New dibenz[b, f]oxepins from Cercis chinensis Bunge

Three new dibenz[b,f]oxepins: 6-methoxy-7-methyl-8-hydroxydibenz[b, f]oxepin (1), 1,8-dimethoxy-6-hydroxy-7-methyldibenz[b, f]oxepin (2), and 1-hydroxy-6,8-dimethoxy-7-methyldibenz[b,f]oxepin (3), along with two known dibenz[b,f]oxepins pacharin (4) and bauhiniastatin 4 (5), were isolated from Cercis chinensis Bunge (Leguminosae). Their structures were elucidated on the basis of spectroscopic evidence (EI-MS, UV, IR, (1)H, (13)C and 2D NMR). Compounds 1-5 were isolated from the Cercis genus for the first time.     

New anthraquinones from Gladiolus gandavensis

Two new anthraquinones, methyl 8-hydroxy-3-methoxy-6,7-methylenedioxy-1-methylanthraquinone-2-carboxylate (gandavensin A, 1) and methyl 8-hydroxy-3,6,7-trimethoxy-1-methylanthraquinone-2-carboxylate (gandavensin B, 2), have been isolated from the light petroleum extract of the subterranean corm of Gladiolus gandavensis Van Houtt., along with methyl 8-hydroxy-3,6-dimethoxy-1-methylanthraquinone-2-carboxylate (3), methyl trans-p-methoxycinnamate (4), 5,7-dimethoxy-2-methylchromone (5), and 5-hydroxy-2-hydroxymethyl-7-methoxychromone (6). Their structures were elucidated on the basis of spectral data.     

Two new iridoids from Patrinia scabra

From the roots of Patrinia scabra two new iridoids, 3-methylbutyric acid 7-hydroxy-7-hydroxymethyl-4-(3-methyl-butyryloxymethyl)-6-oxo-1,6,7,7a-tetrahydrocyclopenta[c]pyran-1-yl ester (1) and 6-hydroxy-7-methylhexahydrocyclopenta[c]pyran-3-one (2) have been isolated. Their structures were determined by means of NMR spectra and X-ray crystallographic analysis.     

Anthraquinones from Gladiolus gandavensis

Five new anthraquinones have been obtained from the ethanolic extracts of the subterranean corms of Gladiolus gandavensis Van Houtt. Their structures were elucidated as 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone (gandavensin D, 1), methyl 3,8-dihydroxy-6,7-methylenedioxy-1-methyl-anthraquinone- 2-carboxylate (gandavensin E, 2), 2,3,8-trihydroxy-6-methoxy-1-methoxymethyl-anthraquinone (gandavensin F, 3), 8-hydroxy-3,6-dimethoxy-1-methyl-anthraquinone-2-carboxylic acid (gandavensin G, 4) and 1,7-dihydroxy-3,6-dimethoxy-anthraquinone (gandavensin H, 5) on the basis of spectral data. The known compounds isolated for the first time from this plant have been determined to be methyl 3,6,8-trihydroxy-7-methoxy-1-methyl-anthraquinone-2-carboxylate (6), methyl 3,6,8-trihydroxy-1-methyl-anthraquinone-2-carboxylate (7), 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone-2-carboxylic acid (8), 3,6,8-trihydroxy-1-methyl-anthraquinone-2-carboxylic acid (9), 6,8-dihydroxy-3-methoxy-1-methyl-anthraquinone-2-carboxylic acid (10), methyl 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone-2-carboxylate (11) and methyl 3,7,8-trihydroxy-1-methyl-anthraquinone-2-carboxylate (12).     

Two new isoprenyl chalcones from Hedysarum gmelinii

Two new isoprenyl chalcones, 1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-3-butenyl)phenyl]-3-(2,2-dimethyl-2H-benzopyran-6-yl)-2-propen-1-one (1) and 1-[4-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-benzofuran-5-yl]-3-[3-(3-methyl-2-butenyl)-4-hydroxy-phenyl]-2-propen-1-one (2), named hedysarumine A and hedysarumine B, along with a known isoprenyl chalcone paratocarpin E (3) were isolated from the roots of Hedysarum gmelinii for the first time. Their structures were elucidated based on NMR and MS spectral analyses.     

New 2-(2-Phenylethyl) Chromones from Bothriochloa Ischaemum

Two new 2-(2-Phenylethyl) chromones were isolated from Bothriochloa ischaemum (Gramineae). They were characterized as 5-hydroxy-6-methoxy-2-[2-(2-hydroxyphenyl)-ethyl]-chromone(1) and 5-hydroxy-2-[2-(2-hydroxyphenyl)-ethyl]-chromone(2) by means of spectroscopic analysis, especially 2D-NMR experiments.     

