Tropane alkaloids from Anthocercis and Anthotroche

In addition to known tropane alkaloids, 3α-iso-butyryloxytropan-6β-ol and 3α-n-butyryloxytropane have been characterized as respective components of the aerial parts of two subspecies of Anthocercis albicans. Aponoratropine, not previously recorded as a natural product, has been detected in the leaves of Anthotroche myoporoides and A. walcottii; similarly aponorhyoscine is indicated as a component of the roots of a subspecies of Anthocercis genistoides.     

Interconversion of trans, trans and cis, trans farnesol by enzymes from Andrographis

When trans, trans-farnesol [4,8,12-¹⁴C₃,1-³H₂] is isomerized to cis, trans-farnesol by soluble enzymes from Andrographis paniculata tissue cultures, 50% of the tritium label is lost. The same loss is observed when isomerization occurs in the opposite direction. This is in accordance with the proposed mechanism for isomerization via aldehydes.     

Diterpenes from Marrubium sericeum, Marrubium supinum and Marrubium alysson

From some Marrubium species endemic in the Iberian Peninsula, four new diterpenoids, 6-acetyl-marrubenol, 19-acetyl-marrubenol, premarrubenol and 6-acetyl-premarrubenol, have been isolated. The previously known diterpenes marrubiin and marrubenol have also been obtained from the same sources.     

Neoxanthin from Helianthus,Taraxacum and Impatiens

Neoxanthin has been isolated from petals of Helianthus annuus, Taraxacum officinale and Impatiens nolitangere. It is identical with authentic neoxanthin from Euglena gracilis. MS and IR spectra were recorded, showing typical fragmentation patterns of neoxanthin, and an allene group. A pigment with the properties of deepoxineoxanthin and polar xanthophylls, which absorbed at very short wavelengths, were also isolated.     

Germacranolides from Perymenium klattianum and Perymeniopsis ovalifolia

The aerial parts of Perymenium klattianum afforded, in addition to kaurane and beyerane derivatives, three germacranolides, two of them isolated for the first time. The structures were elucidated by spectroscopic methods and by some chemical transformations, which in part gave unusual products. Perymeniopsis ovalifolia gave known compounds only.     

Germacranolides from Melampodium americanum and Melampodium pilosum

Chemical analysis of Melampodium americanum yielded, besides the known melampodinin A, four new melampolides, melampodinin B, melampodinin C, 9-des     

Flavonoids from Artemisia ludoviciana var. ludoviciana

Nineteen flavonoids were isolated from Artemisia ludoviciana var. ludoviciana, including a new 2′- hydroxy- 6-methoxyflavone, 5,7,2′,4′-tetrahydroxy-6,5′-dimethoxyflavone. The known compounds include quercetagetin 3,6,3′,4′-tetramethyl ether, eupatilin, 5,7-dihydroxy-3,6,8,4′-tetramethoxyflavone, luteolin 3′,4′-dimethyl ether, jaceosidin, 5,7,4′-trihydroxy-3,6-dimethoxyflavone, tricin, hispidulin, chrysoeriol, kaempferol 3-methyl ether, apigenin, axillarin, eupafolin, selagin and luteolin together with three flavones which were previously isolated for the first time from Artemisia frigida: 5,7,4′-trihydroxy-6, 3′,5′-trimethoxyflavone, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone and 5,7,3′,4′-tetrahydroxy-6,5′- dimethoxyflavone.     

Benzoxazinones from Coix lachryma-jobi var. ma-yuen

The absolute configurations of 2-O-β-D-glucopyranosyl-7-methoxy-1,4(2H)-benzoxazin-3-one and three congeners isolated from Coix lachryma-jobi var. ma-yuen were determined by X-ray analysis and chemical correlation as the 2R type. ¹³C NMR spectra of all congeners and coixol were fully assigned.     

Diterpenoids from Salvia oxyodon and Salvia lavandulifolia

Three new diterpenoids have been detected in Salvia oxyodon and identified as 3β-hydroxy-dehydroabietic acid, 3β-acetoxy-abieta-8(14)-en-18-oic acid 9α,13α-endoperoxide and 3β-hydroxy-abieta-8(14)-en-18-oic acid 9α,13α-endoperoxide. Salvia lavandulifolia yielded two known compounds ursolic acid and galdosol.     

New 8-hydroxyflavonoids from Solanum section Androceras

Five new 8-hydroxyflavonoids have been identified from leaves of Solanum section Androceras: 8-methoxymyricetin 3,7,4′-trimethyl ether; 8-hydroxymyricetin 3,7,4′-trimethyl ether; 8-hydroxymyricetin 8-O-glucosylxyloside 3,7,4′-trimethyl ether; 8-hydroxychrysoeriol 7-methyl ether; 8-hydroxychrysoeriol 7-O-glucoside.     

The anamorphic genus Monotosporella (Ascomycota) from Eocene amber and from modern Agathis resin

The anamorphic fungal genus Monotosporella (Ascomycota, Sordariomycetes) has been reco-vered from a piece of Early Eocene Indian amber, as well as from the surface of extant resin flows in New Caledonia. The fossil fungus was obtained from the Tarkeshwar Lignite Mine of Gujarat State, western India, and was part of the biota of an early tropical angiosperm rainforest. The amber inclusion represents the second fossil record of Sordariomycetes, as well as the first fossil of its particular order (either Savoryellales or Chaetosphaeriales). The fossil fungus is distinguished from extant representatives by possessing both short conidiophores and small two-septate pyriform conidia, and is described as Monotosporella doerfeltii sp. nov. Inside the amber, the anamorph is attached to its substrate, which is likely the degraded thallus of a cladoniform lichen. The extant New Caledonian species is assigned to Monotosporella setosa. It was found growing on semi-solidified resin flows of Agathis ovata (Araucariaceae), and is the first record of Monotosporella from modern resin substrates.     

