Lycopodium Complanatum Research Articles

Patterns in Genome-Wide Codon Usage Bias in Representative Species of Lycophytes and Ferns.

The latest research shows that ferns and lycophytes have distinct evolutionary lineages. The codon usage patterns of lycophytes and ferns have not yet been documented. To investigate the gene expression profiles across various plant lineages with respect to codon usage, analyze the disparities and determinants of gene evolution in primitive plant species, and identify appropriate exogenous gene expression platforms, the whole-genome sequences of four distinct species were retrieved from the NCBI database. The findings indicated that Ceratopteris richardii, Adiantum capillus-veneris, and Selaginella moellendorffii exhibited an elevated A/U content in their codon base composition and a tendency to end with A/U. Additionally, S. capillus-veneris had more C/G in its codons and a tendency to end with C/G. The ENC values derived from both ENC-plot and ENC-ratio analyses deviated significantly from the standard curves, suggesting that the codon usage preferences of these four species were primarily influenced by genetic mutations and natural selection, with natural selection exerting a more prominent influence. This finding was further supported by PR2-Plot, neutrality plot analysis, and COA. A combination of RSCU and ENC values was used as a reference criterion to rank the codons and further identify the optimal codons. The study identified 24 high-frequency codons in C. richardii, A. capillus-veneris, and Diphasiastrum complanatum, with no shared optimal codons among the four species. Arabidopsis thaliana and Ginkgo biloba exhibited similar codon preferences to the three species, except for S. moellendorffii. This research offers a theoretical framework at the genomic codon level for investigating the phylogenetic relationships between lycophytes and ferns, shedding light on gene codon optimization and its implications for genetic engineering in breeding.

Extraordinary preservation of gene collinearity over three hundred million years revealed in homosporous lycophytes

Homosporous lycophytes (Lycopodiaceae) are a deeply diverged lineage in the plant tree of life, having split from heterosporous lycophytes (Selaginella and Isoetes) ~400 Mya. Compared to the heterosporous lineage, Lycopodiaceae has markedly larger genome sizes and remains the last major plant clade for which no chromosome-level assembly has been available. Here, we present chromosomal genome assemblies for two homosporous lycophyte species, the allotetraploid Huperzia asiatica and the diploid Diphasiastrum complanatum. Remarkably, despite that the two species diverged ~350 Mya, around 30% of the genes are still in syntenic blocks. Furthermore, both genomes had undergone independent whole genome duplications, and the resulting intragenomic syntenies have likewise been preserved relatively well. Such slow genome evolution over deep time is in stark contrast to heterosporous lycophytes and is correlated with a decelerated rate of nucleotide substitution. Together, the genomes of H. asiatica and D. complanatum not only fill a crucial gap in the plant genomic landscape but also highlight a potentially meaningful genomic contrast between homosporous and heterosporous species.

A new abietane diterpenoid from Lycopodium complanatum

A new abietane diterpenoid, 1β, 11-epoxyabieta-12-hydroxy-8, 11, 13-triene-7-one (1), along with three known compounds (2–4), was isolated from Lycopodium complanatum. Their structures were confirmed by the analysis of 1D, 2D NMR and HRESIMS data, and comparison with previous spectral data. All compounds were tested for inhibitory activities against A549, HepG2 and MCF-7 tumor cell lines.

Сосудистые растения и мохообразные памятника природы «Петровское болото» (Россия, Брянская область): предварительные списки

