Structure elucidation and NMR spectral assignments of three new lignan glycosides from Akebia trifoliata

Three new lignan glycosides (1-3) were isolated from the stems of Akebia trifoliata. Their structures were elucidated as (7R,8R,7'R,8'R)3,3',5,5'tetramethoxy-4,4'dihydroxy-7,9':7',9-diepoxylignan-4-O-beta-D-glucopyranoside (1), (7S,8S,8'R)-4,4',9-trihydroxy-3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (2), (7R,8R,8'S)-4,4',9-trihydroxy3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (3) by spectral analyses, primarily NMR, MS and CD. The NMR assignments for the compounds were carried out using 1H, 13C, DEPT, COSY, HSQC, HMBC and ROESY NMR experiments.     

Anti-inflammatory and antioxidant components from Hygroryza aristata

Twenty-six known compounds and two new compounds, including a new lignan, (7S*,8R*,7'R*,8'S*)-icariol A?-9-O-β-xylopyranoside (1), and a new indole alkaloid, hygarine (2), were isolated from the extracts of Hygroryza aristata (Gramineae). The structures of all compounds were elucidated on the basis of NMR spectral analysis. The compounds (-)-epigallocatechin-3-O-gallate (4) and (-)-epicatechin-3-O-gallate (5) possess free radical scavenging activities and compound 1 could inhibit superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils with IC?? values of 19.33 ± 0.86 and 24.14 ± 1.59 μM, respectively.     

Isolation and characterization of new ceramides from aerial parts of Lepidaploa cotoneaster

Two new ceramides were isolated from the bulbs of Lepidaploa cotoneaster (Willd. ex Spreng.) H. Rob. [Vernonia cotoneaster (Willd. ex Spreng.) Less.)], in addition to germanicol, beta-sitosterol, stigmasterol, 3-beta-O-beta-D-glucopyranosyl-sitosterol, lupeol, lupeoyl acetate and tiliroside. The structures of the new compounds were elucidated by spectral techniques (MS, 1H NMR, 13C NMR, HSQC, HMBC, DEPT, and TOCSY) and were compared with data reported in literature, and were established as 2S*,2'R*,3S*,4R*,11E)-N-[2'-hydroxyhenicosanoyl]-2-amino-nonadec-11-ene-1,3,4-triol (1) and (2S*,2'R*,3S*,4R*,8E)-N-[2'-hydroxytricosanoyl]-2-amino-nonadec-8-ene-1,3,4-triol (2). To establish the structure and to locate the double bond, the methyl ester of the fatty acid and dimethyl disulfide (DMDS) derivatives were prepared for both ceramides.     

A new bisbenzylisoquinoline alkaloid from Plumulanelumbinis

One new bisbenzylisoquinoline alkaloid, neferine N-oxide(1), along with three known compounds,neferine(2), liensinine(3), and isoliensinine(4), were isolated from Plumulanelumbinis – the embryo of the seed of Nelumbonucifera. Their structures were elucidated by extensive spectroscopic analysis(MS,UV, IR, NMR), and the absolute configurations were determined by experimental circulardichroism(CD)spectra. Compound 1 is a new naturally occurring bisbenzylisoquinoline alkaloid with an N-oxide functionality, and the CD spectrum of(1R, 1'R) neferine is first reported. The antioxidant activities of compounds 1–4 were evaluated using the ORAC assay, which illustrated that all these compounds showed the different levels of oxygen radical absorbance capacity.     

远东疣柄牛肝菌的化学成分

从远东疣柄牛肝菌(Leccinum extremiorientale)子实体中提取分离得到13个 化合物，通过理化常数和波谱数据分析，它们的结构被鉴定为：麦角甾-7，22-二 烯-3β，5α，6β-三醇（1），麦角甾醇过氧化物（2），麦角甾醇（3），麦角甾 -4，6，8（14），22-四烯-3-酮（4），麦角甾-5，7-二烯-3β-醇（5），棕榈酸 （6），（2S，3S，4R，2’R）-2-（2’-羟基二十四碳酰胺）十八烷-1，3，4-三 醇（7），脑苷脂B（8），脑苷脂D（9），尿嘧啶（10），肌苷（11），腺苷（12 ），D-阿洛醇（13），利用2D NMR（~1H-~1H COSY，HMBC，HMQC）技术首次对化合 物8和9的氢谱和碳谱数据进行了全归属。在浓度为100 μg/mL时，化合物2，7和8 表现出选择性地抗蛇毒Crotalus adamenteus分泌的磷脂酶A_2活性，而对蜂毒 Apis mellifcra磷脂酶A_2却无活性。此外，远东疣柄牛肝菌提取物对粘虫拒食率 和小莱蛾死亡率分别为67%和55%。     

Isolation and characterization of dinochrome A and B,anti-carcinogenic active carotenoids from the fresh Water red tide Peridinium bipes

Two epimeric carotenoids, named dinochromes A (2) and B (3), were isolated from the fresh water red tide Peridinium bipes, as anti-carcinogenic compounds. The stereostructure of dinochrome A and B were characterized to be (3S,5R,6R,3'S,5'R,8'R)- and (3S,5R,6R,3'S,5'R,8'S)-5',8'-epoxy-6,7-didehydro-5,6,5',8'-tetrahydro-beta,beta-carotene-3,5,3'-triol 3-O-acetate, respectively by (1)H- and (13)C-NMR, and circular dichroism (CD) data. Dinochromes A (2) and B (3) inhibit 12-O-tetradecanoyl phorbol 13-acetate (TPA)-stimulated (32)P-incorporation into the phosholipids of HeLa cells. Furthermore, dinochrome A was found to inhibit the proliferation of human malignant tumor cells, such as GOTO, OST and HeLa cells.     

