[Chemical constituents from Paris rugosa rhizomes and their antimicrobial activities].

Paris rugosa(Melanthiaceae) only grows in Yunnan province of China at present, and its chemical constituents have not been systematically studied. In this study, nine compounds, including one new compound pariposide G(1) and eight known compounds of cerin(2), stigmast-4-en-3-one(3), ß-ecdysone(4), ophiopogonin C'(5), methyl protogracillin(6), gracillin(7), parissaponin H(8), and parisyunnanoside G(9), were isolated and identified from the ethanol extract of P. rugosa rhizomes by column chromatography methods and semi-preparative high-performance liquid chromatography(HPLC). Compounds 1-9 were isolated from this plant for the first time. The antibacterial and antifungal activities of all the compounds were evaluated. The results showed that ophiopogonin C' had strong inhibitory effects on Candida albicans [MIC_(90)=(4.68±0.01) µmol·L~(-1)] and the fluconazole-resistant strain of C. albicans [MIC_(90)=(4.66±0.02) µmol·L~(-1)].

A new amide from the fruiting bodies of Tricholoma bakamatsutake.

A new amide tricholomine C was isolated from the dried fruiting bodies of Tricholoma bakamatsutake. Its structure was identified by a combination of nuclear magnetic resonance spectroscopic analysis and electronic circular dichroism (ECD) calculations. The ethyl alcohol crude extract and tricholomines A-C from T. bakamatsutake were evaluated for neuroprotective activities. Of these substances, the crude extract showed weak neurite outgrowth-promoting activity in rat pheochromocytoma (PC12) cells, as well as weak inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).

Heterodimers with a cucurbitane-type triterpenoid skeleton from the branches of Elaeocarpus dubius.

Four undescribed and two known cucurbitane-type triterpenoids, including two heterodimers, elaeocarpudubins A and B, were isolated from the branches of Elaeocarpus dubius (Elaeocarpaceae). The chemical structures of these undescribed isolates were determined by analyses of 1D and 2D NMR and MS data, electronic circular dichroism (ECD) calculations, and chemical transformation. Biogenetically, elaeocarpudubins A and B might be derived from cucurbitacin F through Michael addition with vitamin C and (-)-catechin, respectively. These six isolates were evaluated for their cytotoxic activities against human leukemia HL-60, human lung adenocarcinoma A549, human hepatoma SMMC-7721, human breast cancer MCF-7, human colon cancer SW480, and paclitaxel-resistant A549 (A549/Taxol) cell lines, for their antioxidant properties using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and for their differentiation effects on nerve growth factor (NGF)-mediated neurite outgrowth in rat pheochromocytoma PC12 cells. Cucurbitacins F (IC50 of 4.98-38.11 µM) and D (IC50 of 0.03-4.40 µM) showed growth-inhibitory activities against these six cancer cell lines. Elaeocarpudubin B (IC50 of 61.04 µM) and elaeocarpudoside B (IC50 of 6.93 µM) showed antioxidant activities. Elaeocarpudubin B and elaeocarpudoside B also showed neurite outgrowth-promoting activities in PC12 cells at a concentration of 10 µM.

Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis.

Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis (Lour.) Spreng. (Thymelaeaceae) led to the isolation of a new cucurbitane-type triterpenoid, aquilarolide A (1), along with five known compounds (2-6). The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance (NMR) experiments and mass spectrometry (MS) data and theoretical calculations of its electronic circular dichroism (ECD) spectra. Aquilarolide A, cucurbitacin E (3), cucurbitacin B (4), and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (6) showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1, human lung squamous cell carcinoma NCI-H520, human lung adenocarcinoma A549, and paclitaxel-resistant A549 (A549/Taxol) cell lines. All four active compounds, with IC50 values ranging from 0.002 to 0.91 µM, had better inhibitory activities against A549/Taxol cells than paclitaxel (IC50 = 1.80 µM). Among them, cucurbitacin E (IC50 = 0.002 µM) is the most active. Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms.

Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China.

Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7'R)-7'-hydroxyagarotetrol (1), (5S,6R,7R,8S,7'S)-7'-hydroxyagarotetrol (2), (6S,7S,8R)-2­[2­(4-methoxyphenyl)ethyl]­6,7,8­trihydroxy­5,6,7,8­tetrahydrochromone (3), (6S,7S,8R)-2­(2-phenylethyl)­6,7,8­trihydroxy­5,6,7,8­tetrahydrochromone (4), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone (5), three new sesquiterpenoids, (4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (6), (4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (7), and (4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (8), along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) calculations. The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone. At concentrations from 5 to 40 µM, compounds 4 and 6, agarotetrol (9), and 6-hydroxy-2-(2-phenylethyl)chromone (17) showed significant protective activities against corticosterone-induced PC12 cell injury (P < 0.001).

Wild plants used by the Lhoba people in Douyu Village, characterized by high mountains and valleys, in southeastern Tibet, China.

BACKGROUND: Douyu Village, inhabited by the Lhoba people, is situated within the Eastern Himalayas, in southeastern Tibet, China. The village is located among high mountains and valleys, which feature complex terrain with cold and dry climates and distinctive vegetation types and species. The Lhoba people in this village are isolated from other groups in China. The Lhoba people have lived in this village since the 15th century and mainly depended on gathering, hunting, and swidden agriculture before the 1960s. Because they have a long history and live under extreme climatic, geographical, and ecological conditions, the Lhoba people in Douyu Village may have unique traditional knowledge about wild plants. Thus, this research aims to record the traditional botanical knowledge of the Lhoba people in Douyu. METHODS: An ethnobotanical study was conducted on the Lhoba people in Douyu Village in Longzi County, Tibet, China. Semi-structured interviews and group discussions with informed consent were used in the study. We interviewed 41 informants (14 key informants) between 18 and 75 years of age. All information was collected, organized, and compiled into "use reports" for quantitative analysis. The informant consensus factor (ICF) was used to determine the homogeneity of the informants' knowledge of medicinal plants, while the cultural importance index (CI) was used to estimate the cultural importance of shared species. RESULTS: A total of 91 wild species (90 vascular plants and 1 fungus) belonging to 71 genera and 39 families utilized by the Lhoba people in Douyu were documented. Of these species, Pimpinella xizangense and Wikstroemia lungtzeensis are endemic to Longzi County, while Sinopodophyllum hexandrum and Paeonia ludlowii are endangered species in China. All habitats, from the field vegetation at the valley bottoms to the alpine shrubland and meadows, were used for plant collection, and the numbers of species of plants collected from the various vegetation types (except for fields) decreased with increasing altitude. Our study found that 55 species are edible plants and fungi, 29 species are medicinal plants, and 38 species are used for other purposes. Medicinal plants are used for 11 categories of diseases, among which diseases of blood-forming organs (ICF = 0.96) and gastrointestinal diseases (ICF = 0.95) exhibited the highest ICF values. Based on the CI values, the most important plants in this study area are Berberis xanthophloea, B. kongboensis, Sinopodophyllum hexandrum, Vicatia thibetica, and Hippophae rhamnoides subsp. gyantsensis. Moreover, a comparison of the wild plants used by Lhoba ethnic groups in three counties in China showed significant differences among these regions. CONCLUSIONS: Our study demonstrates that the wild plants utilized by the Lhoba people in Douyu Village are highly diverse, at 90 plant and one fungal species, which reflects not only the number of species but also their diversified functions. The extreme climatic, geographical, and ecological conditions of Douyu within the high mountains and valleys of the Eastern Himalayas potentially affect the Lhoba people's culture, including plant utilization practices, and contribute to the rich diversity of the wild plants used by the local people.

Sesquiterpenoids and 2-(2-Phenylethyl)chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis.

One novel spirolactone, aquilarisinolide (1), three new sesquiterpenoids, (2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one (2), (1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one (3), and (4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one (4), together with 13 known compounds (5-17) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP+), as well as inhibitory activities against BACE1. Compound 4, 5,6-dihydroxy-2-(2-phenylethyl)chromone (5), daphnauranol B (7), 6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone (10), isoagarotetrol (14), and 1-hydroxy-1,5-diphenylpentan-3-one (16) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 µM (P < 0.001). Isoagarotetrol (14) showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20 µM (P < 0.001), while compound 4 showed a moderate activity (P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 µM.

