Flavonoid glucuronides and a chromone from the aquatic macrophyte Stratiotes aloides.
The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-beta-D-glucopyranosiduronic acid-(1-->2)-beta-D-glucopyranoside (1) and chrysoeriol 7-O-beta-D-glucopyranosiduronic acid-(1-->2)-beta-D-glucopyranoside (2), as well as the new 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone (5) and chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside (3), which has been assigned via NMR data for the first time. Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside alpha-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-beta-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50-300 microg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 microM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens.
Conrad
Jürgen
J
Institute für Chemie and Zoologie, Universitat Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany. chemconn@uni-hohenheim.de
Förster-Fromme
Bernhard
B
Constantin
Mihaela-Anca
MA
Ondrus
Vladimir
V
Mika
Sabine
S
Mert-Balci
Fadime
F
Klaiber
Iris
I
Pfannstiel
Jens
J
Möller
Wolfgang
W
Rösner
Harald
H
Förster-Fromme
Karin
K
Beifuss
Uwe
U
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D016972:Enterobacter cloacae / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005618:Fresh Water; D005858:Germany; D005960:Glucosides; D020719:Glucuronides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D031321:Hydrocharitaceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D016958:Pseudomonas putida / Q000187:drug effects; D013237:Stereoisomerism; D014315:Triterpenes
C550783:2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone; D000972:Antineoplastic Agents, Phytogenic; D002867:Chromones; D005419:Flavonoids; D005960:Glucosides; D020719:Glucuronides; D014315:Triterpenes; C516764:cucurbitacin G 2-O-beta-D-glucopyranoside; C550784:luteolin 7-O-beta-D-glucopyranosiduronic acid-(1-2)-beta-D-glucopyranoside