Incarvillea Sinensis Research Articles

Incarvine C and its analogues inhibit the formation of cell cytoskeleton by targeting Rac1

Ras-related C3 botulinum toxin substrate 1 (Rac1) has emerged as a key regulator in the treatment of cancer metastasis because of its involvement in the formation of cell plate pseudopods and effects on cell migration. In this study, we found that incarvine C, a natural product isolated from Incarvillea sinensis, and its seven analogues exhibited antitumour activity by inhibiting cell cytoskeleton formation, with moderate cytotoxicity. Accordingly, these compounds inhibited the cytoskeleton-mediated migration and invasion of MDA-MB-231 cells, with inhibition rates ranging from 37.30 % to 69.72 % and 51.27 % to 70.90 % in vitro, respectively. Moreover, they induced G2/M phase cell cycle arrest in MDA-MB-231 cells. A pull-down assay revealed that the interaction between Rac1 and its downstream effector protein PAK1 was inhibited by these compounds and that the compound Ano-6 exhibited substantial activity, with an inhibition rate of more than 90 %. Molecular docking showed that incarvine C and its analogues could bind to the nucleotide-binding pocket of Rac1, maintaining high levels of inactivated Rac1. As Ano-6 exhibited significant activity in vitro, its anti-cancer activity was tested in vivo. Four weeks of oral treatment with Ano-6 was well-tolerated in mice, and it induced a potential anti-tumour response in xenografts of MDA-MB-231 cells. Further studies demonstrated that Ano-6 was enriched in tumour tissues after 2 h of administration and induced an increase in the number of dead tumour cells. In summary, these findings not only reveal the mechanism of incarvine C but also provide a new molecular template for Rac1 inhibitors and identify a promising candidate for breast cancer treatment.

Shade Increased Seed Yield and Quality of Incarvillea sinensis var. przewalskii.

Incarvillea sinensis var. przewalskii has attracted great attention because of the anticancer value of its alkaloids and the potential use of the species for ecological restoration. However, the scarcity of high-quality seeds has significantly hindered the cultivation and efficient utilization of this species. Understanding how seeds respond to maternal environmental conditions is crucial for developing high-yield and top-notch seed accessions, but the available knowledge in this area is limited. Here, we determined the effect of shading treatments on seed development, seed quality, and yield. Compared to the control, shade significantly increased the seed germination rate and 1000-seed weight by 29.2% and 25.6%, respectively. Regardless of light conditions, the seed germination rate and 1000-seed weight decreased by 7.13% and 37.5%, respectively, as the fruit positioned from base to apical. The seed yield per plant was 27.9% higher under shade than under the control treatment. The structural equation model showed that shade promoted seed yield through increasing flowers per reproductive branch and seed numbers per capsule. These findings suggest that adjusting shading conditions and optimizing inflorescence development can lead to high-yield and high-quality seeds. Additionally, prioritizing the number of flowers per reproductive branch and seeds per capsule in breeding programs can further enhance the seed yield of I. sinensis var. przewalskii.

Mechanisms of reproductive isolation between annual and perennial plants of Incarvillea sinensis

AbstractQuantifying the relative strength of isolating barriers is a major focus of research on plant speciation. Contrasting life histories and mating systems have the potential to limit gene exchange between closely related populations growing in sympatry. However, few studies have quantified reproductive isolating barriers between conspecific annual and perennial populations and their contributions to total reproductive isolation (RI). Incarvillea sinensis Lam. (Bignoniaceae) is an insect‐pollinated herb with largely allopatric annual and perennial populations that differ in mating systems. The perennial populations are primarily outcrossing whereas annual populations are predominantly selfing. At a rare sympatric site in northern China we estimated prezygotic and postzygotic barriers to gene exchange between annual and perennial plants and found complete RI between the two life histories. Annuals exhibited significantly higher ecogeographic isolation than perennials whereas perennials experienced more isolation through pollen–pistil interactions than annuals. Crosses between annuals and perennials demonstrated that postzygotic barriers influencing fruit and seed formation, F1 germination and survival were negligible for annuals but played a small role for perennials. However, F1 hybrids of crosses between annuals and perennials produced no pollen and their ovules were largely sterile. Our study provides insight into the relative importance of prezygotic and postzygotic isolating barriers between closely related annual and perennial populations of I. sinensis and some of these barriers could have been involved with speciation. Annuals and perennials of I. sinensis represent two biological species and thus deserve to be recognized as distinct taxonomic species.