Volatile Constituents of Endophytic Fungi Isolated from Aquilaria sinensis with Descriptions of Two New Species of Nemania.

Algae, bacteria, and fungi, as well as higher plants, produce a wide variety of secondary metabolites known as natural products. Natural products are well known as remarkable sources of many therapeutic agents. The genus Nemania is a wood-decaying fungus that belongs to family Xylariaceae. Nemania is often found as an endophyte in diverse hosts and some species are known to produce useful secondary metabolites. In this study, two Nemania species were isolated as an endophytic fungus from Aquilaria sinensis. Multi-gene phylogenetic studies showed that the newly described strains of Nemania are new to science, and this is the first report of Nemania from the host Aquilaria. One of the fermented species, Nemania aquilariae (KUMCC 20-0268), resulted in five sesquiterpenoids, which were previously reported from agarwood, and their structures were identified by gas chromatography-mass spectrometry (GC-MS). In addition, five different media were investigated in vitro to optimize conditions for growing the fungal biomass of Nemania aquilariae and N. yunnanensis.

Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review.

Dendrobium Sw. is one of the largest genera in the orchidaceous family and includes 900-2000 species. Among them, more than 80 Dendrobium species have been reported in China. However, there are only six Dendrobium species, namely, D. bigibbum var. superbum (syn. D. phalaenopsis), D. chrysanthum, D. fimbriatum, D. loddigesii, D. nobile, and D. officinale (syn. D. candidum), listed in the New Inventory of Existing Cosmetic Ingredients in China Launched. Artificial planting of Dendrobium species has been a great success in China. To better utilize Dendrobium resources for medicinal and cosmetic purposes, we summarize their traditional uses and pharmacologically active compounds for treating dermatological disorders in this review. "Orchidaceae", "Dendrobium", "traditional use", "ethnobotany", "dermatological disorder", and "skin disease" were used as search terms to screen the literature. Cited references were collected between 1970 and 2020 from the Web of Science, China National Knowledge Internet (CNKI), SciFinder, Google Scholar, and Chinese books. From the search, it was found that there are 22 Dendrobium species with traditional uses in dermatological disorders, and 131 compounds from Dendrobium plants have been reported to possess anti-inflammatory, antimicrobial, antioxidant, antiaging, anti-psoriasis, and tyrosinase-inhibitory activities, implying that Dendrobium plants are important resources for the discovery of active compounds and the development of new drugs and cosmetics. D. crepidatum, D. denneanum, D. loddigesii, D. nobile, and D. officinale have been extensively studied. More research on other Dendrobium species is needed. The major active compounds found in Dendrobium species are phenanthrenes, alkaloids, flavonoids, phenylpropanoids, and lignans. Several compounds, such as loddigesiinol A, (S)-5-methoxy-2,4,7,9-tetrahydroxy-9,10-dihydrophenanthrene, (S)-4-methoxy-2,5,7,9-tetrahydroxy-9,10-dihydrophenanthrene, 2,5-dihydroxy-4-methoxy-phenanthrene 2-O-ß-D-glucopyranoside, (9R)-1,2,5,9-tetrahydroxy-9,10-dihydrophenanthrene 5-O-ß-D-glucopyranoside, (+)-homocrepidine A, and vicenin 2, have significant anti-inflammatory activities and inhibit nitric oxide (NO) production with IC50 values less than 5 µM, and these compounds are worthy of further study.

Traditional uses, chemical constituents, pharmacological activities, and toxicological effects of Dendrobium leaves: A review.