According to the results of the study of the flora of the natural monument of regional natural monument «Pe-trovskoe swamp» (Russia, Bryansk Region, Mglinsky district), carried out in 2018–2019, annotated lists of vas-cular plants and bryophytes were compiled. The flora of vascular plants includes 367 species from 80 families. The largest number of species is found in the families Asteraceae (40 species), Poaceae (34), Rosaceae (25), Fabaceae (19), Cyperaceae, Lamiaceae and Apiaceae (17), Caryophyllaceae (13), Ranunculaceae (15), Brassi-caceae and Scrophylariaceae (10). 5 of these species are listed in the regional Red Data Book (Krasnaia..., 2016): Diphasiastrum complanatum, Juniperus communis, Lathyrus pisiformis, Pulsatilla patens, Sanicula europaea. Alien species were recorded, including those spreading from cultivated coenoses in nearby settlements: Acer negundo, Amelanchier spicata, Echinocystis lobata, Helianthus tuberosus, Hemerocallis fulva, Hesperis pycnotricha, Levisticum officinalis, Oxalis stricta, Rudbeckia laciniata, Saponaria officinali, Sorbaria sorbifolia. Bryophytes belong to 107 species in 41 families. New localities of mosses listed in the regional Red Data Book were discovered: Homalia trichomanoides, Neckera pennata, Sphagnum jensenii. Indicator species of old-growth forests were noted: Anomodon longifolius, Homalia trichomanoides, Hypnum cupressiforme, Neckera pennata, Stereodon pallescens.

Complanadine F, a novel dimeric alkaloid from Lycopodium complanatum.

A novel Lycopodium alkaloid, complanadine F (1), seco-complanadine A type was isolated from the club moss Lycopodium complanatum. The planar structure and relative configuration were elucidated based on spectroscopic data.

ОСОБЕННОСТИ МЕСТООБИТАНИЙ И СОСТОЯНИЕ ПОПУЛЯЦИЙ РЕДКИХ ОРХИДЕЙ (ORCHIDACEAE) НАЦИОНАЛЬНОГО ПАРКА «НИЖНЯЯ КАМА» И СОПРЕДЕЛЬНЫХ ТЕРРИТОРИЙ НА СЕВЕРЕ ТАТАРСТАНА (ЕВРОПЕЙСКАЯ РОССИЯ)

The article examines the populations of rare species of orchids Cypripedium calceolus (L.), Epipactis helleborine L., Goodyera repens (L.) R.Br, Neottia nidus-avis (L.) Rich., Neottianthe cucullata (L.) Schlechter, Platanthera bifolia (L.) Rich. on the territory of the Republic of Tatarstan. The temperate continental climate prevails on the territory of Tatarstan, which is typical for the central part and northwestern regions of the Volga and Predkamye. In contrast, the north and northeast of Tatarstan are characterized by a moderately cool climate with a lot of precipitation during the growing season. Small fragments of the southern taiga complexes with green moss spruce and fir are formed in the north, in the Baltasi district. Dark coniferous species – spruce and fir are dominated in the north-east along the river Vyatka in Lubyanskoye forestry in coniferous-deciduous forests. Such habitats are characterized by the predominance of typically boreal and boreal-nemoral species of shrubs, grasses and mosses. Rare species have been recorded: Pyrola media Sw., P. chlorantha Sw., Diphasiastrum complanatum (L.) Holub, Hypopitys monotropa Crantz, Viola selkirkii Pursh ex Goldie. Orchid populations have some features. The development and flowering of Platanthera bifolia and Cypripedium calceolus occur 7–10 days later in comparison with central and northwestern regions of Tatarstan. Virginal and adult vegetative individuals predominate in the population structure. Generative individuals of C. calceolus in spruce-broad-leaved and pine-spruce with fir forests often do not form clones; their share is 72 % of all generative plants. The number of shoots of C. calceolus clones decreases and makes in average 3.2 shoots. On the contrary, the number of shoots in clones of the northwestern populations is equal to 6.5. The share of generative individuals of the studied populations of P. bifolia is 25 % on average and it significantly decreases in the populations of the recreational zone of the National Park. The species grows here in dry pine forests on compacted soil, and, probably, tourists pick flowers up for bouquets. Populations of N. cucullata and G. repens are found only in the protected and buffer zones of the National Park. The age structure is full-term though the share of generative plants is quite low and averages 34 % for N. cucullata, and only 15 % for G. repens. N. cucullata and G. repens have not been found yet in habitats with suitable abiotic and biotic conditions in the north and north-east of Tatarstan. This fact requires further research. The species composition of mosses is almost identical in the habitats of orchids (Pleurozium schreberi (Brid.) Mitt., dominates among mosses in all phytocenoses, but the projective cover and height of the moss tufts differ significantly. Typically boreal and hemiboreal species are registered: P. schreberi Dicranum polysetum Sw., Dicranum scoparium Hedw., Rhytidiadelphus triquetrus (Hedw.) Warnst, Rhodobryum roseum (Hedw.) Limpr., Hylocomium splendens (Hedw.) Bruch et al., Ptilium crista-castrensis (Hedw.) DeNot. A rare species – Plagiomnium drummondii (Bruch&Schimp.) T.J. Kop. is identified in the north of the Republic of Tatarstan. The abundance and development of mosses, as guarantors of humidity and preservation of microclimatic conditions, are important conditions for the growth of symbiotrophic fungi that contribute to the maintenance of orchids and many species of boreal forests on the southern border of their distribution.

