Polyacetylenes in Hawaiian bidens

Leaves and roots of 19 species and six subspecies of Hawaiian Bidens were examined for polyacetylenes. Eleven C₁₃ hydrocarbons, aromatic and thiophenyl derivatives, one C₁₄ tetrahydropyran and three C₁₇ hydrocarbons were isolated all identified. All can be derived from a common precursor, oleic acid. Polyacetylenes were not detected in the leaves of 13 taxa although they are found in the roots of all. The occurrence of 2-[2-phenyl-ethyne-1-yl]-5 acetoxymethyl thiopene in Bidens has not been previously reported. Its ubiquitous presence is consistent with other evidence that the Hawaiian species are all derived from a single ancestral immigrant to the islands. Most taxa could be distinguished by their complement of polyacetylenes in roots and leaves. No variation was found to occur within taxa except in B. torta, in which each population had a unique array of polyacetylenes. Above the species level there appeared to be no taxonomically significant pattern to the distribution of polyacetylenes in this group.     

Flavonoids and polyacetylenes from the aerial parts of Bidens tripartita

Fourteen flavonoids (1–14) and two polyacetylenes (15 and 16) were isolated from the aerial parts of Bidens tripartita. Thirteen compounds (1–7, 9, 11, 12, and 14–16) were isolated from this species for the first time, of which a flavonoid (11) was obtained for the first time from the genus Bidens. The chemotaxonomic significance of these compounds was summarized.     

Sesquiterpene and polyacetylene profile of the Bidens pilosa complex (Asteraceae: Heliantheae) from Southeast of Brazil

The pantropical weed Bidens pilosa (Asteraceae) is a species with several taxonomic problems. Recently it has been shown to be a complex of different species. To shed light on this problem in Brazil, dichloromethane extract of leaves of several populations corresponding to three proposed species for the complex in southeastern Brazil (B. pilosa, Bidens alba and Bidens subalternans) were analyzed by GC–MS. Twenty-four substances were detected, of which four resemble polyacetylenes, the others sesquiterpenes. Five sesquiterpenes tentatively identified as E-caryophyllene, α-humulene, germacrene-D, bicyclogermacrene and α-muurolene were found in all three Bidens species. The polyacetylene phenylhepta-1,3,5-triyne was identified only in B. alba. Multivariate analysis (cluster and principal component analyses) separated the three entities, suggesting that these compounds could represent a useful tool to distinguish species in the B. pilosa complex.     

Anti-diabetic properties of three common Bidens pilosa variants in Taiwan

Bidens pilosa L. var. radiata (BPR), B. pilosa L. var. pilosa (BPP), and B. pilosa L. var. minor (BPM) are common variants of a plant often used as a folk remedy for diabetes in Taiwan. However, the three variants are often misidentified and little is known about their relative anti-diabetic efficacy and chemical composition. In this paper, we have first developed a method based on GC–MS and cluster analysis with visualization to assist in rapidly determining the taxonomy of these three Bidens variants. GC–MS was used to determine the chemical compositions of supercritical extracts, and differences and similarities in the variants were determined by hierarchical cluster analysis. Next, the HPLC profiles of the methanol crude extracts in the Bidens plants and evaluated anti-diabetic effects of methanol crude extracts were compared, as well as three polyacetylenic compounds of the Bidens plants using db/db mice. Single-dose and long-term experiments showed that the BPR extract had higher glucose-lowering and insulin-releasing activities than extracts from the other two variants, and that cytopiloyne was the most effective pure compound among the three polyacetylenic compounds. BPR extract and cytopiloyne also significantly reduced the percentage of the glycosylated hemoglobin A1c in db/db mice. Besides, both animal studies and HPLC analysis demonstrated a good correlation between anti-diabetic efficacy of the Bidens extracts and the particular polyacetylenes present.     

白花鬼针草中多烯炔类成分的分离及其生物活性研究

为了解白花鬼针草(Bidens pilosa var.radiata)的化学成分,采用多种色谱技术从其提取物中分离多烯炔类成分,并对其生物活性进行研究.结果表明,从白花鬼针草乙酸乙酯提取部位中分离鉴定出4个多烯炔类化合物,分别为5-acetoxy-2-phenyl-ethinyl-thiophene(1)、1-phen...     

