Chemosystematic comparison of essential oils from eight species of four genera of the New Zealand Apiaceae

The composition of the essential oils from the seeds of eight species and the leaves of two species of the New Zealand Apiaceae was determined. Gingidia and Scandia species provided seed oils in high yield (>6%) that contained high proportions of phenylpropanoids. Anisotome haastii provided an oil in moderate yield (1.7%), over half of which was comprised of monoterpenoids and no phenylpropanoids. The four Aciphylla species afforded seed essential oils in low yield (0.5%). Three of these contained neither terpenoids nor phenylpropanoids, but contained fatty acids instead. The oil from Aciphylla squarrosa was different as it contained an abundance of phenylpropanoids. The composition of the leaf essential oils of Scandia rosifolia and Gingidia montana differed significantly from those of the corresponding seed oils. Outstandingly, the seed essential oil of G. montana contained 62% estragole and that of Scandia geniculata contained 79% dill apiole. The results of this present work support the conclusions of Mitchell et al. (1998), about the taxonomy of these genera that were drawn from their work with ribosomal DNA sequences viz., that the Gingidia and Scandia genera were closely related to each other and that the Anisotome and Aciphylla genera were not closely related to each other, but were weakly related to the Gingidia and Scandia genera.     

Flavonoid profiles in the Heliohebe group of New Zealand Veronica (Plantaginaceae)

The Heliohebe group of Veronica (sect. Hebe) consists of five species occurring in the South Island of New Zealand. These species and a hybrid were analysed for their flavonoids. Five flavone glycosides were isolated and identified by NMR spectroscopy and three additional glycosides were detected by LC–UV–MS. Luteolin 7-O-, 3′-O- and 4′-O-glucosides and apigenin 7-O-glucoside were present in all six taxa investigated, 6-hydroxyluteolin glycosides were found in five and a luteolin caffeoylglycoside in four taxa, while a hypolaetin 7-O-glycoside was detected only in Veronica pentasepala. The 3′-O- and 4′-O-glucosides of luteolin are also common in other species of Veronica sect. Hebe (restricted to the Southern Hemisphere), but are rare in Northern Hemisphere species of Veronica and thus act as good chemotaxonomic markers for the section. The relatively simple flavonoid profiles found in the Heliohebe group are plesiomorphic and consistent with the group's status as sister to the Hebe clade. Based on the detected flavonoids, two groups could be distinguished within the Heliohebe clade: (1) Veronica hulkeana, Veronica lavaudiana and Veronica raoulii, characterised by luteolin caffeoylglycoside, and (2) V. pentasepala and Veronica scrupea, where this compound is replaced by a 6-hydroxyluteolin dihexoside.     

Chemosystematic evaluation of Aloe section Pictae (Asphodelaceae)

The chemosystematic value of UV-absorbing leaf constituents was considered in previously uncharacterised representatives of Aloe section Pictae, the problematic maculate species complex. Comparative data indicate that the anthrone C-glycoside, 6′-malonylnataloin (7-hydroxychrysaloin 6′-O-malonate) is typical of maculate species in East Africa, but is unconvincing as a synapomorphy for section Pictae. A naphthalene derivative found widely in Aloe, plicataloside, was detected in Aloe greatheadii. Biogeographical trends were observed in the occurrence of the flavonoids isoorientin (luteolin-6-C-glucoside) and isovitexin (apigenin 6-C-glucoside). Isoorientin is a common constituent of tropical and sub-tropical species of Aloe, whereas isovitexin is restricted to a few southern African species. Isoorientin and isovitexin co-occur in the southern African maculate species Aloe parvibracteata, and the disjunct West African maculate species, Aloe macrocarpa. This is the first report of isoorientin and isovitexin in maculate species of Aloe; the presence of flavonoids in section Pictae is of taxonomic interest.     

Fruit anatomy of the genus Pimpinella L. (Apiaceae) in Iran

The genus Pimpinella L., with about 170–180 species in the world, is one of the largest genera of the family Apiaceae (Umbelliferae). Based on the Flora Iranica treatment, this genus has 25 species in the Iranian plateau, including 19 species in Iran, and six of those (P. tragioides, P. deverroides, P. pastinacifolia, P. anisactis, P. khorasanica and P. khayyamii) are endemic.     

Sesquiterpenes and diterpenes from Ambrosia arborescens

Six compounds, eudesm-11(13)-en-4β,9β-diol, 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene, 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene, 1α-hydroxy-7-oxo-iso-anhydrooplopanone, 10α-hydroxy-11,13-dihydro-5-epi-psilostachyin, and 4β-hydroxypseudoguaian-12,6-olide 4-O-β-d-glucopyranoside, together with 12 known sesquiterpenes, were isolated from the leaves of Ambrosia arborescens. Structures were elucidated by 1D and 2D NMR spectroscopy including 1D-TOCSY, DQF-COSY, 2D-ROESY, HSQC, and HMBC experiments, as well as by ESI mass spectrometry. The absolute configuration of the 15,16-diol moiety in 15R,16-dihydroxy-3-oxoisopimar-9(11)-ene and 15S,16-dihydroxy-3-oxoisopimar-9(11)-ene was determined using Snatzke’s method. All compounds were evaluated for antiproliferative activity.     