Coumarins from Coriaria nepalensis

Two new coumarins (1) and (2), along with seven known coumarins 3-9, were isolated from the leaves and stems of Coriaria nepalensis Wall. The two new compounds were established as 7-hydroxy-6-methoxy-3,8-bis(3-methyl-2-butenyl) coumarin (1) and 7-hydroxy-6-methoxy-3-(3-methyl-2-butenyl) coumarin (2), on the basis of 1D and 2D NMR techniques. The known compounds 3, 6-9 were isolated from this plant for the first time.     

Stilbene derivatives from Gnetum cleistostachyum

Three new stilbene derivatives, named gnetucleistol A (1), B (2) and C (3), together with four known compounds, gnetifolin A (4), p-hydroxycinnamic acid (5), piceatannol (6) and resveratrol (7), were isolated from Gnetum cleistostachyum C.Y. Cheng (Gnetaceae). Their structures were elucidated on the basis of spectroscopic evidence (EI-MS, UV, IR, NOE, ¹H, ¹³C and 2D NMR).     

A New Bicoumarin from Stellera Chamaejasme L

Thirteen compounds were isolated from roots of Stellera chamaejasme L. (Thymelaeaceae). They are β-sitosterol (2), simplexin (3), pimelea factor P2 (4), daucosterol (5), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (6), 4-ethoxy-benzoic acid (7), 2,4,6-Trimethoxy-benzoic acid (8), (+)-afzelechin (9), fumaric acid (10), N,N-dimethyl-L-aspartic acid (11), umbelliferone (12), daphniretin (13) and a novel bicoumarin named bicoumastechamin (1). Among the known compounds, 7, 8, 9, 10 and 11 were first isolated from this plant, and 6 was first isolated from the natural resources. Their structures have been elucidated on the basis of spectral data. In vitro bioassays showed that 4 inhibited cancer cell growth, 13 exhibited immunomodulatory activity, and 6 exhibited both immunomodulatory and anti-tumor activity.     

A novel sulphur glycoside from the seeds of Descurainia sophia (L.)

A new sulphur glycoside, named descurainoside (1), and the known compound sinapic acid (2) have been isolated from the seeds of Descurainia sophia (L.) Webb ex Prantl. The structure of 1 has been identified as (1R,6S,8R,9S,10S)-9,10-dihydroxy-4-[(4-hydroxy-3,5-dimethoxyphenyl)methylene]-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4.4.0]decan-3-one by means of physico-chemical properties and spectroscopic methods (1D and 2D NMR, HRMS, ESI-MS).     

One new benzyldihydrophenanthrene from Arundina graminifolia

A novel benzyldihydrophenanthrene named arundinaol (1) has been isolated from the rhizoma of Arundina graminifolia. The structure of 1 has been elucidated as 7-hydroxy-1-(p-hydroxybenzyl)-2,4-dimethoxy-9,10-dihydrophenanthrene on the basis of physical and chemical evidence and spectral analysis.     

Chemical Constituents from the Leaves of Magnolia Denudata

20 compounds were isolated from the leaves of Magnolia denudata including 16 lignans, which belong to 6 structural types. Except for (7R, 8S, 1'S) -δ^8' - 1', 4' - dihydro - 5'- methoxy - 3, 4 -methylenedioxy - 4' - oxo -7.O.2', 8.1' - neolignan (6), magliflonenone (9), 2,5' - diene-2', 8'- epoxy - 5' - methoxy - 8 - methyl - 4' - oxo - 3,4-methylenedioxy - spiro (5,5) - undecane (10), veraguensin (16) and β-sitosterol (20), the other 15 compounds were obtained from this species for the first time. The absolute configurations of 3 compounds (1,4,10) were determined by CD spectroscopy for the first time. The anti-inflammatory activities of compounds 1, 2 and 16 were assessed and 2 was shown to have significant inhibition effect on mice hind-paw edema induced by carrageenan.     

A novel alkaloid from Gaultheria nummularioides

A novel alkaloid, gaultherialine A (1), along with twenty-seven known compounds were isolated from the whole plants of Gaultheria nummularioides D. Don. The structure of the new alkaloid was elucidated as 7,8-dimethoxy-1-(4-methoxyphenyl)-4,5-dihydro-2H-benzo[e]indole-2-one N-oxide (1) on the basis of spectral evidence.     

