41137-85-3

Usage

Uses

Due to the limited information available about 5-Hydroxyplatyphyllone M, it is currently not possible to list its specific applications or uses in various industries. Further research and studies are needed to determine its potential applications and benefits.

Upstream product

• 93559-18-3 4-(2-{2-[4-(4-Benzyloxy-phenyl)-2-hydroxy-butyl]-[1,3]dioxolan-2-yl}-ethyl)-phenol 
• 256946-24-4 5-hydroxy-1,7-bis-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-heptan-3-one 
• 52328-96-8 bis-demethoxycurcumin 
• 123-08-0 4-hydroxy-benzaldehyde 
• 123-54-6 acetylacetone 
• 7074-09-1 4-[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]butan-2-one 
• 113482-94-3 1,7-bis(4-hydroxyphenyl)heptane-3,5-dione 
• 288141-04-8 (S)-1,7-bis-(4-hydroxyphenyl)heptan-3-one-5-O-β-D-xylopyranoside 
• 22608-12-4 bisdemethoxycurcumin 
• 93559-06-9 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 93559-09-2 {2-[2-(4-Hydroxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 
• 93559-11-6 {2-[2-(4-Hydroxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetaldehyde 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 256946-28-8 3-(4'-pyranyloxyphenyl)propanol 

Downstream Products

• 56973-65-0 1,7‐bis(4‐hydroxyphenyl)‐4‐hepten‐3‐one 
• 30359-01-4 (3R)-1,7-bis(4'-hydroxyphenyl)-3-heptanol 
• 1415609-97-0 C₂₉H₂₉F₃O₆ 
• 1415609-96-9 C₂₉H₂₉F₃O₆ 
• 56973-64-9 3,5-dihydroxy-1,7-bis(4-hydroxyphenyl)-heptane 

Relevant academic research and scientific papers

A new diarylheptanoid glycoside from the stem bark of Alnus hirsuta and protective effects of diarylheptanoid derivatives in human HepG2 cells

To search for secondary metabolites of Alnus hirsuta (Betulaceae), various chromatographic separations of the ethyl acetate soluble fraction of the stem bark of A. hirsuta led to the isolation of a new diarylheptanoid glycoside, (3R)-1,7-bis-(4-dihydroxyphenyl)-3-heptanol 3-O-β-D- glucopyranosyl(1→3)-β-D-xylopyranoside (13) and twelve diarylheptanoid derivatives, namely, oregonin (1), rubranoside A (2), hirsutanonol 5-O-β-D-glucopyranoside (3), rubranoside B (4), rubranoside C (5), hirsutanonol (6), hirsutenone (7), (5S)-O-methylhirsutanonol (8), platyphylloside (9), platyphyllonol 5-O-β-D-xylopyranoside (10), aceroside VII (11) and platyphyllenone (12). Isolates were assessed for their hepatoprotective effects against tert-butylhydroperoxide (t-BHP)-induced toxicity in HepG2 cells. Of these isolates, compounds 1 - 8 showed significant hepatoprotective effects on t-BHP-induced damage to HepG2 cells, with 8 exhibiting the greatest protective effect (50.7±3.7% at a concentration of 10 μM).

Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells

The chemically modified analogs, the demethy-lated analogs 4-6, the tetrahydro analogs 7-9 and the hexahydro analogs 10-12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O- demethyldemethoxycurcumin (6) are the two most potent compounds that inhibited NO production. The analogs 5 and 6 were twofold and almost twofold more active than the parent curcuminoids 1 and 2, respectively. Moreover, the mRNA expression level of inducible NO synthase was inhibited by these two compounds. The strong neuroprotective activity of analogs 5 and 6 provide potential alternative compounds to be developed as therapeutics for neurological disorders associated with activated microglia. The Japanese Society of Pharmacognosy and Springer 2011.

Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species

The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1:1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Trypanosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 μM, respectively). Among 43 curcuminoid analogs and 8 pairs of 1:1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in submicromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 ± 0.007 μM; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 ± 0.01 μM). Using a previously characterized diminazene-resistant T. b. brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against T. b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 ± 3 and 37 ± 6 μM, respectively) while the control drug, pentamidine, displayed an EC50 of 16 ± 2 μM. Among the active curcuminoid analogs, four compounds exhibited EC50 values of less than 5 μM against Leishmania major promastigotes and four against L. mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T. b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T. b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold.

Curcuminoids form reactive glucuronides in vitro

Curcumin is of current interest because of its putative anti-inflammatory, anticarcinogenic, and anti-Alzheimer's activity, but its pharmacokinetic and metabolic fate is poorly understood. The present in vitro study has therefore been conducted on the glucuronidation of curcumin and its major phase I metabolite, hexahydro-curcumin, as well as of various natural and artificial analogs. The predominant glucuronide generated by rat and human liver microsomes from curcumin, hexahydro-curcumin, and other analogs with a phenolic hydroxyl group was a phenolic glucuronide according to LC-MS/MS analysis. However, a second glucuronide carrying the glucuronic acid moiety at the alcoholic hydroxyl group was formed from the same curcuminoids, but not hexahydro-curcuminoids, by human microsomes. Curcuminoids without a phenolic hydroxyl group gave rise to the aliphatic glucuronide only. The phenolic glucuronides of curcuminoids, but not of hexahydro-curcuminoids, were rather lipophilic and, in part, unstable in aqueous solution, their stability depending strongly on the type of aromatic substitution. The phenolic glucuronide of curcumin and of its natural congeners, but not the parent compounds, clearly inhibited the assembly of microtubule proteins under cell-free conditions, implying chemical reactivity of the glucuronides. These novel properties of the major phase II metabolites of curcuminoids deserve further investigation.

Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver

Curcumin and its natural congeners are of current interest because of their putative anti-inflammatory and anticarcinogenic activities, but knowledge about their metabolic fate is scant. In the present study conducted with precision-cut liver slices from

Minor diarylheptanoid glycosides of Alnus rubra bark

The diarylheptanoid (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-β-D- xylopyranoside, and two known compounds, 1,7-bis(3,4-dihydroxyphenyl)-heptan- 3-one-5-O-β-D-glucopyranoside and platyphylloside were isolated from Alnus rubra bark. Structures were es

Synthesis and digestibility inhibition of diarylheptanoids: Structure- activity relationship

(±)-5-Hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone (2a), (±)5- hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone (2b), (±)-5-hydroxy-7- (4'-hydroxyphenyl)-1-phenyl-3-heptanone (2c), and (±)-5-hydroxy-1,7- bis(phenyl)-3-heptanone (2d) have been synthesized to study the structure- activity relationship regarding digestibility inhibition in vitro in cow rumen fluid. The activities were compared with the activity of chiral (S)-2a and its glucoside platyphylloside (1), isolated from Betula pendula. Compound 2a was slightly less active, 2b and 2c were more active, and 2d was less active than (S)-2a and platyphylloside.

Absolute Configuration of Platyphylloside and (-)-Centrolobol

The ansolute configuration of platyphylloside was established to be S by 13C NMR spectroscopy.On the basis of this establishment, the S-configuration previously assigned to the chirality at C-3 of (-)-centrolobol was revised to the R-configuration.

NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 47. A GENERAL, EFFICIENT, AND CONVENIENT SYNTHESIS OF DIARYLHEPTANOIDS

An efficient synthesis of physiologically interesting diarylheptanoids has been carried out through direct C-acylation using diethyl phosphorocyanidate (DEPC) followed by Grignard reactions with aldehydes.Keywords - diarylheptanoid; C-acylation; diethyl p