Diterpene resin acids from the needle oleoresin of pinus strobus

The resin acid components of P. strobus needles were isolated, and the major constituents identified as labdenoic diterpenes. In addition to anticopalic and strobic acids previously reported in the needles, 3-oxoanticopalic, 3β-acetoxyanticopalic, 3β-hydroxyanticopalic acids and the 8α-hydroxy derivative of anticopalic acid were found along with two new compounds. The structures of the two new compounds, a cycloanticopalic acid and an abcoanticopalic acid, were determined by NMR. The composition of the diterpene resin acids was obtained for several samples of P. strobus needles from provenance tests.     

Iridoid glucosides in Plantago alpina and P. Altissima

Two species of Plantago, namely P. Alpina and P. altissima were investigated. From the former, nine iridoid glucosides and verbascoside were isolated. Together with the known iridoids gardoside, geniposidic acid, 8-epi-loganic acid, mussaenosidic acid, aucubin, monomelittoside and melittoside, two new glucosides were found: 10-O-acetylgeniposidic acid and alpinoside, another compound with a 10-O-acetyl group. From P. altissima verbascoside and isoverbascoside were isolated together with the known iridoids gardoside, 8-epi-loganic acid, catalpol, aucubin, and hookerioside as well as the new compound desacetylhookerioside.     

Neue cadinen-derivate und andere inhaltsstoffe aus Chromolaena-arten

The investigation of two further Chromolaena species afforded two new cadinene derivatives and a related structure with a degraded cadinene skeleton. Also present were two p-coumaric acid esters and a new flavanone. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Eudesmanolides and diterpenes from Wedelia trilobata and an ent-kaurenic acid derivative from Aspilia parvifolia

The reinvestigation of the aerial parts of Wedelia trilobata afforded, in addition to known compounds, six new eudesmanolides, two ent-kaurenic acid derivatives as well as a degraded one. A corresponding hydroxy compound was present in Gnaphalium undulatum. From Aspilia parvifolia new ent-kaurenic acid epoxides were isolated. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Further sesquiterpene lactones from the genus Dittrichia

The aerial parts of Dittrichia graveolens afforded in addition to compounds isolated previously five new sesquiterpene lactones, two benzoic acid derivatives while D. viscosa gave two further derivatives of costic acid. The structures were elucidated by high field NMR spectroscopy.     

Beyerene derivatives and other constituents from Petunia patagonica

Two new diterpenes of the beyerene type, ent-19-hydroxy-1 7-acetoxybeyer-15-ene and ent-beyer-15-en-17-oic acid, and two previously characterized kauranoids, ent-16β-hydroxy-17-acetoxykaurane and ent-16β,1 7-dihydroxy-kaurane, as well as two known flavonoids, luteolin-7,3′,4′-trimethyl ether and luteolin-7,3′-dimethyl ether, and a triterpenoid, oleanoic acid, were obtained from a chloroform extract of Petunia patagonica. The new structures were elucidated by spectral data and chemical transformations.     

Triterpenoids and glycosides from Geum japonicum

Two new glucosides and two known ester glucosides have been isolated from Geum japonicum. The two new glucosides were isolated by formation of their acetates and were identified as glucosides of 2-isopropyl-5-methylhydroquinone by chemical and spectral studies. The two known ester glucosides were identified as niga-ichigoside F1 and suavissimoside F1 by direct comparison with authentic samples. 2α,19α-Dihydroxyursolic acid and the known glycoside, gein, were also isolated from the same plant, in addition to a mixture of 2α-hydroxyursolic acid and 2α-hydroxyoleanolic acid.     

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.     

Melampolides and germacranolides from Stevia amambayensis

From the aerial parts of Stevia amambayensis in addition to known compounds three new sesquiterpene lactones, a grazielic acid derivative and two melampolides were isolated. The roots gave two new bisabolene derivatives.     

Neue phloroglucin-derivate aus Leontonyx-arten sowie weitere verbindungen aus vertretern der tribus inuleae

The investigation of several South African species of the tribe Inuleae afforded in addition to known compounds 16 new constituents. From Leontonyx a group of 9 new phloroglucinol derivatives, from Stoebe species two new p-hydroxyacetophenone, two thymol and two coumaric acid derivatives and from Relhania a new euparine-derivative were isolated. The structures are elucidated mainly by spectroscopic methods. The chemotaxonomic aspects are discussed briefly. The phloroglucinol derivatives, which in part are derived from geraniol, seem to be especially characteristic.     

Sesquiterpene acids from Inula Viscosa

In addition to known terpenoids and flavonoids two new sesquiterpene acids, viscic acid and viscosic acid, were obtained from the aerial parts of Inula viscosa.     

