Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction

Chemistry & Biodiversity

Bianco

et al. 2017

Stachys palustris, well-known as marsh woundwort, is a perennial herb growing in wet environments of Europe. Its tubers, leaves and seeds are eaten raw or cooked. Alike other Stachys species, the plant is also used as a traditional remedy. Despite S. palustris has been consumed for centuries, little is known about its chemical constituents. In this work the main secondary metabolites of S. palustris from Hungary and France have been analysed. From the plant ethanolic extracts, ethanoid glucosides, isoscutellarein derivatives, caffeoyl-quinic acids and iridoids have been isolated and structurally characterized by NMR. The essential oils were analysed by GC/MS and showed (E)-phytol, fatty acids and carbonylic compounds as the most abundant compounds. The radical scavenging capacity of plant ethanolic extracts, as evaluated by the DPPH assay, was noteworthy, with IC values of 92.08 - 105.42 μg/ml.

Section: Resultssupporting

confidence: 59%

“…Harpagide ( 6 ) and its derivative 8‐ O ‐acetyl‐harpagide ( 7 ) are chemotaxonomic markers for several genera included in the Lamiaceae family. Monomelittoside ( 8 ) was identified in this species for the first time whereas it was already known in other members of the Stachys genus and in the family itself …”

Section: Resultsmentioning

confidence: 84%

Polar Constituents, Essential Oil and Antioxidant Activity of Marsh Woundwort (Stachys palustris L.)

Chemistry & Biodiversity

Bianco

et al. 2017

“…Ajuga tenorei and Ajuga chamaepitys ) [25,26], although its presence was also signaled in a few Lamioideae species as Melittis melissophyllum subsp. melissophyllum [19] and species of the genera Stachys and Sideritis . The occurrence of 1 in the Stachys genus is limited to a few species such as B. officinalis (syn.…”

Section: Discussionmentioning

confidence: 99%

“…The eluting system was a mixture of n -BuOH/H 2 O (82:18 v/v). From this chromatographic separation (Scheme 1) 11 compounds were isolated and identified by comparison with data reported in literature and/or by comparison with pure compounds available in our laboratory: Verbascoside (10, 12.4 mg) [14] from the assembly of fractions 8-15; stachysoside A (11, 11.2 mg) [8,15] in mixture with verbascoside (1:2) in the assembly of fractions 17-24; b-arbutin (9, 3.2 mg) [16] from the assembly of fractions 30-32; reptoside (6) [17] and 6-O-acetyl-ajugol (7) [18] in mixture in ratio 1:1.5 (25.0 mg) from the assembly of fractions 43-45; ajugoside (1, 113.7 mg) [17,19] as pure compound from the assembly of fractions 53-54; 8-O-acetyl-harpagide (2, 1.0 g) [20] from the assembly of fractions 70-88; chlorogenic acid (8) [21] in mixture with 8-O-acetyl-harpagide (2) in ratio 1:2 (109.4 mg) from the assembly of fractions 95-112; harpagide (3) [22] and chlorogenic acid (8) in mixture 3:1 (48.3 mg) from the assembly of fractions 118-122; allobetonicoside (4) and chlorogenic acid (8) in mixture 10:1 (29.1 mg) from the assembly of fractions 133-135; allobetonicoside (4, 100.7 mg) [23] as a pure compound from the assembly of fractions 144-163; 4¢-O-galactopyranosyl-teuhircoside (5) [6] in mixture with allobetonicoside (4) in ratio 3:1 (24.7 mg) from the assembly of fractions 166-169.…”

Section: Methodsmentioning

confidence: 99%

Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

J Intercult Ethnopharmacol

Lorenzetti

et al. 2017

Background:The phytochemical analysis of Stachys alopecuros subsp. divulsa, an endemic Italian species, has been recently reported and has showed the presence of 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), and 4¢-O-galactopyranosyl-teuhircoside (5). In this paper, an in deep study of its glycosidic fraction with the aim to widen the knowledge on its secondary metabolites content is reported.Materials and Methods:Chromatographic techniques were used for the isolation of constituents while spectroscopic and spectrometric techniques were applied for the structures elucidation.Results:Besides the known constituents, all of them reconfirmed, ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7) were also identified among the iridoids while the phenolic components resulted to be chlorogenic acid (8), b-arbutin (9), verbascoside (10), and stachysoside A (11), instead.Conclusion:The iridoid pattern of S. alopecuros subsp. divulsa has been expanded with the identification of not previously reported compounds as well as for the phenolic fraction. Except for the reconfirmed verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported, and both the chemotaxonomic and pharmacological relevance of the isolated compounds is largely discussed.

“…Only a couple of previous works have focused on the composition of the essential oil from this particular subspecies [3,8], while no study has ever been made of the polar fraction. With the idea of completing the molecular pattern of this species and continuing our recent study on this genus [9], which showed the presence of monomelittoside, melittoside, harpagide, 8-O-acetyl-harpagide, ajugoside and allobetonicoside, we have then decided to proceed with the analysis of a sample of subsp. albida collected in Central Italy.…”

mentioning

confidence: 99%

Constituents of Melittis melissophyllum subsp. albida

Natural Product Communications

Caretti

et al. 2016

In this paper, for the first time, we have reported the analysis of the polar fraction of Melittis melissophyllum subsp. albida, a species with ecological relevance which is also used in traditional medicine of Central-Southern Italy. Iridoid glucosides were mainly identified, together with verbascoside, an ubiquitous phenyl-ethanoid glycoside, with chemotaxonomic implications in Lamiales order. The majority of the isolated compounds is endowed with interesting bioactivities and may justify the traditional uses of this plant also from a chemical point of view. Several peculiarities were also recorded in the metabolic pattern of this subspecies, i.e. the presence of virginioside and geniposidic acid, two rare compounds in the Lamiaceae family. The presence of free cinnamic acid was an additional characteristic of this subspecies which showed a specific secondary metabolites content. These phytochemical peculiarities, together with the morphological differences showed by the subsp. albida in respect to the nominal species, may be a base for a reconsideration of the systematic of Melittis melissophyllum subsp. albida.