Liverwort Porella Research Articles

A new sacculatane diterpenoid and a new oplopanone sesquiterpenoid from Porella perrottetiana (Mont.) Trevis. collected in Sapa, Vietnam

From the n-hexane extract of the liverwort Porella perrottetiana collected in Sapa (North Vietnam), a new sacculatane diterpenoid (perrottetianal E (1)) and a new oplopanone sesquiterpenoid ((+)-oplopanone C (2)), along with two known sesquiterpenes (3 and 4), and two known phaeophytins (5 and 6) have been isolated. Their structures were elucidated based on the analysis of NMR spectroscopic data, in combination with HR-ESIMS and the reported data. Compounds 1-4 were evaluated for their cytotoxic activities against three cancer cell lines: KB (human carcinoma in the mouth), HepG2 (human hepatocellular carcinoma), and A549 (human lung carcinoma).

Multiple paternity in the unisexual, haploid, leafy liverwort Porella platyphylloidea

We used isozyme markers to obtain an estimate of multiple paternity (mating of females with multiple males) in the unisexual, haploid leafy liverwort Porella platyphylloidea. From a sample of 119 plants, 15 (12.6%) were non-sex-expressing, 16 (13.4%) were females without sporophytes, 38 (31.9%) were males, and 50 (42.0%) were females bearing sporophytes. Thus, 87.4% of all plants expressed sex, and 73.5% of females bore sporophytes. The overall observed sex ratio was female-biased at 1.74:1. We extracted a total of 121 sporophytes from the 50 fertile females. Using the strict criterion that only female plants bearing two or more sporophytes with different multilocus genotypes represent cases of multiple paternity, our overall estimate is 56.8% (46 out of 81). Spearman rank-order correlation coefficients revealed that plants growing lower on trees were significantly larger than those higher on the tree and that female plants were significantly larger than male plants. Multivariate analysis showed, however, that the primary determinant underlying these correlations was the larger mean size of females.

Phytochemical and cytotoxic investigations of pinguisanoids from liverwort Porella cordaeana

Four new pinguisane derivatives, namely porellacetals A-D (1–4), alongside with two known compounds, phytol (5) and stigmasterol (6), were isolated from an ether extract of Porella cordaeana, guided by cytotoxicity assays against MCF-7, a human breast cancer cell line, and HT-29, a human colorectal cancer cell line. The structures of the isolated compounds were elucidated with the aid of spectroscopic means (UV, IR, NMR, mass spectrometry). The isolated compounds exhibited weak cytotoxic activities against the two aforementioned cancer cell lines.

Organic-Matter Retention and Macroinvertebrate Utilization of Seasonally Inundated Bryophytes in a Mid-Order Piedmont River

Abstract There is increased understanding of the role of bryophytes in supporting invertebrate biomass and for their influence on nutrient cycling and carbon balance in aquatic systems, but the structural and functional role of bryophytes growing in seasonally inundated habitats is substantially less studied. We conducted a study on the Middle Oconee River, near Athens, GA, to assess invertebrate abundance and organic-matter retention in seasonally inundated patches of the liverwort Porella pinnata, a species that tends to be submerged only when water levels in rivers are substantially above base flow. Aquatic invertebrate utilization of these seasonally inundated habitats has rarely been investigated. Macroinvertebrate biomass, insect density, and organic-matter content were significantly greater in patches of P. pinnata than on adjacent bare rock. Bryophyte biomass explained additional variation in organic matter, insect biomass, and density. The most abundant insects in P. pinnata patches were Dipteran...

Immunomodulatory pinguisane-type sesquiterpenes from the liverwort Porella cordaeana (Porellaceae): the “new old” furanopinguisanol and its oxidation product exert mutually different effects on rat splenocytes

α-Furanopinguisanol and furanopinguisanone, two new pinguisane-type sesquiterpenes from the liverwortPorella cordaeana, exert mutually different effects on rat splenocytes.

A new guaiane-type sesquiterpene lactone from the Chinese liverwort Porella acutifolia subsp. tosana

AimTo study the chemical constituents of the Chinese liverwort Porella acutifolia subsp. tosana. MethodsThe compounds were isolated and purified with column chromatography and their structures were determined on the basis of 1D- and 2D-NMR analysis. ResultsThree compounds were obtained and identified as guaian-3-en-2α, 14-6α, 12-diolide (1), (20R)-6β-hydroxystigmasta-4, 22-dien-3-one (2), and (20R)-3β-hydroxystigmasta-5, 22-dien-7-one (3). ConclusionCompound 1 is a new guaiane-type sesquiterpene lactone. Compounds 2 and 3 are known steroids.

