Triterpenoids of Pterocarpus santalinus: Constitution of a new lupene diol

The bark of Pterocarpus santalinus has been found to contain β-amyrone, lupenone, epi-lupeol, lupeol, sitosterol and a new lupene diol whose constitution has been established as lup-(20)29-en-2α,3α-diol.     

Triterpenes of five euphorbiaceae species of Sri Lanka

Five endemic species of Euphorbiaceae have been investigated. Aleuritolic acid and its derivatives were isolated from P. thwaitesii. A. cardiosperma had friedelan derivatives. The Glochidion species contained the same triterpenes, viz. glochidonol, lup-20(29)-ene-3α,23-diol and glochidiol. The bark extractives of a new Glochidion species had, in addition, glochidone and probably lup-20(29)-ene-1α,3α,23-triol. The latter is a new natural product. Glochidone was isolated for the first time outside the genus Glochidion from Bridelia moonii.     

Inhibitory effects of 3α-hydroxy-lup-20(29)-en-23, 28-dioic acid on lipopolysaccharide-induced TNF-α, IL-1β, and the high mobility group box 1 release in macrophages

We investigated the anti-inflammatory effects of 3α-hydroxy-lup-20(29)-en-23, 28-dioic acid (HLEDA)—a lupane-type triterpene isolated from leaves of Acanthopanax gracilistylus W. W.Smith (AGS), as well as the underlying molecular mechanisms in lipopolysaccharide (LPS)-induced RAW264.7 cells. Our results demonstrated that HLEDA concentration-dependently reduced the production of nitric oxide (NO), signi?cantly suppressed LPS-induced expression of TNF-α and IL-1β at the mRNA and protein levels in RAW264.7 cells. Further analysis revealed that HLEDA could reduce the secretion of High Mobility Group Box 1 (HMGB1). Additionally, the results showed that HLEDA efficiently decreased nuclear factor-kappaB (NF-κB) activation by inhibiting the degradation and phosphorylation of IκBα. These results suggest that HLEDA exerts anti-inflammatory properties in LPS-induced macrophages, possibly through inhibition of the NF-κB signaling pathway, which mediates the expression of pro-inflammatory cytokines. These results warrant further studies that would concern candidate therapy for diseases, such as fulminant hepatitis and rheumatology of triterpenoids in AGS.     

Triterpenoids of Salvia horminum,constitution of a new diol

Lupeol, lup-(20)29-ene-2α,3β-diol and a new triterpenic alcohol olean-(13)18-ene-2β,3β-diol were isolated from the petrol extract of air dried Salvia horminum and their structures were determined.     

Two triterpenoid carboxylic acids from Acanthopanax trifoliatus

Two new triterpenoid carboxylic acids have been isolated from leaves of Acanthopanax trifoliatus and their structures elucidated as 3α, 11α-dihydroxylup-20(29)-en-28-oic acid and 30α, 11α,23-trihydroxylup-20(29)-en-28-oic acid by physical data and chemical transformations.     

Triterpenoids from Salvia pinnata

A new and four known triterpenoids have been isolated from the leaves of Salvia pinnata. The structures of these compounds have been established by spectral data and by some chemical reactions.     

A lupenediol from Euonymus revolutus

A new lupane derivative isolated from Euonymus revolutus (Celastraceae) has been established to be 2α,3α-dihydroxy-lup-20(29)-en-28-oic acid on the basis of chemical interconversions and spectroscopic data.     

Two 24-nor-triterpenoid carboxylic acids from acanthopanax trifoliatus

From Acanthopanax trifoliatus the new nor-triterpenes 24-nor-3α, 11α-dihydroxy-lup-20(29)-en-28-oic acid and 24-nor-11α-hydroxy-3-oxo-lup-20(29)-en-28-oic acid were isolated. Their structures were determined on the basis of spectroscopic data, X-ray analysis and chemical transformations.     

A natural triterpene acid from Hyptis suaveolens

A new natural triterpenoid, characterized as 3β-hydroxylup-20(29)-en-27-oic acid, has been isolated from the roots of Hyptis suaveolens in additi     

3α, 11α-Dihydroxy-23-oxo-lup-20(29)-en-28-oic acid from Acanthopanax trifoliatus

The new triterpene 3α,11α-dihydroxy-23-oxo-lup-20(29)-en-28-oic acid was isolated from Acanthopanax trifoliatus. Its structure has been determined on the basis of spectroscopic data and chemical transformations.     

Three triterpenes and other terpenoids from Catha cassinoides

The investigation of stems and leaves of Catha cassinoides afforded, in addition to sitosterol, β-amyrin, ursolic acid, lup-20(29)-en-3β,30-diol and friedelin, three new pentacyclic triterpenes: 30-hydroxyfriedelan-3-one, 29-hydroxyfriedelan-3-one and 3-oxo-friedelan-29-oic acid. The structures ofthese were determined by spectral studies and correlations, and were confirmed by X-ray analysis of 29-hydroxyfriedelan-3-one acetate.     

