Xiachang Wang

Nanjing University of Chinese Medicine · College of Pharmacy

An HPLC method was developed and validated to compare the chemical profiles and tyrosinase inhibitors in the woods, twigs, roots, and leaves of Artocarpus heterophyllus . Five active tyrosinase inhibitors including dihydromorin, steppogenin, norartocarpetin, artocarpanone, and artocarpesin were used as marker compounds in this HPLC method. It was d...

Jatrophalactam (1), a novel diterpenoid lactam possessing an unprecedented 5/13/3 tricyclic skeleton, was isolated from the roots of Jatropha curcas. The structure and relative configuration of jatrophalactam (1) were elucidated by extensive spectroscopic analysis and further determined by a single-crystal X-ray diffraction.

A new dolabrane-type diterpene named tagalsin O 1, together with six known analogues 2-7, were isolated from the aerial part of the mangrove plant Ceriops tagal. The structures and relative configurations were elucidated on the basis of their spectroscopic data. Cytotoxicity of the isolated compounds against HeLa human cervical carcinoma cancer cel...

The phytochemical profiles of Morus nigra roots and twigs were compared by HPLC with those of the old and young twigs of Morus alba which are known to contain oxyresveratrol and mulberroside A as major components. It was found that M. nigra root extract contains some unknown natural products with potential tyrosinase inhibitory activity. The extrac...

Background Gynostemma pentaphyllum (Thunb.) Makino has been linked to a numbers of pharmacological benefits, including hepatoprotective, anti-inflammatory, antioxidative, and antihyperlipidemic activities. Gypenoside XLVI (Gyp XLVI) was a significant triterpenoid saponin reported from a sweet-taste varietas G. pentaphyllum, which has inhibitory eff...

A hydrosulfonylation reaction of unactivated alkenes with sulfinic acids was realized under light irradiation. The reaction features photocatalyst- and additive-free conditions. A diverse set of unactivated alkenes can be transformed...

Six undescribed capnosane-type macrocyclic diterpenes sarcocrassolins A–F (1–6) and one related known analog pavidolide D (7) were isolated from Sarcophyton crassocaule, a soft coral collected off the Nansha Islands, in the South China Sea. Their complete structures, relative configurations and absolute configurations were established through compr...

One of the largest concerns with world health today is still antibiotic resistance, which is making it imperative to find efficient alternatives as soon as possible. It has been demonstrated that microbes are reliable sources for the creation of therapeutic antibiotics. This research intends to investigate the endophytic microorganisms from several...

Gypenosides, structurally analogous to ginsenosides and derived from a sustainable source, are recognized as the principal active compounds found in Gynostemma pentaphyllum, a Chinese medicinal plant used in the treatment of the metabolic syndrome. By bioactive tracking isolation of the plants collected from different regions across China, we obtai...

Liver fibrosis resulting from chronic liver damage is becoming one of the major threats to health worldwide. Active saponin constituents isolated from Gynostemma pentaphyllum were found to possess a protective effect in liver diseases. Here, we obtained a naturally abundant gypenoside, XLVI, and evaluated its liver protection activity in both anima...

Two new prenylated flavonoids named sinoflavonoids NJ and NK (1-2), along with ten known compounds were isolated from the fruits of Podophyllum hexandrum Royle. The chemical structures were determined through NMR spectroscopic data and MS analysis. Sinoflavonoid NJ (1) with an unusual 5,11-dioxabenzo[b]fluoren-10-one skeleton was firstly reported f...

It is well known that the processing method of herbal medicine has a complex impact on the active components and clinical efficacy, which is difficult to measure. As a representative herb medicine with diverse processing methods, Radix Paeoniae Alba (RPA) and its processed products differ greatly in clinical efficacy. However, in some cases, differ...

Since the current identification method for Paeoniae Radix Alba is complex in operation and long time-consuming with high requirements for technicians, the present study employed Heracles NEO ultra-fast gas phase electronic nose(E-nose) technology to identify raw and sulfur-fumigated Paeoniae Radix Alba decoction pieces in order to establish a rapi...

Three new polyketide dimers named huoshanmycins A‒C (1–3) were isolated from a plant endophytic Streptomyces sp. HS-3-L-1 in the leaf of Dendrobium huoshanense, which was collected from the Cultivation base in Jiuxianzun Huoshanshihu Co., Ltd. The dimeric structures of huoshanmycins were composed of unusual polyketides SEK43, SEK15, or UWM4, with a...

On the basis of the one strain-many compounds (OSMAC) strategy, two new hygromycin A derivatives (3, 4), together with six known compounds were isolated from a medicinal plant inter rhizospheric Streptomyces in Pulsatilla chinensis. The structures of 3 and 4 were elucidated using NMR and HRESIMS analyses. A plausible biosynthetic pathway for these...