Forest typological and phytosozological assessment of forest vegetation of Slobozhansky National Park

Forest typological and phytososological biodiversity of forest vegetation of Slobozhansky National Park is shown. The park covers 5244 hectares and includes the main parts of the run off valleys of the left-bank Merla River tributary, which belongs to the Vorskla River basin in the Kharkiv region. The main forest-forming species of the Slobozhansky National Nature Park are Pinus sylvestris L. (2779.3 hectares, 59.84%), Quercus robur L. (1451.8 hectares, 31.26%). Minor areas are occupied by Betula pendula Roth (138.3 hectares, 2.98%), Alnus glutinosa (L.) P. Gaertn. (122.5 hectares, 2.64%), Populus tremula L. (45.0 hectares, 0.97%) and other species. Areas covered with forest vegetation are represented by 16 edatopes: all trophotope and almost all hygrotopes, except very dry. Among the trophotopes subors (2015.2 hectares, 43.39%), oak wood (1504.4 hectares, 32.39%) and sugruds (1042.2 hectares, 22.44%) predominate, and the part of pine forest is insignificant (82.5 hectares, 1.78%). Among hygrotopes, the majority are with fresh conditions (4060.6 hectares, 87.43%), much smaller areas are dry (268.4 hectares, 5.78%), damp (184.3 hectares, 3.97%), moist (124.4 hectares, 2.68%) and wet (6.6 hectares, 0.14%) conditions. There are 17 types of forests in the Slobozhansky National Park areas covered with forest vegetation. Fresh oak-pine forest (1780.6 hectares, 38.35%), fresh maple-linden forest (1453.6 hectares, 31.30%), fresh linden-oak-pine sugrud (756.8 hectares, 16.30%) are dominated. Pinus sylvestris plantations grow in 10 forest types. The most common types of pine forests are fresh oak-pine and fresh linden-oak-pine sugrud. Quercus robur growth in 7 forest types, the most common of which is fresh maple-linden oak wood. The distribution of forest typological differences on the territory of the park of vascular plants rare species populations, which have different sozological status is analyzed. Annex I to Resolution 6 of the Berne Convention includes the following species: Dracocephalum ruyschiana L., Jurinea cyanoides (L.) Rchb., Iris pineticola Klokov. A number of species have the appropriate conservation status in Ukraine (Diphasiastrum complanatum (L.) Holub, Lycopodium annotinum L., Dracocephalum ruyschiana, Pulsatilla pratensis (L.) Mill. Sl, Allium ursinum L., Iris furcata M. Bieb., Iris pineticola, Fritillaria meleagris L., F. ruthenica Wikstr., Tulipa quercetorum Klokov & Zoz, Epipactis helleborine (L.) Crantz, Listera ovata (L.) R. Br., Neottia nidus-avis (L.) Rich., Platanthera bifolia (L.) Rich., Stipa borysthenica Klokov ex Prokudin) and 22 species at the regional range.