Diterpenes from Sideritis trojana

Six known ent-kaurene, a new ent-kaurane and a new pimarane diterpenes were isolated from Sideritis trojana. The structures of new compounds were determined as ent-7alpha-15beta,16beta-epoxykaurane (1), and ent-2alpha-hydroxy-8(14),15-pimaradiene (2) along with the known compounds siderol (3), sideridiol (4), 7-epicandicandiol (5), isocandol B (6), candol A acetate (7) ent-7alpha-acetoxykaur-15-ene (8) by IR, 1D and 2D NMR techniques and HRMS.     

Novel dammarane-type glycosides from Gynostemma pentaphyllum

Three new dammarane glycosides (1-3), together with five known compounds, gypenoside LXIX (4), gylongiposide I (5), gypenoside XLVIII (6), allantion (7) and vitexin (8) were isolated from the MeOH extract of the aerial parts of Gynostemma pentaphyllum. Compounds 5, 7, and 8 were isolated from this plant for the first time. Their structures were elucidated by 1D and 2D NMR spectra interpretation as well as by chemical degradation.     

Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp

Six new ceramide dihexosides, amphimelibiosides A-F (1-6), were isolated from a Japanese marine sponge Amphimedon sp. The structure of amphimelibioside C (3), which is a major component of amphimelibiosides, was determined by 2D NMR techniques, chemical degradation, and a semisynthetic method to be 1-O-[beta-D-glucopyranosyl-(1-->6)-alpha-D-galactopyranosyl]-(2S,3S,4R,6E)-2-[(2'R)-2-hydroxydocosanoyl]-2-amino-6-octadecene-1,3,4-triol. The structures of the other constituents were elucidated by a combination of mass spectra, (1)H NMR, and GC-MS analysis.     

Ceramide constituents from five mushrooms

Five mushrooms, Panellus serotinus, Lyophyllum connatum, Amanita pantherina, Sarcodon aspratus and Lepista nuda, have been investigated chemically. Two new ceramides, (2S,3R,4E,8E)-N-hexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (1) and (2S,3R,4E,8E,9'Z,12'Z)-N-9',12'-octadecadienoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lyophyllum connatum. Two new ceramides, (2S,2'R,3R,4E,8E)-N-2'-hydroxypentadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (4) and (2S,2'R,3R,4E,8E)-N-2'-hydroxytetradecanoyl-2-amino-9-methyl-4,8-octadeca-diene-1,3-diol (5), have been isolated from Amanita pantherina with (2S,2'R,3R,4E,8E)-N-2'-hydroxyhexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (3), a known synthetic compound. Compounds 3 and 4 were also isolated from Sarcodon aspratus and compound 3 was isolated from Lepista nuda. The structures of the new compounds were elucidated on the basis of their spectral data.     

NEOLIGNANS FROM PIPER KADSURA(Ⅱ)

Two new bicyclo[3,2,1]octanoid neolignans,named as kadsurenin I andkadsurenin J were isolated from Piper kadsura(Choiey)Ohwi.Based on the spectros-copic analysis(UV,IR,MS and NMR)and chemical derivatization,their structures wereestablished as 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy-2'-hydroxy-1',2',3',4'-tetrahydro-4'-oxo-7.3',8.1'-neolignan and 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy-2'-acetoxy-1',2',3',4'-tetrabydro-4'-oxo-7.3',8.1'-neolignan respectively.     

Iridoids from Neopicrorhiza scrophulariiflora and their hepatoprotective activities in vitro

Four new non-glycosidic iridoids, piscrocins D (1), E (2), F (6), and G (7), as well as two new iridoid glycosides, piscrosides A (8) and B (9), were isolated from the roots of Neopicrorhiza scrophulariiflora (Scrophulariaceae), together with seven known iridoids. The structures of the isolated compounds were established by means of 1D and 2D NMR spectroscopy and chemical methods. The hepatoprotective activities of these compounds were evaluated by measuring their effects on CCl(4)-induced hepatocytes damage in vitro, and the structure-activity relationships were also discussed.     

Studies on the constituents of Swertia japonica Makino II. On the structures of new glycosides

Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alco-hol glycoside, 3-butenyl 6'-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (3), and a new lignan glycoside, 7R,7'R,8S,8'S-(+)-neo-olivil-4-O-beta-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica Makino. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.     