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.     

Structure-function relationships in the phototoxicity of acetylenes from the Asteraceae

Structure-function relationships of a series of polyacetylenes and thiophene derivatives from the plant family Asteraceae were examined in relation to their photosensitizing activity to E. coli and S. cerevisiae cultures. The thiophenes were generally found to be more phototoxic than the polyacetylenes, with increasing activity with increasing number of thiophene rings. With the polyacetylenes there was a general trend of increasing toxicity with increasing acetylene bonds in the molecule. An assessment of the relative phototoxicities of the test compounds revealed a positive correlation between phototoxicity and water-octanol partition coefficients with yeast and to a lesser extent with E. coli. Thiophenes were found to have a higher relative light absorption than acetylenes, but considering all the compounds together there was little correlation between phototoxicity and photon absorption. These results are discussed in relation to modes of action and ecological significance of these phototoxic protective agents.     

Acetylenes from the callus of Panax ginseng

Two new polyacetylenes were isolated from dried callus of Panax ginseng. The structures of the polyacetylenes were confirmed as heptadeca-3-oxo-4,6-diyne-9,10-diol and its dihydro derivative by their IR, ¹H NMR, ¹³C NMR and mass spectra, and some chemical reactions. The new acetylenes exhibited growth inhibition against Yoshida sarcoma cells in tissue culture.     

The flavonoids of Megalodonta beckii and isolation of 2′-3-Dihydroxy-4-methoxy-4′-glucosyl chalcone

A new naturally occurring chalcone glycoside, $\text{2′,-}\text{dihydroxy}\text{-4-}\text{methoxy}\text{-4′-O-β-}\text{d}\text{-}\text{glucosyl}$ chalcone, and other chalcones, aurones, flavonols, and anthocyanins are reported from Megalodonta (Bidens) beckii. The plan is an amphibious aquatic with heterophyllous leaves, but the presence of certain flavonoids is correlated with vegetative versus floral tissues rather than vegetative leaf form. The implications of flavonoid chemistry with respect to the relationship of M. beckii to several sections of Bidens are discussed.     

New ways to look at the architecture of plant cell walls : localization of polygalacturonate blocks in plant tissues

We report the use of Ni²⁺ and Co²⁺ on free-hand sections of soybean (Glycine max L.) and Bidens sp to localize polygalacturonates. In soybean only the hourglass cells of the seedcoat stain intensely. In the pod the epidermis of the outer pod wall and a few layers of subepidermal cells stain lightly, while that part of the funiculus adjacent to the seedcoat palisade epidermal cells stains heavily and the neck of the funiculus close to the pod also stains. In Bidens stem sections, the walls of the collenchyma stain most intensely.     

Die GattungBidens L. in der Tschechoslowakei

Im ersten Teil dieser Arbeit werden die Studienergebnisse über die Verbreitung einzelner Arten der GattungBidens aus den Jahren 1962—1965 angeführt. Im zweiten Teil werden die Wege sowie die Art und Weise veranschaulicht, wie sich die adventiven Arten der GattungBidens in Mitteleuropa verbreiteten.     

Polyacetylenes of Artemisia vulgaris

During a re-examination of Artemisia vulgaris, a series of new acetylenic products, in addition to those previously known, was found. Trideca-1,3,5-triene-7,9,11-triyne and tetradeca-4,6-diene-8,10,12-triyne-1-ol, new compounds to the species, were fully characterized from the root extract, and heptadeca-1,7,9-triene-11,13,15- triyne, cis-dehydromatricaria ester and tetradeca-6-ene-8,10,12-triyne-3-one were found in the flowers, previously stated to contain no polyacetylenes. Three further polyacetylenes, known from related plants of the Anthemideae, were not fully characterized, but their presence was indicated.     