A New Monoterpene Alkaloid from Incarvillea sinensis with Migration Inhibitory Activity on Cancer Cell.

A novel monoterpene alkaloid, named incarvine G, was isolated from the Incarvillea sinensis Lam. Its chemical structure was elucidated using comprehensive spectroscopic methods. Incarvine G is an ester compound comprised of a monoterpene alkaloid and glucose. This compound showed evident inhibition on cell migration, invasion, and cytoskeleton formation of human MDA-MB-231 with low cytotoxicity.

Characterization of the chloroplast genome and its inference on the phylogenetic position of Incarvillea sinensis Lam. (Bignoniaceae)

Incarvillea sinensis Lam. is the type of the genus Incarvillea Juss., and it is widely distributed, relative to other members of the genus. In this paper, we sequenced, assembled and annotated the chloroplast genome of Incarvillea sinensis. The complete chloroplast genome is 162,088 bps in size, with overall GC content of 39.4%. We annotated 113 unique genes in the plastome sequence, including 79 protein coding genes, 30 tRNA genes, and four rRNA genes. The phylogenetic analysis based on chloroplast genome sequences resulted in a different resolution on the relationships among subgenera from the former.

Do annual and perennial populations of an insect-pollinated plant species differ in mating system?

Theory predicts that outcrossing should be more prevalent among perennials than annuals, a pattern confirmed by comparative evidence from diverse angiosperm families. However, intraspecific comparisons between annual and perennial populations are few because such variation is uncommon among flowering plants. Here, we test the hypothesis that perennial populations outcross more than annual populations by investigating Incarvillea sinensis, a wide-ranging insect-pollinated herb native to China. The occurrence of both allopatric and sympatric populations allows us to examine the stability of mating system differences between life histories under varying ecological conditions. We estimated outcrossing rates and biparental inbreeding in 16 allopatric and five sympatric populations in which both life histories coexisted using 20 microsatellite loci. In each population we measured height, branch number, corolla size, tube length and herkogamy for ~30 individuals. In a sympatric population, we recorded daily flower number, pollinator visitation and the fruit and seed set of annual and perennial plants. As predicted, outcrossing rates (t) were considerably higher in perennial (mean = 0.76) than annual (mean = 0.09) populations. This difference in mating system was also maintained at sympatric sites where plants grew intermixed. In both allopatric and sympatric populations the degree of herkogamy was consistently larger in outcrossing than selfing plants. Perennials were more branched, with more and larger flowers than in annuals. In a sympatric population, annuals had a significantly higher fruit and seed set than perennials. Genetically based differences in herkogamy between annuals and perennials appear to play a key role in governing outcrossing rates in populations, regardless of variation in local ecological conditions. The maintenance of mating system and life history trait differentiation between perennial and annual populations of I. sinensis probably results from correlated evolution in response to local environmental conditions.

Cross genera transferability of microsatellite markers from other members of family Bignoniaceae to Tecomella undulata (Sm.) Seem

Transferability of SSR markers from related species/genera is a rapid and cost-effective method to enhance genomic database of genetically neglected crops. Monotypic genus Tecomella undulata, a pharmacologically important endangered timber tree, found in hyper arid regions is one such genetic resource limited species, wherein neither SSR identification nor cross transferability studies have been initiated. Transferability of 69 cross-genera SSR primers selected from other members of family bignoniaceae (Incarvillea sinensis, I. mairei, Jacaranda copaia, Tabebuia aurea and Arrabidaea chica) showed 40.58% (28 primers) transferability amplifying 1–10 amplicons ranging in the size from 80to 600 bp in 24 accessions of T. undulata. Per cent marker transferability varied from 66.67% (A. chica) to 38.89% (J. copaia) among the genera tested while no transferable markers could be identified from I. sinensis. Transferability of simple di-/tri-nucleotide repeat (34.2–37.5%) and complex nucleotide sequence (60.0%) based SSR motifs were higher as compared to penta-/hexa-nucleotide based repeat motifs. Within the 28 transferable markers, 26 (92.86%) were polymorphic while 2 (7.14%) were monomorphic. Average number of alleles per primer was 5.39 while average polymorphic alleles per locus were 5.11. The PIC values of SSR markers ranged from 0.23 to 0.85 with an average of 0.59. Efficiency of the identified cross species SSR markers was tested for diversity analysis using a set of 24 trees (8 each of yellow, orange and red flower colour morphotypes). The 24 samples clustered into six groups with similarity coefficient ranging from 0.29 to 0.67, while six accessions formed distinct out groups. Distribution of accessions in the SSR dendrogram showed no correlation with flower colour. More diversity (99%) was observed within populations compared to that existing between populations (1%). The present study can enrich the genomic background of T. undulata by identifying suitable polymorphic markers from confamiliar species that can be applied for genetic diversity studies, mapping of QTLs and cultivar identification as well.

