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Two new polyphenols, talaversatilis A (

Penicildiones A-D (1-4), four new steroids derivatives together with three known compounds including 16α-methylpregna-17α,19-dihydroxy-(9,11)-epoxy-4-ene-3,18-dione-20-acetoxy (5), stachybotrylactone B (6) and stachybotrin (7) were isolated from the soft coral-derived fungus Penicillium sp. SCSIO41201, cultured in the 1% NaCl PDB substrate. Their structures were determined through spectroscopic methods and X-ray crystallography. Biological evaluation results revealed that 6 exhibited significant cytotoxic activity against HL-60, K562, MOLT-4, ACHN, 786-O, and OS-RC-2 cell lines with IC50 values of 5.23, 4.12, 4.31, 23.55, 7.65 and 10.81 μmol·L-1, respectively, while other compounds showed weak or no cytotoxicity at 50 μmol·L-1.

Introduction Conbercept is a new anti-vascular endothelial growth factor drug approved for the treatment of age-related macular degeneration by the China Food and Drug Administration (CFDA) in 2013. In this study, we for the first time evaluated the concentrations of vascular endothelial growth factor (VEGF) and placental growth factor (PlGF) after patients with proliferative diabetic retinopathy were treated with intravitreal conbercept (IVC) injection. Methods Sixteen patients with proliferative diabetic retinopathy were randomly divided into two equal groups (A and B). Nine patients with rhegmatogenous retinal detachment were used as the control group. The patients in group A received 0.5 mg IVC and their aqueous humor was collected. After 7 days, all patients underwent vitrectomy, and their aqueous and vitreous humor were collected. Results In the aqueous humor, the concentrations of VEGF and PlGF were higher pre- than post-IVC injection in group A. Similarly, the concentrations of VEGF and PlGF in group A (pre-IVC) and group B were higher than those in the control group. In vitreous humor, the concentrations of VEGF and PlGF were higher in group B than those in the control group, and the concentrations of VEGF were lower in group A (post-IVC) than those in group B. Conclusions Our study proved that the concentration of VEGF and PlGF reduced after IVC injection in aqueous humor. However, the concentration of PlGF did not reduce after IVC injection in vitreous humor.

The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From Persicaria chinensis, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-O-galloyl-4,6-(S)-dehydrohexahydroxydiphenoyl-d-glucose. Interestingly, acid hydrolysis of this compound afforded ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of Polygonum runcinatum var. sinense, a large amount of granatin A, along with minor ellagitannins, helioscpoinin A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin A was determined to be 1,6-(S)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-d-glucopyranose. These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, oligomeric proanthocyanidins of Persicaria capitatum and P. chinensis were characterized by thiol degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins., Molecules, 26(2), art.no.337; 2021

A new anthraquinone, cappariquinone A (1), along with four known compounds, 2-hydroxy-1-methoxy-3-methylanthraquinone (2), vanillic acid (3), pyrogallic acid (4), and ergosterol (5), were isolated from the whole plant of Capparis himalayensis. The compounds 2, 4, and 5 are reported from this species for the first time.

Barnacle is a unique sessile crustacean, which produces a multi-protein complex historically called barnacle cement to attach to diverse immersed materials permanently. The proteinaceous cement exhibits powerful adhesive property and special waterproof capability to cure at solid-liquid boundaries, which makes it ideal biomaterial for technical, medical and dental applications. It has been proved that a 19 kDa protein component, termed cp-19k in the cement plays a key role in surface coupling during underwater attachment. To verify whether the bacterial recombinant 19 kDa protein retains the adhesive ability, we cloned and sequenced the Bacp-19k gene in Balanus albicostatus. It encodes 173 amino acid residues, with seven biased ones, Thr, Lys, Gly, Ala, Val, Ser and Leu, comprising about 80% of the total. Two amino acid substitutions (F69L, I106L) were discovered in Bacp-19k due to the polymorphisms in barnacle cp-19ks, compared with the submitted one (GenBank: AB242295.1). Recombinant Bacp-19k was highly expressed in host strain Escherichia coli BL21 (DE3) and purified by affinity chromatography. Adsorption of recombinant Bacp-19k to glass substrata was examined by Coomassie brilliant blue staining. Future study will reveal the relationship between specific structures and functions for molecular design of novel biomimetic underwater adhesives.

