Aliphatic hydroxy-ketones from Curculigo orchioides rhizomes

Two new aliphatic hydroxy-ketones, isolated from the rhizomes of Curculigo orchioides, have been characterized as 27-hydroxytriacontan-6-one and 23-hydroxytriacontan-2-one, respectively, by spectral data and chemical studies.     

Occurrence of Potential Brassinosteroid Precursor Steroids in Seeds of Wheat and Foxtail Millet

Triticum aestivum L.) and foxtail millet (Setaria italica Beauv.) were found by GC-MS to contain, in addition to bulk sterols, 4-en-3-one steroids including 24-ethylcholesta-4,24(28)Z- dien-3-one (a new steroid), 24-methylcholest-4-en-3-one, 24-ethylcholesta-4,22E-dien-3-one and 24-ethylcholest-4-en-3-one, as well as 5α-steroidal 3-one compounds including 24-methyl-5α-cholestan-3-one, 24-ethyl-5α-cholestan-3-one and 24-ethyl 5α-cholest-22E-en-3-one (in S. italica only). Analysis of free sterol and steryl ester fractions indicated that campestanol and sitostanol were present at high levels in both seeds. These results suggest that the seeds of T. aestivum and S. italica synthesize campestanol from campesterol via 24-methylcholest-4-en-3-one and 24-methyl-5α-cholestan-3-one as has already been demonstrated in Arabidopsis thaliana L., and also produce sitostanol from sitosterol via 24-ethylcholest-4-en-3-one and 24-ethyl-5α-chotestan-3-one. Biosynthetic relationships of campestanol and sitostanol with C₂₈ and C₂₉ brassinosteroids are discussed. Received 4 September 1998/ Accepted in revised form 26 November 1998     

An N-glycoside and steroids from Aristolochia indica

A phenanthrene derivative, aristololactam N-β-d-glucoside, and the steroids 3β-hydroxy-stigmast-5-en-7-one and 6β-hydroxy-stigmast-4-en-3-one have been isolated from Aristolochia indica.     

Aliphatic compounds from Costus speciosus roots

Two new compounds G and H isolated from the roots of Costus speciosus have been characterized as 8-hydroxytriacontan-25-one and Me tritriacontanoat     

Aliphatic compounds from Curculigo orchioides rhizomes

21-Hydroxytetracontan-20-one and 4-methylheptadecanoic acid have been isolated from the rhizomes of Curculigo orchioides and characterized on the basis of chemical and spectroscopic evidence.     

3-methoxy-4,6-dihydroxymorphinandien-7-one,an alkaloid from Croton bonplandianum

A new alkaloid, 3-methoxy-4,6-dihydroxymorphinandien-7-one, and norsinoacutine have been isolated from extracts of Croton bonplandianum.     

1-Hydroxycanthin-6-one,an alkaloid from Ailanthus giraldii

A new alkaloid has been isolated from the heartwood of Ailanthus giraldii and its structure determined as 1-hydroxycanthin-6-one.     

Sesquiterpenes from severinia buxifolia

Three new sesquiterpenes were isolated from Severinia buxifolia, and identified as α-santalen-11-one, dihydro-α-santalen-12-one, and 12,13-epoxy-α-santalene, respectively. α-Photosantalol A, Δ^13,14-iso-α-santalol, α-santalene and (E)-5-(2,3-dimethyl-3-nortricyclyl)pent-3-en-2-one were also isolated and characterized.     

Heptatriacontan-4-one,tetratriacontanyl octacosanoate and other constituents from Pedalium murex

Two new compounds isolated from the fruits of Pedalium murex are characterized as heptatriacontan-4-one and tetratriacontanyl octacosanoate by spectral studies. Pentatriacontane, sitosterol, hexatriacontanoic acid, hentriacontanoic acid, ursolic acid and vanillin have also been isolated and identified.     

Aliphatic constituents from Duboisia myoporoides

Four new compounds, isolated from the leaves and stems of Duboisia myoporoides have been characterized as 6-methyldotriacontane, hentriacontanyl tetratriacontanoate, 3-hydroxydotriacontan-28-one and 4-pentatriacontanone, respectively, by spectral data and chemical studies.     

Sulphides and furanones from steam volatile oils of Allium fistulosum and Allium chinense

The constituents of the steam volatile oils from two kinds of Allium fistulosum, A. fistulosum var. caespitosum and A. chinense, have been investigated by GC and spectral techniques (IR, UV, GC/MS, ¹H NMR and ¹³C NMR). The compounds identified from the neutral fraction of each volatile oil included sulphides, thiolanes, alcohols, aldehydes, ketones, furanones and others. Among the sulphur compounds, dipropyl disulphide comprised ca 28% of A. fistulosum oil, ca 23% of A. fistulosum var. caespitosum oil and ca 30% of A. chinense oil. A. fistulosum oil was characterized by a large quantity of tridecan-2-one (ca 52%) and 2,3-dihydro-2-octyl-5-methylfuran-3-one (ca 16%). Also, a large amount of 2,3-dihydro-2-hexyl-5-methylfuran-3-one (ca 20%) was isolated from A. chinense oil.     