Response of understory species distribution of Robinia pseudoacacia plantation to environmental factors in loess hilly region, China.

We explored the distribution characteristics and influencing factors of understory species in Robinia pseudoacacia plantation in Wuqi, Ansai, Mizhi, Yichuan and other places, in combination with niche breadth, soil, altitude and other environmental factors. We analyzed the response mechanism of species distribution to environmental factor to provide a scientific basis for the mana-gement of R. pseudoacacia plantation in loess hilly region. The results showed that the broadly distributed understory species in R. pseudoacacia plantation were Setaria viridis, Heteropappus altaicus, Artemisia scoparia, Poa sphondylodes, Artemisia leucophylla, Ixeris sonchifolia, and Incarvillea sinensis. With the increasing rehabilitationage, the dominant understory species distribution followed the order: Artemisia capillaries → P. sphondylodes → A. scoparia → others (Rubia cordifolia, Rosa rubus and so on) → A. leucophylla → S. viridis. Results from principal component analysis showed that soil total phosphorus (25.6%), altitude (20.3%) and soil total nitrogen (19.3%) were the key factors influencing understory species distribution in R. pseudoacacia plantation. Soil organic carbon content, soil total nitrogen content, soil total phosphorus content, soil water content and the number of understory species distribution in R. pseudoacacia plantation were generally positively correlated with the degree of correlation varying across different species. There was no correlation between the slope aspect and the understory species distribution in R. pseudoacacia plantation. In conclusion, topography and soil factors played important roles in driving understory species distribution. The steeper the slope, the higher the altitude, the fewer understory species in R. pseudoacacia plantation. Understory species distribution was mainly affected by soil total phosphorus content and altitude. The understory species distribution reflected the differences of soil nutrient status, which had a certain guiding role in the management of R. pseudoacacia plantation.

Natural product incarvillateine aggravates epileptic seizures by inhibiting GABAA currents

A natural monoterpene alkaloid incarvillateine isolated from the plant Incarvillea sinensis is known to relieve inflammatory and neuropathic pain. However, the molecular target for the action of incarvillateine remains elusive. Here, we report that incarvillateine exacerbates epileptic seizures by inhibiting subtypes of γ-Aminobutyric acid type A (GABAA) receptors. Two-electrode voltage clamp recordings of α1β3γ2, α2β3γ2, α3β3γ2 and α5β3γ2 subtypes expressed in Xenopus oocytes revealed that incarvillateine inhibited the GABAA currents with IC50 of 25.1 μM, 43.1 μM, 105.1 μM and 93.7 μM, respectively. Whole-cell patch clamp recordings of hippocampal slices confirmed that incarvillateine inhibited spontaneous inhibitory postsynaptic currents (IPSCs), and miniature IPSCs and tonic currents. Moreover, inhibition of GABAA currents and spontaneous IPSCs by incarvillateine persisted even in the presence of blockers of adenosine receptors. In addition, incarvillateine enhanced epileptic discharges induced by Mg2+-free artificial cerebrospinal fluid (ACSF) in hippocampal slices. Furthermore, intracerebral ventricular injections of incarvillateine increased the severity of seizures induced by kainic acid in a dose-dependent manner. Taken together, our data demonstrate that incarvillateine aggravates seizures by inhibition of GABAA currents and GABAergic synaptic transmissions.

