Steroidal Alkaloid Glycosides from Tomato (Lycopersiconesculentum)

Abstract

Three new steroidal alkaloid glycosides, lycoperosides F-H (1-3), were isolated from tomato fruits (Lycopersicon sculentum) along with lycoperosides A-D, esculeoside A, and rutin. The structures of these glycosides were characterized as the 3-O-beta-lycotetraosides of 23(R)-23-acetoxy-27-hydroxy-27-O-beta-d-glucopyranosyltomatidine (1), (23S,24R)-23-acetoxy-24-O-beta-d-glucopyranosylsoladulcidine-24-ol (2), and 22-isopimpifolidine (3), by means of their spectroscopic data. Also obtained was the new natural product lycoperodine-1 (4).

Profiling of secondary metabolites in root exudates of Arabidopsis thaliana

“…In addition, a simple b-carboline alkaloid (10) previously reported to accumulate in tomato fruits (Yahara et al, 2004) was identified using a synthetic reference compound prepared from Trp and formaldehyde (Tilstra et al, 1990). While other proteinogenic amino acids were not detected using the established analytical method, the more hydrophobic side chain-elongated Met homologs (11, 12) and their Soxides (13, 14) were putatively identified based on the elemental composition, the presence of three exchangeable protons and the occurrence of characteristic neutral losses of 46.01 Da (HCOOH) and 48.00 Da (CH 3 SH)/64.00 Da (CH 3 SOH) in the CID mass spectra of the [M+H] + ions.…”

(R/S)‐BINOL‐α‐Phosphoryloxy Enecarbamate‐Mediated and (R/S)‐Titanium(IV) BINOLates‐Catalyzed Enantioselective Intramolecular Heck/Aza‐Diels–Alder Cycloaddition (IHADA): An Expedient Methodology

“…Similar results were obtained in the absence of imine (dienophile) where the [4p + 2p] cycloadduct was formed between the two molecules of chiral aPPC2a enantioselectively and afforded the stereoisomers tHP2a and tHP2b in a 97.5:2.5 ratio. The stereochemistry of the obtained tHP1a-2a was determined through converting them to their deprotected analogues (S)-2,3,4,9-tetrahydro-1H-pyrido-A C H T U N G T R E N N U N G [3,4-b]indole-3-carboxylic acid [21] known in the literature by treating them with HCl-dioxane followed by basic hydrolysis. Utilization of different imines D3-D18 (Table 3) as dienophile imine, provided moderate to good yields with excellent enantioselectivities for the compounds tHP3a-10a and oHPP1a-17a [22] under the optimized reaction conditions.…”

New Solanocapsine-Type Tomato Glycoside from Ripe Fruit of Solanum lycopersicum

“…1. [6][7][8] Esculeoside B-1 (2) corresponds to an isomer of esculeoside A (1).9) Detailed investigation of the constituents of local Italian tomatoes, processed tomato products, and imported canned tomatoes, tomato juice, and ketchup is currently in progress. Esculeoside B-1 (2) is the first example of a solanocapsine-type steroidal alkaloid glycoside, the fundamental skeleton of which is very rare and interesting in terms of its chemical structure and unknown pharmacological activity.…”

“…1. [6][7][8] Esculeoside B-1 (2) corresponds to an isomer of esculeoside A (1). 9) Detailed investigation of the constituents of local Italian tomatoes, processed tomato products, and imported canned tomatoes, tomato juice, and ketchup is currently in progress.…”