Sempervirenic acid,a diterpene acid from Solidago sempervirens

Sempervirenic acid, a new diterpene has been isolated from Solidago sempervirens and its structure determined by spectroscopic methods and chemical conversions to be 3β-acetoxy-labda-7,13-diene-15-oic acid.     

3β-hydroxy-21β-e-cinnamoyloxyolean-12-en-28-oic acid,a triterpenoid from enterolobium contorstisiliquum

The triterpenes 3β-hydroxy-21β-E-cinnamoyloxyolean-12-en-20-oic acid, 3β,21β-dihydroxyolean-12-en-28-oic acid (machaerinic acid) and its lactone (3β-hydroxyolean-12-en-21β→28-lactone) were isolated from the fruits of Enterolobium contorstisiliquum. Methyl and ethyl esters of 3β,21β-dihydroxyolean-12-en-oic acid were isolated and characterized as artifacts. The structures of these triterpenes have been established by a study of their chemical and spectroscopic (IR, MS and NMR) data.     

A novel abscisic acid metabolite from seeds of Robinia pseudacacia

Abscisic acid and its novel metabolise, which was a conjugated form of hydroxyabscisic acid (Metabolite C), were isolated from seeds of Robinia pseudacacia L. The structure of the conjugate was shown to be (+)-3-methyl-5 - [1(S),6(R) - 2,6 - dimethyl - 1 - hydroxy - 6 - (3 - hydroxy - 3 - methyl - 4 - carboxybutanoyloxymethyl) - 4 - oxo-cyclohex-2-enyl]-2-Z-4-E-pentadienoic acid and tentatively named β-hydroxy-β-methylglutarylhydroxyabscisic acid.     

The structure and stereochemistry of barrigenic acid,a new triterpene acid sapogenin from Barringtonia acutangula

A new triterpene acid, barrigenic acid, was isolated from the fruits of Barringtonia acutangula. Its structure was established as 2α,3β,19β-trihydroxyolean-12-en-23,28-dioic acid.     

Oxidative dimerization of ferulic acid by extracts from Sorghum

Extracts from leaves and first internodes of Sorghum bicolor catalyze the conversion of ferulic acid to a β-β-coupled dimer, the dilactone dimer of ferulic acid. The dilactone is then hydrolyzed, probably non-enzymatically, to a blue fluorescing compound, tentatively identified as a β-β-coupled dimer with at least one lactone ring opened to form a carboxylic acid. Both the initial enzymatic and the subsequent non-enzymatic steps are greater at pH 8 than pH 6. The most active preparation is a crude particulate fraction from leaves obtained by centrifugation at 37000 g; white light increases the amount of dimer formed.     

The neurolathyrogen, α-amino-β-oxalylaminopropionic acid in legume seeds

The neurotoxic lathyrogen, α-amino-β-oxalylaminopropionic acid (β-oxalyldiaminopropionic acid, ODAP) accumulates in the seeds of 13 species of Crotalaria and 17 species of Acacia as well as in seeds of Lathyrus. The compound was not detected in seeds representing 250 other legume genera—these are listed.     

Distribution of α-amino-β-methylaminopropionic acid in Cycas

α-Amino-β-methylaminopropionic acid, previously isolated from seeds of Cycas circinalis, has now been identified either free or bound in all th     

6β-Hydroxyursolic acid and other triterpenoids of Enkianthus cernuus

From the leaves of Enkianthus cernuus forma rubens, a new triterpene, 6β-hydroxyursolic acid, was isolated together with several known compounds     

Jessic acid and related acid triterpenoids from combretum elaeagnoides

A novel triterpenoid acid, jessic acid, was extracted from the leaves of Combretum elaeagnoides, where it was found together with its methyl ester and its α-L-arabinopyranoside, all three compounds occurring in significantly large amounts. Jessic acid is 1α,3β-dihydroxy-23-oxo-24-methylenecycloartan-30-oic acid.     

Three new oxygenated triterpenoids of the lupane series from Gymnosporia wallichiana

Two new epimeric triterpenoid acids, gymnosporic acid, 3β-hydroxy-(20R)-lupan-29-oic acid, wallichianic acid, 3β-hydroxy-(20S)-lupan-29-oic acid and a new diol wallichianol, (20S)-lupane-3β,29-diol have been isolated from Gymnosporia wallichiana, in addition to β-amyrin, friedelin, 3β-hydroxy-29-norlupan-20-one and dulcitol.     

