[Two pairs of phloroglucinol enantiomers from Hypericum wightianum and their stereochemical structures].

The chemical constituents in the ethanol extract of Hypericum wightianum(Hypericaceae) were purified by column chromatography and identified via magnetic resonance imaging(NMR), high-resolution mass spectrum, and circular dichroism. A total of 22 compounds were identified, including eight polyprenylated phloroglucinols(1-8), three chromones(9-11), and three terpenoids(14-16) and so on. Among them, compounds 16 and 17 were first reported in the genus Hypericum, and compounds 1-11, 14, 15, and 19 were first isolated from H. wightianum. Compounds 1-4 were previously reported as two pairs of enantiomers. This study reported the chiral resolutions and absolute configurations of compounds 1-4 for the first time.

Fire-prone Rhamnaceae with South African affinities in Cretaceous Myanmar amber.

The rapid Cretaceous diversification of flowering plants remains Darwin's 'abominable mystery' despite numerous fossil flowers discovered in recent years. Wildfires were frequent in the Cretaceous and many such early flower fossils are represented by charcoalified fragments, lacking complete delicate structures and surface textures, making their similarity to living forms difficult to discern. Furthermore, scarcity of information about the ecology of early angiosperms makes it difficult to test hypotheses about the drivers of their diversification, including the role of fire in shaping flowering plant evolution. We report the discovery of two exquisitely preserved fossil flower species, one identical to the inflorescences of the extant crown-eudicot genus Phylica and the other recovered as a sister group to Phylica, both preserved as inclusions together with burned plant remains in Cretaceous amber from northern Myanmar (~99 million years ago). These specialized flower species, named Phylica piloburmensis sp. nov. and Eophylica priscastellata gen. et sp. nov., exhibit traits identical to those of modern taxa in fire-prone ecosystems such as the fynbos of South Africa, and provide evidence of fire adaptation in angiosperms.

Genetic Diversity Evaluation and Conservation of Kam Fragrant Glutinous Rice (Oryza sativa L.) Germplasm in Southeast Guizhou, China.

The genetic diversity of rice germplasm is the basis for increases in rice yield and quality. The collection, assessment, and protection of the genetic diversity of rice germplasm is important for achieving sustainable agriculture and assuring food security. Many underdeveloped indigenous areas have abundant and valuable rice germplasm resources. However, in-depth assessments of the genetic diversity of rice germplasm from these areas and studies related to protecting these traditional cultures are not available. In this study, from 2005 to 2016, the authors have conducted in-depth evaluation of the genetic diversity of Kam fragrant glutinous rice germplasm resources in southeast Guizhou by using multidisciplinary comprehensive methods such as ethnobotany, cultural anthropology, and modern molecular markers. In total, 376 Kam fragrant glutinous rice samples from 42 villages in the Dong community in southeast Guizhou were collected. Agronomic traits of panicles were complex and exhibited diversity. Some varieties had good disease resistance and adaptation to cold and wet climates. The Dong people named the Kam fragrant glutinous rice varieties by using seven elements, including diverse traits, growth environment, and origin. Traditional folk classification, in addition to morphology and biological analysis using molecular markers, indicates that Kam fragrant glutinous rice includes 91 varieties. Kam fragrant glutinous rice comprises a very high number of varieties, most of which are japonica-type and exhibit a high level of genetic diversity. The traditional folk classification of Kam fragrant glutinous rice by the Dong community is consistent with the biological classification. The traditional naming of Kam fragrant glutinous rice provides an important reference for understanding its genetic diversity. The high level of genetic diversity in Kam fragrant glutinous rice is not only related to the natural environment of the area but also tightly linked with the abundant and diverse Dong ethnic traditional cultures, which has led to protection of Kam fragrant glutinous rice's genetic diversity.

Utricularia lihengiae (Lentibulariaceae), a new species from Northwest Yunnan, China.

Utricularia lihengiae, a new species from the Dulongjiang region of northwest Yunnan, China, is here described and illustrated. The new species belongs to the section Oligocista and is similar to U. bifida L. and U. scandens Benj., from which it can be easily distinguished by the dark purple stripe on the corolla. The new species also differs in its shorter inflorescence and the shape of the calyx lobes.