Coumarins from the Malagasy Cedrelopsis rakotozafyi Cheek and Lescot (Rutaceae)

A phytochemical analysis of the bark of the Malagasy Cedrelopsis rakotozafyi Cheek and Lescot (Rutaceae) yielded the novel 8-hydroxy-7-methoxy-6-(2R-hydroxy-3-methylbut-3-enoxy)-2H-1-benzopyran-2-one, and 7-hydroxy-6-(2R-hydroxy-3-methylbut-3-enoxy)-2H-1-benzopyran-2-one, 5,6,7-trimethoxy-2H-1-benzopyran-2-one, scoparone, scopoletin, lupeol and β-amyrin. The placement of Cedrelopsis within the Rutaceae is supported phytochemically by the typically Rutaceous coumarins isolated.     

A caryophyllene derivative from Fleischmannia pycnocephaloides

A new caryophyllene derivative, 15-acetoxy-5,6-dihydro-6,7-dehydrocaryophyllen-5-one, has been isolated from the roots of Fleischmannia pycnocephaloides. Other Fleischmannia sp. yielded previously known compounds.     

5-Methoxy-2,2,8-trimethyl-10-senecioyl-2H,6H-benzo(1,2-b; 5,4-b')dipyran-6-one from Spathelia wrightii

From leaflets of Spathelia wrightii a new pyranochromone has been isolated, the spectroscopic properties of which are in accordance with the structure 5-methoxy-2,2,8-trimethyl-10-senecioyl-2H,6H-benzo(1,2-b, 5,4-b')dipyran-6-one (1).     

Secondary metabolites from Mycosphaerella ligulicola

(+)-Epoxydon, together with the new (+)-epoxydon monoacetate, 3-methylidene-6-methoxy-1,4-benzodioxan-2-one and 2-(2-hydroxy-5-methoxyphenoxy)-acrylic acid, has been isolated and identified from the mycelium of Mycosphaerella ligulicola grown on Sabouraud-maltose 4 %-agar.     

Anti-inflammatory,antimicrobial and acetylcholinesterase inhibitory activities of friedelanes from Maytenus robusta branches and isolation of further triterpenoids

The new pentacyclic triterpenoids friedel-1-en-3,16-dione (1), 1α,29-dihydroxyfriedelan-3-one (2) and 16β,28,29-trihydroxyfriedelan-3-one (3) were isolated from Maytenus robusta branches in addition to the known, but new for this species, triterpenoid 12α,29-dihydroxyfriedelan-3-one (4). The structures and stereochemistry of the novel triterpenoids were established by IR, 1D/2D NMR and HR-APCIMS spectral data. In addition, the biological activity of compound 2 and the previously isolated friedelanes 5–8 (friedelan-3,16-dione, 29-hydroxyfriedelan-3-one, 29-hydroxyfriedelan-3,16-dione and 16β,29-dihydroxyfriedelan-3-one) was investigated. Compounds 2 and 8 were tested for their acetylcholinesterase properties and antimicrobial activity against the bacteria Staphylococcus aureus, Pseudomonas aeruginosa, Listeria monocytogenes, Citrobacter freundii, and the fungus Candida albicans. Compound 2 was the most active compound for both assays, with values of 32.3% acetylcholinesterase inhibition, 42% activity against the fungus Candida albicans and 34% against the bacterium Pseudomonas aeruginosa. Compounds 5–8 were assayed for their antiedematogenic activity using the carrageenan-induced paw edema assay. At maximum inflammation after three hours, compounds 6 and 8 showed 42% and 57% activity, respectively. After four hours, compounds 5 and 7 showed activity of 71% and 75% compared to 79% of the control indomethacin.     

The isolation of lanosta-7,9(11),24-trien-3β,21-diol from the fungus ganoderma australe

The lipid-soluble fraction of the fungus Ganoderma australe belonging to the family Polyporaceae has yielded ergosterol palmitate, ergosta-7,22-dien-3-one, ergosterol and lanosta-7,9(11),24-trien-3β,21-diol. This fungus is the second reported natural source of the latter compound whose structure is now established on the basis of spectral data.     

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.     

13C NMR Spectra of some D:A-friedo-oleananes

The ¹³C NMR signals of D:A-friedo-olean-7-one, putranjivadione, D:A-friedo-olean-22-one, D:A-friedo-olean-3,22-dione, and Salacia triterpene R have been assigned using off-resonance decoupling and lanthanide induced shift techniques. ¹³C NMR data provide further evidence for the boat-boat conformation for the D and E rings of D:A-friedo-oleananes in solution.     

Lactones,flavonoids and benzophenones from Garcinia conrauana and Garcinia mannii

Two novel lactones have been isolated from the stem barks of Garcinia conrauana and G. mannii. The major component of the bark of G. conrauana was identified as 3-(3$\text{,}\text{?}$ 3″-dimethylallyl)-conrauanalactone [4-hydroxy-3-(3″, 3″-dimethylallyl)-6-pentadecylpyran- 2-one] by comparison of spectral data of the isolated compound and two methylethers with that obtained for the previously isolated conrauanalactone. A minor component of the bark of G. mannii was tentatively identified as 3-α-hydroxy-5-(heptadec-8′-enyl)-tetrahydro- furan-2-one on the basis of spectral data from the isolated compound and its monoacetate. The distributions of biflavonoids and related compounds and benzophenones in the stem bark, heartwood, seeds and leaves of the two species are reported.