Rheum palmatum is one of the three genuine Rhubarb in Chinese Pharmacopeia and widely used in clinic as a purgative medicine. To effective quality evaluation of R. palmatum, a UPLC fingerprint method was established. Twenty batches of R. palmatum were analyzed, together with R. tanguticum, R. officinale and Polygonum cuspidatum. Fourteen common pea...

Twelve guaianolide-type sesquiterpene oligomers with diverse structures were isolated from the whole plants of Ainsliaea fragrans, including a novel trimer (1) and two new dimers (2, 3). The chemical structures of the new compounds were elucidated through spectroscopic data interpretation and computational calculations. Ainsfragolide (1) is an unus...

Two new cadinane sesquiterpenes named myrrhterpenes A and B (1, 2), along with eighteen known analogs were isolated from the resin of Commiphora myrrha. Their structures were determined by various NMR and MS spectrometry analysis, as well as by comparison with related compounds. Anti-inflammatory activity with LPS-induced RAW 264.7 macrophages reve...

Iridin, one of the main bioactive components isolated from Belamcanda chinensis (L.) DC, exerts various pharmacological activities, such as anti-inflammation, antioxidant, and antitumor. However, the metabolism and pharmacokinetics of iridin are still unknown. After 100 mg/kg administration of iridin orally, the plasma, urine, and fecal bio-samples...

A novel octahydroindolizine alkaloid, named dendrocrepidamine (1) with an unusual 18,19,19′-cyclopropanone-dendrocrepine skeleton, was isolated from the ethanol extract of the roots of Dendrobium crepidatum, along with six known compounds (2–7). The structure of 1 was elucidated through HR-ESIMS, NMR spectroscopic data and computational calculation...

Two new terragine analogs (1‒2) with special succinimide and aminopentane moieties were isolated from the fermentation broth of Bacillus sp. SH-1.2-ROOT-18, an endophyte previously discovered from the root of Dendrobium officinale. The structures were elucidated base on comprehensive 1 D/2D NMR and MS data analysis. Complete NMR assignments for the...

Abstract: Objective To explore the protective effect of pedunculoside (PE) on myocardial ischemia/reperfusion injury. Methods Rat model of acute myocardial ischemia reperfusion injury was prepared by ligating the left anterior descending coronary artery (LAD) of the heart for 30 min and reperfusion for 24 h, and the rats were randomly divided into...

Background Cytokine release syndrome (CRS) is a potentially life-threatening complication of chimeric antigen receptor T (CAR-T) cell therapy. Recent studies indicated critical roles of macrophages and monocytes in CAR-T induced CRS. Here, we report rapid dissipation of CAR-T induced CRS in two patients after receiving Tripterygium glycosides (TG)....

Background: The pathogenesis of inflammatory bowel disease (IBD) is linked to an intricate association of environmental, microbial, and host-related factors. Polysaccharide affects host immunity by regulating the composition and metabolism of gut microbiota is the common mechanism of disease resistance. However, the efficacy and mechanism of Schisa...

ABSTRACT: OBJECTIVE To establish the HPTLC identification, HPLC fingerprint and multi-components quantitative analysis methods of Notopterygium incisum (NI), for the quality evaluation of 18 batches NI from different origins and to provide a reference for improvement of NI quality standards. METHODS HPTLC method was applied for NI identification. H...

Gypenosides, extracts of Gynostemma yixingense, have been traditionally prescribed to improve metabolic syndrome in Asian folk and local traditional medicine hospitals. However, the mechanism of its action remains unclarified. In this work, our results indicated that chronic administration of 2α-OH-protopanoxadiol (GP2), a metabolite of gypenosides...

Several nucleoside antibiotics are structurally characterized by a 5″-amino-5″-deoxyribose (ADR) appended via a glycosidic bond to a high-carbon sugar nucleoside (5′S,6′S)-5′-C-glycyluridine (GlyU). GlyU is further modified with an N-alkylamine linker, the biosynthetic origin of which has yet to be established. By using a combination of feeding exp...

Natural products and natural product‐derived compounds have been widely used for pharmaceuticals for many years, and the search for new natural products that may have interesting activity is on going. Abyssomicins are natural product molecules that have antibiotic activity via inhibition of the folate synthesis pathway in microbiota. These compound...

The cover shows a novel 6/6/5/6 tetracyclic polyketide, chartspiroton, isolated from an endophytic Streptomyces residing in the medicinal plant Dendrobium officinale. Chartspiroton features an unprecedented naphthoquinone derivative spiro-fused with a benzofuran lactone. A plausible polyketide biosynthetic pathway for 1 suggests intriguing oxidativ...