Triterpenoids of Akebia quinata callus tissue

From tissue culture of Akebia quinata, three new triterpenes were isolated together with two known triterpenes, oleanolic acid and mesembryanthemoidgenic acid. The new triterpenes were characterized by spectroscopic means as 3β-hydroxy-30-norolean-12,20(29)-dien-28-oic acid, 3-epi-30-norolean-12,20(29)-dien-28-oic acid and 3β-hydroxy-29(or 30)-al-olean-12-en-28-oic acid.     

Two sesquiterpene and three diterpene lactones from Acanthospermum australe

The aerial parts of Acanthospermum australe afforded two new sesquiterpene lactones, an acid and a cis,cis-germacranolide, as well as three diterpene lactones of a new type, most probably formed by intermolecular nucleophilic attack of the carboxyl group of an acid epoxide derived from geranylgeraniol. The structures were proposed on the basis of spectroscopic studies.     

Grindelane diterpenoids from grindelia squarrosa and G. Camporum

An acid fraction of the dichloromethane extract of Grindelia squarrosa and a neutral fraction of the ethyl acetate extract of Grindelia camporum yielded a number of previously known grindelane diterpenoids and flavonoids. Along with the known isolates, two new grindelane diterpenoids, 13-isogrindelic acid and 17-grindeloxy grindelic acid, from G. squarrosa were isolated and identified spectroscopically.     

Furanediterpenes from Baccharis thymifolia

From the aerial part of Baccharis thymifolia two new furanediterpenoids have been isolated besides previously know flavonoids. The structure of thymifodioic acid and 17-acetoxymethylthymifodioic acid, were established by spectroscopic data and chemical transformations.     

Substrate-like water soluble lipase inhibitors from Filipendula kamtschatica

Filipendula kamtschatica is a plant utilized as a traditional medicine by Ainu people in Japan, but its chemical constituents are not much studied. Pancreatic lipase inhibitors are a promising tool for the treatment of obesity. We searched for natural lipase inhibitors from F. kamtschatica and two new compounds were isolated along with the known flavonoid glycoside. The structure elucidation of new compounds revealed these two to be 2-O-caffeoyl-4-O-galloyl-l-threonic acid and 3-O-caffeoyl-4-O-galloyl-l-threonic acid, which can be recognized as a pancreatic lipase’s substrate-like structure. The isolated compounds all showed an inhibitory activity against porcine pancreatic lipase and one of the isomer, 3-O-caffeoyl-4-O-galloyl-l-threonic acid, possessed the most potent activity with IC₅₀ value showing an order lower value compared to others. The substrate-like structure of the new compounds seemed to be important for their activity.     

Xanthones from formosan Gentianaceous plants

A reinvestigation of the whole plants ofTripterospermum lanceolatum gave, in addition to compounds isolated previously, two new xanthones, named lanceolin and methyllanceolin, respectively. The compound previously reported to be oleanolic acid was re-examined and identified as ursolic acid by a¹³C NMR study. An isomeric mixture, oleanolic acid and ursolic acid, and sweroside were isolated from the whole plants ofSwertia arisanensis.     

A new triterpenoid and other constituents from Lepidogrammitis drymoglossoides

Phytochemical investigation of a Chinese fern Lepidogrammitis drymoglossoides led to the isolation of five compounds, including one triterpenoid, two lignans and two glycosides. Their structures were determined to be filic-3-ene-28-oic acid (1), (−)-syringaresinol-4-O-beta-d-glucopyranoside (2), lyoniresinol (3), 4-O-beta-d-glucopyranosyl caffeic acid (4) and n-butyl-O-beta-d-fructopyranoside (5) on the basis of mass and NMR spectra and chemical and physical properties. Filic-3-ene-28-oic acid (1) is a new triterpenoid, while compounds 2–5 were isolated from the genus Lepidogrammitis for the first time. Chemotaxonomic significance of this investigation is summarized.     

Viscidic acid A and B,two ent-labdane derivatives from Chrysothamnus viscidiflorus

The chemical investigation of Chrysothamnus viscidiflorus afforded, in addition to known bisabolene derivatives, elemicin and p-hydroxyacetophenone, two new diterpene acids. Their structures were determined, by spectroscopic methods and some chemical transformations, as ent-labd-8(17),13E-dien-15-ol-18-oic acid (viscidic acid A) and ent-labd-8(17),13E-dien-15-acetoxy-18-oic acid (visidic acid B).     

Mutation at the am locus of Neurospora crassa

Forty-eight new mutations at the am locus of Neurospora crassa have been characterized. Nineteen mutations were induced by UV; of these, eight were missense, two were frameshifts, two were nonsense, three were deletions and four were unidentified. Twenty-nine mutations were induced with nitrous acid; of these, twenty-one were missense, three were frameshifts, one was nonsense, two were deletions and one was genetically unstable.