From the commercially available starfish Archaster typicus, five new (1–5) and 14 known (6–19) metabolites were isolated and identified. Detailed 1D and 2D NMR spectroscopic data, including 1H, 13C, DEPT, HSQC, HMBC, and NOESY, established the structures of the new metabolites as sodium 5α-cholesta-9(11),24-dien-3β,6α,20β-triol-23-one 3-sulphate (1), sodium 5α-cholesta-9(11)-en-3β,6α,20β-triol-23-one 3-sulphate (2), sodium (25R)-5α-cholestane-3β,4β,6α,8,14α,15β,26-heptaol-15-sulphate (3), sodium (25R)-5α-cholestane-3β,6α,8,14α,15β,26-hexaol 15-sulphate (4), and sodium cholest-25(27)-ene-3β,4β,5α,6α,7β,8β,14α,15α,24,26-decanol 6-sulphate (5). Other spectroscopic techniques, including IR, ESI–MS, and HR-ESI–MS, were also adopted to further confirm the structures of the metabolites. These five steroids (1–5) are reported in nature for the first time. All of the steroids found in A. typicus (1–12) were tested for anticancer activities against MDA-MB-435 and Colo205 tumour cells. However, only sodium 5α-cholesta-9(11)-en-3β,6α,20β-triol-23-one 3-sulphate (2) and 27-nor-5α-cholestane-3β,4β,5,6α,7β,8,14,15α,24α-nonaol (6) exhibited weak activities.

A convenient and effective 'ultrasonic dispersion method' was used to fabricate vector/DNA complexes encapsulated microspheres. Polyamidoamine (PAMAM) dendrimer/DNA complexes protected by a water-soluble polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-L-aspartamide] (PHEA), were encapsulated in a polymer film mainly composed of cholic acid functionalized star poly(DL-lactide), which degraded through surface erosion mechanism with a fast degradation rate. The PAMAM/DNA complexes encapsulated polymer film was then immersed in ethanol and ultrasonicated to afford the microspheres. The in vitro gene transfections showed PAMAM/DNA complexes protected by PHEA exhibited a much higher transfection activity compared with PAMAM/DNA complexes without the protection by PHEA. The expressions of pGL3-Luc in HEK293 cells could be effectively mediated by the polymer film and microspheres with the presence of PHEA. The ultrasonic dispersion method, which did not involve toxic organic solvents, could keep the bioactivity of DNA and offer good control over the size of microspheres.

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-D-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-D-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1-4 were tested against H(2)O(2)-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.

Two new triterpenoid saponins, oleiferoside N and oleiferoside O, were isolated from the EtOH extract from the roots of Camellia oleifera C. Abel. Their structures were elucidated as 16α-acetoxy-21β,22α-O-diangeloyloxy-23,28-dihydroxyolean-12-ene 3β-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 3)-β-D-glucuronopyranoside (1), 16α-acetoxy-21β-O-angeloyloxy-23,28-dihydroxy-22α-O-(2-methylbutanoyloxy)olean-12-ene 3β-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 3)-β-D-glucuronopyranoside (2), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and acid hydrolysis. Both were characterized to be oleanane-type saponins with sugar moieties linked to C-3 of the aglycone. Cytotoxic activities of two saponins were evaluated against four human tumor cell lines (A549, B16, BEL-7402, and MCF-7) by using the MTT in vitro assay. Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines.

Two new triterpenoid saponins, zygophylosides O (1) and P (2), have been isolated from the barks of Zygophyllum fabago L. Their structures were elucidated as 3beta-[(2-O-sulfo-beta-D-xylopyranosyl)oxy]urs-12-ene-27,28-dioic acid and 3beta-[(2-O-sulfo-beta-D-xylopyranosyl)oxy]urs-12-ene-27,28-dioic acid 28-beta-D-glucopyranoside, respectively, by spectral and chemical evidence. Compound 1 showed weaker Nitric Oxide (NO) inhibitory activity.

This review presents the most recent chemical and biological investigations on one of the marine invertebrates, gorgonian octocoral. It summarizes all 432 new compounds published in 2002-2009, which consists of 46 sesquiterpenoids (including 2 new natural products, NNP), 282 diterpenoids (including 4 from Pennatulacea octocoral and one artifact), 76 steroids, and 29 alkaloids or other types (2 NNP included). In this paper, according to the structure division, the new compounds are described in combination with the taxonomy of the investigated animals, and its simultaneous bioactivity results. Novel skeletons and complex structures are paid most emphasis on its features, means of structural elucidation and the proposed biogenesis pathway. The source of all new compounds and the different diterpenoid skeleton types are all listed and analyzed, as well as the commonly used Chinese names or some proposed ones for diterpenoid skeletons. Furthermore, this papers deals with all biological test toward the gorgonian new metabolites, i.e. anti-cancer, anti-inflammatory, anti-bacterial(against Staphylococcus aureus bacteria, Mycobacterium tuberculosis etc), anti-malaria, and anti-fouling as well, in which anti-cancer activity and cytotoxicity were additionally, a discussion and prospect are proposed regarding chemical overview on gorgonian. This review, hopefully, can be useful in proving data and references for further chemical and biological research of China sea gorgonian, for the studies on chemical ecology, and for the discovery of new and bioactive compounds or the marine-derived leading targets.

A highly oxygenated racemate with C8 skeleton, menellin A (I), and a polyhydroxylated steroid, menellsteroid C (II) are isolated as along with eight known natural products.

