-11..
S. pulmosa	Flavonoid heterozoids	Isoscutellarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	*Marin et al., 2004Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253.; Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
	Phenylethane heteroids	Acteoside; Martinoside; Forsythoside B	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Diterpenes	Labdane	*Paternostro et al., 2000*Paternostro KP, Maggio AM, Piozzi F, Servettaz O. Labdane diterpenes froom Stachys pulmosa. J Nat Prod . 2000;63(8):1166-1167..
S. recta	Flavonoid heterozoids	Isoscutellarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methylisoskutelarein 7-O- [6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside; 4'-O-Methyl hypo ethanol 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)]-β-D-glucopyranoside	*Marin et al., 2004Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253.; Lenherr, Meier, Sticher, 1984aLenherr A, Meier B, Sticher O. Modern HPLC as a tool for chemotaxonomical investigations: Iridoid glucosides and acetylates flavonoides in the group of Stachys recta. Planta Med. 1984a;50(5):403-409.; Lenherr, Lahloub, Stcher, 1984b*Lenherr A, Lahloub M, Stcher O. Three flavonoid glycosides containing acetylated allose from Stachys recta. Phytochemistry . 1984b;23(10):2343-2345..
	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside; Apigenin 7-O-(3 ''-p-coumaroyl)-β-D-glucopyranoside	*Karioti et al., 2010*Karioti A, Bolognesi L, Vincieri FF, Bilia AR. Analysis of the constituents of aqueous preparations of Stachys recta by HPLC-DAD and HPLC-ESI-MS. J Pharm Biomed Anal. 2010;53(1):15-23..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; p-Coumaric acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Czigle et al., 2007*Czigle S, Háznagy-Radnai E, Tóth J, Máthé I, Grančai D. Rosmarinic acid in the genus Stachys L. Rev Med Farm. 2007;53:343-346..
	Diterpenes	Clerodan	*Adinolfi et al., 1984*Adinolfi M, Barone G, Lanzetta R, Laonigro G, Mangoni L, Parrilli M. Diterpenes from Stachys recta. J Nat Prod. 1984;47(3):541-543..
S. sylvatica	Flavonoid heterozoids	4'-O-Methylisoskutelarein 7-O-[6 '' '- acetyl-β-D-allopyranosyl (1-2)] - β-D-glucopyranoside	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Flavonoids	Apigenin 7-O-(6 ''-p-coumaroyl)-β-D-glucopyranoside	*Marin et al., 2004*Marin PD, Grayer RJ, Grujić-Jovanović S, Kite GC, Veitch NC. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry . 2004;65(9):1247-1253..
	Phenylethane heteroids	Acteoside; Martinoside; Forsythoside B	*Bankova et al., 1999*Bankova V, Koeva-Todorovska J, Stambolijska T, Ignatova-Groceva M-D, Todorova D, Popov S. Polyphenols in Stachys and Betonica species (Lamiaceae). Z Naturforsch C. 1999;54(11):876-880..
	Phenol carboxylic acids	Caffeic acid; Chlorogenic acid; Rosmarinic acid; p-Coumaric acid; Protocatechuic acid; Sinapic acid	Buchwald, Czapska, 1995Buchwald W, Czapska A. Tannins and phenolic acids content in herb of domestic species of Betonica L. and Stahys L. genera. Herba Pol. 1995;41(4):198-202.; *Bilušić Vundać et al., 2005Bilušić Vundać V, Maleš Ž, Plazibat M, Golja P, Cetina-Čižmek B. HPTLC determination of flavonoides and phenolic acids in some Croatian Stachys taxa. J Plan Chromatogr - Mod TLC. 2005;18(4):269-273.; Czigle et al., 2007*Czigle S, Háznagy-Radnai E, Tóth J, Máthé I, Grančai D. Rosmarinic acid in the genus Stachys L. Rev Med Farm. 2007;53:343-346..
	Diterpenes	Kauran; Clerodan	Popa, Pasechnik, 1974Popa DP, Pasechnik GS. Structure of stachysic acid, a new diterpenoid of the kaurane series. Chem Nat Comp . 1974;10:447-451.; Piozzi, Bruno, 2011Piozzi F, Bruno M. Diterpenoids from roots and aerial parts of the genus Stachys. Rec Nat Prod . 2011;5(1):1-11..

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[1] *Correspondence: N. M. Zlatić. Department of Biology and Ecology. Faculty of Science. University of Kragujevac. Radoja Domanovića 12, 34000 Kragujevac, Republic of Serbia. Phone: +381-34-336223. E-mail: nenad.zlatic@pmf.kg.ac.rs.