Terpenoids and aromatic compounds from selected East Malaysian liverworts

Nine East Malaysian liverworts have been investigated chemically. Frullania serratta produces eudesmane-, germacrane-, eremophilane and elemane-type sesquiterpenoids and bibenzyls and is classified as chemotype I of the Frullaniaceae. Wiesnerella denudata elaborates not only germacranolides but also cyclic bis(bibenzyls), marchantins A and B. The major components of Trichocolea pluma is prenyl 3,4-dimethoxybenzoates, the chemical markers of the Trichocoleaceae. Mastigophora species are chemically almost identical to those of Herbertus because both genera produce unique isocuparene-type sesquiterpenoids and isocuparene dimers. Chandonathus, Heteroscyphus, Lepidozia, Scapania and Schistochila species produce various types of sesquiterpenoids which have been widely distributed in the other liverworts.     

Sesquiterpenes of nine european liverworts from the genera, Anastrepta,bazzania, jungermannia,lepidozia and Scapania

The essential oils of fourteen liverwort specimens from nine species of the Jungermanniales have been examined as to their sesquiterpenes. The barbatenes prove to be present in detectable amounts in all but one species. Bazzanene is frequently found with the barbatenes and new chemical evidence does not support the previously assigned structure but is consistent with a structure diastereomeric to trichodiene. This is consistent with a biogenetic rationale for the barbatene skeleton. Anasterptene, a novel crystalline tetracyclic hydrocarbon, has been found in numerous oils, and chemical degradation established a common skeleton with myliol. The samples of genus Scapania elaborate sesquiterpenes of the enantiomeric humulene-longifolene sequence. New members of this group found are (?)-β-longipinene, (?)-longipipanol, and (+)-γ-himachalene. The related germacrene series is represented by a cadinene, (?)-α-ylangene, and (?)-sativene. A series of cis-fused selinenes have also been found, which are more closely allied to the germacrene-sativene group than to typical trans-fused selinenes. One of these selinenes is shown to be the same as the material previously designated as sibirene. Scapania undulata also elaborates (+)-α- and β-chamigrene, and a number of novel hydrocarbons of still unknown structure.     

Cuparane- and isocuparane-type sesquiterpenoids in liverworts of the genus Herbertus

Canadian and Japanese Herbertus aduncus, Japanese H. sakuraii and Colombian H. subdentatus belonging to the Jungermanniales (Hepaticae) were chemically investigated. The previously known entcuparane- and novel isocuparane-type sesquiterpenoids are the major components which are of importance as chemical markers in the Herbertaceae.     

Sesquiterpenes of thalloid liverworts of the genera Conocephalum,Lunularia, Metzgeria and Riccardia

Thalloid liverworts of orders Metzgeriales and Marchantiales elaborate essential oils distinguishable from those of the Jungermanniales by the absence of β-barbatene and anastreptene. Riccardia sinuata elaborates a novel tricyclic exomethylene sesquiterpene of as yet undetermined structure. Conocephalum conicum elaborates cadinene-type sesquiterpenes. β-Cadinene from the latter species is clearly enantiomeric to the same product from vascular plants.     

A survey of alkaloids in the genera Harpalyce and Brongniartia (Fabaceae—Brongniartieae)

The presence of alkaloids in six species of Brongniartia and three species of Harpalyce is reported. This survey revealed remarkable qualitative differences in the alkaloid profiles of these two genera. B. discolor, B. lupinoides, B. sousae and B. intermedia showed a typical -pyridone pattern, with cytisine, anagyrine and baptifoline as major alkaloids. In leaves of the first three species ormosanine-type alkaloids occurred additionally. B. flava and B. vazquezii are devoid of -pyridones, but accumulate lupanine, hydroxylated lupanines and ester alkaloids. All three species of Harpalyce were similar in accumulating -pyridones, but H. formosa differed from H. brasiliana and H. pringlei in the presence of epilupinine. In general the alkaloid profiles of Brongniartia and Harpalyce show similarities to those of the Australian genera Hovea, Lamprolobium, Plagiocarpus and Templetonia and support therefore the actual concept of the enlarged tribe Brongniartieae.     

