Terpenoids from Wedelia buphthalmiflora

A series of known di- and triterpenoids were characterized in the whole plant of Wedelia buphthaimiflora.     

Triterpenes from Periandra dulcis roots

Three oleanane triterpenes were isolated from the roots of Periandra dulcis,and identified as 3β-hydroxy-25-al-olean-18-en-30-oic acid (periandric acid I), 3β-hydroxy-25-al-olean-12-en-30-oic acid (periandric acid II) and 3-oxo-25-hydroxy-olean-12-en-30-oic acid. The former two compounds (periandric acids I and II) were identical with the aglycones obtained by hydrolysis of periandrin I and II, respectively and the latter one was a new triterpene.     

Triterpenes from periandra dulcis roots

Two new triterpenes from the root of Periandra dulcis were found to be 3,25-dioxoolean-12(13)-en-30-oic acid and 3,25-dioxoolean-18(19)-en-30-oic acid.     

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.     

Triterpenoids from two Mallotus species: a nor-triterpene and two new acids

The carbonyl compound, previously isolated from the stems of Mallotus paniculatus, has been proved to be 29-nor-21αH-hopane-3,22-dione. The light petrol extracts of both the leaves and stems of M. hookerianus have been found to contain friedelin, friedelan- 3β-ol and sitosterol, and the ethanol extract of the former two new triterpene acids, 3-oxours-12-ene-27,28-dioic and 3β,28-dihydroxyurs-12-en-27-oic acids.     

Acid-catalyzed transformation of 13(S)-hydroperoxylinoleic acid into epoxyhydroxyoctadecenoic and trihydroxyoctadecenoic acids

Acid treatment of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid in tetrahydrofuran-water solvent afforded mainly (11R,12R,13S)-(Z)-12,13-epoxy-11-hydroxy-9-octadecenoic acid, diastereomeric (Z)-11,12,13-trihydroxy-9-octadecenoic acids and four isomers of (E)-9,12,13(9,10,13)-trihydroxy-10(11)-octadecenoic acid. Other minor products were oxooctadecadienoic, (E)-9(13)-hydroxy-13(9)-oxo-10(11)-octadecenoic and (E)-12-oxo-10-dodecenoic acids. A heterolytic mechanism for acid catalysis was indicated, even though most of the products characterized also have been observed as a result of homolytic decomposition of the hydroperoxide via an oxy radical. Most of the products found in this study have been observed as metabolites of (13S)-(9Z,11E)-13-hydroperoxy-9,11-octadecadenoic acid in biological systems, and analogous compounds have been reported as metabolites of (12S)-(5Z,8Z,10E, 14Z)-12-hydroperoxy-5,8,10,14-hydroperoxy-5,8,10,14-eicosatetraenoic acid in either blood platelets or lung tissue.     

Labdane Diterpenoids from Coleus forskohlii （Willd.） Briq.

in order to investigate the active substances of Coleus forskohlii（Wiiid.） Brlq., a new labdane dlterpenold, 12- hydroxy-8,13E-labdadlen-15.olc acid, together with two 8,13-epoxylabd-14-ene-11-one dlterpenolds, 6-acetyl-1- deoxyforskolln and 6-acetyl-1,9-dldeoxyforskolln, was Isolated on the basis of various chromatographic technlques and spectroscopic methods.     

Kolavane and kaurane diterpenes from the stem bark of Xylopia aethiopica

The stem bark of Xylopia aethiopica has yielded four diterpenes, two of them novel. Three of the diterpenes were identified as (?)-kaur-16-en-19-oic acid and its 7-oxo and 7β-hydroxy derivatives. The fourth was the novel kolavane derivative 2-oxo-kolav-3,13-dien-15-oic acid, a type of compound not previously recorded in the Annonaceae.     

Oral administration of (11E)-13-oxo-15,16-dinorlabda-8(20),11-dien-19-oic acid strongly reduces photocarcinogenesis in mouse skin exposed to UV-B irradiation

(11E)-13-Oxo-15,16-dinorlabda-8(20),11-dien-19-oic Acid (1), obtained either from the stem bark of Thuja standishii or readily prepared in larger quantities from the related constituent 2, was found to significantly reduce the formation of papilloma in an in vivo two-stage mouse-skin-carcinogenesis model. Carcinogenesis was initiated by skin exposure to UV-B irradiation and promoted by topical application of 12-O-tetradecanoylphorbol-13-acetate (TPA). Oral administration of 1, starting one week before and ending one week after irradiation, exhibited remarkable effects. First, papilloma formation started two weeks later than in the control group (lacking 1). Second, the average number of skin papilloma after 20 weeks was reduced by ca. 50% in the test group relative to the control.     