Ferulic acid dimer as a non-opioid therapeutic for acute pain

PurposeSearch for alternate pain medications has gained more importance in the past few years due to adverse effects associated with currently prescribed drugs including nervous system dysfunction with opioids, gastrointestinal discomfort with nonsteroidal anti-inflammatory drugs, and cardiovascular anomalies with cyclooxygenase-2 (COX-2) inhibitors. Phytomedicine has been explored for the treatment of pain, as these have been used for generations in regional communities and tend to lack major side effects in general. One such phytomedicine, incarvillateine (INCA), derived from the Chinese herb Incarvillea sinensis has its primary antinociceptive action through the adenosine receptor, a novel pain target. We hypothesized that derivatives of cinnamic acid dimers, which are structurally similar to INCA, would show potent antinociceptive action and that their effect would be mediated through adenosine receptor action.Materials and methodsDimers of cinnamic acid (INCA analogs) were synthesized using cavitand-mediated photodimerization (CMP) method, which utilizes a macromolecule (γ-cyclodextrin) to control excited state reactivity of photoactive compounds. Acute pain response was assessed by using formalin-induced licking behavior in hind paw of mice, and neurologic function was monitored through locomotor activity, mechanical hyperalgesia, and thermal sensitivity upon administration of test compound. For mechanistic studies, binding to adenosine receptor was determined by using computer modeling.ResultsFerulic acid dimer (FAD), which has the same chemical functionalities on the aromatic ring as INCA, showed significant suppression of formalin-induced acute pain. Antinociceptive effect was observed primarily in the inflammatory phase, and no apparent behavioral changes related to the nervous system were noticeable. Inhibition of opioid receptor did not reverse antinociceptive response, and modeling data suggest adenosine 3 receptor binding.ConclusionFAD (INCA analog) shows potent nonopioid antinociceptive action mediated predominantly through A3AR – adenosine 3 receptor action. Further characterization and selection of such INCA analogs will help us generate a new class of antinociceptives with precise chemical modifications by using CMP methodology.

Cinnamic Acid Derivatives as Novel Antinociceptives for Acute Pain

Search for alternate pain medications has gained more importance in the past few years due to nervous system related side‐effects with opioids, gastrointestinal dysfunction associated with non‐steroidal anti‐inflammatory drugs (NSAIDs), and cardiovascular anomalies with cyclo‐oxygenase‐2 inhibitors (COX‐2). Phytomedicine has been quite effective for treatment of pain, as these have been used for generations in regional communities, and tend to lack any major side‐effects. A dimer of cinnamic acid, Incarvillateine (INCA), derived from the Chinese herb Incarvillea sinensis, has its primary antinociceptive action through the adenosine receptor. Adenosine‐mediated analgesia has become an attractive target as it has the least side‐effects. We hypothesized that derivatives of cinnamic acid dimers, which structurally mimic INCA, show potent antinociceptive action, and their effect is mediated through adenosine receptor action. Compounds were synthesized using novel cavitand‐mediated photodimerization method, which utilizes a macromolecule (gamma‐cyclodextrin) to control the excited state reactivity of photoactive compounds to yield target tetra‐substituted cyclobutanes (dimers). The dimers generated so far show significant suppression of formalin‐induced acute pain in mice hind paw. Antinociceptive effect of ferulic acid dimer and 3‐methoxy cinnamic acid dimer was observed primarily in the inflammatory phase, and the dimer binds to the adenosine 3 receptors (as revealed by computer modeling). The pain suppressing response of these dimers was similar to that observed with indomethacin, an anti‐inflammatory drug. Even though morphine was more effective than the synthesized dimers in reducing neurogenic and inflammatory pain, there was no visible neurogenic side‐effects observed with administration of the dimers as commonly observed with morphine, which suggests a primary non‐opioid action. Our further characterization and selection of INCA analogs, with predominant adenosine receptor action, will help us to generate a new class of antinociceptives with precise chemical modifications using CMP methodology.Support or Funding InformationUNK Undergraduate Research Fellowship (AP, MH, WM, CC); Great Plains IDeA CTR Pilot Grant (MP, SC)This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal.

Effects of distinct pollinators on the mating system and reproductive success inIncarvillea sinensis, an annual with large floral displays

Effects of distinct pollinators on the mating system and reproductive success in<i>Incarvillea sinensis</i>, an annual with large floral displays

Gram Scale Syntheses of (-)-Incarvillateine and Its Analogs. Discovery of Potent Analgesics for Neuropathic Pain.

(-)-Incarvillateine (INCA) is the major antinociceptive component of Incarvillea sinensis, which has been used to treat rheumatism and relieve pain in traditional Chinese medicine. We have developed a concise and general synthetic approach for INCA, which enabled gram-scale asymmetric syntheses of (-)-INCA, (-)-incarvilline, (-)-isoincarvilline, and six other INCA analogues. The synthesis of isoincarvilline was reported for the first time. Three structurally simplified analogues of INCA were also synthesized. In vivo screening found that INCA and two structurally optimized analogues were efficacious in preventing the acetic acid-induced writhing response. Moreover, their analgesic efficacy was demonstrated in formalin induced pain model. More importantly, administration of 20 or 40 mg/kg INCA and two structurally optimized analogues showed strong analgesic effects in spared nerve injury (SNI) model, and their effective doses were lower than the current gold standard, gabapentin (100 mg/kg in this model).

