Flavonoid p-coumaroylglucosides and 8-hydroxyflavone allosylglucosides in some labiatae

doi:10.1016/0031-9422(92)83452-5

Phytochemistry

Volume 31, Issue 9, September 1992, Pages 3097-3102

https://doi.org/10.1016/0031-9422(92)83452-5 Get rights and content

Abstract

The occurrence of flavonoid p-coumaroylglucosides and 8-hydroxyflavone 7-allosylglucosides is restricted, in the Labiatae, to some genera of subfamily Lamioideae (tribe Stachydeae). Generally both types of compounds do not co-occur in the same species. Thus, flavonoid p-coumaroylglucosides are present in all the species studied of the genera Ballota, Phlomis and Marrubium, and are universally present in the subgenus Marrubiastrum of Sideritis, in subgenus Galeopsis and in section Betonica of genus Stachys, while 8-hydroxyflavone 7-allosylglucosides accumulate in the other Sideritis, Stachys and Galeopsis species. Amongst the flavonoid p-coumaroylglucosides, the apigenin derivatives occur most frequently but also the corresponding luteolin, chrysoeriol, kaempforol and isorhamnetin glycosides have been detected. The 8-hydroxyflavone allosylglucosides occur as such and also as the monoacetylated and diacetylated derivatives. The presence of p-coumaroylglucosides and/or 8-hydroxyflavone allosylglucosides shows the affinities of Anisomeles, Pogostemon, and Leonurus species with Ballota, Marrubium, Phlomis, Sideritis, Stachys and Galeopsis species. These results suggest that flavonoid p-coumaroylglucosides are valuable markers for chemotaxonomic studies.

References (22)

F.A. Tomás-Barberán et al.
Phytochemistry
(1988)
M.A.M. Nawwar et al.
Phytochemistry
(1989)
F. Tomás et al.
Phytochemistry
(1986)
A. Lenherr et al.
Phytochemistry
(1987)
A. Lenherr et al.
Phytochemistry
(1984)
M.A. El-Ansari et al.
Phytochemistry
(1991)
J.B. Harborne et al.
Phytochemistry
(1986)
F.A.T. Barberán et al.
Phytochemistry
(1984)
F.A. Tomás-Barberán et al.
Phytochemistry
(1991)
S.I. El-Negoumy et al.
Phytochemistry
(1986)

R. Kumar et al.

Phytochemistry

(1985)

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Citation Excerpt :
Samples UG3-12 and UG3-13 are located in positive part of PC1 as a result of the very high amount of apigenin 7-O-(4″-p-coumaroylglucoside) (31) and a significant portion of phenylethanoids and flavonoids. Apigenin 7-O-glucoside has been previously found in the samples of S. taurica (Aboutabl et al., 2002), S. syriaca (Armata et al., 2008) and together with apigenin 7-(4″-p-coumaroylglucoside) (31) have been identified in Spanish Sideritis samples (Barberán et al., 1992; Gil et al., 1993). But, Barberán et al. (1992) did not report apigenin 7-O-glucoside (20) and apigenin 7-(4″-p-coumaroylglucoside) (31) in the species belonging to the Empedoclea section (S. syriaca, S. scardica) and Sideritis section.
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Eight compounds were detected in all analyzed Sideritis samples: 5-caffeoylquinic acid, lavandulifolioside, verbascoside, isoscutellarein 7-O-allosyl(1→2)glucoside, hypolaetin 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside, isoscutellarein 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside, 3′-O-methylhypolaetin 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside and 4′-O-methylhypolaetin 7-O-[6‴-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glucoside). They present from 50 to 80% of total phenolic content in S. scardica, S. raeseri, S. syriaca and S. taurica and up to 90% in S. lanata and the similarity of their polyphenolic profiles implies that they are systematically very closely related.
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The obtained results demonstrate considerable degree of similarity between S. scardica, S. raeseri and Bulgarian S. syriaca that give contribution to the dilemma that Bulgarian S. syriaca is very similar to Turkish S. taurica and suggest further verification of its taxonomic status.

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