[Traditional medicinal knowledge in Lancang-Mekong River:a case study in Lancang Lahu autonomous county].

Lancang Lahu autonomous county, where the Lancang-Mekong River flows by, was selected as the case site to investigate the traditional medicinal knowledge(TMK). A comparison of TMK between Lancang county and other places in the Lancang-Mekong sub-region was conducted. Research on TMK has been seldom reported although there are abundant medicinal resources in this sub-region. The key informant interview and other methods have been adopted in the field surveys in the past six years. The investigation revealed that there was rich TMK and various herbal medicine resources in Lancang county. A total of 220 folk prescriptions have been collected, which were normally simple with easy processing methods and usages, and most raw materials were freshly used. As for medicinal plants, 121 species in 67 families have been documented. Other findings included that TMK in Lancang county was remained at the level of medication based on experience only. The processing methods of herbal medicines were simple and the bioactive ingredients were not clear. Without text and cultural support for self-teaching, coupled with conservative inheritance, it resulted in massive losses of TMK. The folk doctors have accumulated their factions based on self-study or ancestral experience. There was different treatment experience among folk doctors, but the safety and effectiveness should be paid attention to. The folk doctors used various herbal medicines, but there was a lack of standards or specifications for quality control. Given the problems existing in inheritance and development, conservation strategies were proposed in the present study.

[Chemical constituents of Hypericum stellatum and their antioxidant bioactivities].

Hypericum stellatum is an important ethnomedicinal plant endemic to southwest China. Ultra high performance liquid chromatography with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) was applied to analyze the chemical constituents of H. stellatum. Seventeen compounds from H. stellatum were tentatively identified using UPLC-Q-TOF-MS data. Antioxidant activity and total phenolic content were investigated by DPPH assay and Folin-Ciocalted methods. The EtOAc extract with high total phenolic content showed prominent antioxidant activity. The EtOAc extract of H. stellatum was separated and purified by column chromatography, including silica gel, Sephedex LH-20, and RP-HPLC. The isolates were defined by 1D, 2D NMR data. As a result, ten compounds were isolated and assigned as quercetin (Ⅰ), quercetin 3-O-ß-D-glucopyranoside (Ⅱ), 1,3,6,7-tetrahydroxylxanthone (Ⅲ), 1,3,5,6-tetrahydroxyxanthone (Ⅳ), 1,3,7-trihydroxyxanthone (Ⅴ), 3, 6, 7-trihydroxy-1-methoxyxanthone (Ⅵ), calycinoxanthon D (Ⅶ), caffeic acid ethyl ester (Ⅷ), chlorogenic acid (Ⅸ) and chlorogenic acid ethyl ester (Ⅹ). This is the first report on chemical constituents and bioactivity of H. stellatum. The antioxidant activity of chemical constituents was tentatively found, which provided a foundation for further researches on the genus Hypericum and the traditional uses of H. stellatum.

Amides, Isoquinoline Alkaloids and Dipeptides from the Aerial Parts of Piper mullesua.

One undescribed amide, pipermullesine A, two undescribed isoquinoline alkaloids, pipermullesines B and C, and six undescribed dipeptides, pipermullamides A-F, along with 28 known compounds, were isolated from the aerial parts of Piper mullesua. The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data. Furthermore, the structures of pipermullesines A-C were confirmed by single crystal X-ray diffraction analysis. All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin (IIa) or platelet-activating factor (PAF). (-)-Mangochinine, pellitorine, and (2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF, with IC50 values of 470.3 µg/mL, 614.9 µg/mL, and 579.7 µg/mL, respectively.

[Studies on volatile oils compounds of Acorus macrospadiceus based on GC-MS, an ethnomedicinal and food plant used by local people in southwest China].

