Allium Species from Central and Southwest Asia Are Rich Sources of Marasmin

Abstract

Marasmin, which is especially known from the two South African species Tulbaghia alliacea and Tulbaghia violacea , but was also described for the garlic mushroom Marasmius alliaceus , is the precursor of the thiosulfinate marasmicin. Marasmicin has attracted considerable attention because of its antifungal and tuberculostatic activities. However, many Allium species of the subgenus Melanocrommyum, especially Allium suworowii , are also very rich in marasmin. A. suworowii revealed concentrations of marasmin up to 1.6%, related to the fresh weight of bulbs, and up to 3.0%, related to air-dried fruiting bodies, of the corresponding γ-glutamylmarsmin was found in M. alliaceus. Both species show much higher amounts of marasmin as Tulbaghia and could be considered as natural sources for the isolation of this compound. Further promising Allium species with considerable amounts of marasmin besides other cysteine sulfoxides are Allium stipitatum and Allium altissimum . (R(S),R(C))-Marasmin is typical for the investigated species of the subgenus Melanocrommyum, whereas γ-glutamyl-(S(S),R(C))-marasmin is the only cysteine sulfoxide for the genus Marasmius known until now. Both cysteine sulfoxides were isolated and described as o-phthaldialdehyde (OPA) derivatives. Furthermore, the cysteine sulfoxides methiin, propiin, S-(2-pyrrolyl)-cysteine sulfoxide, eventually S-(2-pyridyl)-cysteine sulfoxide and S-(2-pyridyl)-L-cysteine N-oxide were found.

Flavor Precursors and Sensory-Active Sulfur Compounds in Alliaceae Species Native to South Africa and South America

“…1 seems to be present abundantly in all Allioideae species, including members of the Allium subgenera Melanocrommyum, Caloscordum, and Nectaroscordum. 4,[6][7][8][9][10][13][14][15][16][17]37,38 On the contrary, the present study revealed that Tulbaghioideae and Gilliesioideae plants accumulate 1 only at trace levels (if at all) and 11 is the principal derivative present in these species. Furthermore, the threecarbon side chain derivatives [i.e., 3, 4, and propiin (5)] are present only in Allium species, excluding members of the subgenera Nectaroscordum, Caloscordum, and Melanocrommyum which do not contain 3−5 at significant levels.…”

“…siculum and A. tripedale) are significantly distinct from all other alliaceous species in their ability to synthesize two four-carbon side chain derivatives, namely, S -butyl- and ( E )- S -(1-butenyl)cysteine S- oxides ( 7 and 8 , butiin and homoisoalliin, respectively). − Finally, subgenus Melanocrommyum species are characterized by the presence of 11 and two unusual heterocyclic derivatives, i.e., S -(2-pyrrolyl)cysteine S -oxide ( 9 ) and S -(2-pyridyl)cysteine N -oxide ( 10 ). ,, …”

Identification and expression analysis of S-alk(en)yl-L-cysteine sulfoxide lyase isoform genes and determination of allicin contents in Allium species

“…Allium L. is one of the largest genera in the family of the Amaryllidaceae, encompassing over 900 species [1,2]. The main center of its diversity is central Asia, including the territory of Iran and the Mediterranean, while the second distribution center for garlic and many Allium is western North America [3][4][5][6].…”

Allium ekimianum: a new species (Amaryllidaceae) from Turkey

“…The genus Allium L. is one of the largest monocotyledonous genera with c. 900 species distributed world-wide (Govaerts et al 2013, Keusgen et al 2011). The genus was formerly included in the Liliaceae family, but the (APG)Angiosperm Phylogeny Group reassessed the taxonomic position of this genus and finally Allium was placed in the Amaryllidaceae family (APG III 2009).…”