A New Naphthoquinone from Bombax Malabaricum

A new naphthoquinone 1 together with 7-hydroxycadalene (2) and 8-formyl-7-hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone (3) were isolated from the heartwood of Bombax malabaricum. The new naphthoquinone was characterized as 7-hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone (1) based on spectral and chemical studies.     

Total synthesis of two new dihydrostilbenes from Bulbophyllum odoratissimum

A total synthetic route of two new dihydrostilbenes 5-(2-benzo[1,3]dioxole-5-ylethyl)-6-methoxy benzo[1,3]dioxole-4-ol (1) and 5-(2-benzo[1,3]dioxole-5-ylethyl)benzo[1,3]dioxole-4,7-diol (2), which were isolated from Bulbophyllum odoratissimum Lindl. with significant cytotoxicity toward human cancer cell lines, was developed via Horner reaction etc. The natural products 1 and 2 were obtained in 10.5% and 3.3% overall yield, respectively.     

Studies on chemical constituents from Ilex pubescens

Two new phenolic glycosides, ilexpubsides A and B, along with four known lignan glycosides were isolated from the roots of Ilex pubescens. By spectral evidence, the structures of the new compounds were elucidated as 4-O-β-D-[6'-O-(4'-O-β-D-glucopyranosylvanilloyl)glucopyranosyl] vanillic acid (1) and syringinic 6'-O-β-D-xylopyranoside (2). The known compounds were identified to be liriodendrin (3), (-)-olivil (4), tortoside A (5) and (+)-cyclo-olivil (6). All compounds were first isolated from Ilex pubescens.     

Triterpene saponins from Lysimachia christinae

Seven triterpene saponins were isolated from Lysimachia christinae and identified as lysichriside A (1), lysichriside B (2), primulanin (3), lysikokianoside 1 (4), anagallisin C (5), ardisiacrispin A (6), and ardisicrenoside B (7). Compounds 1 and 2 are new triterpene saponins, compounds 3, 5, and 7 were isolated from this genus, and compounds 4 and 6 were isolated from this species for the first time. Their structures were elucidated by means of 1D and 2D NMR experiments.     

Triterpenes from Tripterygium wilfordii Hook

Two new friedelane-type triterpenes, tripterfrielanons A (1) and B (2), along with six known triterpenoids, friedelin (3), canophyllal (4), canophyllalic acid (5), 3-oxo-29-hydroxyfriedelane (6), wilforlide A (7), wilforlide B (8), have been isolated from the EtOH extract of the roots of Tripterygium wilfordii Hook.f. Compounds 4, 5, 6 were isolated for the first time from this plant. The new triterpenes 1 and 2 exhibited mild cytotoxic activity against human Hela cell lines in vitro. The assay showed the IC₅₀ of 1 and 2 were 8.5 and 25 μg/mL, respectively.     

Three new and two rare furanoeremophilanes from Senecio asirensis

Three new furanoeremophilanes have been obtained from the aerial parts of Senecio asirensis (N. O. Asteraceae), and characterized as 6-hydroxylmethyl-9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, designated asirensane-a (1), 6-hydroxyl-1,2-dimethoxyl-4,6,11-trimethyl-6-hydronaphtho[2,3-a]furan-7-one, named asirensane-b (2), and (6,12-dihydroxyl-9-methoxyl-4-methyl-11-acetyl-3,4-dihydronaphtho[2,3-b]furan-3-yl)methyl (2'Z)-2'-methylbut-2'-enoate, designated asirensane-c (3). In addition, two rare furanoeremophilanes have also been isolated and characterized from this source, namely 9-methoxyl-4,11-dimethylnaphtho[2,3-b]furan, named 14-nordehydrocalohastine (4), and 4,11-dimethylnaphtho[2,3-b]furan-6,9-dione, designated as maturinone (5). Their structures have been elucidated on the basis of spectral analysis. The alcoholic extract was also tested for anti-inflammatory activity, which decreased edema by 22% at a dose of 500 mg kg^-1 after 3 h with respect to the control group treated only with carrageenan, while the standard drug phenylbutazone showed a 50% decrease at a dose of 100 mg kg^-1, indicating that the extract has moderate anti-inflammatory activity.     

Two new constituents from mangrove Bruguiera gymnorrhiza

A lignan and two aromatic compounds were isolated from the branches of the mangrove plant, Bruguiera gymnorrhiza. They were brugunin A (1), bruguierol D (2) and 2,3-dimethoxy-5-propylphenol (3). Among them, 1 and 2 were new compounds; 3 was isolated from a natural source for the first time. The structures of these compounds were determined by NMR spectroscopic studies as well as chemical evidence.