Dianthramides A and B,two N-benzoylanthranilic acid derivatives from elicited tissues of Dianthus caryophyllus

Two new phenolic derivatives, dianthramide A and B, were isolated from Dianthus caryophyllus tissues elicited with mycelial extracts of Phytophthora parasitica. The purified substances were identified on the basis of their spectral data and were characterized as N-salicyl-4-methoxyanthranilic acid (dianthramide A) and N-salicyl-4-hydroxyanthranilic acid methyl ester (dianthramide B). Dianthramides A and B co-occur in carnation tissues with the known phytoalexin dianthalexin.     

Viscidic acid A and B,two ent-labdane derivatives from Chrysothamnus viscidiflorus

The chemical investigation of Chrysothamnus viscidiflorus afforded, in addition to known bisabolene derivatives, elemicin and p-hydroxyacetophenone, two new diterpene acids. Their structures were determined, by spectroscopic methods and some chemical transformations, as ent-labd-8(17),13E-dien-15-ol-18-oic acid (viscidic acid A) and ent-labd-8(17),13E-dien-15-acetoxy-18-oic acid (visidic acid B).     

(−)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscula

(?)-trans-7(S)-Methoxytetradec-4-enoic acid and the related amides, malyngamides A, B and C, were found as constituents of shallow-water varieties of the marine blue-green alga Lyngbya majuscule.     

Pendulaosides A and B. Two acylated triterpenoid saponins from Harpullia pendula seed extract

Two new acylated triterpenoid saponins named pendulaosides A and B as well as the known phenolic compounds methyl gallate, gallic acid, 1,2,3,6-tera-O-galloyl-β-d-glucose and 1,2,3,4,6-penta-O-galloyl-β-d-glucose, were isolated from the seeds of Harpullia pendula. The structures of pendulaosides A and B were determined using extensive 1D and 2D NMR analysis and mass spectrometry as well as acid hydrolysis, as 3-O-β-d-glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β-d-glucuronopyranosyl-22-O-angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and 3-O-β-d-glucopyranosyl-(1→2)-[α-L-arabinofuranosyl-(1→3)]-β-d-glucuronopyranosyl-16-O-(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene, respectively. To the best of our knowledge the two triterpene parts 22-O-angeloyl-3β,16α,22α,24β,28-pentahydroxylolean-12-ene and16-O-(2-methylbutyroyl)-3β,16α,22α,24β,28-pentahydroxylolean-12-ene have never been characterized before. The two isolated saponins were assayed for their in-vitro cytotoxic activity against the three human tumor cell lines HepG2, MCF7 and PC3. The results showed that pendulaoside A exhibited moderate activity on PC3 cell line with IC50value equal to 13.0 μM and weak activity on HepG2 cell line with IC50 value equal to 41.0 μM. Pendulaoside B proved to be inactive against the three used cell lines.     

Abeliosides A and B,secoiridoid glucosides from Abelia grandiflora

Twp new secoiridoid glucosides, abeliosides A and B, were isolated along with cantleyoside and sylvestroside II from Abelia grandiflora. On the basis of spectral and chemical evidence, these new glucosides were identified as esters of secologanic acid with an iridoid lactone which may arise from loganin. Cantleyoside was also isolated from A. spathulata and A. serrata.     

Phenolic acid glycosides from Parmentiera cereifera Seem. (Candle tree)

Two new phenolic acid glycosides, parmentins A (1) and B (2) were isolated from the methanolic extract of the leaves and stems of candle tree (Parmentiera cereifera Seem). These compounds were accompanied by a mixture of β-sitosterol and stigmasterol (3), β-sitosterol glucoside (4), isovanillic acid (5), vanillic acid (6), and p-hydroxybenzoic acid (7). The structures of the isolated compounds were determined on the basis of physical and spectroscopic analyses, including 1D and 2D NMR (¹H, ¹³C, COSY, HSQC and HMBC) and mass spectrometry (HR-ESI-MS).     

Further triterpenoids and 13C NMR spectra of oleanane derivatives from Phytolacca acinosa

In addition to five known triterpenoids, namely acinosolic acid, phytolaccagenin, phytolaccagenic acid, esculentic acid and jaligonic acid, three new oleanane derivatives, designated as phytolaccagenin A, acinosolic acid A and acinosolic acid B, have been isolated and characterized from the defatted berries of Phytolacca acinosa. The new compounds have been identified as 3β-acetoxy-3β-methyloleanate-12-en-2β,23α-diol-28β-oic acid, 3β-acetoxy-28β-methyloleanate-12-en-2β-ol-30β-oic acid and 2β-acetoxy-28β-methyloleanate-12-en-3β-ol-30β-oic acid, respectively.     