Chemical classification of the essential oils of the Iranian Salvia species in comparison with their botanical taxonomy

The essential oils of eight Salvia species collected from different localities in Iran were analyzed by gas chromatography/mass spectrometry (GC/MS). The analytical results were compared with those previously published for related Iranian sage species in order to identify chemical markers for these species. Salvia eremophila, S. hypoleuca, and S. reuteriana are endemic, while S. atropatana, S. chloroleuca, S. santolinifolia, S. aegyptiaca, and S. macrosiphon also grow wild in neighboring countries. We categorized the Iranian Salvia species into four main chemotypes according to their essential-oil constituents: those which are dominated by 1) monoterpenes, 2) mono- and sesquiterpenes, or 3) sesquiterpenes as the major constituents, and 4) those containing low-molecular-weight acids, aldehydes, and esters, and green-leaf volatiles (GLVs). Likely due to the chemical diversity of different Salvia chemotypes, this categorization was supported by principal component analysis (PCA) for the group sampled here, but not for the values reported in the literature. We identified the following chemical markers: α-pinene, β-pinene, 1,8-cineol, linalool, and borneol in monoterpene-rich species, or β-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, and caryophyllene oxide in sesquiterpene-rich species. Among these, α-pinene, β-caryophyllene, and germacrene D are the most common and abundant in the Salvia species investigated. In accordance with their close biological taxonomy, the chemical similarity of the essential oils of S. santolinifolia and S. eremophila is so high that we may consider them chemically identical.     

香根草挥发物化学成分的分析

The chemical components of the volatiles from Vetiveria zizanioides were analyzed by SPME and GC-MS. In the roots, the main component was valencene (30.36%) abstract, while in the shoots and leaves, they were 9-octadecenamide (33.50%) abstract, 2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene (27.46%) abstract, and 1,2-benzendicarboxylic acid, diisooctyl ester(18.29%) abstract The results showed that there were many terpenoids in the volatils. In shoot volatiles, there existed 3 monoterpenes, 2 sesquiterpenes and 1 triterpene. Most of the volatiles in roots were sesquiterpenes.     

Evidence for conspecificity of Piper methysticum forst. f. and Piper wichmannii C. DC

Morphological, chemical, cytological and genetic evidence demonstrating the absence of taxonomic distinction between Piper methysticum and Piper wichmannii are reviewed. Piper methysticum is not a separate species, but rather a group of sterile cultivars selected from somatic mutants of P. wichmannii. As P. methysticum was described first (1786), it has priority and P. wichmannii (1910) is superfluous. A new subspecific classification is suggested that makes a distinction between the sterile cultivars (P. methysticum var. methysticum) and the wild populations (P. methysticum var. Wichmannii).     

Flavonoids of the annual Muhlenbergia

Whole plant flavonoids were characterized from 152 populations representing 15 species of the annual Muhlenbergia. Flavonoids are predominantly based on luteolin and tricin. Glycosides are linked at position 6 C-glycosyl and 7 O-glycosyl. There is considerable variation in flavonoid patterns within and among species. Phenetic analyses of flavonoid data support recognition of three closely related groups in these 15 species of Muhlenbergia.     

Constituents of the essential oils from three tetraploid species of Chrysanthemum

The chemical constituents of the volatile oils from Chrysanthemum indicum, C. yoshinaganthum and C. cuneifolium, three botanically related tetraploid species, are described. By spectroscopic methods, 42 compounds were identified, including 22 monoterpenoids, 17 sesquiterpenoids and 3 acetylenic compounds. The sesquiterpenoids estafiatin (C. yoshinaganthum) and valeranone (C. indicum) have been found for the first time in Chrysanthemum species.     

Phytoalexin induction and its chemosystematic significance in the genus Trigonella

Using the drop-diffusate technique, a number of isoflavonoid phytoalexins have been obtained from the excised, fungus-inoculated leaflets of 41 species belonging to the legume genus Trigonella. Leaf diffusates variously contained pterocarpan (medicarpin and maackiain) and isoflavan (vestitol and sativan) derivatives previously associated with genera closely allied to Trigonella. In diffusates from T. calliceras, medicarpin was accompanied by a phytoalexin (designated TC-1) provisionally identified as a new hydroxylated pterocarpan. Most of the Trigonella species were also examined for their ability to release coumarin upon tissue maceration. The combined phytoalexin/coumarin data suggest that three major intrageneric chemical divisions occur in Trigonella; two of these apparently link the genus to Medicado/Factorovskya and Melilotus respectively, whilst the third provides some evidence for a connection with Trifolium. The taxonomic aspects of these findings are discussed in the light of earlier morphological studies which provided evidence for a distinct floral dichotomy amongst Trigonella species.     

