Norditerpenoid alkaloids from Delphinium species

From the aerial parts of four Delphinium species 11 known and 3 new norditerpenoid alkaloids have been isolated: from D. dissectum Huth: delavaine A/B, deoxylycoctonine, methyllycaconitine; new: 10-hydroxymethyllycaconitine; from D. excelsum Reichenb.: delcaroline, delectinine, delterine, methyllycaconitine; new: 10-hydroxymethyllycaconitine, 18-O-methyldelterine and 10-hydroxynudicaulidine; from D. grandiflorum L.: delcosine, deltatsine, grandiflorine, methyllycaconitine; from D. triste Fisch.: delcosine, macrocentridine, 14-dehydrodelcosine. The structures of the new alkaloids were established on the basis of MS, 1H, 13C, DEPT, homonuclear COSY, HMQC and HMBC NMR spectroscopic techniques.     

Six alkaloids from Papaver species

Papaver fugax produced the new alkaloids (−)-narcotinehemiacetal and (−)-papaveroxine. New alkaloids from P. pseudo-orientale are (−)-narcotinediol, (+)-macrantaldehyde, (−)-papaveroxinoline, (−)-narcotolinol and (−)-narcotinehemiacetal.     

Insecticidal sesquiterpene pyridine alkaloids from Euonymus species

Three insecticidal sesquiterpene pyridine alkaloids with a beta-dihydroagarofuran sesquiterpene skeleton, euoverrine A (1), B (2), and euophelline (3), and a known compound, euojaponine C (4), were isolated from the root bark of Euonymus verrucosides, E. fortunei and E. phellomana by bioassay-guided fractionation. Their chemical structures were elucidated mainly by analyses NMR and MS spectral data.     

Isoquinoline alkaloids isolated from three Guatteria species

The chemical investigation of the aerial parts of Guatteria ferruginea collected in the National Park of Serra dos Órgãos, Teresópolis, Brazil and of Guatteria latifolia and Guatteria sellowiana collected in the National Park of Itatiaia, Itatiaia, Brazil resulted in the isolation and identification of six isoquinoline alkaloids, two aporphine alkaloids 3-hydroxy-nornuciferine (1), nornuciferine (2) and four oxoaporphine alkaloids lysicamine (3), isomoschatoline (4), liriodenine (5) and O-methylmoschatoline (6). The isoquinoline alkaloids were found in the species G. ferruginea, G. latifolia and G. sellowiana for the first time and they support the taxonomic position within the genus Guatteria. Isoquinoline alkaloids (5–6) can be considered chemotaxonomic markers of the subfamily Annonoideae.     

Flavonoids from four compositae species

The isolation of umbelliferone from Eupatorium angustifolium, of alnustin, 5,7,8-trimethoxyflavone, 7-hydroxy-3,5,8-trimethoxyflavone and 3,5,7,8-tetramethoxyflavone from Achyrocline satureoides var. albicans; of cirsimaritin from Baccharis eleagnoides; and of genkwanin from Symphyopappus polystachyus is reported.     

Sterols from four species of liliaceae

Fractionation of the sterol mixture from Tristagma uniflorum, Nothoscordum gramineum var. philippianum, Nothoscordum inodorum, and Nothoscordum montevidense were achieved by means of preparative TLC. Analysis of the fractions by GC and GC-MS allowed the identification of Δ⁰, Δ⁵, and Δ⁷ sterols. The unusually high proportion of cholestan-3β-ol seems to be biogenetically related to the C₂₇ steroidal sapogenins contained in those plants.     

An annotated checklist of Pythium species from Iran

The genus Pythium, with slightly over 280 described species has been classified traditionally with other filamentous, coenocytic, sporangia-producing fungi as “Phycomycetes”. However, with recent advances in chemical, ultrastructural and molecular studies Pythium spp. are now considered as “fungus-like organisms” or “pseudo-fungi” and are placed in the kingdom Chromista or kingdom Straminopila, distinct from the true fungi or the kingdom Fungi. Little is known about the biodiversity of Pythium in Iran. This paper attempts to assess the position of the genus Pythium and provides details of the historical development of the study of Pythium in Iran. The survey list contains 33 species, 4 species groups and 1 unknown species of Pythium.     

Further pyrrolizidine alkaloids and furoeremophilanes from Senecio species

The investigation of 17 Senecio species afforded in addition to 14 known pyrrolizidine alkaloids 20 new ones, including some compounds of a novel type with an additional lactone moiety. Furthermore seven known and 11 new furoeremophilanes, two known and a new eremophilone, a further shikimic acid derivative and an acetylenic compound, most likely formed by intramolecular Diels-Alder reaction were isolated. The structures were elucidated by spectroscopic methods, especially high field ¹H and ¹³C NMR and NOE difference spectroscopy. The configuration of the seneremophilondiol esters has been corrected.     

Essential oils from two endemic species of Apiaceae from Iran

The composition of essential oils of Leutea glaucopruinosa (Rech.f.) Akhani & Salimian comb. nov., and Zeravschania (Boiss. & Hausskn.) Salimian & Akhani comb. nov. were analysed by GC-MS. 49 compounds are identified in the former and 33 compounds in the latter, comprising a total of 76 compounds in both species. Both species were originally described under Peucedanum, which are transferred in this paper into Leutea and Zeravschania, respectively. The chemical compounds of the essential oils show that there are only seven common compounds between two species. The major compounds of L. glaucopruinosa are mostly monoterpene hydrocarbons and oxygenated monoterpenes, in which alpha-pinene (31.5%), sabinene (9.7%), beta-pinene (9.2%), exo-fenchyl acetate (4.5%) are dominant. In Z. pastinacifolia sesquiterpene hydrocarbons and phenylpropanoids dominate with beta-bisabolene (37.3%), 3,1-butyl-1,2-dimethoxy benzene (14.9%), 10,11-dimethylbicyclo[6.3.0]undec-(8)-en-9-one (12.9%), 4-t-butyl-1,2-dimethoxy benzene (6.8%), (E)-asarone (5.1%) and elemicine (4.1%) as major compounds.     