Bioactive Sesqui- and Diterpenoids from the Argentine Liverwort Porella chilensis

Four fusicoccane-type diterpenoids (1-4), including the new 1 and 2; four pinguisane-type sesquiterpenoids (5-8); and two aromadendrane-type sesquiterpenoids (9 and 10) were isolated from an Argentine collection of the endemic liverwort Porella chilensis. The biofilm formation of the human pathogen Pseudomonas aeruginosa was inhibited by compounds 3 (53 and 47%), 9 (45 and 41%), and 10 (48 and 37%) at 50 and 5 μg/mL, respectively. Compounds 3, 9, and 10 also produced a slight decrease in bacterial growth and interfere with the process of quorum sensing at the same doses.

High levels of genetic variation in the haploid leafy liverwort Porella platyphylla from the southeastern United States

The few studies that have investigated levels of genetic variation in liverworts have found very little polymorphism. Our electrophoretic data show, however, that the leafy liverwort Porella platyphylla maintains high levels of genetic variation in at least some natural populations from the southeastern United States. Within a single population from southwestern North Carolina, we detected 26 distinct multilocus genotypes and more than 80% of the enzyme loci we surveyed were polymorphic. It seems likely that earlier studies of mostly thalloid species from glaciated regions of Europe have presented a biased picture of levels of variation in liverwort populations.

A fossil Porella (Porellaceae, Hepaticae) in Eocene Baltic amber

Description and illustration are given of the liverwort Porella subgrandiloba Grolle & M. L. So sp. nov. from Baltic amber (Eocene), the first fossil record for the Porellaceae.

Africane-type sesquiterpenoids from the Argentine liverwort Porella swartziana and their antibacterial activity.

Seven africanes (1, 2a,b, 3-6), two of them new (1, 2a), three secoafricanes (7-9), one of them new (7), and two norsecoafricanes (10, 11a), one of them new (10), all of them swartzianin-type, have been isolated from an Argentine collection of the endemic liverwort Porella swartziana. The structures of the new compounds were established by extensive 1D and 2D NMR spectroscopic data. Absolute configurations of compounds 2a, 2b, and 10 were derived on the basis of CD spectra. The compounds were tested for activity against a variety of microbes, but none were found to exhibit significant antibacterial activity.

Pinguisane-type sesquiterpenes from the South American liverwort Porella recurva (Taylor) Kuhnemann.

The chemical composition of a dichloromethane extract of the South American liverwort Porella recurva has been examined. Two new pinguisane-type norsesquiterpenoid natural products were isolated: 6,11-epoxy-15-nor-3,4-dioxo-5,10-pinguisadien-12-acetate and 6,11-epoxy-15-nor-4-oxo-5,10-pinguisadien-12-acetate. In addition two known pinguisane-type sesquiterpenes were also isolated: norpinguisone and norpinguisone methyl ester. All structures were elucidated by means of NMR spectroscopic techniques and mass spectrometry.

Genetic diversity of the Macaronesian leafy liverwort Porella canariensis inferred from RAPD markers.

Plant colonization of the North Atlantic raises the intriguing question of the relationships between extant island species with their continental counterparts (European, African, and American), which may provide clues to past geographic distribution and colonization history. It has been suggested that during past glaciations, many plant species with typical Mediterranean distributions survived in the Atlantic islands that belong to what is today known as Macronesia. We used random amplified polymorphic DNA (RAPD) markers to study 12 populations of the liverwort Porella canariensis partly covering its present-day distribution (Azores, Madeira, Canary and Cape Verde Islands, and Iberian Peninsula). Unweighted pair-group (UPGMA) and principal component (PCO) analyses showed a similar geographical pattern that suggested a close relationship between Iberian populations and those from the Canaries and Cape Verde Islands. Populations from Madeira had more genetic variation than those from the Azores, a result from either a richer diversity of habitats in Madeira, which prompted more population diversification, successive colonization waves from different origins, or an older colonization of Madeira. The data show that continuous patches of liverworts are often comprised of more than one individual. Finally, RAPDs can be used to investigate intraspecific diversity within a comparatively large geographic area and, with utmost care, can be used to infer a historic context to explain the patterns observed.