A comparative study on the alkaloids of Zanthoxylum leprieurii, Z. lemairei and Z. rubescens from Ghana

Previous reports on the alkaloids of Z. leprieurii, Z. lemairei and Z. rubescens are reviewed. The alkaloids from nine specimens collected in Ghana have been examined chromatographically and the implications of the findings discussed, with special reference to the distinction between Z. leprieurii and Z. rubescens. In addition three further compounds, dihydrochelerythrine, lupeol and sesamin are reported for the first time from Z. leprieurii. The overall value of alkaloids as systematic markers in Zanthoxylum in Africa is briefly discussed.     

Chemical and behavioral defenses of the neotropical harvestman Camarana flavipalpi (Arachnida: Opiliones)

The defensive secretion of the harvestman Camarana flavipalpi (Gonyleptidae) was chemically characterized, revealing the presence of a single, highly volatile component (2-methyl-5-ethyl-phenol). Individuals do not frequently use chemical defenses and rely mainly on thanatosis as defense. Two types of emission of secretions were recorded: a globule at the gland opening without liquid displacement and liquid displacement along the lateral margins of the dorsal scute with accumulation of fluid at the lateroposterior area of the body. The anterior opening of the ozopore is covered by an integumentary dome that faces the laterodorsal area of the scute. The lateral channel is well defined near the opening of the ozopore and along the lateral margin of the dorsal scute as rows of small granules. The ozopore morphology of C. flavipalpi is similar to closely related species and simplified when compared with other species that promptly release chemical secretions.     

Neurotrophic secoaromadendrane-type sesquiterpenes from the liverwort Plagiochila fruticosa

A new sesquiterpene dialdehyde, plagiochilal B, isolated from the liverwort Plagiochila fruticosa exhibits not only acceleration of neurite sprouting but also enhancement of choline acetyltransferase activity on a neuronal cell culture of fetal rat cerebral hemisphere at 10⁻⁵ M. Additionally, two new secoaromadendranes, plagiochilines J and K were isolated. The structures of the new secoaromadendrane-type sesquiterpenes were established by extensive 2D NMR data and chemical correlation with plagiochiline A.     

Phylogenetic relationships among Chilean Sophora species

Phylogenetic affinities among Chilean Sophora species are not clear. We suggest a new hypothesis for the origin of the section Edwardsia on the basis of parsimony analysis, which allows a South American origin to be established for the species of this section. The seed alkaloid composition did not provide useful information for the filiation of Edwardsia species, and the shortest tree was obtained using morphological characters only. Two branches are clearly distinguishable by the pubescence of the leaflets and the flag/wings length ratio: one of them includes S. chrysophylla, S. tetraptera, S. toromiro, S. howinsula and S. denudata; the other one includes S. macnabiana, S. microphylla, S. masafuerana, S. prostrata and S. fernandeziana. In contrast, S. macrocarpa, an ancient element of the South American flora, is closely related to species belonging to the section Sophora represented in the region by S. tomentosa, S. linearifolia and S. rhynchocarpa. Sections Calia and Styphnolobium are clearly related to each other, both morphologically and chemically.     

Comparative dynamics of ptaquiloside and pterosin B in the two varieties (caudatum and arachnoideum) of neotropical Bracken Fern (Pteridium aquilinum L. Kuhn)

Significant chemical differences have been observed among the two neotropical varieties of bracken, caudatum and arachnoideum. Trans-o-hydroxycinnamic acid and coumarin have been found only in the caudatum variety. The concentration changes of ptaquiloside and pterosin B with blade growth were markedly different in caudatum and arachnoideum. In the newly emerged croziers where the concentration of these compounds was highest the former exhibited from 1.98 to 3.9 mg of ptaquiloside per gram of biomass (mg/gbm) while arachnoideum possessed only between 0.032 and 0.66 mg/gbm. These concentrations decreased consistently with the unfurling of the blade. Pterosin B was found in approximately one-tenth of the ptaquiloside concentration in most stages, suggesting that these compounds are chemically related in vivo. Caudatum, in retaining a much higher concentration of these toxins than arachnoideum in the full grown frond poses a higher risk of exposure to farm grazing animals that the latter, where ptaquiloside and pterosin B are almost absent.     