Abstract: Traditional Chinese medicine (TCM) decoction pieces are the intermediate link of the three major Chinese medicine industrial chains of “Medicinal materials-Decoction pieces-Preparations”. In recent years, people have gradually realized the importance of the quality control of decoction pieces. Q-marker of TCM have been widely studied afte...

Background Pedunculoside (PE) is a triterpene saponin from the barks of Ilex rotunda, a Traditional Chinese Medicine called Jiubiying, which is used for the treatment of cold and fever, tonsillitis, sore throat, acute and chronic hepatitis, etc. Previous studies have confirmed that crude extract orally has a significant therapeutic effect on myocar...

Six pairs of octahydroindolizine-type alkaloid enantiomers (1-6) including three new compounds [(-)-1/(+)-1, 2] were isolated from the stems of Dendrobium crepidatum. Their structures including the absolute configurations were elucidated by extensive spectroscopic analyses and comparison between the experimental and calculated electronic circular d...

Background: Endophyte has now become a potential source for the discovery of novel natural products, as they participate in biochemical pathways of their hosts and produce analogous or novel bioactive compounds. As an epiphytic plant, Dendrobium officinale is one of precious Chinese medicines with various activities. It is well known for containin...

A novel 6/6/5/6 tetracyclic polyketide named chartspiroton (1) was isolated from a medicinal plant endophytic Streptomyces in Dendrobium officinale. The complete structure assignment with absolute stereochemistry was elucidated through spectroscopic data, computational calculations, and single-crystal X-ray diffraction. Chartspiroton features an un...

The discovery of new, safe, and effective pesticides is one of the main means for modern crop protection and parasitic disease control. During the search for new insecticidal secondary metabolites from endophytes in Stemona sessilifolia (a traditional Chinese medicine with a long history as an insecticide), 10 new insecticidal endostemonines A-J (1...

We report the isolation and characterization of three new nybomycins (nybomycins B-D, 1-3) and six known compounds (nybomycin, 4; deoxynyboquinone, 5; α-rubromycin, 6; β-rubromycin, 7; γ-rubromycin, 8; and [2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol, 9) from the Rock Creek (McCreary County, KY) underground coal mine acid reclamation site isola...

Objective To explore the potential Q-markers between crude Schisandrae Chinensis Fructus (SCF) and vinegar-processed Schisandrae Chinensis Fructus (VSCF) based on multivariate statistical analysis and network pharmacology. Methods UPLC-Q/TOF-MS was used to analyze the main lignans in SCF and VSCF, and the potential differences of chemical component...

A new diterpenoid named jatrophacine (1), with an unusual 4,5-seco- rhamnofolane skeleton, was isolated from the roots of Jatropha curcas, together with eleven known diterpenoids. The structure of the new compound was elucidated through a detailed analysis of its 1 D- and 2 D-NMR spectra. The X-ray structure of jatrophol (2) is also presented. Anti...

The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-...

The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A–C, 1–3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-...

Peroxiredoxin 1 (Prx1) and glutaredoxin 3 (Grx3) are two major antioxidant proteins that play a critical role in maintaining redox homeostasis for tumor progression. Here, we identify the prototypical pyranonaphthoquinone natural product frenolicin B (FB) as a selective inhibitor of Prx1 and Grx3 through covalent modification of active-site cystein...

An efficient and convenient method for the synthesis of oxazole derivatives from enamides has been established via an inexpensive Ruthenium-catalyzed C-O cyclization. This protocol allows for a wide functional group compatibility, broad substrate scope and easy operation. The catalytic method is also applicable to other 5-member O-containing and S-...

The isolation and structure elucidation of four new naturally occurring amino-nucleoside [puromycins B-E (1-4)] metabolites from a Himalayan isolate ( Streptomyces sp. PU-14-G, isolated from the Bara Gali region of northern Pakistan) is reported. Consistent with prior reports, comparative antimicrobial assays revealed the need for the free 2″-amine...

Muraymycins are antibacterial natural products from Streptomyces sp. that inhibit translocase I (MraY) involved in cell wall biosynthesis. Structurally, muraymycins consist of a 5′- C -glycyluridine (GlyU) that is appended with a 5″-amino-5″-deoxyribose (ADR), forming a disaccharide core that is found in several peptidyl nucleoside inhibitors of Mr...

