50940-26-6

Upstream product

• 108-24-7 acetic anhydride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 141-82-2 malonic acid 
• 540-38-5 p-Iodophenol 
• 79-10-7 acrylic acid 
• 114916-04-0 N¹,N⁵-di-(E)-coumaroyl-spermidine 
• 50-99-7 D-glucose 
• 105-53-3 diethyl malonate 
• 3943-97-3 methyl p-hydroxycinnamate 
• 578-86-9 liquiritigenin 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 7400-08-0 p-Coumaric Acid 
• 29588-94-1 N-phthaloyl-L-tyrosine 
• 1225064-68-5 kankanoside H₂ 

Downstream Products

• 76457-47-1 4-(3-oxy-[1,2,3]oxadiazol-5-yl)-phenol 
• 140170-46-3 8-acetyl-3,4-dihydro-5,7-dihydroxy-6-methyl-4-(4-hydroxyphenyl)coumarin 
• 140170-45-2 6-acetyl-3,4-dihydro-5,7-dihydroxy-8-methyl-4-(4-hydroxyphenyl)coumarin 
• 140170-39-4 methyl 3-(5-acetyl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadienyl)-3-(4-hydroxyphenyl)propanoate 
• 188707-50-8 Heptanoic acid 4-((E)-2-carboxy-vinyl)-phenyl ester 
• 52820-26-5 4-hydroxyphenylacryloyl chloride 
• 140654-51-9 Heptanoic acid 4-((E)-2-chlorocarbonyl-vinyl)-phenyl ester 
• 140654-52-0 Octanoic acid 4-((E)-2-chlorocarbonyl-vinyl)-phenyl ester 

Relevant academic research and scientific papers

Metabolites of orally administered Perilla frutescens extract in rats and humans

As a part of our search for bioactive substances from the leaves of Perilla frutescens BRITTON var. acuta KUDO, (Perillae Herba, Labiatae), the aqueous extract was orally administered to rats and humans, and metabolites in the urine, plasma, and/or bile were analyzed by a high-performance liquid chromatograph (HPLC) equipped with a photodiode array detector. When the extract was administered to rats, 10 metabolites, trans-caffeic acid-4-O- sulfate (1), trans-p-coumaric acid-4-O-sulfate (2), trans-ferulic acid-4-O- sulfate (3), trans-m-coumaric acid-3-O-sulfate (4), trans-caffeic acid (5), m-hydroxyphenylpropionic acid (6), trans-p-coumaric acid (7), trans-m- coumaric acid (8), luteolin (9), and apigenin (10) were detected in the urine, whereas four metabolites, scutellarein-6, 7-di-O-β-glucuronide (11), apigenin-4'-O-sulfate-7-O-β-glucuronide (12), apigenin-7-O-β-glucuronide (13), and diosmetin-7-Oβ-glucuronide (14) were found in the bile. Compounds 1-8 and 11-14 were also found in the plasma. When the extract was given to humans, however, two metabolites, 1-O-(2,4,5-trimethoxycinnamoyl)-β- glucuronic acid (15) and apigenin-4'-O-β-glucuronide (16), were found in the urine and plasma. Thus, a species difference in the metabolism of the extract constituents was observed between rats and humans. Structures 1-16 were identified based on their chemical and spectral data.

Saponins and acylated saponins from Dizygotheca kerchoveana

Nine saponins and two acylated saponins were isolated from the leaves and the stem of branches of Dizygotheca kerchoveana. Their structures were established by chemical and spectroscopic means. Four new triterpenoid saponins were isolated from the leaves and stem of branches of Dizygotheca kerchoveana along with seven known ones. The new saponins were respectively characterized as 3-O-[β-d-glucopyranosyl-(1 → 3)]-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl echinocystic acid, 3-O-[β-d-glucopyranosyl- (1 → 3)]-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl echinocystic acid 28-O-[α-l-rhamnopyranosyl-(1 → 4)-β-d- glucopyranosyl-(1 → 6)-β-d-glucopyranosyl] ester, 3-O-[β-d-3-O- trans-p-coumaroyl-glucopyranosyl-(1 → 3)]-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl echinocystic acid 28-O-[α-l- rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl] ester and 3-O-[β-d-3-O-cis-p-coumaroyl- glucopyranosyl-(1 → 3)]-[β-d-glucopyranosyl-(1 → 2)]-α-l-arabinopyranosyl echinocystic acid 28-O-[α-l- rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl] ester. Their structures were elucidated by 1D and 2D NMR experiments, FAB-MS as well as chemical means.

Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana

A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana resulted in the isolation and characterization of two new triterpenoids, 23-trans-p-coumaroyloxy-2α,3α-dihydroxyolean-12-en-28-oic acid (1), and 23-cis-p-coumaroyloxy-2α,3α-dihydroxyolean-12-en-28-oic acid (2), along with seven known triterpenoids (3-9). The structures of the new compounds were determined on the basis of spectroscopic analyses including 2D NMR. The cytotoxic activities of the triterpenes (1-9) were evaluated by determining their inhibitory effects on human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) using the SRB assay. Compounds 5 and 6 showed potent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines (IC50 (5): 4.37, 7.04, 9.72, and 5.83 μM, and IC50 (6): 5.57, 7.84, 13.29, and 5.61 μM, respectively).