Excretion of norsteroids’ phase II metabolites of different origin in human

The urinary phase II metabolites of norsteroids, 19-norandrosterone, 19-noretiocholanolone and 19-norepiandrosterone glucuronide and sulphate, were analyzed in samples collected during the pregnancy, following the administration of norsteroids or the consumption of edible parts of non-castrated pig and in athletes’ samples in which they were found during routine controls. The level of the sulfo- and glucuroconjugated metabolites was precisely determined by GC/HRMS, after selective hydrolysis. The goal was to evaluate whether the fine analysis of the norsteroid conjugates produced and excreted in different conditions would show a pattern that could be linked to their origin. The delta ¹³C values of the metabolites formed following the ingestion of edible parts of non-castrated pig were measured by isotope ratio mass spectrometry. Our results indicated that it is not possible to determine the origin of the urinary metabolites based upon the sole evaluation of the different metabolites and conjugates. The GC/C/IRMS is the only method permitting to distinguish between the exogenous and endogenous origin of the metabolites.     

Structure of terminic acid,a dihydroxytriterpene carboxylic acid from Terminalia arjuna

The structure of terminic acid, a new dihydroxytriterpene carboxylic acid isolated from the roots of Terminalia arjuna, has been established as 3β, 13β-dihydroxylup-20(29)-en-28-oic acid by a study of its chemical reactions and spectroscopic data. Terminic acid and its derivatives were found to undergo skeletal rearrangement under protonic conditions to yield oleanene lactone.     

Fern constituents: Cycloartane triterpenoids and allied compounds from Polypodium formosanum and P. niponicum

From the rhizomes of Polypodium formosanum, new triterpenoids of the cycloartane group, (24R)-cyclolaudenol and (24R)-cyclomargenol, were isolated as the corresponding acetates, alcohols and ketones, and their structures were established. Also, from the rhizomes of P. niponicum eight acetates of cycloartane derivatives and two acetates of new methyl sterols were isolated and characterized.     

Metabolism and conjugation of [4-14C]progesterone by bovine liver and adipose tissues, in vitro

The ability of bovine liver and fat to metabolize progesterone and also to form glucuronide conjugates with these progestins $\text{in vitro}$ was investigated. Tissue supernatants were incubated with [4-¹⁴C] progesterone, UDP-glucuronic acid, and a NADPH generating system for 5 hr, at 37°C. Steroids were identified by thin-layer chromatography, high performance liquid chromatography, and recrystallization to a constant specific activity. The total original radioactivity which could not be removed by exhaustive ether extraction (presumptive conjugates) was 44.7 ± 14.2% in liver, 5.0 ± 3.6% in subcutaneous fat, and 3.7 ± 2.2% in kidney fat samples. Progestins identified in liver samples include 5β-pregnane-3α, 20α-diol (free and conjugate), 5β-pregnane-3α, 20β-diol (free and conjugate), 3α-hydroxy-5sB-pregnan-20-one (free and conjugate), 3β-hydroxy-5β-pregnan-20-one (free), 5β-pregnane-3, 20-dione (free), and progesterone (conjugate). Progestins identified in both the free and conjugate fractions of subcutaneous fat and kidney fat samples include progesterone, 3α-hydroxy-5β-pregnan-20-one, 20β-hydroxy-4-pregnen-3-one, and 20α-hydroxy-4-pregnen-3-one. Differences due to sex of bovine used were noted. These results confirm the ability of bovine liver to readily metabolize progesterone and form glucuronide conjugates of these compounds and suggest that adipose tissues take an active role in these actions in cattle.     

Biotransformation of progesterone by suspension cultures of Digitalis purpurea cultured cells

It has been shown that the cultured cells of Digitalis purpruea are capable of transforming progesterone (I) to 5α-pregnane-3,20-dione (II), 5α-pregnan-3β-ol-20-one (III), its glucoside (IV), 5α-pregnane-3β,20α-diol (V), its glucoside (VI), 5α-pregnane-3β,20β-diol (VII), its glucoside (VIII), Δ⁴-pregnen-20α-ol-3-one (IX), its glucoside (X), Δ-pregnen-20β-ol-3-one (XI) and its glucoside (XII). 5α-Pregnan-3β-ol-20-one glucoside (IV), 5α-pregnane-3β,20α-diol glucoside (VI), 5α-pregnane-3β,20β-diol glucoside (VIII), Δ⁴-pregnen-20α-ol-3-one glucoside (X) and Δ⁴-pregnen-20β-ol-3-one glucoside (XII) have been found for the first time as new metabolises by plant tissue cultures. A scheme for the biotransformation of progesterone (I) has been proposed, and the reduction and glucosidation activities distinctly have been observed in these cultured cells.     

Configuration at C-24 of sterols from the liverwort Palavicinnia lyellii

The 4-desmethylsterol fraction of the liverwort Palavicinnia lyellii is composed of 36% 24β-methylcholest-5-en-3β-ol (dihydrobrassicasterol), 16% 24α-methylcholest-5-en-3β-ol (campesterol), 33% 24α-ethylcholest-5-en-3β-ol (sitosterol) and 15% 24ξ-ethylcholesta-5,22-dien-3β-ol.