Seasonal variation in the mating system of a selfing annual with large floral displays.

Flowering plants display considerable variation in mating system, specifically the relative frequency of cross- and self-fertilization. The majority of estimates of outcrossing rate do not account for temporal variation, particularly during the flowering season. Here, we investigated seasonal variation in mating and fertility in Incarvillea sinensis (Bignoniaceae), an annual with showy, insect-pollinated, 'one-day' flowers capable of delayed selfing. We examined the influence of several biotic and abiotic environmental factors on day-to-day variation in fruit set, seed set and patterns of mating. We recorded daily flower number and pollinator abundance in nine 3 × 3-m patches in a population at Mu Us Sand land, Inner Mongolia, China. From marked flowers we collected data on daily fruit and seed set and estimated outcrossing rate and biparental inbreeding using six microsatellite loci and 172 open-pollinated families throughout the flowering period. Flower density increased significantly over most of the 50-d flowering season, but was associated with a decline in levels of pollinator service by bees, particularly on windy days. Fruit and seed set declined over time, especially during the latter third of the flowering period. Multilocus estimates of outcrossing rate were obtained using two methods (the programs MLTR and BORICE) and both indicated high selfing rates of ∼80 %. There was evidence for a significant increase in levels of selfing as the flowering season progressed and pollinator visitation declined. Biparental inbreeding also declined significantly as the flowering season progressed. Temporal variation in outcrossing rates may be a common feature of the mating biology of annual, insect-pollinated plants of harsh environments but our study is the first to examine seasonal mating-system dynamics in this context. Despite having large flowers and showy floral displays, I. sinensis attracted relatively few pollinators. Delayed selfing by corolla dragging largely explains the occurrence of mixed mating in I. sinensis, and this mode of self-fertilization probably functions to promote reproductive assurance when pollinator service is limited by windy environmental conditions and competition from co-occurring flowering plants.

Targeting Fatty Acid Binding Protein (FABP) Anandamide Transporters – A Novel Strategy for Development of Anti-Inflammatory and Anti-Nociceptive Drugs

Fatty acid binding proteins (FABPs), in particular FABP5 and FABP7, have recently been identified by us as intracellular transporters for the endocannabinoid anandamide (AEA). Furthermore, animal studies by others have shown that elevated levels of endocannabinoids resulted in beneficial pharmacological effects on stress, pain and inflammation and also ameliorate the effects of drug withdrawal. Based on these observations, we hypothesized that FABP5 and FABP7 would provide excellent pharmacological targets. Thus, we performed a virtual screening of over one million compounds using DOCK and employed a novel footprint similarity scoring function to identify lead compounds with binding profiles similar to oleic acid, a natural FABP substrate. Forty-eight compounds were purchased based on their footprint similarity scores (FPS) and assayed for biological activity against purified human FABP5 employing a fluorescent displacement-binding assay. Four compounds were found to exhibit approximately 50% inhibition or greater at 10 µM, as good as or better inhibitors of FABP5 than BMS309403, a commercially available inhibitor. The most potent inhibitor, γ-truxillic acid 1-naphthyl ester (ChemDiv 8009-2334), was determined to have Ki value of 1.19±0.01 µM. Accordingly a novel α-truxillic acid 1-naphthyl mono-ester (SB-FI-26) was synthesized and assayed for its inhibitory activity against FABP5, wherein SB-FI-26 exhibited strong binding (Ki 0.93±0.08 µM). Additionally, we found SB-FI-26 to act as a potent anti-nociceptive agent with mild anti-inflammatory activity in mice, which strongly supports our hypothesis that the inhibition of FABPs and subsequent elevation of anandamide is a promising new approach to drug discovery. Truxillic acids and their derivatives were also shown by others to have anti-inflammatory and anti-nociceptive effects in mice and to be the active component of Chinese a herbal medicine (Incarvillea sinensis) used to treat rheumatism and pain in humans. Our results provide a likely mechanism by which these compounds exert their effects.

Phylogeographic analysis reveals significant spatial genetic structure of Incarvillea sinensis as a product of mountain building.