Identification by gas chromatography-mass spectrometry of intermediates in the aromatization of modified C19 steroids by human placental microsomes

Analogs of 4-androstene-3,17-dione and testosterone were tested as substrates for the aromatizing enzyme complex of human placenta. Compounds modified in rings B, C and D were found to be aromatized via a pathway similar to that postulated for 4-androstene-3,17-dione and testosterone, in which oxidation to the 19-hydroxy and 19-oxo (or corresponding gem-diol) intermediates occurs. No evidence of additional intermediates was obtained.     

Deactivation of the effects of F-Met-Leu-Phe and leukotriene B4 on calcium mobilization in rabbit neutrophils

Preincubation of rabbit neutrophils with the synthetic chemotactic factor f-Met-Leu-Phe has been found to diminish the ability of these cells to mobilize calcium upon subsequent stimulation by f-Met-Leu-Phe or by leukotriene B₄. The preexposure of the neutrophils to leukotriene B₄ on the other hand results in a diminished subsequent response to itself but an unaltered response to f-Met-Leu-Phe. These results demonstrate that deactivation can be observed at the level of calcium mobilization, strengthen the postulated second messenger role of calcium in neutrophils and imply that neutrophil activation by chemotactic factors can bypass the arachidonic acid metabolic pathway.     

New neutral diterpenes from southern pine tall oil

Five new diterpene natural products isolated from southern pine (Pinus spp.) tall oil were characterized as 8(14),15-pimaradiene-3β,18-diol, 19-hydroxy-15,16-dinorlabd-8(17)-en-13-one, 8,13β-epoxy-14-labden-6α-ol, 8,11, 13-abietatriene-15,18-diol and 9,10-secoabieta-8,11,13-trien-18,10-olide.     

Myrianthic acid: a triterpene acid from the rootwood of Myrianthus arboreus

Arjunolic acid and a new triterpene acid, myrianthic acid, were isolated from the rootwood of Myrianthus arboreus. The structures of the two compounds were elucidated by IR, ¹H NMR and mass spectroscopy.     

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.     

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.     

Two New Triterpenoids from the Roots of Sanguisorba officinalis L.

Two new triterpenoids, octanordammar-1,11,13(17)-trien-17-ol-3,16-dione (1) and lup-12-en-15α,19β-diol-3,11-dioxo-28-oic acid (4), as well as 13 known compounds were isolated from the roots of Sanguisorba officinalis L. (Rosaceae). Their structures were determined using spectroscopic methods.     

Chemical Constituents from Fruits of Rosa davidii

From the fruit of Rosa davidii Crep., eleven compounds were isolated and identified by spectral evidence, viz. 2α,3β,19β-trihydroxyl-olean-12-en-28-oic acid (1), 2α,3β-dihydroxyl-urs-28(13)-lactone (2), arjunic acid (3), euscaphic acid (4), 2α,3β-dihydroxyl-urs-12-en-28-oic acid (5), oleanolic acid (6), kaempferol (7), tiliroside (8), quercetin (9), daucosterol (10) and β-sitosterol (11). Among them, 1 and 2 were new compounds.     

Triterpenes from Euonymus revolutus

Fourteen pentacyclic triterpenes, which included ten D:A-friedooleananes, three lup-20(29)-enes and 2α,3α-dihydroxy-olean-12-en-28-oic acid, were isolated from the stem bark extract of Euonymus revolutus.     

Eremophilane Sesquiterpenoids from Coleus xanthanthus (in English)

A new eremophilane sesquiterpenoid, along with two known ones, was isolated from the ethyl acetate soluble fraction of the aerial part of Coleus xanthanthus C. Y. Wu et Y. C. Huang. Their structures were elucidated as 4,5,11-trimethyl-8,9-seco-1(10),7(11)-eremophiladien-8,12-olid-9-oic acid (1), 2,9-dioxoeuryopsin (2) and 9-oxoeuryopsin (3) by spectral methods. The H-NMR and 13C-NMR data of compounds 1, 2 and 3 were unambiguously assigned on the basis of two-dimensional NMR spectroscopy.     

3α-Hydroxy-multiflora-7,9(11)-dien-29α-oic acid,a new triterpene from Bryonia dioica

The structure of a new triterpene acid from the roots of Bryonia dioica is shown on the basis of chemical and spectroscopic evidence to be 3α-hydroxy-multiflora-7,9(11)-dien-29α-oic acid. This is the first report of a naturally occurring Δ^7,9(11) -multiflorene compound.