NITROGEN CYCLING IN A FOREST STREAM DETERMINED BY A15N TRACER ADDITION

Nitrogen uptake and cycling was examined using a six-week tracer addition of 15N-labeled ammonium in early spring in Walker Branch, a first-order deciduous forest stream in eastern Tennessee. Prior to the 15N addition, standing stocks of N were determined for the major biomass compartments. During and after the addition, 15N was measured in water and in dominant biomass compartments upstream and at several locations downstream. Residence time of ammonium in stream water (5–6 min) and ammonium uptake lengths (23–27 m) were short and relatively constant during the addition. Uptake rates of NH4 were more variable, ranging from 22 to 37 μg N·m−2·min−1 and varying directly with changes in streamwater ammonium concentration (2.7–6.7 μg/L). The highest rates of ammonium uptake per unit area were by the liverwort Porella pinnata, decomposing leaves, and fine benthic organic matter (FBOM), although epilithon had the highest N uptake per unit biomass N. Nitrification rates and nitrate uptake lengths and rates were ...

Pinguisane and dimeric pinguisane-type sesquiterpenoids from the Japanese liverwort Porella acutifolia subsp. tosana

Two new pinguisane-type, three new Diels–Alder reaction-type dimeric pinguisane sesquiterpenoids and known sesqui and diterpenoids were isolated from the ether extract of the Japanese liverwort Porella acutifolia subsp. tosana. Their absolute stereostructures were established by a combination of extensive 2D-NMR, CD spectra, X-ray crystallographic analysis, modified Mosher’s method and chemical correlation.

苔類ジャゴケ及びフジウロコゴケの植物化学的研究

Four hundred samples of Conocephalum conicum, collected in various places have been analyzed by GC-MS. This resulted in the presence of three chemo-types of C. conicum. One of them elaborate (-)-sabinene (type-I) as a major compound. The other two types characteristically contained (+)-bornyl acetate (type-II) and methyl cinnamate (type-III) as major constituent respectively. The structures of three new monoterpenic esters, isolated from the ether extract of C. conicum (type-I and/or II) have been established by chemical and spectral means. They were shown to be monoterpenic esters of (+)-borneol and p-coumaric acid derivatives. The ether extract of the liverwort Chiloscyphus polyanthos afforded sesquiterpenoids which are enantiomeric to those found in another liverwort Lepidozia vitrea. The absolute configurations of the sesquiterpenoids found in the C. polyanthos were determined by spectroscopic evidence, chemical derivatization and/or x-ray crystallographic analysis. The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. +28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed.

A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

Abstract The ether extract of the liverwort Porella perrottetiana afforded (−)-α-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (−)-α-eudesmol strongly suggested that the positive values (e.g.+28.5°) described in many previous papers should be revised. Since the absolute configuration of (−)-α-eudesmol was identical to that of (+)-β-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (−)-α-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (−)-α-eudesmol will be discussed.

Sesquiterpenoids from the Liverwort Porella canariensis

From the liverwort Porella canariensis, collected in Madeira, Portugal, nine pinguisanes, four drimanes, including the pungent polygodial, two germacranes, and two aromadendranes were isolated. The major compounds were the arom adendrane ent-cyclocolorenone and the nor-pinguisane norpinguisone. Three hydrocarbons were isolated by low temperature column chrom atography. One germacrane and one pinguisane proved to be new natural products.

Pinguisane sesquiterpenes from the liverwort porella Navicularis

Four new pinguisanes, 5-pinguisen-11-ol, 6 α-methoxy-pinguis-5(10)-en-11,6-olide, 6 α-methoxy-pinguis-5(10)-en-11,6-olide-15-carboxylic acid and 5 α,10 α-epoxy-pinguisane-11,6-olide-15-carboxylic acid methyl ester, have been isolated from the North American liverwort Porella navicularis along with two known pinguisane-type sesquiterpenes, the drimane albicanol, allo-cedrol and the known diterpenes naviculide and trans-communic acid. The structures were elucidated by spectroscopic methods. Furthermore, sesquiterpene and diterpene hydrocarbons were identified by GC-MS analysis.

Grandilobalides A, B and C, sesquiterpenes from the liverwort Porella grandiloba

Three new pinguisane-type sesquiterpenes, named grandilobalide A, B, and 6α-hydroxy-4,8-dimethoxycarbonyl-pinguis-11,6-olide, and a new rearranged pinguisane-type, named grandilobalide C, together with six known sesqui- and diterpenes, have been isolated from the liverwort Porella grandiloba grown in the field. Their structures have been elucidated on the basis of spectroscopic evidence and chemical correlation.

Two novel Diels-Alder reaction-type dimeric pinguisane sesquiterpenoids and related compounds from the liverwort Porella acutifolia subsp. tosana

Abstract From the ether extract of the liverwort Porella acutifolia subsp. tosana , two new pinguisane-type and two novel Diels-Alder reaction-type dimeric pinguisane sesquiterpenoids have been isolated. Their absolute structures were determined by a combination of 2D-NMR and CD spectra, X-ray crystallographic analysis, modified Mosher's method, and chemical degradation.