BackgroundIncarvillea sinensis is widely distributed from Southwest China to Northeast China and in the Russian Far East. The distribution of this species was thought to be influenced by the uplift of the Qinghai-Tibet Plateau and Quaternary glaciation. To reveal the imprints of geological events on the spatial genetic structure of Incarvillea sinensis, we examined two cpDNA segments ( trnH- psbA and trnS- trnfM) in 705 individuals from 47 localities.ResultsA total of 16 haplotypes was identified, and significant genetic differentiation was revealed (GST =0.843, NST = 0.975, P < 0.05). The survey detected two highly divergent cpDNA lineages connected by a deep gap with allopatric distributions: the southern lineage with higher genetic diversity and differentiation in the eastern Qinghai-Tibet Plateau, and the northern lineage in the region outside the Qinghai-Tibet Plateau. The divergence between these two lineages was estimated at 4.4 MYA. A correlation between the genetic and the geographic distances indicates that genetic drift was more influential than gene flow in the northern clade with lower diversity and divergence. However, a scenario of regional equilibrium between gene flow and drift was shown for the southern clade. The feature of spatial distribution of the genetic diversity of the southern lineage possibly indicated that allopatric fragmentation was dominant in the collections from the eastern Qinghai-Tibet Plateau.ConclusionsThe results revealed that the uplift of the Qinghai-Tibet Plateau likely resulted in the significant divergence between the lineage in the eastern Qinghai-Tibet Plateau and the other one outside this area. The diverse niches in the eastern Qinghai-Tibet Plateau created a wide spectrum of habitats to accumulate and accommodate new mutations. The features of genetic diversity of populations outside the eastern Qinghai-Tibet Plateau seemed to reveal the imprints of extinction during the Glacial and the interglacial and postglacial recolonization. Our study is a typical case of the significance of the uplift of the Qinghai-Tibet Plateau and the Quaternary Glacial in spatial genetic structure of eastern Asian plants, and sheds new light on the evolution of biodiversity in the Qinghai-Tibet Plateau at the intraspecies level.

Development of polymorphic microsatellite markers for Incarvillea sinensis (Bignoniaceae)

Microsatellite markers were developed for Incarvillea sinensis var. sinensis (Bignoniaceae), an annual herb endemic to Inner Mongolia, to study the degree to which delayed self-fertilization is favored. Eight polymorphic primer sets were isolated and characterized in two Inner Mongolia populations of I. sinensis var. sinensis with a relatively simple and fast subcloning method. Numbers of alleles per locus ranged from 2 to 7, with observed and expected heterozygosities ranging from 0 to 0.261 and from 0 to 0.778, respectively. These markers will be useful for future studies of self-fertilization adaptability in I. sinensis var. sinensis.

Biodiversity Conservation of the Genus Incarvillea Juss. (Bignoniaceae) Based on Molecular Diversity and Species Richness Assessment

Incarvillea is a genus with considerable ornamental and medicinal value, yet many of its 16 species are threatened in the wild and two (Incarvillea forrestii and Incarvillea altissima) may be extinct. An extensive field survey of the Chinese species has shown that logging is the greatest threat to woodland margin species, while overgrazing by cattle endangers species from alpine meadows. To aid the setting of conservation priorities, we used phylogenetic weighting of species, based on the molecular phylogeny of both nuclear (nrITS) and chloroplast (trnL-F region) gene regions. We estimated molecular diversity with measures for genetic diversity (GD) and phylogenetic diversity (PD). PD/GD values highlighted the importance of Incarvillea sinensis and two Central Asian species, Incarvillea semiretschenskia and Incarvillea olgae from Kazakstan and Kirghizia, for which little is known. This combination of phylogenetic and complementarity analyses focused on the provinces of Sichuan, Yunnan, and Qinghai, with Yunnan having the only adequately protected areas for that genus.

Two New Alkaloids from Incarvillea sinensis

AbstractTwo new alkaloids, incarvines E (1) and F (2), were isolated from the EtOH extract of the whole plant of Incarvillea sinensis. Their structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR.

Synthesis of (-)-Incarvillateine

Incarvillateine is an alkaloid extracted from the Chinese plant Incarvillea sinensis, used in folk medicine for treating rheumatism and as a pain killer. The compound showed some potent analgesic properties and probably works via an adenosine receptor mechanism. This concise synthesis features a Rh-catalyzed intramolecular alkylation, installing two stereogenic centers (D → H).