Mosquito larvicidal activity of polyacetylenes from species in the Asteraceae

Twenty-four polyacetylenes isolated from species in the Asteraceae were screened for their near-UV-mediated larvicidal properties to the mosquito, Aedes aegypti. Dosage resonse lines for three of the most active compounds were prepared. One of these, σ-terthienyl from Tagetes was more toxic than DDT when near-UV radiation was provided. A scaled up trial with this compound in a simulated field situation demonstrated its potential as a larvicide. The effects of the radiation dose on larval survival were studied and the action spectra for the phototoxic effects of three compounds on larvae were obtained with narrowband interference filters. Because of the close agreement between the action and absorption spectra, it appears most probable that the polyacetylene is the primary absorbing compound. The potential of polyacetylenes as larvicides and their role in plant herbivore relations are discussed.     

Bio-guided isolation of leishmanicidal and trypanocidal constituents from Pituranthos battandieri aerial parts

Protozoan pathogens that cause neglected tropical diseases are a major public health concern in tropical and developing countries. In the course of our ongoing search for new lead compounds as potential antiprotozoal agents, this study aims to perform a bio-guided fractionation of Pituranthos battandieri, using an in vitro assay against Leishmania amazonensis and Trypanosoma cruzi. Two known polyacetylenes, (−)-panaxydiol (1) and (−)-falcarindiol (2) were identified from the ethanolic extract of the aerial parts of P. battandieri as the main bioactive constituents. Compounds 1 and 2 showed similar potency (IC₅₀ values of 5.76 and 5.68 μM, respectively) against L. amazonensis to miltefosine (IC₅₀ value of 6.48 μM), the reference drug, and low toxicity on macrophage cell lines J774. Moreover, compound 1 exhibited moderate activity (IC₅₀ 23.24 μM) against T. cruzi. In addition, three known furanocoumarins, 8-geranyloxypsoralen (3), 8-geranyloxy-5-methoxypsoralen (4), and phellopterin (5) were isolated. Their structures were elucidated by NMR and MS analysis. Compounds 1 and 2 are described for the first time in the Pituranthos genus, and this is the first report on their antiprotozoal activity. These results highlight this type of polyacetylenes as an interesting scaffold for the development of novel antiparasitic drugs.     

The generic placement of a morphologically enigmatic species in Asteraceae: evidence from ITS sequences

 Bidens cordylocarpa is a high polyploid species restricted in distribution to stream sides in the mountains of Jalisco, Mexico. The morphologically enigmatic species was originally described as a member of the genus Coreopsis, but later transferred to Bidens, largely because the involucral bracts appear most similar to Bidens. Characters of the cypselae, often useful in generic placement, are of no value for this species because the fruits have features not detected in either Bidens or Coreopsis. Sequences from the internal transcribed spacer region of nuclear ribosomal DNA (ITS) were used to assess the relationships of Bidens cordylocarpa. The molecular phylogeny places B. cordylocarpa in a strongly supported clade of Mexican and South American Bidens, and provides more definitive evidence of relationships than morphology, chromosome number, or secondary chemistry. Molecular, morphological, and chromosomal data suggest that B. cordylocarpa is an ancient polyploid, perhaps the remnant of a polyploid complex. Received August 28, 2000 Accepted February 11, 2001     

Polyacetylenes of Dahlia

Two Dahlia sherffii strains and three Dahlia pinnata strains and Dahlia rudis Sorensen have been investigated for polyacetylenes. A great number of acetylenic compounds, characterized earlier from other Dahlia species was determined. The two Dahlia sherffii strains and the three Dahlia pinnata strains contain 1-phenylhept-5-ene-1,3-diyne and 1-phenyl-hepta-1,3,5-triyne and derivatives which have previously been found in one Dahlia coccinea strain and in a horticultural form. A comparison between this group of dahlias with others previously investigated, show characteristic differences in the chemical pattern. Dahlia rudis is thus closer to the D. imperialis and the D. tenuicaulis and three of the Dahlia coccinea strains. Dahlia merckii exhibits a quite unique pattern of polyacetylenes.     

Genetic relationships between Bidens forbesii and six species in the Hawaiian and the Marquesas Islands

A crossing program was carried out between the Kauai endemicB. forbesii and six other Polynesian species, five of which are Hawaiian and one Marquesan. All crosses produced vigorous F₁ hybrids, portraying a strong genetic relationship betweenB. forbesii and the other species. The results indicate a close systematic relationship among the Polynesian species ofBidens placed by Sherff in sect.Campylotheca and strengthen the argument that this group dispersed from North America to the Hawaiian Islands, then from Hawaii to the Marquesas Islands.     