Acorus macrospadiceus is a common medicinal and food plant used different ethnic groups in Guizhou and surrounding areas. In this paper, the leaf and rhizome tissues of A. macrospadiceus were hydro-distilled to extract the volatile oils. The chemical constituents of these oils were analyzed by GC-MS and identified using the NIST 14.0 & NIST 14.0s mass spectral libraries. The relative contents of chemical constituents from the different plant parts were determined by area normalization. The analysis of A. macrospadiceus volatile oils resulted in the identification of 25 compounds from the leaf and 36 compounds from the rhizome. The identified compounds accounted for 97.85% of the leaf essential oil content and 97.18% of the rhizome essential oil content. The main volatile constituent of A. macrospadiceus was identified as estragole (93.56% of total oil content in leaf and 71.62% of total oil content in rhizome). Fourteen compounds were found to be common to essential oils of both leaf and rhizome. However, the relative amounts of these compounds were significantly different between the plant parts; the remaining identified compounds were unique to each part. This comparison of volatile oils from the different parts of A. macrospadiceus can serve as a reference for future development. Because of the higher estragole content and better harvesting sustainability of the leaves compared to rhizomes, the leaves of A. macrospadiceus deserve consideration for sustainable development. However, when we use it as a medical plant, we should draw a distinction between it with A. tatarinowii.

Cytotoxic garcimultiflorones K-Q, lavandulyl benzophenones from Garcinia multiflora branches.

Seven undescribed lavandulyl benzophenones garcimultiflorones K-Q, and fourteen known compounds were isolated from the CHCl3 soluble fraction of 95% EtOH extract of Garcinia multiflora branches. Their structures and absolute configurations were determined by spectroscopic techniques including NMR spectroscopy, MS analysis, and ECD calculations. Seven isolated compounds expect for garcimultiflorone L and garcimultiflorone O exhibited cytotoxic activities in vitro against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480). It is worth mentioning that garcimultiflorone Q exhibited most significant cytotoxicities against five cancer cell lines with IC50 values ranging from 3.07-12.56 µM.

Modified Abietane Diterpenoids from Whole Plants of Selaginella moellendorffii.

A new modified abietane diterpenoid, (3S,4S,5R,10S)-18(4→3)-abeo-3,4,12,18-tetrahydroxy-8,11,13-abietatrien-7-one (1), and two novel dimers, selaginedorffones A (2) and B (3), featuring a new cyclohexene moiety that was biogenetically constructed from two modified abietane diterpenoids through a Diels-Alder reaction were obtained from a methanolic extract of Selaginella moellendorffii, a traditional Chinese herb. The structures of 1-3 were identified by a combination of NMR spectroscopic analysis and ECD calculations. In the present study, diterpenoids were identified from S. moellendorffii for the first time, which supports the presence of diterpene synthases in this plant. These three diterpenoids (1-3) were evaluated for their growth-inhibitory activities against several human cancer cell lines. Of these substances, selaginedorffone B (3) showed cytotoxicity against the MCF-7 human-breast-cancer-cell line (IC50 9.0 µM).

Gaultheria Ethnobotany and Bioactivity: Blueberry Relatives with Anti-inflammatory, Antioxidant, and Anticancer Constituents.

Gaultheria, a genus belonging to the Ericaceae family, is typically a shrub that produces berries, and closely resembles the blueberry genus Vaccinium. Gaultheria species are used worldwide especially as food and medicine in China. Certain Gaultheria species are biologically active, as antioxidants, anti-inflammatories, and cytotoxic agents. Through literature searches and field surveys, the results of ethnobotanical uses, especially in China, as well as in vitro and in vivo studies are reviewed critically. This review examines the chemistry and bioactivity of this under-studied plant genus, and thus lays the groundwork for its future development for human health.

New aporphine alkaloids from the aerial parts of Piper semiimmersum §.

Two new aporphine alkaloids, semiimmersumines A (1) and B (2), along with 20 known compounds, were isolated from the aerial parts of Piper semiimmersum (Piperaceae). The structures of the new compounds were elucidated based on the analysis of 1D and 2D NMR, MS, and CD data. The absolute configuration of semiimmersumine A (1) was determined by single crystal X-ray diffraction analysis using anomalous dispersion with copper radiation. The effects of all compounds from the plant on rabbit platelet aggregation induced by thrombin (IIa) or PAF were also evaluated.

Using Ultra-Performance Liquid Chromatography Quadrupole Time of Flight Mass Spectrometry-Based Chemometrics for the Identification of Anti-angiogenic Biflavonoids from Edible Garcinia Species.