ETHNOPHARMACOLOGICAL RELEVANCE: In China, shi hu (stems of Dendrobium chrysotoxum Lindl, D. fimbriatum Hook. D. huoshanense Z.Z. Tang & S.J. Cheng, or D. nobile Lindl) and tie pi shi hu (stems of D. officinale Kimura et Migo) are famous traditional medicines and are listed in the Chinese Pharmacopoeia. However, the leaves of these Dendrobium plants are largely discarded. AIM OF THE STUDY: To better utilize Dendrobium leaves, we summarize their traditional uses, chemical constituents, pharmacological activities, and toxicological effects. MATERIALS AND METHODS: "Orchidaceae", "Dendrobium", "leaf", "traditional use", and "ethnobotany" were used as search terms to screen the literature. Cited references were collected between 1960 and 2020 from the Web of Science, China National Knowledge Internet (CNKI), SciFinder, and Google Scholar, primarily in English and Chinese. RESULTS: Traditional uses of leaves from 16 Dendrobium species were identified in the literature. The major uses of Dendrobium leaves include treatments for dermatologic disorders, metabolic syndromes, nervous system disorders, and musculoskeletal system disorders. More than 50 chemical compounds have been identified in the leaves of 10 Dendrobium species, which primarily include flavonoids, bibenzyls, coumarins, N-containing compounds, and polysaccharides. Antihyperlipidemia, antihypertensive, antihyperuricemia, anti-inflammatory, antimicrobial, antioxidant, cytotoxic and antitumor, hepatoprotective, immunomodulatory, lipase-inhibitory, and/or tyrosinase-inhibitory activities have been reported for the leaves of six Dendrobium species. D. officinale leaves have been shown to exhibit no reproductive toxicity against male rats, while D. speciosum Sm. leaves have been observed to exhibit slight genotoxicity in an in vitro study. Among Dendrobium species, D. officinale leaves are the most widely studied. CONCLUSIONS: D. officinale leaves represent a good example of the utilization of leaf resources of the Dendrobium genus. In the future, more extensive research for the development of Dendrobium leaves is needed.

A new p-terphenyl derivative from the fruiting bodies of Sarcodon imbricatus (L.) P. Karst.

A new p-terphenyl, 2',3'-diacetoxy-4,5,5',6',4'',5''-hexahydroxy-p-terphenyl (1), along with 12 known compounds were isolated from the fruiting bodies of Sarcodon imbricatus (Bankeraceae). Their structures were confirmed on the basis of extensive spectroscopic analysis and comparison with the spectral data in the literature. Compound 1 exhibited weak cytotoxicity against colon cancer SW480 and leukemia HL-60 cell lines, with IC50 values of 55.02 ± 1.79 µM and 44.71 ± 2.15 µM, respectively.

Tricholomines A and B, two new amides from the fruiting bodies of Tricholoma bakamatsutake.

Two new amides tricholomines A (1) and B (2), along with nine known compounds, were isolated from the dried fruiting bodies of Tricholoma bakamatsutake. Their structures were determined on the basis of extensive spectroscopic analysis or comparison with the data in the literatures. The absolute configuration of 1 was confirmed by single crystal X-ray diffraction analysis.

A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar.

One new sesquineolignan, piperneolignan A (1), four new neolignans, piperneolignans B-E (2-5), and eight known compounds were isolated from the leaves of Piper betle (Piperaceae) collected from Myanmar. These new structures were determined by analysis of MS and NMR data, and the absolute configuration of piperneolignan A was elucidated by electronic circular dichroism (ECD) calculations. Piperneolignan A (1), piperneolignan B (2), hydroxychavicol (6), p-hydroxycinnamaldehyde (10), and diallylcatechol (13) possessed anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells with IC50 values of 9.87, 45.94, 4.80, 26.40, and 40.45 µM, respectively, compared with the positive control NG-monomethyl-l-arginine (l-NMMA, IC50 = 33.84 µM). The two hydroxy groups in the structure of hydroxychavicol are essential for activity, and dimerization or trimerization of hydroxychavicol decreases activity.

Neuroprotective compounds from the resinous heartwood of Aquilaria sinensis.