薇甘菊挥发油的化学成分及其对昆虫的生物活性

用GC/MS分析了薇甘菊挥发油的化学成分,共鉴定了22个化合物,单萜和倍半萜及其醇和酮的衍生物是其主要成分,并研究了薇甘菊挥发油对昆虫的生物活性.结果表明,在5～10μl·株^-1的用量时,它们对小菜蛾、黄曲条跳甲和猿叶虫有显著的产卵驱避作用.同时也具有一定的触杀毒力,在500、750、1000mg·L^-1浓度时,对萝卜蚜的校正虫口减退率分别为50.0%、59.86%和62.51%.然而,在500mg·L^-1浓度时,对萝卜蚜、小菜蛾和黄曲条跳甲等不同受试虫态却无熏蒸毒杀作用.     

Species of Colletotrichum on Agavaceae

Species of Colletotrichum cause diseases on a wide range of hosts, frequently infecting plants in the Agavaceae (monocotyledons: Liliales). Three species of Colletotrichum restricted to the Agavaceae were detected through morphological studies of specimens and molecular sequence analyses of the LSU of the nu-rDNA and the ITS region of the nu-rDNA from cultures. Colletotrichum agaves on Agave is fully described and illustrated. Colletotrichum dracaenophilum is described as a new species for isolates having long conidia and occurring on Dracaena sanderiana from China. Colletotrichum phormii and Glomerella phormii are determined to be the correct scientific names for the asexual and sexual states, respectively, of a species commonly referred to as C. rhodocyclum and G. phacidiomorpha occurring mainly on Phormium. In addition, C. gloeosporioides and C. boninense were isolated from plants in the Agavaceae. All species of Colletotrichum described on Agavaceae were evaluated based on type specimens. A key to the five species of Colletotrichum on Agavaceae is included. This paper includes one new species, Colletotrichum dracaenophilum, and three new combinations, Colletotrichum phormii, Glomerella phormii, and Phaeosphaeriopsis phacidiomorpha.     

Chloroplast DNA and the determination of species status in the Disa tripetaloides complex (Orchidaceae), and its relationships to three species Racemosae, section Disa

Disa cardinalis and three populations within the D. tripetaloides species complex contain variation in their chloroplast DNA (cpDNA) variability. All four taxa possessed unique cpDNAs and sequence divergence values ranged from 0.34 to 1.03%. A phylogeny of these genomes was reconstructed, along with the genomes of three other species, D. racemosa, D. uniflora and D. venosa, all of which are also section Disa and series RAcemosae, to determine the relationship of these closely related species to the D. tripetaloides complex. A phylogeny of the taxa using morphological data was also reconstructed. Outgroup comparison was made with D. sagittalis, a member of section Coryphaea. Although the molecular and morphological data were not completely congruent, both data types revealed D. cardinalis, rather than D. tripetaloides ssp. aurata, to be more closely allied with D. tripetaloides ssp. tripetaloides, suggesting that D. tripetaloides ssp. aurata should be elevated to species rank. Additionally, the high sequence divergence observed between the Natal and Cape populations, coupled with their geographical isolation and alternate flowering seasons, suggests that these two D. tripetaloides ssp. tripetaloides populations may, in fact, be more appropriately ranked as subspecies.     

First report of non-mycorrhizal plant mutants (Myc) obtained in pea (Pisum sativum L.) and fababean (Vicia faba L.)

Genetic resistance to vesicular-arbuscular (VA) mycorrhiza formation has been obtained in spontaneous or chemically induced mutants of two mycorrhiza-forming species (Pisum sativum L. and Vicia faba L.). The eight mutants, termed myc⁻, are characterized by aborted infections limited to one or two host cells. Expression of the myc⁻ character is associated with that of the nod⁻ character in both legumes, and is likewise under recessive genetic control. Preliminary analysis of the genetic behaviour of the myc⁻ mutants in diallel crosses has shown that at least three genes are involved in VA mycorrhiza infection.