Serratane triterpenoids from Lycopodium complanatum and their anti-cancer and anti-inflammatory activities

Phytochemical investigation of the ethyl acetate fraction of Lycopodium complanatum led to eight new serratane triterpenoids (lycomplanatums A-H, 1–8), along with five known analogues (9–13). Their structures were elucidated by extensive spectroscopic methods, including 1D/2D NMR, HRESIMS, and DFT GIAO 13C NMR calculation. Among them, compounds 2 and 13 showed moderate antiproliferative effects against seven human cancer cell lines, especially for MCF-7 with IC50 values of 13.8–44.7 μM. Additionally, the compounds were screened for anti-inflammatory effects based on their inhibitory activities of nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW264.7 cells, and compounds 2 and 13 diminished NO production more potently than others in a concentration-dependent manner.

Progress towards the Total Syntheses of Lycopodium Alkaloid, Lycopladine A

AbstractSeveral alkaloids derived from discrete Lycopodium species can treat Alzheimer's disease and increase the efficiency of learning and memory in animals. Thus, Lycopodium alkaloids bearing amazingly unique hetero‐polycyclic ring scaffolds persuaded scientists to look upon its biogenetic and biosynthetic pathways and to design its ambitious total syntheses. Recently, a C16N type Lycopodium alkaloid, (+)‐lycopladine A; isolated from the club moss Lycopodium complanatum, showed selective but modest cytotoxicity towards murine lymphoma L1210 cells (IC50 7 μg/mL). Owing to its dense array of stereochemical features, as well as intriguing biological activity, lycopladine A has been an important synthetic target for last 12 years. An overview of the synthetic studies of lycopladine A is presented, covering literature from 2006 until March 2019.

Cytotoxic polyhydroxy serratene triterpenoids from Lycopodium complanatum

Phytochemical investigation of the 70% aqueous EtOH extract of Lycopodium complanatum led to six new polyhydroxy serratene triterpenoids (serrat A-F, 1–6), along with a known analogue (7). Their structures and configurations were elucidated by data analysis of HRESIMS, 1D and 2D NMR, in combination with comparisons of reported experimental spectroscopic data. All the isolates were evaluated cytotoxic activities against HepG2 cells, MCF-7 cells and series human lung cancer cell lines A549, Calu-6, NCI-H441, NCI-H226 and NCI-H1975. The results indicated that certain compounds inhibited proliferation of human cancer cells. Moreover, all compounds possessed selective cytotoxic activities on MCF-7 cells. Further, possible biosynthesis pathways of these compounds were proposed.

Ground vegetation composition and diversity in drained Norway spruce (Picea abies (L.) Karst.) stands 50 years after whole-tree harvesting management: case study in Latvia

Abstract The long-term (50 years) effect of whole-tree harvesting (stump harvesting) on ground vegetation in experimental drained Norway spruce (Picea abies (L.) Karst.) stands was studied. We used a chronosequence approach to assess the long-term impact of whole-tree harvesting (WTH) on stands’ ground vegetation. WTH stands were compared with four control stands with different age and with the same forest type: young stand (15 years), middle-aged stand (45 years), mature stand (110 years) and over-mature stand (140 years). Species richness was similar between the WTH stand and middle-aged stand (61 and 60 species, respectively). Shannon-Wiener diversity indices in the WTH and middle-aged stand (3.40 and 3.19, respectively) indicated that the stands were similar to each other. A community similarity analysis showed that the composition of vegetation was similar between the WTH and middle-aged stand, although some species like Lycopodium clavatum and Diphasiastrum complanatum occurred only in the WTH stand. The study showed that a period of 50 years is sufficient for ground vegetation of a typical drained spruce forest to recover after WTH management.

