946831-51-2

Upstream product

• 1386974-96-4 rhamnocitrin-3-O-{(3S)-hydroxy-3-methyl-5-[(S)-1-phenylethylamino]glutaryl-(1->6)}-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 
• 1391144-82-3 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->4)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 
• 1391144-83-4 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-β-D-galactopyranoside 
• 1391144-84-5 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-β-D-galactopyranoside-4'-O-β-D-glucopyranoside 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 129724-80-7 (3R)-5-O-acetyl-1-<(S)-phenylethyl>-mevalonamide 

Relevant academic research and scientific papers

C-Methylated flavanones from the rhizomes of Matteuccia intermedia and their α-glucosidase inhibitory activity

One new flavanonol, demethylmatteucinol (1), and nine new flavanone glucoside derivatives, matteflavosides H-J (2–4) and matteuinterates A-F (5–10), were isolated from the rhizomes of Matteuccia intermedia C.Chr., along with 21 known flavanones (11?31). N

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America

A chemical investigation on the fruiting bodies of Fomitopsis pinicola led to the isolation and identification of 28 lanostane triterpenoids including 11 new compounds (1-11) and 17 known analogues (12-28). Their structures were elucidated by extensive on

Eudesmane Glycosides from Ambrosia artemisiifolia (Common Ragweed) as Potential Neuroprotective Agents

In Alzheimer's disease, amyloid-β (Aβ) accumulation in the brain results in neuronal cell death and is one of the major causes of dementia. Because the current therapeutic agents are not yet sufficiently effective or safe, there have been attempts to find

New C-2 diastereomers of flavanone glycosides conjugated with 3-hydroxy-3-methylglutaric acid from the pericarp of Citrus grandis (L.) Osbeck

Two new 3-hydroxy-3-methylglutaryl (HMG) flavanone 7-O-diglycosides, cigranosides A and B (1 and 2), the known naringenin 7-(2′′-α-rhamnosyl-6′′-(3′′′′-hydroxy-3′′′′-methylglutaryl)-glucoside (melitidin, 3), their common biosynthetic precursor flavanone 7-O-diglycoside (naringin, 4), and one known flavone 7-O-diglycoside (rhoifolin, 5) were isolated from the pericarp of Citrus grandis (L.) Osbeck. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The relative ratios and absolute configurations of the C-2 diastereomers of compounds 1, 2 and 4 were determined by online normal-phase HPLC-CD using a Chiralcel column. The absolute configuration of the HMG fragment in compounds 1–3 was assigned to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. The NO inhibitory activities of compounds 1–5 were evaluated using lipopolysaccharide-induced RAW264.7 cells. Compounds 1–5 were not cytotoxic to RAW264.7 cells at 10 μM.

C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus

Thirteen C-methylated flavonoid glycosides (1-13), along with 15 previously known flavonoids (14-28), were isolated from rhizomes of Pentarhizidium orientale. Among these compounds, matteuorienates D-K (1-8) were obtained as analogues of matteuorienates A-C (14-16), which contain a characteristic 3-hydroxy-3-methylglutaryl (HMG) moiety. The structures of 1-13 were characterized by spectroscopic analysis and chemical derivatization. The isolates were evaluated for their antiviral activities against influenza virus (H1N1), with compounds 21, 22, 23, 25, and 26 showing inhibitory effects (IC50 of 23.9-30.3 μM) against neuraminidases.

Flavonoids and a Limonoid from the Fruits of Citrus unshiu and Their Biological Activity

The fruits of Citrus unshiu are one of the most popular and most enjoyed fruits in Korea. As we continue to seek for bioactive metabolites from Korean natural resources, our study on the chemical constituents of the fruits of C. unshiu resulted in the isolation of a new flavonoid glycoside, limocitrunshin 1, along with seven other flavonoids 2-8 and a limonoid 9. All structures were identified by spectroscopic methods, namely 1D and 2D NMR, including HSQC, HMBC, and 1H-1H COSY experiments, HRMS, and other chemical methods. Compounds 3, 5, and 9 are reported to be isolated from this fruit for the first time. The isolated compounds were applied to activity tests to verify their inhibitory effects on inflammation and nephrotoxicity. Compounds 6 and 9 showed the most potent inhibitory activity on renal cell damage and nitric oxide production, respectively. Thus, the fruits of C. unshiu could serve as a valuable natural source of bioactive components with health benefits for potential application in functional foods.

Lanostane Triterpenes from the Tibetan Medicinal Mushroom Ganoderma leucocontextum and Their Inhibitory Effects on HMG-CoA Reductase and α-Glucosidase

(Chemical Equqation Presented). Sixteen new lanostane triterpenes, ganoleucoins A-P (1-16), together with 10 known tripterpenes (17-26), were isolated from the cultivated fruiting bodies of Ganoderma leucocontextum, a new member of the Ganoderma lucidum complex. The structures of the new compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The inhibitory effects of 1-26 on HMG-CoA reductase and α-glucosidase were tested in vitro. Compounds 1, 3, 6, 10-14, 17, 18, 23, 25, and 26 showed much stronger inhibitory activity against HMG-CoA reductase than the positive control atorvastatin. Compounds 13, 14, and 16 presented potent inhibitory activity against α-glucosidase from yeast with IC50 values of 13.6, 2.5, and 5.9 μM, respectively. In addition, the cytotoxicity of 1-26 was evaluated against the K562 and PC-3 cell lines by the MTT assay. Compounds 1, 2, 6, 7, 10, 12, 16, 18, and 25 exhibited cytotoxicity against K562 cells with IC50 values in the range 10-20 μM. Paclitaxel was used as the positive control with an IC50 value of 0.9 μM. This is the first report of secondary metabolites from this medicinal mushroom.

3-hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata

Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

A refined method for determining the absolute configuration of the 3-hydroxy-3-methylglutaryl group

A refined method for the determination of the absolute configuration of the 3-hydroxy-3-methylglutaryl group in natural products was developed. An interchange between the order of reduction with lithium borohydride and amidation with a chiral amine descri

Revised chirality of the acyl group of 8′-O-(3-hydroxy-3- methylglutaryl)-8′-hydroxyabscisic acid

The chirality of the acyl group 8′-O-(3-Hydroxy-3-methylglutaryl)- 8′-hydroxyabscisic acid was revised to S based on an HPLC analysis of the diastereomer derived from mevalonolactone obtained by reduction of the conjugate with lithium borohydride. 8′-O-(3