Muraymycins belong to a family of nucleoside antibiotics that have a distinctive disaccharide core consisting of 5-amino-5-deoxyribofuranose (ADR) attached to 6′-N-alkyl-5′-C-glycyluridine (GlyU). Here we functionally assign and characterize six enzymes from the muraymycin biosynthetic pathway involved in the core assembly that starts from UMP. The...

The Cover Feature shows a naturally occurring muraymycin nucleoside antibiotic blocking the reaction mediated by the bacterial membrane protein MraY. MraY catalyzes the formation of the membrane‐bound intermediate lipid I and therefore a key step in peptidoglycan biosynthesis. In the corresponding paper by Koppermann, Ducho et al., a range of muray...

Type 2 diabetes mellitus (T2DM) is a chronic, complex and multifactorial metabolic disorder, and targeting gluconeogenesis inhibition is a promising strategy for anti-diabetic drug discovery. This study discovered a new class of thieno[2,3-b]pyridine derivatives as hepatic gluconeogenesis inhibitors. First, a hit compound (DMT: IC50 = 33.8 μM) char...

Muraymycins are nucleoside antibiotics isolated from Streptomyces sp. NRRL 30471 and several mutant strains thereof that were generated by random, chemical mutagenesis. Reinvestigation of two mutant strains using new media conditions led to the isolation of three new muraymycin congeners, named B8, B9, and C6 (1–3), as well as a known muraymycin, C...

Muraymycins are a subclass of antimicrobially active uridine-derived natural products. Biological data on several muraymycin analogues have already been reported, including some inhibitory in vitro activities towards their target protein, the bacterial membrane enzyme MraY. However, a structure-activity relationship (SAR) study on naturally occurri...

A series of LX2343 derivatives were designed, synthesized and evaluated as neuroprotective agents for Alzheimer's disease (AD) in vitro. Most of the compounds displayed potent neuroprotective activities. Especially for compound A6, exhibited a remarkable EC50 value of 0.22 μM. Further investigation demonstrated that compound A6 can significantly re...

The structures of 12 new "enantiomeric"-like abyssomicin metabolites (abyssomicins M-X) from Streptomyces sp. LC-6-2 are reported. Of this set, the abyssomicin W (11) contains an unprecedented 8/6/6/6 tetracyclic core, while the bicyclic abyssomicin X (12) represents the first reported naturally occurring linear spirotetronate. Metabolite structure...

Four cyclopentenone-containing ansamycin polyketides (mccrearamycins A–D), and six new geldanamycins (Gdms B–G, including new linear and mycothiol conjugates), were characterized as metabolites of Streptomyces sp. AD-23-14 isolated from the Rock Creek underground coal mine acid drainage site. Biomimetic chemical conversion studies using both simple...

Four cyclopentenone-containing ansamycin polyketides (mccrearamycins A-D), and six new geldanamycins (Gdms B-G, including new linear and mycothiol conjugates), were characterized as metabolites of Streptomyces sp. AD-23-14 isolated from the Rock Creek underground coal mine acid drainage site. Biomimetic chemical conversion studies using both simple...

The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6-8] and 11 previously reported bacterial metabolites (1, 3, 9-12a, and 14-18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectromet...

Four new Y-type actinomycin analogues named Y6-Y9 (1-4) were isolated and characterized from the scale-up fermentation of the Streptomyces sp. strain Gö-GS12, as well as actinomycin Zp (5), which was, for the first time, isolated as a natural product. Structures of the new compounds were elucidated by the cumulative analyses of NMR spectroscopy and...

The first enantioselective total synthesis of griseusin A, griseusin C, 4'-deacetyl-griseusin A, and two non-native counterparts in 11-14 steps is reported. This strategy highlights a key hydroxy-directed CH olefination of 1-methylene isochroman with an α,β-unsaturated ketone followed by subsequent stereoselective epoxidation and regioselective cy...

Actinomadura melliaura ATCC 39691, a strain isolated from a soil sample collected in Bristol Cove, California, is a known producer of the disaccharide-substituted AT2433 indolocarbazoles (6-9). Reinvestigation of this strain using new media conditions led to >40-fold improvement in the production of previously reported AT2433 metabolites and the is...

Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5-8. E...

Two new cyclopeptides, mullinamides A [cyclo-(-L-Gly-L-Glu-L-Val-L-Ile-L-Pro-)] and B [cyclo-(-L-Glu-L-Met-L-Pro-)] were isolated from the crude extract of terrestrial Streptomyces sp. RM-27-46 along with the three known cyclopeptides surugamide A [cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D-Ala-)], cyclo-(-L-Pro-L-Phe-) and cyclo-(-L-Pro-L...