Bis-sesquiterpenes and diterpenes from Chloranthus henryi

Bis-sesquiterpenes, henriols A (1), B (2), C (3), and D (4), and three diterpenes, henrilabdanes A (5), B (6), and C (7), together with two known bis-sesquiterpenes and three known labdane diterpenes, were isolated from the ethanol extract of the roots of Chloranthushenryi. Their structures and absolute configurations were elucidated by NMR spectroscopic, X-ray crystallographic and CD analyses. Compounds 1, 5, 6 and 7 showed moderate hepatoprotective activities with IC₅₀ values of 0.19, 0.66, 0.09 and 0.18 μM, respectively. They were not studied further due to the weak effects noted. Compounds 3 and 8 exhibited cytotoxic activities against three types of cancer cell lines including the hepatoma (BEL-7402), human gastric carcinoma (BGC-823), and colon cancer (HCT-8).     

The microbiological transformation of the diterpenes dehydroabietanol and teideadiol by Mucor plumbeus

The microbiological transformation of dehydroabietanol (18-hydroxy-dehydroabietane) by Mucor plumbeus led to 2alpha,18-dihydroxy-abieta-8,11,13,15-tetraene, 2alpha,15-dihydroxy-dehydroabietanol, 2alpha-hydroxy-15-methoxy-dehydroabietanol, 7beta-hydroxy-2-oxo-dehydroabietanol, 15-hydroxy-2-oxo-dehydroabietanol and 15,16-dihydroxy-2-oxo-dehydroabietanol, whilst that of teideadiol (1alpha,18-dihydroxy-dehydroabietane) gave 2alpha-hydroxy-teideadiol, 7alpha-hydroxy-teideadiol and 7beta-hydroxy-teideadiol. Thus, 2alpha- and 7beta-hydroxylation occur in both biotransformations and the 15-hydroxylation is inhibited in the biotransformation of teideadiol by the presence of a 1alpha-alcohol.     

Labdane diterpenes from Leonurus japonicus leaves

Three labdane diterpenes 15,16-epoxy-6-hydroxylabda-5,8,13(16),14-tretraen-7-one (leojaponin), (9alpha,13S);15,16-diepoxy-7beta-hydroxylabd-14-en-6-one (13-epi-preleoheterin), and (9alpha,13R);15,16-diepoxy-6beta-hydroxylabd-14-en-7-one (iso-preleoheterin) were isolated from the leaves of Leonurus japonicus, in addition to the previously reported preleoheterin. The structure elucidations were made based on analysis of their spectroscopic data.     

Nor-ent-kaurane diterpenes and hydroxylactones from Antennaria geyeri and Anaphalis margaritacea

In a study of Pacific Northwest plants of the Asteraceae family, a nor-ent-kaurane diterpene and a known diterpene, both displaying antibacterial activities, were isolated together with scopoletin and sitosterol-3-O-beta-glucopyranoside from the aerial parts of Antennaria geyeri. Anaphalis margaritacea afforded two hydroxylactones. The structures were established by one and two dimensional NMR techniques, IR and CIMS.     

Chromosome numbers of South African Umbelliferae (Apiaceae)

Chromosome numbers are reported for 12 species from nine genera of South African Umbelliferae, of which seven species and one genus (Itasina) are recorded for the first time. A detailed list of all published chromosome counts for southern African species is also presented, together with a review of the literature. The new data obtained are briefly discussed in the context of the taxonomy and relationships of local Umbelliferae. The counts agree with previous reports except that Annesorhiza appears to have 2n = 22, with or without one additional B-chromosome, and not 2n = 24 as reported in the literature. The number for Itasina (2n = 24) is of considerable interest and indicates that a detailed chromosome study of the South African genera Annesorhiza and Chamarea may yield valuable taxonomic information.     

Azorellane diterpenes from Azorella cryptantha

Azorella cryptantha yielded the diterpenes, azorellolide and the dihydroderivative, dihydroazorellolide, together with the known yaretol and 1alpha,10beta,4beta,5alpha-diepoxy-7alpha-germacran-6beta-ol. Both possess a carbon skeleton type that may originate from rearrangement of the mulinane skeleton.     