Comparative capitular morphology and anatomy of Coreopsis L. and bidens L. (compositae), including a review of generic boundaries

The capitular and floral morphology and anatomy ofBidens L. andCoreopsis L. were studied. All the North American species ofCoreopsis were studied. Selected species ofBidens from North and South America andCoreopsis from South America were included. The results were compared with previous observations on African species ofBidens (incl.Coreopsis). Emphasis was given to character states of the ray florets, paleae, stylearm apices, outer phyllaries, achenes, and pollen grains. Some of the character states are unique features ofCoreopsis, e.g., globular and elongately conical receptacles, deltoid outer phyllaries, truncate and indistinctly 3–5-dentate, 3–4-lobed ray florets, narrowly spathulate paleae, subulate paleae with linear-filiform upper half, hairy and apically 3-cleft paleae, truncate, convex or shallowly conical stylearm apices with the sweeping hairs limited to the area above the stigmatic surfaces and the orbicular to circular achenes. The cylindric setaceous pappus bristles so commonly encountered inBidens are unknown inCoreopsis. The pappus bristles inCoreopsis are paleaceous but similar, though thicker ones are also found in African species ofBidens (incl.Coreopsis) with winged achenes. Twin-celled hairs (setulae) with differing degrees of wall thickness are found on the achenes ofCoreopsis sect.Pseudoagarista (Mexico and South America),Coreopsis sect.Pugiopappus (California), AfricanBidens with winged achenes (e.g.,B. prestinaria, B. macroptera) and some North AmericanBidens (e.g.,B. aristosa). Similar sclerotic parenchyma make up the achenial wings of species in both genera. These may be interpreted as homologous structures, indicating the underlying similarity of these taxa and their derivation from a common ancestral stock.     

Area and the rapid radiation of Hawaiian Bidens (Asteraceae)

Aim To estimate the rate of adaptive radiation of endemic Hawaiian Bidens and to compare their diversification rates with those of other plants in Hawaii and elsewhere with rapid rates of radiation. Location Hawaii. Methods Fifty‐nine samples representing all 19 Hawaiian species, six Hawaiian subspecies, two Hawaiian hybrids and an additional two Central American and two African Bidens species had their DNA extracted, amplified by polymerase chain reaction and sequenced for four chloroplast and two nuclear loci, resulting in a total of approximately 5400 base pairs per individual. Internal transcribed spacer sequences for additional outgroup taxa, including 13 non‐Hawaiian Bidens, were obtained from GenBank. Phylogenetic relationships were assessed by maximum likelihood and Bayesian inference. The age of the most recent common ancestor and diversification rates of Hawaiian Bidens were estimated using the methods of previously published studies to allow for direct comparison with other studies. Calculations were made on a per‐unit‐area basis. Results We estimate the age of the Hawaiian clade to be 1.3–3.1 million years old, with an estimated diversification rate of 0.3–2.3 species/million years and 4.8 × 10^?5 to 1.3 × 10^?4 species Myr^?1 km^?2. Bidens species are found in Europe, Africa, Asia and North and South America, but the Hawaiian species have greater diversity of growth form, floral morphology, dispersal mode and habitat type than observed in the rest of the genus world‐wide. Despite this diversity, we found little genetic differentiation among the Hawaiian species. This is similar to the results from other molecular studies on Hawaiian plant taxa, including others with great morphological variability (e.g. silverswords, lobeliads and mints). Main conclusions On a per‐unit‐area basis, Hawaiian Bidens have among the highest rates of speciation for plant radiations documented to date. The rapid diversification within such a small area was probably facilitated by the habitat diversity of the Hawaiian Islands and the adaptive loss of dispersal potential. Our findings point to the need to consider the spatial context of diversification – specifically, the relative scale of habitable area, environmental heterogeneity and dispersal ability – to understand the rate and extent of adaptive radiation.