Garcinia xanthochymus fruits are edible and also used in traditional medicine. Our previous work showed that the isolated natural products from G. xanthochymus fruits have displayed antioxidant activity and cytotoxicity in the colon cancer cells. In this study, we developed a strategy to correlate a zebrafish angiogenesis assay with ultra-performance liquid chromatography quadrupole time of flight mass spectrometry-based chemometric analysis to identify potential anti-angiogenic activity compounds from G. xanthochymus fruits. Primary bioactivity results showed that the methanolic extracts from aril and pericarp but not from seed have significant inhibitory effects on the growth of subintestinal vessels (SIVs) in zebrafish embryos. A total of 13 markers, including benzophenones and biflavonoids, were predicted by untargeted principal component analysis and orthogonal partial least squares discriminate analysis, which were tentatively identified as priority markers for the bioactivity related in aril and pericarp. Amentoflavone, a biflavonoid, has been found to significantly inhibit the growth of SIVs at 10 and 20 µM and downregulate the expressions of Angpt2 and Tie2 genes of zebrafish embryos. Furthermore, seven biflavonoids, volkensiflavone, fukugetin, fukugeside, GB 1a, GB 1a glucoside, GB 2a, and GB 2a glucoside, isolated from Garcinia species were evaluated for their structure-activity relationship using the zebrafish model. Only fukugetin, which was previously shown to be anticancer, was active in inhibiting the SIV growth. In this report, both amentoflavone and fukugetin, for the first time, displayed anti-angiogenic effects on zebrafish, thus demonstrating an effective and rapid strategy to identify natural products for anti-angiogenesis activity.

Amides and neolignans from the aerial parts of Piper bonii.

Six amides, piperbonamides A-F, three neolignans piperbonins A-C, and 11 known compounds were isolated from the aerial parts of Piper bonii (Piperaceae). The structures of piperbonamides A-F and piperbonins A-C were elucidated based on the analysis of 1D and 2D NMR and MS data. Piperbonin A, (+)-trans-acuminatin, (+)-cis-acuminatin, (+)-kadsurenone, and pipernonaline showed weak activity against platelet aggregation with IC50 values of 118.2, 108.5, 90.02, 107.3, and 116.3 µM, respectively, as compared with the positive control, tirofiban, with an IC50 value of 5.24 µM. Piperbonamides A-F were inactive against five tumor cell lines at concentrations up to 40 µM.

Neolignans from Selaginella moellendorffii.

Two new neolignans selaginellol (1) and selaginellol 4'-O-ß-D-glucopyranoside (2), together with seven known compounds (3-9), were isolated from the whole plant of Selaginella moellendorffii. The structures of the new isolates were determined through spectroscopic data analysis. Compounds 1-9, as well as compounds 10-18 previously isolated from the species, were measured for the activity against platelet aggregation induced by ADP or collagen. Three neoligans (8, 11, and 12), one flavanone (14), and one alkaloid (16) showed inhibitory activity against ADP- or collagen-induced platelet aggregation as compared with tirofiban. The dihydrobenzofuran neolignans (8, 11, and 12) are more potent than the benzofuran neolignan (13) and other types of neolignans (1-7). Glucosidation of the dihydrobenzofuran neolignans (11 and 12) is helpful for the activity. Two new neolignans selaginellol (1) and selaginellol 4'-O-ß-D-glucopyranoside (2) were isolated from the whole plant of Selaginella moellendorffii. Several compounds from this plant showed the activity against platelet aggregation induced by ADP or collagen.

Ethnobotanical approaches of traditional medicine studies in Southwest China: A literature review.

