Glucosinolates of Lepidium graminifolium L. (Brassicaceae) from Croatia

Abstract

The glucosinolate (GSL) profiles (inflorescence, stem, root, and fruit) of the wild-growing plant Lepidium graminifolium L. (Brassicaceae) from Croatia was established by LC-MS analysis. During this investigation, we confirmed the presence of benzyl-(1), 3-methoxybenzyl-(2), 4-hydroxybenzyl-(4), 4methoxyindol-3-ylmethyl-(7) GSLs and reported for the first time in the plant the presence of (2R)-hydroxybut-3-enyl-(11), (2S)-hydroxybut-3-enyl-(12), but-3-enyl-(13), and 2-phenylethyl-(14) GSLs. Finally, 3-hydroxybenzyl GSL (3) was isolated for the first time from L. graminifolium inflorescence and characterized by spectroscopic data interpretation.

Glucosinolates in Wild-Growing Reseda spp. from Croatia

“…Fragments from the elimination of anhydrorhamnose, anhydroglucose, and thioglucose (fragment h ) were observed, with the characteristic fragment m / z 334 resulting from the loss of glucose ( m / z 180). Glucolepigramin ( 22 ) was identified only in the flower (8.66 µmol g − 1 DW) using desulfoglucolepigramin as a standard isolated from Lepidium graminifolium [ 38 ], corroborating a recent discovery [ 29 ].…”

“…The specimen vouchers were stored under numbers ZOKRA1, ZOKRL1, and ZOKRF1. Sinigrin, DEAE-Sephadex A-25 (GE Healthcare), and sulfatase (type H-1 from Helix pomatia) were purchased from Sigma-Aldrich (St. Louis, MO, USA); glucotropaeolin ( 11 ), glucobrassicin ( 43 ), N -methoxyglucobrassicin ( 47 ), and gluconasturtiin ( 105 ) were obtained from Phytoplan Diehm & Neuberger GmbH (Heidelberg, Germany); while glucolepigramin ( 22 ) was previously isolated from L. graminifolium [ 38 ]. All other chemicals and reagents were of analytical grade.…”

Lepidium graminifolium L.: Glucosinolate Profile and Antiproliferative Potential of Volatile Isolates

“…The major GSL in the root from the Split sample was benzyl GSL ( 9 ), followed by 3,4,5-trimethoxybenzyl GSL ( 11 ) and 7 , with 61.69, 35.20 and 20.56 μmol/g of DW, respectively. Highly substituted arylaliphatic GSLs are usually restricted to a few genera (e.g., Matthiola , Lepidium ) [ 5 , 16 ]. To our knowledge, however, 11 was reported only in Lepidium species : L. hyssopifolium Desv., L. coronopus (L.) Al-Shebbaz, L. sordidum A.…”

“…Indol-3-ylmethyl GSL, 4-methoxyindol-3-ylmethyl GSL, and 1-methoxyindol-3-ylmethyl GSL were also detected by HPLC analysis of seedlings [ 15 ]. A systematic qualitative investigation of the GSL profile of L. graminifolium wild-growing in Croatia was performed using LC-MS of intact GSLs, and the major GSL, 7 , was isolated and characterized using spectroscopic techniques [ 16 ]. The presence of 6 , 9 , 12 and 4-methoxyindol-3-ylmethyl GSL was confirmed, while the presence of ( 2R )-hydroxybut-3-enyl GSL ( 1 ), ( 2S )-hydroxybut-3-enyl GSL ( 3 ), but-3-enyl GSL ( 4 ), and 2-phenylethyl GSL ( 13 ) was reported for the first time [ 16 ].…”

“…A systematic qualitative investigation of the GSL profile of L. graminifolium wild-growing in Croatia was performed using LC-MS of intact GSLs, and the major GSL, 7 , was isolated and characterized using spectroscopic techniques [ 16 ]. The presence of 6 , 9 , 12 and 4-methoxyindol-3-ylmethyl GSL was confirmed, while the presence of ( 2R )-hydroxybut-3-enyl GSL ( 1 ), ( 2S )-hydroxybut-3-enyl GSL ( 3 ), but-3-enyl GSL ( 4 ), and 2-phenylethyl GSL ( 13 ) was reported for the first time [ 16 ]. However, all previous reports provided no information on the GSL quantity in L. graminifolium , especially important due to the presence of non-ubiquitous substituted benzylic-type GSLs.…”