Furanocoumarins from Dorsteniafoetida

The linear furanocoumarins 5-(2,3-epoxy-3-methyl-butoxy)-chalepensin, 5-methoxy-3-(3-methyl-2,3-dihydroxybutyl)-psoralen-diacetate (7), 5-methoxy-3-[3-(β-d-glucopyranosyloxy)-2-acetyloxy-3-methyl-butyl]-psoralen and 5-(3-methyl-2,3-dihydroxybutyloxy)-3-[3-(β-d-glucopyranosyloxy)-2-hydroxy-3-methyl-butyl]-psoralen, and the coumarin derivative 7-hydroxy-5-methoxy-6-carboxymethyl-3-[3-(β-d-glucopyranosyloxy)-2-hydroxy-3-methyl-butyl]-coumarin were isolated from the leaves of Dorstenia foetida (Moraceae) along with the known compounds psoralen, bergapten, isopimpinellin, phellopterin, 5-methoxychalepensin and turbinatocoumarin. Further furanocoumarins were characterized by ESI-MS/MS investigations. The nonpolar extracts of D. foetida exhibit antifungal, antibacterial and cytotoxic activity, however, no anthelminthic activity.     

Coumarins from Pterocaulon balansae and P. lanatum

Analysis of the petrol-diethyl ether extracts of Pterocaulon balansae and P. lanatum aerial parts afforded, besides puberulin, scopoletin-[2′     

Bitter diterpenoids from Isodon shikokianus var. Intermedius

Four new diterpenoids were isolated from the aerial parts of Isodon shikokianus var. intermedius. The structures of two of them, shikodokaurin A and B, were established.     

Isoflavan phytoalexins from Anthyllis,lotus and Tetragonolobus

Two previously unreported phytoalexins, 7,4′dihydroxy-2′-methoxy- and 7,2′,4′-trihydroxyisoflavan, have been isolated from the fungus-inoculated leaves of Anthyllis vulneraria and 5 Tetragonolobus species. Examination of Lotus corniculatus revealed the co-occurrence of the latter with the known isoflavans, vestitol and sativan. Only 7,2′4′-trihydroxyisoflavan and vestitol were produced by the closely related L. uliginosus.     

Starch synthetases from Vitis vinifera and zea mays

ADPglucose: α-1,4-glucan α-4-glucosyltransferases (starch synthetases) from leaves of Vitis vinifera and leaves and kernels of Zea mays were chromatographed on DEAE-cellulose columns. One form of the enzyme was present in grape leaves having activity both in the presence and absence of primer. Two forms were present in both leaves and kernels of maize. The second peak of activity in maize leaves and the first peak in maize kernels synthesized a polyglucan in the absence of primer. A peak of branching enzyme (Q-enzyme) occurred between the two starch synthetase peaks with both tissues. When fractions containing starch synthetase and branching enzyme were added to the first leaf starch synthetase peak, up to 100-fold activation of the unprimed reaction occurred. Branching enzyme did not stimulate the unprimed activity of the first kernel peak and no branching enzyme could be detected in this peak. The unprimed product was a branched polyglucan with mainly α-1,4-links.     

Daucane esters from Ferula communis subsp. communis

Fourteen daucane esters together with a known propiophenone 3,4-methylenedioxy-5-hydroxy-propiophenone, were isolated from Ferula communis subsp. communis. Except for the 6-(p-anisic acid) ester of jaeschkeanadiol all these esters are new. Structures were elucidated using spectral properties of the esters and their partial hydrolysis products. X-ray diffraction analysis of one of the compounds confirmed its structure including the stereochemical assignments made on the basis of spectral data.     

Aromatic compounds from Artemisia campestris subsp. Glutinosa

From the weakly acid fraction of the hexane extract from Artemisia campestris subsp. glutinosa, five new aromatics have been isolated. They hav     

Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum

Roots of Podophyllum hexandrum and P. peltatum contain the same range of ten aryltetralin lignans: podophyllotoxin, 4′-demethylpodophyllotoxin, α-peltatin, β-peltatin, desoxypodophyllotoxin, podophyllotoxone, isopicropodophyllone, 4′-demethyldesoxypodophyllotoxin, 4′-demethylpodophyllotoxone and 4′-demethylisopicropodophyllone, although the relative proportions are markedly different. The latter two compounds are previously unreported natural products, but 4′-demethylisopicropodophyllone may well be an artefact resulting from epimerization of 4′-demethylpodophyllotoxone. The peltatins have not previously been isolated from P. hexandrum.     

Chlorinated withanolides from Withania somnifera and Acnistus breviflorus

The structure of a new chlorinated withanolide isolated from the hybrid plants of Withania somnifera, chemotypes III (Israel) by Indian I, is established as the chlorohydrin of withanolide D (6α-chloro-4β,5β,20α_F-trihydroxy-l-oxo-22R-witha-2,24-dienolide). Two other known chlorinated withanolides had been isolated from different sources and additional data are provided, including the X-ray diffraction study of 4-deoxyphysalolactone (chlorohydrin of withanolide E). All available data are used for comparative analysis of the six known chlorinated withanolides. The origin of the chlorine atom in these compounds in the plants has been determined by carrying out a simple reaction of withanolide D with NaCl on silica gel.