Records of Natural Products Articles

The roots of Stemona tuberosa ha ve been used as an antitussive and insecticide remedy for thousands of years. On the chemical investigation of the roots of S . tuberosa , two new tuberostemonine-type alkaloids, epoxy-tuberostemonol (1), and neotuberostemoenone (2), together with a known alkaloid, n eotuberostemonine, were isolated and identified. The structures of new alkaloids were established on the basis of 1D and 2D NMR and other spectroscopic analyses.

Three new secondary metabolites kermesoside (1), cocciferoside (2) and (-)-8-chlorocatechin (3), were isolated from the the stems with barks of Quercus coccifera along with five known phenolic compounds, 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one (4) and 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-propan-1-one (5), trans-resveratrol-3-O-β-glucopyranoside (6) lyoniresinol-9-O-β-xylopyranoside (7), lyoniresinol-9-O-β-glucopyranoside (8). The structure elucidation of the isolated compounds was performed by spectroscopic methods (UV, 1D- and 2D- NMR and HR-MS).

A new eudesmane-type sesquiterpene, 11 -hydroxy capitulatin B (1) , along with a known related sesquiterpene, capitulatin B (2), was isolated from the endophytic fungus Nigrospora oryzae A8 from Aquilaria sinensis, the only plant resource for agarwood production in China. This research demonstrates that the endophytic fungi from A. sinensis might play a role in the formation of agarwood.

Phytochemical study on the ethanol extract of the Curcumae Radix pieces, authenticated as the radixes of Curcuma wenyujin Y.H. Chen et C. Ling, led to the isolation of two new sesquiterpen e s , (1R,4R,5S,7S)-curwenyujinone ( 1 ) and zedoalactone H (2) , along with five known sesquiterpenes , zedoalactone E (3) , zedoarolide B ( 4), gwei curculactone (5), curdionolide A (6), c urcumenone (7) and one diterpene compound, curcuminol D (8). Their structures were elucidated on the basic of extensive spectroscopic analysis and computational ECD simulations.

Two new alkaloids, cuspidatin (1) and cuspidatinol (2), were isolated from Antidesma cuspidatum M.A. (Euphorbiaceae). The structures were determined by means of spectroscopic analysis (IR, MS, and NMR spectroscopy). The results of cytotoxicity evaluation showed that compounds 1 and 2 were inhibitory to L1210 cells, with IC 50 values 8.41 and 6.36 µg/mL respectively.

Four new natural compounds, namely 2-deprenyl-7-hydroxy-rheediaxanthone B, (2E)-2-(hydroxyl hexyliden)-cyclopropyl-1 ® 3-diglucoside and (6E)-6[2-( β -gluco­pyranosyloxy)-cyclopropyliden] hexanoic acid methylester as well as the first glucocerebroside from a fern, (4E)-1-O-(β-glucopyranosyl)-N-(2’-hydroxy­tetra­cosanoyl)-4,8-sphingadienine (d18:2/h24:0-GlcCer) , were isolated for the first time from the rootlets of the tree fern Metaxya rostrata C. Presl. Two of these compounds contain a very rare cyclopropyliden structure which until now is only known from two other compounds from this plant. In addition, this is the first report of the tannin pro­anthocyanidin A2 and the triterpenes squalene and fern-9(11)-ene in this tree fern, of which the two latter were isolated from the leaves. The structures of all compounds were elucidated on the basis of detailed spectroscopic and mass spectrometric analyses, including 1D-, 2D-NMR and HR Q-TOF-MS.

One new sulfated saponin 3β,23,30-trihydroxyurs-20-en-28-al-23-sulfate 3-O-β- D -xylopyranoside (Zygofaboside C; 1) was purified from the water soluble fraction of ethanolic extract of the aerial parts of Zygophyllum fabago Linn. The structure of the compound was elucidated through spectral studies, especially 1D- and 2D-NMR, HR-FAB mass spectrometry, and comparison with literature data.

 Commercial geranium oil samples, steam-distilled oils of authenticated plant samples, and a reference sample were investigated by GC/MS to determine the validity and applicability of a series of chemical and stereochemical tests that have been proposed in the literature to identify the country of origin, phytochemical identity or authenticity of geranium oils. The chemical tests evaluated include the ratio of the concentrations of geraniol to citronellol and the presence or absence of certain sesquiterpenes, viz., (-)- guaia-6,9-diene and (-)-10-epi-γ-eudesmol. The stereochemical tests include the stereochemical distribution of i) citronellol, ii) menthone and isomenthone, and iii) rose oxides. The most reliable chemical test was the presence or absence of the sesquiterpene probes. The stereochemical tests proved to be less reliable. Most of the tests could be used to classify geranium oils into general types; however, none of the tests provided a foolproof method to distinguish cultivars or country of origin. During this study, the ambiguity in the absolute stereochemistry of (-)-10-epi-γ-eudesmol and (-)-guaia-6,9-diene was addressed, and these two sesquiterpenes could serve as effective markers for the authentication of P. graveolens essential oils.

In the present work three subspecies of Helichrysum plicatum DC. (Helichrysum plicatum DC. subsp. plicatum, Helichrysum plicatum DC. subsp. polyphillum (Ledeb) P.H.Davis & Kupicha and Helichrysum plicatum DC. subsp. isauricum Parolly) were investigated for the essential oil chemical compositions. The volatiles were obtained by conventional hydrodistillation of aerial parts and microdistillation of inflorescences. Subsequent gas chromatography (GC-FID) and gas chromatography coupled to mass spectrometry (GC/MS) revealed chemical diversity in compositions of the volatiles analyzed.