ETHNOPHARMACOLOGICAL RELEVANCE: The ethnopharmacology of Southwest China is extremely interesting because of the region's high level of cultural and medicinal plant diversity. Little work has been done to document the traditional medicinal practices in this area. This review aims to provide an overview of the current knowledge of how medicinal plants in this area are utilized, and conserved, in order to better understand the medicinal flora, identify research gaps, and suggest directions for further research. MATERIAL AND METHODS: A literature review was conducted that included peer reviewed journals, website, books, theses and scientific reports from 1979 to 2014. The distribution and characteristics of medicinal plant knowledge in each province, methods applied in research, and the fluctuations of literature in 5 year intervals were analyzed. The distribution research on different plant groups including fungi, ferns, mosses, and vascular plants were also analyzed. RESULTS AND DISCUSSION: A total of 436 publications from 1979 to 2014 were selected for analysis. References were classified into three stages: discovery stage, utilization stage and conservation stage. Detailed results about the focus of the references, the methods applied, the development and relationship among all folk medicine in Southwest China, Daodi ethnomedicinal resources, Pharmacological studies and Toxicology studies were discussed. While, compared to the rich medicinal flora, the complex demographics and cultural diversity, a large gap still exist to fully understand and document the medicinal flora. CONCLUSIONS: Based on the review results, most research efforts in Southwest China focused on the first step: discovery of traditional usage, geographical distribution, and taxonomy of medicinal species. Only a small percentage of traditional uses or treatments have been tested by modern ethnobotanical approaches. Further research needs to put more emphasis on identifying adulterations, evaluating of Daodi medicine, and elucidating effective compounds from traditional drugs, using molecular and phytochemical approaches. Knowledge on ethnic and cultural aspects of medicinal plant species, to develop effective conservation and sustainable use protocols is lacking.

Comparative UPLC-QTOF-MS-based metabolomics and bioactivities analyses of Garcinia oblongifolia.

Garcinia oblongifolia Champ. ex Benth. (Clusiaceae) is a well-known medicinal plant from southern China, with edible fruits. However, the phytochemistry and bioactivity of the different plant parts of G. oblongifolia have not been studied extensively. Comparative metabolic profiling and bioactivities of the leaf, branch, and fruit of G. oblongifolia were investigated. A total of 40 compounds such as biflavonoids, xanthones, and benzophenones were identified using UPLC-QTOF-MS and MS(E), including 15 compounds reported for the first time from this species. Heatmap analyses found that benzophenones, xanthones, and biflavonoids were predominately found in branches, with benzophenones present in relatively high concentrations in all three plant parts. Xanthones were found to have limited distribution in fruit while biflavonoids were present at only low levels in leaves. In addition, the cytotoxic (MCF-7 breast cancer cell line) and antioxidant (ABTS and DPPH chemical tests) activities of the crude extracts of G. oblongifolia indicate that the branch extract exhibits greater bioactivity than either the leaf or the fruit extracts. Orthogonal partial least squares discriminate analysis was used to find 12 marker compounds, mainly xanthones, from the branches, including well-known antioxidants and cytotoxic agents. These G. oblongifolia results revealed that the variation in metabolite profiles can be correlated to the differences in bioactivity of the three plant parts investigated. This UPLC-QTOF-MS strategy can be useful to identify bioactive constituents expressed differentially in the various plant parts of a single species.

Parallel reductions in phenolic constituents resulting from the domestication of eggplant.

Crop domestication is often accompanied by changes in metabolite compositions that alter traits such as flavor, color, or other beneficial properties. Fruits of eggplants (Solanum melongena L.) and related species are abundant and diverse in pharmacologically interesting phenolic compounds, particularly hydroxycinnamic acid (HCA) conjugates such as the antioxidant caffeoylquinic acids (CQA) and HCA-polyamine amides (HCAA). To understand metabolite variability through the lens of natural and artificial selection, HPLC-DAD was used to generate phenolic profiles for 32 compounds in fruits from 93 accessions representing 9 Solanum species. Profiles were used for identification of species-level and infraspecific chemical patterns across both genetic distance and landscape. Sampling of plant lines included the undomesticated progenitor of eggplant and Asian landraces with a genetic background associated with three Asian regions near proposed separate centers of domestication to test whether chemical changes were convergent despite different origins. Results showed ten compounds were unique to species, and ten other compounds varied significantly in abundance among species. Five CQAs and three HCA-polyamine conjugates were more abundant in wild (undomesticated) versus domesticated eggplant, indicating that artificial selection may have led to reduced phenolic levels. No chemical abundance patterns were associated with site-origin. However, one genetically distinct lineage of geographically-restricted SE Asian eggplants (S. melongena subsp. ovigerum) had a higher HCAA content and diversity than other lineages, which is suggested to be related to artificial selection for small, firm fruit. Overall, patterns show that fruit size, palatability and texture were preferentially selected over health-beneficial phytochemical content during domestication of several nightshade crops.