Six undescribed compounds, including three sesquiterpenoids [(4S,5S,7S,8S,11R)-7-hydroxyguai-1(10)-en-8,12-olide, aquilarisinone, and 2Z,7(13),9E-humulatrien-12-ol-5-one], one diphenylpentanone [1-(2-hydroxyphenyl)-5-phenylpentan-3-one], and two 2-(2-phenylethyl)chromones (6-epiagarotetrol and triepoxyhexahydrochromone A), along with 15 known compounds, were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). Their structures were determined by mass (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configuration of (4S,5S,7S,8S,11R)-7-hydroxyguai-1(10)-en-8,12-olide was confirmed by X-ray diffraction analysis, and the configurations of (4S,7S,8S,10R,11R)-7,10-epoxyguai-1(5)-en-8,12-olide, aquilarisinone, 6-epiagarotetrol, and triepoxyhexahydrochromone A were confirmed by electronic circular dichroism (ECD) calculations. The neuroprotective activities of the compounds were evaluated using models of BACE1 inhibition and PC12 cells with corticosterone- and 1-methyl-4-phenylpyridine ion (MPP+)-induced damage. At concentrations of 1, 2, and 5 µM, triepoxyhexahydrochromone A, (+)-(7R,10R)-selina-4,11(13)-diene-12,15-dial, (-)-(5R,7R,10R)-12,15-dioxo-α-selinene, and (+)-(1R,4S,5R)-1ß-hydroxyeremophila-7(11),9-dien-8-one exerted significant protective effects (p < 0.01) on PC12 cell injury induced by corticosterone, while triepoxyhexahydrochromone A and (-)-(5R,7R,10R)-12,15-dioxo-α-selinene exerted significant protective effects (p < 0.01) on MPP+-induced PC12 cell injury at concentrations of 1, 2, and 5 µM. No compounds produced significant inhibitory effects on BACE1, with inhibition rates of less than 20% observed at a concentration of 20 µM.

Chemical Constituents from the Whole Plant of Cuscuta reflexa.

Two new 2H-pyran-2-one glucosides, cuscutarosides A (1) and B (2), and one new steroidal glucoside, 7ß-methoxy-ß-sitosterol 3-O-ß-glucopyranoside (3), together with 12 known compounds (4-15) were isolated from the whole plant of Cuscuta reflexa (Convolvulaceae) collected from Myanmar. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. The antiobesity activity of these isolates was evaluated using porcine pancreatic lipase (PPL), and the antiplatelet aggregation activity was screened using rabbit platelets induced by thrombin, platelet-activating factor (PAF), arachidonate (AA), or collagen. 7ß-Methoxy-ß-sitosterol 3-O-ß-glucopyranoside (3) showed weak PPL inhibitory activity. Cuscutaroside A (1), its acetylated derivative (1a), and scrophenoside B (8) showed weak inhibitory activity against rabbit platelet aggregation induced by collagen. Compound 1a also showed inhibitory activity against rabbit platelet aggregation induced by AA.

Medicinal and edible plants used by the Lhoba people in Medog County, Tibet, China.

ETHNOPHARMACOLOGICAL RELEVANCE: The Lhoba people are a small, ancient, tribal ethnic group from the Himalayas and are located in the Tibet Autonomous Region of China. Medog County is rich in biocultural diversity. For a long time, Medog has been almost isolated from the outside world. The Lhoba people, who live in Medog, have maintained a relatively unique lifestyle and have accumulated rich traditional knowledge (TK), especially about medicinal and edible plants. Currently, there is very little documentation of the plants traditionally used by the local Lhoba communities. AIM OF THE STUDY: Our investigation aimed to (i) document the species of medicinal and food plants used by the Lhoba people in Medog County, Tibet, China; (ii) screen the most important plant taxa for specific medicines, and identify the aliments treated to further contribute to drug and food supplement research; and (iii) examine whether the ethnobotanical knowledge of the Lhoba is similar among different tribes and discuss traditional uses in the health practices and livelihoods of the local communities. METHODS: Ethnobotanical data were recorded through semi-structured interviews, guided field trips, and quantitative analysis. The informant consensus factor (FIC) was used as a quantitative index. RESULTS: Ninety-one informants (61 men and 30 women) were interviewed. A total of 75 species, including 37 medicinal plants for 14 categories of diseases and 57 edible plants from six types of food, were recorded. Among the usage types of medicinal plants, the highest FIC values were recorded for antidotes (FIC = 0.98), anthelmintics (FIC = 0.98), and treatments of gastrointestinal problems (FIC = 0.93). The FIC values for different types of edible plants were very similar. The most frequently used medicinal and food plants in the studied communities are Zanthoxylum motuoense, Crassocephalum crepidioides, and Swertia nervosa. According to the comparative study, few differences in the use of wild plants were found. There appeared to be more overlapping species between two Lhoba tribes in Medog, named Mixingba and Miguba, with 46 (61%) common species, compared with the Bo'gaer tribe in Milin, which had only two (2.7%) overlapping species. This might be due to the different geographical environments, vegetation types, and different influences of other ethnic cultures. CONCLUSIONS: The Lhoba people in Medog County, Tibet, China, have rich TK about the uses of wild plants. However, the TK is seriously threatened due to environmental degradation and acculturation, and it showed signs of being forgotten and abandoned by the younger generation. Therefore, measures are urgently needed to document and protect the TK of the uses of the wild plant resources; and (i) the most frequently used medicinal and/or edible plants; (ii) the plants used to treat the most commonly mentioned diseases; and (iii) the endemic species that are widely used in Medog, which should be assessed for their potential future as food supplements and therapeutic products.