A total of 199 compounds were identified representing 73.9-98.3% of the volatiles compositions. High abundance of fatty acids and their esters (24.9-70.8%) was detected in the herb volatiles of H. plicatum subsp. polyphyllum and H. plicatum subsp. isauricum.

The inflorescences of Helichrysum subspecies were found to be rich in monoterpenes (15.0-93.1%), fatty acids (0.1-36.3%) and sesquiterpenes (1.1-25.5%). The inflorescence volatiles of H. plicatum subsp. isauricum were distinguished by predomination of monoterpene hydrocarbons (93.1%) with fenchene (88.3%) as the major constituent

The essential oil obtained from hydrodistillation of Zornia diphylla (L.) Pers (whole plant) was analyzed by gas chromatographic techniques. Thirty seven compounds comprising 96.3% of the oil were identified by GC-MS. Monoterpenoids predominated the oil (83.9%) and the major constituent was sabinene (43.1%) followed by terpinene 4-ol (13.2%). The oil was screened for antibacterial, antifungal, anti-inflammatory and cytotoxic activities. Sabinene was tested for its anti-microbial property. The essential oil showed significant in vitro antibacterial activity against Salmonella typhi, one of the causative organisms of food poisoning. Sabinene exhibited promising anti-bacterial and anti-fungal activities. The essential oil showed anti-inflammatory activity against carageennan-induced paw edema in rats. The oil (50 µg/mL) was devoid of any significant in vitro cytotoxicity to thymocytes, macrophages and Dalton’s lympohoma ascitis cells. This is the first report on the essential oil constituents of Zornia diphylla (L.) Pers.

In this study, Ginkgo biloba products used for the same purpose, but licensed to varying authorities were analyzed in point of similarity to each other. A group of these products were licensed from health authorities as herbal medicinal product (HMP), while the other groups of products were licensed as the food supplement (FS). The evaluation of their phytoequivalence was carried out comparing the chromatographic fingerprint profiles. Furthermore, ginkgolides (ginkgolides GA, GB, GC, and GJ) and flavonoid aglycones (quercetin, kaempferol, and isorhamnetin) were quantitatively analyzed by using liquid chromatography–mass spectrometry (LC-MS) and HPLC-diode Array detector (HPLC-DAD) assays. All six herbal medicinal products and two food supplements were found to be phytoequivalent to each other, but five of the seven food supplements did not possess similar content as herbal medicinal products, and the quantity of ginkgolides and flavonoid aglycones per tablet/capsule was found to be lower than declared on the labels. In addition, food supplements were found to be adultered with rutin to reach expected total flavonoid glycosides amount.

A new acylated flavonol glycoside, namely gomphrenol-3-O-( 5 '''-O-E-feruloyl)-β-D-apiofuranosyl-(1→2)[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (1) was isolated from the aerial parts of Chenopodium foliosum Asch. The structure of 1 was determined by means of spectroscopic methods (1D and 2D NMR, UV, IR, and HRESIMS). Radical scavenging and antioxidant activities of 1 were established using DPPH and ABTS radicals, FRAP assay and inhibition of lipid peroxidation (LP) in linoleic acid system by the ferric thiocyanate method. Compound 1 showed low activity (DPPH and ABTS) or lack of activity (FRAP and LP). In combination with CCl 4, 1 reduced the damage caused by the hepatotoxic agent and preserved cell viability and GSH level, decreased LDH leakage and reduced lipid damage. Effects were concentration dependent, most visible at the highest concentration (100 µg/m L ), and similar to those of silymarin .

: Two new O-acetyl derivatives of pentacyclic triterpenic acids, 3α-acetoxyurs -5:12-dien-24-oic acid ( 1 ) and 3α-acetoxylup -12:20 (29)-dien-24-oic acid ( 2 ) were isolated from Omani frankincense of Boswellia sacra Flueckiger along with four known compounds: commic acid-D (3), 9,11-dehydro-β-boswellic acid (4), 3β-Hydroxy-11-oxours-12-ene (5), and 11β-Hydroxy-3-oxours-12-ene (6) . The structures of new compounds 1 and 2 were elucidated on the basis of detailed mass and NMR spectroscopic analysis using 1H NMR, 13C NMR, HMQC, HMBC, COSY, and HREIMS techniques. The relative configurations of 1 and 2 were assigned by comparative analysis of the NMR spectral data with the related known triterpenoids together with NOESY experiments. The structures of the known compounds 3-6 were confirmed by the comparative analysis of the reported mass and NMR data.

A new indigoferamide-A (1) along with three new source compounds dotriacontanoic acid (2), quercetin (3) and formononetin “4-hydroxy-4-methyl-2-pentanone” (4) were isolated from the seeds of Indigofera heterantha Wall. The structures of all these compounds were determined by using mass spectrometry, 1D-and 2D NMR techniques. The structure of the new indigoferamide-A was established by methanolysis as well as by GC-MS analysis.

Four sesterterpenoids were isolated from a South China marine sponge of the genus Hyrtios, and their chemical structures were elucidated by extensive investigation of HRMS and 2D-NMR spectrum. Two of the compounds were new natural products and characterized to be scalarinether (1) and 21-hydroxy-16-deacetyl-12-epi-scalarafuran acetate (2). Two known sesterterpenes were identified as scalarin (3) and isoscalara furan-A (4).

A new dammarane-type triterpene glycoside (1) and compounds Ginsenoside F 5 (2) , Ginsenoside F 3 (3), Ginsenoside F 2 (4) , Ginsenoside Rg 2 (5) were isolated from the root of Aralia elata Seem.. The new compound was established as 12-oxo-3β, 6α, 20 (S)-trihydroxydammar-24-ene-3-O-β- D -gluco pranos yl (1→2) β- D -glucopyranoside . All the structures of the compounds were elucidated on the basis of extensive spectral and chemical evidence.