Sequestration of polyacetylenes by the parasite Orobanche hederae (Orobanchaceae) from its host Hedera helix (Araliaceae)

Orobanche hederae Duby and its host Hedera helix L. were collected in the North Italian Trentino-Südtirol region and analyzed for their content of polyacetylenes. Both, the host plant (Hedera) and the parasite (Orobanche) contained the polyacetylene falcarinol and two of its dehydroderivatives. The contents of polyacetylenes in Hedera decrease from roots via stems to leaves and contents in Orobanche are only about one-tenth of the contents in the Hedera roots it parasites on. Moreover, relative contents of the more polar polyacetylenes are higher in Orobanche than in Hedera, implying a bias toward the sequestration of more polar compounds.     

Tagalsins A-H, dolabrane-type diterpenes from the mangrove plant, Ceriops tagal

From the stems and twigs of the mangrove plant, Ceriops tagal, seven dolabrane-type diterpenes, namely tagalsins A-G (1-7), and the norditerpene tagalsin H (8) were isolated. Their structures were established on the basis of extensive spectroscopic analysis.     

Ent-pimarane type diterpenes from Gnaphalium gaudichaudianum

Fractionation of the methanol extract of Gnaphalium gaudichaudianum DC afforded one new and six known ent-pimarane diterpenes together with velutin, squalene and stigmasterol. The structure of the new compound was established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. Two of the isolated compounds exhibited moderate toxicity in the Artemia salina toxicity test.     

Essential oil composition of nine Apiaceae species from western United States that attract the female Indra Swallowtail butterfly (Papilio indra)

Aletes acaulis, Cymopterus hendersonii, Cymopterus panamintensis var. acutifolius, Lomatium rigidum, Lomatium scabrum var. tripinnatum, Musineon tenuifolium, Sphenosciadium capitellatum, Tauschia arguta and Tauschia parishii are among the twenty-two species of the Apiaceae family to which female Indra Swallowtail butterflies (Papilio indra: Lepidoptera) are attracted for oviposition. Because plant volatile oils are known to be attractants for female butterflies, the percent composition of the essential oils of each species was studied. Amongst the nine host plants 168 essential oil components were identified representing between 84% and 99% of the oils. Principal Components Analysis and hierarchical cluster analysis on the essential oil compositions of the larval host plants against four non-larval host plants separated the hosts from the non-hosts into distinct clusters. Volatile components of the oils common to the nine species of Apiaceae are correlated with the expression of physiological attraction behavior by the butterfly.     

Genetic and pathogenic diversity of Neofusicoccum parvum in New Zealand vineyards

Genetic diversity of 50 isolates of Neofusicoccum parvum, the predominant species of the Botryosphaeriaceae recovered from grapevines displaying symptoms of dieback and decline in New Zealand, was compared to that of isolates from Australia, South Africa, and California. The eight universally primed polymerase chain reaction (UP-PCR) primers distinguished 56 genotypes, with only four clonal pairs found. Seven main groups were identified in a neighbour-joining (NJ) tree with isolates from different regions and vineyards of New Zealand, Australia, and California distributed in different groups, indicating a high level of intra and intervineyard genetic variation. All of the South African isolates were positioned in a separate UP-PCR group, indicating that these isolates were less related to the other N. parvum isolates. When compared to fungi that reproduce sexually the genetic diversity and Shannon diversity indices were low (0.076-0.249; 0.109-0.367, respectively), genetic identity levels were high (0.76-0.95), and genetic distance levels were low (0.04-0.27). The large number of genotypes and the low number of clones in the New Zealand N. parvum populations may be explained by parasexual recombination as anastomosis was observed between nonself pairings. Pathogenicity tests using isolates from different UP-PCR groups inoculated onto either green shoots or 1-y-old grapevines detected virulence diversity, indicating intra and intervineyard variation between isolates, however, no correlation was detected between UP-PCR group and virulence.     

ent-Isopimarane-type diterpenoids from the New Zealand liverwort Trichocolea mollissima

Two ent-isopimarane-type diterpenoids were isolated from the New Zealand liverwort Trichocolea mollissima (Hook. f. and Tayl.) Gott., together with a known 1alpha-hydroxy-ent-sandaracopimara-8(14),15-diene. Their absolute structures have been established by modified Mosher's method, X-ray crystallography and by analyses of their CD spectra.     

Labdane diterpenes from Marrubium velutinum and Marrubium cylleneum

From the aerial parts of Marrubium velutinum and Marrubium cylleneum, seven labdane diterpenes, velutine A, 15-epi-velutine A, velutine B, 15-epi-velutine B, velutine C, cyllenine A and 15-epi-cyllenine A, have been isolated together with five known diterpenes and four known flavones. The structures of the isolated compounds were established by means of NMR [(1)H-(1)H-COSY, (1)H-(13)C-HMQC, HMBC, HMQC-TOCSY, NOESY] and MS spectral analyses. Complete NMR assignments are reported for known compounds.