A chemical investigation on a South China Sea gorgonian, Menella sp. resulted in the isolation and elucidation of menellin A (1), a highly oxygenated racemate with C(8) skeleton, and a polyhydroxylated steroid, menellsteroid C (2), along with eight known compounds (3-10). The structures of the new compounds were elucidated by means of MS, 1D and 2D NMR spectra, and the relative stereochemistry of 1 was determined by X-ray single-crystal diffraction analysis. In addition, compound 7 was isolated as a new natural product. Compounds 1-3 and 7 were selected to test the anti-inflammatory inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 1 and 3 exhibited modest inhibitory effects with IC(50) of 71.3, 33.9 µM, respectively, compared to the positive control aminoguanidine (IC(50) 25.0 µM).

To study the chemical constituents from the marine sponge Iotrochota sp.The compounds were isolated and purified by various column chromatography methods, and their structure wer identified cholesterol (1), nonadecyl ethers of glycerol (2), p-hydroxybenzaldehyde (3), (E)-4-(3,4-dihydroxyphenyl) but-3-en-2-one (4), 3,4-dihydroxybenzaldehyde (5), ethyl vanillin (6), hendecanoic acid (7), tricosane (8).All compounds are isolated from marine sponge Iotrochota sp. for the first time.

To study the chemical constituents in the fresh marine sponge Spongilla Wagner.Compounds were separated and purified through various chromatographic methods and their structures were identified by spectroscopic data.Seven compounds were isolated and identified as 4-hydroxybenzoic acid (I), p-hydroxycinnamic acid (II), Pyrimidine-2, 4 (1H, 3H)-dione (III), Ferulic acid methyl ester (IV), Dodecyl ethers of glycerol (V), Tetracosane( VI).All compounds are isolated from this sponge for the first time.

Two new alkaloids, Capparin A (1) and B (2), along with seven known compounds 6-methoxyindoline-2,3-dione (3), wogonin (4), oroxylin A (5), kaempferol (6), apigenin (7), quercetin (8) and luteolin (9), were isolated from the whole plant of Capparis himalayensis. Their structures have been established on the basis of spectral methods and the structure of 1 was confirmed by X-ray crystallographic analysis.

Two new alkaloids, Capparin A (1) and B (2), along with seven known compounds 6-methoxyindoline-2,3-dione (3), wogonin (4), oroxylin A (5), kaempferol (6), apigenin (7), quercetin (8) and luteolin (9), were isolated from the whole plant of Capparis himalayensis. Their structures have been established on the basis of spectral methods and the structure of 1 was confirmed by X-ray crystallographic analysis.

Low transfection efficiency and inactivation by serum are the major drawbacks for cationic polymers when used as non-viral gene vectors. Here, a series of N-succinyl-chitosan-graft-polyethylenimine (NSC-g-PEI) copolymers with different compositions were synthesized through grafting low molecular weight PEI (800 Da) to N-succinyl-chitosan. An agarose gel electrophoresis assay showed NSC-g-PEIs had good binding capability with DNA and the particle size of the NSC-g-PEI-DNA complexes was between 150 to 300 nm as determined by a Zeta sizer. In vitro transfection of NSC-g-PEI-DNA complexes for 293T, HeLa and CHO cells was investigated. It was found that the transfection efficiency of NSC-g-PEI-DNA complexes was higher than that of DNA combined PEI (25 kDa) and the transfection efficiency increased with the increasing GD of PEI. More importantly, the NSC-g-PEI-DNA complexes were stable and the transfection efficiency was not affected obviously in the presence of serum with different concentrations. In addition, NSC-g-PEIs had a lower cytotoxicity than PEI (25 kDa) and the toxicity increased with increasing GD of PEI. The NSC-g-PEI copolymers will have a good potential as efficient non-viral gene vectors in the presence of serum.

We prepared Ca-P/DNA co-precipitates deposited and encapsulated in polymer films for substrate-mediated gene delivery. The polymer films were composed of fast-degrading functionalized star poly(DL-lactide) CA-PDLLA and block copolymer poly(L-lactide)-poly(ethylene glycol)-poly(L-lactide) (PLLA-PEG-PLLA). The in vitrogene transfections of pGL3-Luc and pEGFP-C1 plasmids in HEK293T cells mediated by different films were studied. The effect of presence of a water-soluble polymer, poly-α,β-[N-(2-hydroxyethyl)-L-aspartamide], on the transfection activity of the film-mediated transfection was studied. The gene expressions could be effectively mediated by the Ca-P/DNA co-precipitates deposited and encapsulated in polymer films. During the cellular transfection, the fast-degrading films rapidly released Ca-P/DNA co-precipitates to mediate gene transfection, and the degradation products did not show any negative effects on the gene expression. The Ca-P/DNA co-precipitates deposited and encapsulated in films have promising applications in substrate-mediated gene delivery.