Characterization of protamines from four avian species

No data are available on the protamines of birds, with the exception of galline. We have characterized the protamines from four species of birds belonging to four different orders. All of them have very similar properties. They have been purified by carboxymethylcellulose chromatography and analyzed with respect to amino acid composition and electrophoretic behaviour. They are very arginine-rich proteins (63.4-67.3%) but do not contain lysine. Serine (12.0-18.2%), tyrosine (5.8-9.0%) and glycine (4.5-7.1%), along with arginine, make up the bulk of the amino acid residues in these molecules. The electrophoretic mobility of bird protamines in acetic acid-urea-polyacrylamide gels is intermediate between that of somatic histones and salmine. The molecular size, estimated from amino acid analysis and electrophoretic migration, is 65 +/- 5 amino acid residues.     

Three new species of the genus Leveillula from Iran

 Based on molecular and morphological studies, Leveillula guilanensis sp. nov. on Chondrilla juncea, L. lactucae-serriolae sp. nov. on Lactuca serriola, and L. mindii sp. nov. on Mindium laevigatum are described from Iran. Received: May 7, 2002 / Accepted: September 5, 2002 Correspondence to:S. Takamatsu     

Glycopentanolones A-D,four new geranylated quinolone alkaloids from Glycosmis pentaphylla

The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC₅₀ values between 0.05 and 4.28 μM.     

Benzophenanthridine alkaloids from the stem bark of a Zanthoxylum species

From the stem bark of a Zanthoxylum species collected on Grand Cayman Island 12 benzophenanthridine alkaloids have been isolated of which five are new. The novel alkaloids have been identified on the basis of spectral analysis as decarine acetate, 6-carboxymethyldihydrochelerythrine, 6-(4-methyl-2-oxopentanyl)dihydrochelerythrine; chelelactam, 6-[3′-(2-oxopyrrolidinyl)]-dihydrochelerythrine and caymandimerine, 2,2-di[6′-(dihydrochelerythryl)]-acetaldehyde.     

New chromosome counts in nine endemic species from Iran

Original meiotic chromosome counts are presented for nine endemic species in seven families of Angiosperms from Iran including:Arum giganteum Ghahr. (Araceae) (n=14),Caccinia actinobole Bunge (Boraginaceae) (n=8),Delphinium aquilegifolium (Boiss.)Bornm. (Ranunculaceae) (n=8),Diplotaenia damavandica Mozaff., Hedge etLamond (Apiaceae) (n=11),Gypsophila caricifolia Boiss. (Caryophyllaceae) (n=17),Iphiona arachnoidea (Boiss.)Anderb. (Asteraceae) (n=9),Moltkia gypsacea Rech. f. etAellen (Boraginaceae) (n=20),Onobrychis gaubae Bornm. (Fabaceae) (n=8) andOnosma platyphyllum Riedl (Boraginaceae) (n=9). Eight counts are reported for the first time. Furthermore, the previous chromosome count forIphiona aracnoidea is corrected. Based on cytological data the species status ofMoltkia gypsacea is confirmed; it is not merely synonymous withM. coerulea (Willd.)Lehm. The basic chromosome number n=11 is reported in the genusDiplotaenia for the first time.     

New chromosome counts in some species of Asteraceae from Iran

Seven chromosome counts of six species from the family Asteraceae are reported. All taxa were collected from Hamedan province, Iran. One count is a new report (viz Inula aucheriana ), three are not in accordance with previous counts (viz Senecio glaucus, Tanacetum chiliophyllum and Tanacetum polycephalum ) and the others (viz Tripleurospermum disciforme, Tanacetum polycephalum , T. parthenium ) are confirmations of very limited (one to eight records) previous data. Most of the studied taxa have the basic number x=9, but Senecio glaucus has x = 10, with ploidy levels ranging from 2x to 8x. Both diploidy and triploidy were found in T. chiliophyllum and may be regarded as a sign of ongoing speciation.     

Karyotypes of four wild Paeonia species from Greece

The karyotypes of eight wild Greek Paeonia taxa were studied, viz. P. clusii ssp. clusii (2n = 10, 20), P. clusii ssp. rhodia (2n = 10), P. mascula ssp. mascula (2n = 20), P. mascula ssp. hellenica (2n = 20), P. mascula ssp. icarica (2n = 20), P. mascula ssp. russi (2n = 10), P. peregrina (2n = 20) and P. parnassica (2n = 20). P. mascula and P. clusii have a very similar haploid chromosome complement, x = 5, including three metacentric chromosomes, one submetacentric and one subtelocentric. In the chromosome complements of the tetraploid P. peregrina and P. parnassica the same chromosome types are included but their karyotype differ from those of the former two species by a number of characters. The main karyotype differences are concerned with the size differentiation of the chromosomes which in the case of P. peregrina has resulted in the diploidization of the tetraploid karyotype.
From the individuals examined, six were found to have abnormal karyotypes suggesting chromosomal exchanges. These structural aberrations in which mainly submetacentric and subtelocentric chromosomes are involved have also been described and discussed.