Trinorditerpenes from the roots of Flueggea virosa

Two trinorditerpenes, flueggrenes A and B (1 and 2), have been isolated from the roots of Flueggea virosa. Their structures were established by extensive analyses of spectroscopic data. The isolates were evaluated for anti-HCV activity, as well as the inhibition of superoxide anion generation and elastase release in response to FMLP/cytochalasin B.     

High prevalence Giardia duodenalis assemblage B and potentially zoonotic subtypes in sporadic human cases in Western Australia

Giardia duodenalis is a widespread parasite of mammalian species, including humans. Fecal samples from sporadic human clinical cases of giardiasis in Western Australia were analysed at two loci; 18S rRNA and glutamate dehydrogenase (gdh), and G. duodenalis assemblage B isolates were identified in 75% of isolates. Sequence analyses of 124 isolates at the 18S rRNA locus identified 93 isolates as assemblage B and 31 as assemblage A. Analyses of 109 isolates at the gdh locus identified 44 as B3, 38 as B4 and 27 were A2. Infection with Giardia was highest amongst children <5 years of age, with >56% of infections in this age group. The majority of the isolates were from rural areas (91/124) compared with urban areas (33/124). The assemblage A isolates were completely homogenous genetically at the gdh locus, while assemblage B isolates showed variability at the nucleotide but not at the amino acid level at this locus. Some of the assemblage B3 and B4 subtypes identified in humans were previously identified in marsupials in Australia and in a fox, indicating potential zoonotic transmission.     

New cytotoxic protolimonoids from the stem bark of Aglaia argentea (Meliaceae)

Two new protolimonoid compounds, namely, argentinin A (1) and B (2) along with five known triterpenoid compounds, dammar-24-en-3α-ol (3), 3-epi-cabraleahydroxy lactone (4), (E)-25-hydroperoxydammar-23-en-3β,20-diol (5), mixture of eichlerianic acid and shoreic acid (6a and 6b), and dammar-24-en-3α,20-diol (7), were isolated from the stem bark of Aglaia argentea. The structure of new compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis. All of the compounds were tested for their cytotoxic effects against P-388 murine leukemia cells in vitro. Among those isolated compounds, argentinin A (1) showed the strongest activity with an IC₅₀ value of 1.27 μg/mL (3.05 μM).     

Cyanogenic glycosides of Malesherbia

Twenty-eight species of Malesherbia were tested and found to be cyanogenic. Analysis of HPLC, GC, NMR and comparisons of R_f values on paper chromatograms showed all to possess tetraphyllin A and B as major cyanogens, with epitetraphyllin B and deidaclin being present occasionally. These data confirm the close relationship of this family with other families which produce structurally related cyanogens, the Passifloraceae, Turneraceae and Flacourtiaceae. In none of these families is tetraphyllin A the major cyanogen, however. The genus Gynopleura, sometimes segregated from Malesherbia, does not differ in this character.     

Two new saponins from Paronychia capitata

Two new oleanane-type triterpene glycosides, 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→2)˗β˗D˗xylopyranosyl˗(1→6)˗β˗D˗glucopyranosyl]medicagenic acid (1) and 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→6)˗β˗D˗glucopyranosyl˗(1→2)˗ β˗D˗xylopyranosyl]oleanolic acid (2), named capitatosides A and B respectively, were isolated from the butanol extract of Paronychia capitata (L.) Lam., along with seven known compounds. The structures of the isolated compounds were established by spectroscopic methods, mainly HRMS, 1D and 2D NMR (¹H, ¹³C, COSY, HSQC, HMBC and NOESY) techniques, whereas those of the known compounds were identified by spectral comparison with reported literature data.     

Lignans of haplophyllum tuberculatum

Tuberculatin, a new lignan apioside, was isolated from Haplophyllum tuberculatum. Chemical transformations and spectral evidence established its structure as 4-O-(β-d-apiofuranosyl)-6,7-dimethoxy-1-(3′, 4′-methylene-dioxyphenyl)-3-hydroxymethylnaphthalene-2-carboxylic acid lactone. Three other known 1-aryl-2,3-naphthalide lignans, diphyllin, justicidin A and B occurring with tuberculatin were isolated and characterized.     

Separation of the pentacyclic triterpenes tylolupenols A and B from Tylophora kerrii

Tylolupenols A and B from Tylophora kerrii were separated and identified as D:C-friedolup-8(9)-en-3β-ol and D:C-friedolup-9(11)-en-3β-ol, respectively.     