Abietane diterpenoids from Lycopodium complanatum

Five new abietane diterpenoids (complanatins A-E, 1–5) have been isolated from the club moss Lycopodium complanatum, along with two known abietane diterpenoids (xanthoperol and sugiol). Their structures were determined by comprehensive analysis of 1D, 2D NMR, CD and HRESIMS data. The cytotoxic effects of five compounds (1–4, 7) were evaluated in three human lung cancer cell lines (MSTO-211H, NCI-H2052 and NCI-H226). Compounds 3 and 4 exhibited cytotoxic activities against the three cell lines. In addition, a plausible biogenetic pathway of compounds 1–7 was proposed.

Lycoplanines B-D, Three Lycopodium Alkaloids from Lycopodium complanatum

A novel C17N Lycopodium alkaloid (LA), lycoplanine B (1), containing an unusual formyl group, along with two new LAs, lycoplanines C (2) and D (3), were isolated from the whole plant of Lycopodium complanatum. Their structures were elucidated by extensive NMR techniques, including 1D- and 2D-NMR experiments, as well as comparing their spectral data with those of the known analogues. A possible biogenetic pathway for 1 was also proposed.Graphical

Lycogladines A-H, fawcettimine-type Lycopodium alkaloids from Lycopodium complanatum var. glaucum Ching

Five new fawcettimine-type alkaloids (1–5) and three new natural products (6–8), along with four known analogues, fawcettimine (9), fewcettidine (10), lycopoclavamine B (11), and lycopladine B (12), were isolated from the whole plant of Lycopodium complanatum var. glaucum Ching. The structures of lycogladines A-H (1–8) were determined based on HRESIMS, 1D and 2D NMR spectroscopic analysis, as well as single-crystal X-ray diffraction. Compound 1 possesses a new ring system that is formed through the linkage of C-13-OC-2, which is rarely present in Lycopodium alkaloids (LAs). Compounds 1–8 were tested for their β-site amyloid precursor protein (APP)-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AChE) inhibitory activities.

Lycoplanine A, a C16N Lycopodium Alkaloid with a 6/9/5 Tricyclic Skeleton from Lycopodium complanatum.

Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.

4 アスヒカズラ(Lycopodium complanatum)由来新規アルカロイドの構造(口頭発表の部)

4 アスヒカズラ(Lycopodium complanatum)由来新規アルカロイドの構造(口頭発表の部)

Inhibitory effects of serratene-type triterpenoids from Lycopodium complanatum on cholinesterases and β-secretase 1

Phytochemical investigation of Lycopodium complanatum whole plants led to the isolation of two new serratene-type triterpenoids (1 and 2) along with eight known triterpenoids (3–10). Their structures were established using 1D and 2D NMR spectroscopic techniques and mass spectrometry. These compounds did not inhibit acetylcholinesterases (AChE) and butyrylcholinesterase (BChE), but did inhibit β-secretase 1 (BACE1). Compounds 1 and 6 showed potent BACE1 inhibition with IC50 values of 2.79 ± 0.28 and 2.49 ± 0.12 μM, respectively. The kinetic study of BACE1 inhibition revealed that compound 1 showed competitive inhibition, whereas 6 showed mixed-type inhibition. Furthermore, molecular docking results showed that the tested inhibitors 1 and 6 exhibited good binding affinities toward BACE1, with binding energies of −8.8 and −10.3 kcal/mol, respectively.

Lyconadins G and H, Two Rare Lyconadin-Type Lycopodium Alkaloids from Lycopodium complanatum.

Two rare lyconadin-type Lycopodium alkaloids, lyconadins G (1) and H (2), together with four known ones (3–6), were isolated from Lycopodium complanatum. The structures were determined on the basis of their spectroscopic analyses, and the absolute configuration of 1 was established by an X-ray crystallographic analysis. It is the first time to establish the absolute configuration of lyconadin-type Lycopodium alkaloid by an X-ray diffraction experiment. In addition, these findings may provide more information for the biosynthesis of lyconadins.Graphical Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0111-9) contains supplementary material, which is available to authorized users.