Alkaloids from the Branches and Leaves of Elaeocarpus angustifolius.

Nine new alkaloids, (+)-1, (-)-1, 2, (+)-3, (-)-3, and 4-7, along with five known compounds (8-12), were obtained from the branches and leaves of Elaeocarpus angustifolius. The alkaloids were structurally characterized by NMR and MS data. The absolute configurations of (+)-1, (-)-1, (+)-3, and (-)-3 were determined by comparing their experimental and computed electronic circular dichroism spectra. (±)-8,9-Dehydroelaeocarpine (5), (±)-9-epielaeocarpine cis-N-oxide trifluoroacetate (6), and (±)-elaeocarpine trifluoroacetate (9) exerted weak inhibitory activities against butyrylcholinesterase with IC50 values of 39, 29, and 35 µM, respectively, while that of tacrine, the positive control, was 0.07 ± 0.01 µM. This is the first report of the cholinesterase inhibitory activities of Elaeocarpus alkaloids.

Ochrocephalamines B-D, Three Alkaloids from Oxytropis ochrocephala Bunge.

Ochrocephalamines B-D (1-3), composed of fused quinolizidine and octahydroquinoline rings, were isolated from Oxytropis ochrocephala Bunge. Ochrocephalamine B (1) has a unique bridged tetracyclic ring skeleton fused with a lactam ring. The structures of 1-3 were elucidated using spectroscopic and computational approaches. Ochrocephalamine C (2) and D (3) demonstrated potent anti-HBV activities and are more potent against the secretion of HBeAg than that of HBsAg.

Chemical Constituents from Ethanoic Extracts of the Aerial Parts of Leea aequata L., a Traditional Folk Medicine of Myanmar.

We aimed at reporting the chemical constituents and antimicrobial activities of Leea aequata L., a traditional folk medicine used in Myanmar for the treatment of wounds and skin diseases. A new neolignan, (7S,8R)-9'-O-acetylcedrusin (1), a new lactam, (3S,4S)-4-chloro-3-hydroxypiperidin-2-one (2), along with 21 known compounds, including five lignans (3-7), four flavonoid glycosides (8-11), and others (12-23), were isolated from the ethanoic extract of the aerial parts of L. aequata. The structures of the new compounds were determined by NMR, MS, and ECD spectra. For all the antimicrobial tests of the 23 compounds, only 3,4,5-trihydroxybenzoic acid ethyl ester (17) showed weak inhibitory activities against Escherichia coli and Salmonella enterica subsp. enterica.

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum.

Two new amides (E)-N-cinnamoyl-2-methoxypiperidine (1) and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one (2), four new amide glucosides, retrofractosides A-D (3-6), and two new phenylpropanoid glucosides, retrofractosides E (7) and F (8), together with 24 known compounds (9-32) were isolated from the fruits of Piper retrofractum. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates (1-32) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2. (E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide (9) showed a weak inhibitory effect, with an inhibition ratio of 52.0% at a concentration of 150 µM.