The isolation and structural elucidation of a new tetracyclic polyketide (ruthmycin) from Streptomyces sp. RM-4-15, a bacteria isolated near thermal vents from the Ruth Mullins underground coal mine fire in eastern Kentucky, is reported. In comparison to the well-established frenolicin core scaffold, ruthmycin possesses an unprecedented signature C...

Venturicidin C (1), a new 20-membered macrolide along with the known venturicidins A (2) and B (3) were isolated from the crude extract of the Appalachian bacterial strain Streptomyces sp. TS-2-2. Additionally, nine other known compounds namely nocardamine, dehydroxynocardamine, desmethylenylnocardamine, ferrioxamine E, adenosine, riboflavin, cyclo...

We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characteri...

An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor anal...

Bacterial strains belonging to the class actinomycetes were isolated from the soil near a thermal vent of the Ruth Mullins coal fire (Appalachian Mountains of eastern Kentucky). High-resolution electrospray ionization mass spectrometry and ultraviolet absorption profiles of metabolites from one of the isolates (Streptomyces sp. RM-7-15) revealed th...

Appalachian active coal fire sites were selected for the isolation of bacterial strains belonging to the class actinobacteria. A comparison of high-resolution electrospray ionization mass spectrometry (HRESIMS) and ultraviolet (UV) absorption profiles from isolate extracts to natural product databases suggested Streptomyces sp. RM-4-15 to produce u...

Three new lupane-type triterpenes, 3 alpha-O-trans-feruloylbetulinic acid (1), 3 alpha-O-trans-coumaroylbetulinic acid (2) and 3beta-O-cis-feruloylbetulin (3), together with 10 known triterpenes (4-13), were isolated from the aerial parts of the mangrove plant Ceriops tagal. The structures of the three new compounds were established by means of spe...

Five new terpenoids, including four eudesmane-type sesquiterpenoids, 1–4, and one labdane-type diterpenoid, 6, together with ten known compounds, were isolated from the roots of Chloranthus spicatus. The structures and their relative configurations were mainly established by 1D- and 2D-NMR spectra, and MS experiments.

magnified image Four new compounds, including one new sesquiterpene dimer, i.e. , shizukaol P ( 1 ), one new dimeric sesquiterpene glycoside, i.e. , 9‐ O ‐ β ‐glucopyranosylcycloshizukaol A ( 2 ), and two new sesquiterpenes, i.e. , shizukanolides G and H ( 3 and 4 , resp.), together with eight known compounds, were isolated from the aerial part of...

AIMTo study the chemical constituents of the roots of Chloranthus fortunei.METHODSThe chemical constituents were isolated and purified using column chromatographies and the structures were elucidated on the basis of spectral analysis.RESULTSFive compounds were obtained and their structures were identified as chloranthatone (1), atractylenolactam (2...

Two new guaiane sesquiterpenoids named jatrophaols A and B (1, 2), along with three known analogues, were isolated from the roots of Jatropha curcas. Their structures were determined by spectroscopic methods, including 1D and 2D NMR spectroscopy, HR-EI-MS, HR-ESI-MS, and X-ray diffraction, as well as by comparison of their spectral data with those...

Two new xanthone glycosides, 8-hydroxy-3-methyl-6-methoxyxanthone-1-O- β-D-glucopyranosyl-(1→6)-β-D-glucopyranose (1) and 8-hydroxy-3-methyl-6-methoxyxanthone-1-O-α-L-rhamnopyranosyl-(1→6) -β-D-glucopyranose (2), together with two known anthraquinones, 1,8-dihydroxy-3-methylanthraquinone (3) and 1,3,8-trihydroxy-6- methylanthraquinone (4), were iso...

Five new lindenane sesquiterpene dimers ( 1- 5), named shizukaols K-O, and eight known sesquiterpene dimers were isolated from the roots of Chloranthus fortunei. The structures of 1- 5 were elucidated using spectroscopic data, mainly 1D NMR, 2D NMR, and mass spectra.

A new diterpenoid, guan fu diterpenoid A (1), and a new diterpenoid alkaloid, guan fu base S (2), were isolated from the Chinese medicinal herb Aconitum coreanum (Lèvl.) Rapaics, together with five known diterpenoid alkaloids guan fu base P, guan fu base R, guan fu base G, guan fu base F, and guan fu base Z. The structures of the two new compounds...

Aim: To make comparative study on HPLC fingerprint for 10 batches of Aconitum coreanum produced in the Northeast of China. Method: Diamonsil C18 column was used with a mobile phase of (A) 2 mg/mL sodium 1-heptanesulfonate (including 0.2% triethylamine and the pH was adjusted to 3.0 with phosphoric acid)-(B)acetonitrile in a gradient mode. The flow...