COVID-19 Survivor Patients Carrying the Rs35705950 Risk Allele in MUC5B Have Higher Plasma Levels of Mucin 5B

Background: Genetic susceptibility to infectious diseases is partly due to the variation in the human genome, and COVID-19 is not the exception. This study aimed to identify whether risk alleles of known genes linked with emphysema (SERPINA1) and pulmonary fibrosis (MUC5B) are associated with severe COVID-19, and whether plasma mucin 5B differs according to patients’ outcomes. Materials and methods: We included 1258 Mexican subjects diagnosed with COVID-19. We genotyped rs2892474 and rs17580 of the SERPINA1 gene and rs35705950 of MUC5B. Based on the rs35705950 genotypes, mucin 5B plasma protein levels were quantified. Results: Homozygous for the risk alleles of the three polymorphisms were found in less than 5% of the study population, but no statistically significant difference in the genotype or allele association analysis. At the protein level, non-survivors carrying one or two copies of the risk allele rs35705950 in MUC5B (GT + TT) had lower levels of mucin 5B compared to the survivors (0.0 vs. 0.17 ng/mL, p = 0.0013). Conclusion: The polymorphisms rs28929474 and rs17580 of SERPINA1 and rs35705950 of MUC5B are not associated with the risk of severe COVID-19 in the Mexican population. COVID-19 survivor patients bearing one or two copies of the rs35705950 risk allele have higher plasma levels of mucin 5B.     

Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Two new cyclohexene long-chain fatty acid esters, namely Dulcisenes A and B, were isolated from the twigs of the Uvaria dulcis together with seven known compounds, uvarigranol E, (−)-zeylenol, ellipeiopsol B, 5,7-dihydroxyflavone, 8-hydroxy-5,7-dimethoxyflavanone, lupeol, and benzyl benzoate. The structures of the isolated compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D, 2D NMR and HR TOF MS. Several of these metabolites were tested for cytotoxicity against HepG2, A549, S102, HuCCA-1, HeLa, MDA-MB-231, T47D, HL-60, and P388 cell lines.     

Antibacterial endiandric acid derivatives from Beilschmiedia anacardioides

Three endiandric acid derivatives, beilschmiedic acids A, B and C were isolated from the stem bark of Beilschmiedia anacardioides together with the known β-sitosterol. Their structures were established by means of modern spectroscopic techniques. The relative configuration of compound 1 was determined by single crystal X-ray analysis. The antibacterial activities of compounds A,B,C were evaluated in vitro against five strains of microbes. Compound C showed strong activity against Bacillus subtilis, Micrococcus luteus and Streptococcus faecalis (MICs below 23 μM). This Compound was more active than the reference antibiotic ampicillin against B. subtilis and M. luteus.     

Violacin A,a new chromanone produced by Streptomyces violaceoruber and its anti-inflammatory activity

A new chromanone derivative, named violacin A (1), was isolated from the fermentation broth of Streptomyces violaceoruber as a potential anti-inflammatory compound. The structure of violacin A was established using comprehensive NMR spectroscopic data analysis together with UV, IR, and MS data. The anti-inflammatory effects and action mechanisms of violacin A were investigated in vitro. The results demonstrated that violacin A attenuated the production of NO, IL-1β, IL-6, and TNF-α as well as inhibited the expression of iNOS in LPS-induced RAW 264.7 cells. Additionally, Western blot and qRT-PCR results revealed that 1 down-regulated pro-inflammatory cytokines expression correlated with the suppression of NF-κB signaling pathway.     

Novel γ-lactone derivatives from Trigonostemon heterophyllus with their potential antiproliferative activities

Two novel γ-lactone derivatives, trigoheterophines A (1) and B (2), together with four known furan derivatives (3–6), were isolated from the stems and leaves of Trigonostemon heterophyllus. The structures of 1 and 2 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparing with the data reported in literature. Among them, trigoheterophines A (1) and B (2) represent an unusual type of γ-lactone derivatives, possessing 21 carbon atoms on the carbon skeleton, and known compouds (3–6) are rare furan derivatives in the plant kingdom with diverse long-chain hydrocarbyl groups as substituents at C-4. All isolated compounds were evaluated for their antiproliferative activities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1–6 showed significant antiproliferative effects against various human cancer cell lines with IC₅₀ values ranging from 0.28 to 12.06 μM. These findings suggest that the discoveries of these novel γ-lactone derivatives and furan derivatives with significant antiproliferative activities isolated from T. heterophyllus could be of great importance to the development of new anticancer agents.     

Two new flavonol glycosides from the leaves of Cleome viscosa L.

From the leaves of Cleome viscosa L., two new flavonol glycosides, named visconoside A (1) and visconoside B (2), together with six known flavonol glycosides, vincetoxicoside A (3), vincetoxicoside B (4), kaempferitrin (5), kaempferide 3-O-β-d-glucopyranoside 7-O-α-l-rhamnopyranoside (6), kaempferol 3-O-β-d-glucopyranoside 7-O-α-l-rhamnopyranoside (7), and isorhamnetin 3-O-β-d-glucopyranoside (8) were isolated by various chromatography methods. Its chemical structure was elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with literatures.