Potent effects of alkaloid-rich extract from Huperzia selago against sodium nitroprusside-evoked PC12 cells damage via attenuation of oxidative stress and apoptosis.

Imbalance between production and scavenging of free radicals and other reactive oxygen species (ROS) is a component of many diseases, but it is especially important in aging-related diseases of the central nervous system. Oxidative stress-induced neuronal dysfunction plays an important role in the pathomechanism of neurodegenerative disorders, including Alzheimer's and Parkinson's disease. Experimental data showed that free radical scavengers may protect the brain against oxidative modifications. The need for efficient and safe antioxidants with therapeutic potential stimulated the rise of interest in the medicinal plant products, which are a rich source of phytochemicals possessing biological activity. In our studies we focused on alkaloid fractions (AFs) isolated from club moss, Huperzia selago and Diphasiastrum complanatum, due to their beneficial activity and exclusive chemical structure. Our previous study demonstrated that selected alkaloids from Huperzia selago effectively protect macromolecules from oxidative damage. Therefore, in the present study we investigated the effects and mechanisms of action of AFs isolated from Huperzia selago and Diphasiastrum complanatum against sodium nitroprusside (SNP)-induced oxidative injury in PC12 cells. The results demonstrated that the selected AFs via reduction of nitric oxide (NO) liberation protected cells against oxidative stress, DNA and mitochondrial damage, as well as apoptosis caused by SNP. Selected AF notably decreased SNP-evoked mitochondrial polymerase γ (Polg) up-regulation. Furthermore, AF which contains Lycopodine, Serratidine, Lycoposerramine-G and (probably) Cermizine B completely inhibited the SNP-induced expression of interferon-γ (Ifng) and cyclooxygenase 2 (Ptgs2) as well as significantly down-regulated the expression of 12/15-lipoxygenase (Alox12) and tended to decrease the mRNA level of interleukin-6 gene (Il6). In conclusion, these results suggest that the AFs from Huperzia selago effectively protect PC12 cells against SNP-induced oxidative damage by adjusting the level of reactive nitrogen species, suppression of apoptosis and down-regulation of proinflammatory genes. The compounds present in these AFs could be potential candidates to develop successful drugs preventing oxidative damage and apoptosis in age-related neurodegenerative disorders.

Новые разновидности Diphasiastrum zeilleri (Rouy) Holub (Lycopodiaceae)

Diphasiastrum zeilleri (Rouy) Holub is a hybrid species, with the formula D. complanatum (L.) Holub × D. tristachyum (Pursh) Holub. A high variability of D. zeilleri is due to environmental conditions (light and shadow ecological forms) and probably to introgressive hybridization with the parental species. Intermediate forms between D. zeilleri, D. complanatum and D. tristachyum are quite rare, that allows to treat the three taxa as separate species. D. zeilleri is missing in subarctic regions of Europe and North America, and some degree of its resemblance with D. complanatum subsp. montellii Kukk. is convergent. Lycopodium complanatum f. polystachyum H. Lindb. is considered to belong to D. zeilleri, and an appropriate conbination is published, Diphasiastrum zeilleri var. polystachyum (H. Lindb.) Ivanenko. A new variety Diphasiastrum zeilleri (Rouy) Holub var. ramistachyum Ivanenko is described, differing by sessile strobili formed on the basal part of fertile branches during one growing season. The structure, the base of which is a fertile branch, and the upper part is strobilus (strobili), is proposed to term «strobilus branch». Besides D. zeilleri var. ramistachyum, the strobilus branches are produced by D. issleri (Rouy) Holub, D. oellgaardii Stoor, Boudrie, Jérôme, K. Horn et Bennert, and rarely by D. alpinum (L.) Holub and D. complanatum.