Triterpenoids from enkianthus campanulatus

From the leaves of Enkianthus campanulatus were isolated three new triterpenes, 3-oxo-19,23,24-trihydroxyurs-12-en-28-oic acid, 3β,6β, 19,23-tetrahydroxyurs-12-en-28-oic acid and 3β,6β,23-trihydroxyurs-12-en-28-oic acid.     

7β-Acetoxytrachyloban-18-oic acid from the stem bark of Xylopia quintasii

A novel diterpene has been isolated from the stem bark of Xylopia quintasii and identified as 7β-acetoxytrachyloban-18-oic acid. The taxonomic si     

Occurrence of betulinic acid in different callus cultures of Solanum aviculare

Betulinic acid (3β-hydroxy-lup-20(29)-en-28-oic acid) was obtained from in vitro cultures of Solanum aviculare in yields up to 3% of the dry weight. This is a further example of overproduction by cells cultured in vitro of a product not found in the original parent plant.     

Microbiological conversion of 12-oxygenated and other derivatives of ent-kaur-16-en-19-oic acid by Gibberella Fujikuroi, mutant B1-41a

The metabolism of several ring C and D-functionalized ent-kaur-16-en-19-oic acids by cultures of Gibberella fujikuroi, mutant B1-41a, to the corresponding derivatives of the normal fungal gibberellins (GAs) and ent-kaurenoids is described. A range of 12α- and 12β-hydroxyGAs and ent-kaurenoids are characterized by their mass spectra and GC Kovats retention indices. The mass spectral and GC data are used to identify the 12α-hydroxy derivatives of GA₁₂, GA₁₄, GA₃₇ and GA₄ (GA₅₈), and of the 12β-hydroxy derivatives of ent-7α-hydroxy- and ent-6α, 7α-dihydroxykaurenoic acids, in seeds of Cucurbita maxima. Similarly the metabolites of GA₉, formed in seeds of Pisum sativum and cultures of G.fujikuroi, mutant B1-41a, are identified as 12α-hydroxyGA₉. ent-11β-Hydroxy- and ent-11-oxo-kaurenoic acids are metabolized by the fungus to the corresponding 11-oxygenated derivatives of the normal fungal ent-kaurenoids and some C₂₀-GAs; no 11-oxygenated C₁₉-GAs are formed. Grandiflorenic acid, 11β-hydroxygrandiflorenic acid, attractyligen and ent-15β-hydroxykaurenoic acid are metabolized to unidentified products.     

Sapogenins from Guaiacum officinale

Acid hydrolysis of the saponins from the stem bark of Guaiacum officinale yielded the new sapogenin 3β,20η-dihydroxy-30-norolean-12-en-28-oic acid and the artifacts 3β-hydroxy-30-norolean-12,19-dien-28-oic acid and its methyl ester. Larreagenin, sitosterol and oleanolic acid were also isolated.     

Isolation of a natural sterol and an aliphatic acid from Vernonia cinerea

From the roots of Vernonia cinerea a new natural sterol and a new aliphatic acid characterized as stigmast-5,17(20)-dien-3β-ol and 26-methylheptacosanoic acid, respectively, have been isolated together with stigmasterol and sitosterol.     

Two quassinoid glycosides and a β-carboline-1-propionic acid from hannoa klaineana

Among the polar constituents of Hannoa klaineana roots, two new quassinoid glycosides, 15-O-β-D-glucopyranosyl-21-hydroxyglaucarubolone, 15-O-α-D-xylofuranosyl(1 → 6)-β-D-glucopyranosyl-21-hydroxy-glaucarubolone, an alkaloid, β-carboline-1-propionic acid and a coumarin glycoside, scopolin were isolated and their structures elucidated.     

Triterpenoids from guettarda angelica

From the root bark of Guettarda angelica were isolated 3-O-β-d-glucopyranosyl-quinovic acid and its aglycone. The root wood gave the same glucoside, rotundic acid, hederagenin and 3β,23-dihydroxyurs-12-en-28-oic acid.     

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     

Methoxylation of 3β,7α-dihydroxychol-5-en-24-oic acid,a key intermediate of chenodeoxycholic acid biogenesis,compared with that of its 7β-epimer

The conventional methods of gas liquid chromatography or mass spectrometry failed to be useful for the identification of the biliary 3β, 7α-hydroxychol--en-24-oic acid, a key intermediate of chenodeoxycholic acid biogenesis. It has been preliminarily reported that this acid in human bile was successfully identified by gas chromatography-mass spectrometry, after the methoxylation of its allyl alcohol group. Physical as well as spectral properties of the methoxylation products derived from the acid were reported, compared with those from its 7β-epimer.