Cytotoxic cembranoids from the Red Sea soft coral Sarcophyton glaucum

One new cembrane diterpene, 2R,7R,8R-dihydroxydeepoxysarcophine (1), together with three known compounds, 7alpha,8beta-dihydroxydeepoxysarcophine (2), 7beta-acetoxy-8alpha-hydroxydeepoxysarcophine (3), and sarcophine (4), have been isolated from the Red Sea soft coral Sarcophyton glaucum. Their structures were determined using 1D and 2D NMR spectroscopy. 7beta-Acetoxy-8alpha-hydroxydeepoxysarcophine (3) exhibits cytotoxic activity against HepG2, HCT-116, and HeLa cells with IC50 values of 3.6, 2.3, and 6.7 microg/mL, respectively.     

A new triterpene from Scorzonera latifolia (Fisch. and Mey.) DC

A novel triterpene 1 (3-β-hydroxy-fern-7-en-6-one-acetate) together with four known compounds, urs-12-en-11-one-3-acetyl (2), 3-β-hydroxy-fern-8-en-7-one-acetate (3), olean-12-en-11-one-3-acetyl (4) and leucodin (5) were obtained from the S. latifolia roots. All compounds were isolated from the n-hexane extract of S. latifolia roots using several chromatographic techniques. The structure of the isolated compounds was elucidated on the basis of (1)H-NMR, (13)C-NMR and 2D NMR data (HMBC, HMQC, COSY, TOCSY, NOESY, DEPT) as well as GC EITOF-HRMS.     

Complete 1H and 13C data assignments of two new guaianolides isolated from Ainsliaea fragrans

Two new guaianolides, 8alpha-hydroxy-11alpha,13-dihydroglucozaluzanin C and 11alpha,13-dihydroglucozaluzanin C, were isolated from Ainsliaea fragrans, along with two known guaianolides, 8alpha-hydroxy-11alpha,13-dihydrozaluzanin C and glucozaluzanin C. The structures of the new compounds were unambiguously established by HR-ESI-MS, one-dimensional (1D) (DEPT), two-dimensional (2D) ((1)H-(1)H COSY, HSQC, HMBC, ROESY) NMR experiments and by comparison with structurally related compounds. The known compounds were identified by comparison of spectral data with published references. Some NMR data of the known compounds were reported for the first time.     

New triterpenoids isolated from the root bark of Ulmus pumila L

Three new triterpenoids, 1-3, were isolated from the dried root bark of Ulmus pumila. Along with the three new compounds, six known triterpenoids, epifriedelanol (4), friedelin (5), oleanolic acid (6), maslinic acid (7), camaldulenic acid (8), and arjunolic acid (9) were also isolated. The structures of new compounds were established as ulmudiol (bauer-7-ene-1alpha,3beta-diol, 1), dehydroulmudiol [bauer-7,9(11)-diene-1alpha,3beta-diol, 2], and ulmuestone [3alpha-hydroxy-11alpha-(4'-hydroxy-3'-methoxy)benzoyloxybauer-1-one, 3], on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. In addition, the cytotoxic activities of these compounds are also reported.     

Structure elucidation and NMR spectral assignment of five new xanthones from the bark of Garcinia xanthochymus

Five new xanthones, namely Garcinexanthones A-E (1-5), were isolated from the barks of Garcinia xanthochymus. Their structures were elucidated by spectral analysis, primarily NMR, MS, and UV. The complete assignments of the (1)H NMR and (13)C NMR chemical shifts for the compounds were achieved by using 1D and 2D NMR techniques, including DEPT, HSQC, and HMBC NMR experiments.     

Phenolic constituents from the rhizomes of Gastrodia elata

Gastrodia elata Bl. (Orchidaceae) is an important traditional medicinal plant as well as a famous foodstuff in China. In the present article, the HPLC chromatograms of different preparation processes were reported, and structures of nine phenolic compounds, isolated from Gastrodia elata, were assigned. The isolated compounds were identified as 1,3-bis(4-hydroxybenzyl)citrate (1), gastrodin (2), 4-hydroxybenzyl alcohol (3), 1-(4-beta-D-glucopyranosyloxybenzyl)citrate (4), 4-hydroxybenzaldehyde (5), parishin B (6), 4-hydroxybenzyl methyl ether (7), 4-hydroxybenzyl ethyl ether (8), and 4-(4'-hydroxybenzyl)phenol (9). Compounds 1 and 4, named as parishin D and E, were new. Their structures were elucidated on the basis of spectral analyses, including 2D NMR spectroscopy.     

Three new compounds from the leaves of Acanthopanax senticosus Harms

<正>Three new compounds named(2E)-prenyl benzoate-4-O-α-L-arabinopyranosyl(1→6)β-D-glucopyranoside(1),7-methoxy-8- O-β-D-glucopyranosyl coumarin(2),and 3,4'-dihydroxy-3'-methoxy benzenepentanoic acid(3) were isolated from the leaves of Acanthopanax senticosus Harms.The structures of new compounds were determined by means of 2D NMR experiments and chemical methods.