Phytochemical study of Juglans regia L. leaves

A methanolic extract of Juglans regia L. leaves was fractioned by various chromatographic techniques yielding a total of 40 metabolites belonging to megastigmane, tetralone, phenylpropanoid, neolignane and juglone glycosides. Ten unknown megastigmane glucoside derivatives (juglanionosides A-K, 1–10) and six unknown tetralone glucoside derivatives (juglanosides J-O, 11–16) together with 24 known compounds - among them 16 described for the first time in Juglans - were isolated. As characteristic structural feature, the previously undescribed compounds showed acylation of the sugar units with sinapic, ferulic, coumaric, benzoic or salicylic acid. Their chemical structures were elucidated on the basis of 1D and 2D NMR techniques, HRESIMS as well as CD spectroscopy. Absolute stereochemistry was revealed by mild alkaline hydrolysis and comparison of CD and polarimetric data to literature values.

A new phenolic glycoside from Spiraea prunifolia var. simpliciflora twigs

The phytochemical investigation of the methanol extract from the twigs of Spiraea prunifolia var. simpliciflora (Rosaceae) using column chromatography led to the isolation of a new phenol glycoside, 1-O-(E)-caffeoyl-2-O-p-(E)-coumaroyl-β-d-glucopyranose (1), together with 16 known phenolic compounds (2-17). The structure of this new compound was elucidated by analysis of spectroscopic data including 1D, 2D nuclear magnetic resonance and HR-FAB-MS data. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using the sulforhodamine B bioassay.

Black goji as a potential source of natural color in a wide pH range

Lycium ruthenicum Murr. is a traditional Chinese herb widely distributed in Tibet. The fruit, known as black goji, is popular in traditional Chinese medicine. The objective of this study was to investigate its anthocyanin profile (by HPLC coupled to PDA and MS detectors) and the colorimetric and spectrophotometric properties. Black goji extracts contained abundant petunidin derivatives, with cis and trans isomers of petunidin-3-p-coumaroyl-rutinoside-5-glucoside. The colorimetric and spectrophotometric traits of black goji anthocyanins were significantly impacted by solid-phase-extraction, pH, and acylation. MCX cartridge removed considerable polyphenolics from fruit extracts, but attenuated the saturation of color expression. Petunidin-3-trans-p-coumaroyl-rutinoside-5-glucoside contributed most of the color expression of the black goji extract, and showed superior stability compared to other extracts over time. Acylation strengthened the petunidin derivatives color retention, and enhanced the color intensity and stability. Black goji anthocyanins produced various vivid hues over wide ranges of pH, making them promising candidates for natural colorants.

Cytotoxic phenolic compounds in leaf buds of Populus tremuloides

Phytochemical investigations of the EtOH extract of Populus tremuloides leaf buds led to the isolation of 19 phenolic compounds. Among them, (1S,2S)-1-[4-0-E-coumaroyl-β-D-glucopyranosyloxy]cyclohexanediol was reported for the first time, and its structur

Hybrid biosynthesis of roseobacticides from algal and bacterial precursor molecules

Roseobacticides regulate the symbiotic relationship between a marine bacterium (Phaeobacter inhibens) and a marine microalga (Emiliania huxleyi). This relationship can be mutualistic, when the algal host provides food for the bacteria and the bacteria produce growth hormones and antibiotics for the algae, or parasitic, when the algae senesce and release p-coumaric acid. The released p-coumaric acid causes the bacteria to synthesize roseobacticides, which are nM-μM toxins for the algae. We examined the biosynthesis of roseobacticides and report that all roseobacticide precursors play critical roles during the mutualist phase of the symbiosis. Roseobacticides are biosynthesized from the algal growth promoter, the major food molecule provided by the algal cells, and the algal senescence signal that initiates the mutualist-to-parasite switch. Thus, molecules that are beneficial during mutualism are diverted to the synthesis of toxins during parasitism. A plausible mechanism for assembling roseobacticides from these molecules is proposed.

Revelation of the Balanol Biosynthetic Pathway in Tolypocladium ophioglossoides

A cryptic gene cluster, bln, was activated by genome mining in Tolypocladium ophioglossoides. This activation led to the production of balanol and eight other metabolites. Gene disruption and metabolite profile analysis showed that the biosynthesis of balanol involved the convergence of independent PKS and NRPS pathways, and a biosynthetic pathway for balanol was proposed.

Covalently linked anthocyanin-flavonol pigments from blue Agapanthus flowers

The structures of the two major anthocyanins in blue Agapanthus flowers have been determined to be a p-coumaroylated delphinidin diglycoside attached to a flavonol triglycoside via a succinic acid diester link. The structure has been determined unambiguously through degradation studies, glycosidic analysis and NMR experiments. These compounds represent unique examples of anthocyanin pigments where both types of co-pigment, an aromatic acyl group and a flavonoid co-pigment, are attached covalently to the anthocyanin. (C) 2000 Elsevier Science Ltd.