Seven new meroditerpenoids, from the marine sponge Strongylophora strongylata, that inhibited the maturation of starfish oocytes

Seven new meroditerpenoids, strongylophorines 13-19 (1-7), have been isolated together with the four known strongylophorines 2 (8), 3 (9), 4 (10), and 8 (11) by a screening method using oocytes of the starfish Asterina pectinifera from a marine sponge Strongylophora strongylata collected at Iriomote Island, Okinawa, Japan. The structures were assigned according to their spectral data. Ten strongylophorines inhibited the maturation of starfish oocytes in the range 1.1-37.6 μM (IC₅₀), while strongylophorine 4 (10) was not active at 250 μM.     

Steroidal saponins from Lysimachia Paridiformis

A new steroidal saponin, paridiformoside B (1), was obtained from the EtOH extract of the whole plant of Lysimachia Paridiformis Franch, togerher with one steroidal sapogenin (7) and seven known steroidal saponins (2-6, 8-9). Their structures were elucidated using extensive spectroscopic techniques including 1D and 2D NMR spectra.     

Antibacterial constituents from Stemona sessilifolia

Bioassay-guided fractionation led to the isolation of eight compounds from Stemona sessilifolia. Of the eight isolates, three new bibenzyls, stilbostemins M-O (1-3), and a new tocopherol, 6-methoxy-3,4-dehydro-δ-tocopherol (4) were revealed together with four known compounds 3,5-dihydroxy-2'-methoxy bibenzyl (5), 3,5-dihydroxy bibenzyl (6), β-tocopherol (7), and γ-tocopherol (8). Compounds 5, 6, and 8 exhibited strong antibacterial activities against Staphylococcus aureus and S. epidermidis.     

Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum

Three new germacrane sesquiterpenes, eupalinolides C-E (1-3), along with three known germacrane sesquiterpenes, eupalinolide A (4), eupalinolide B (5), and 3β-acetoxy-8β-(4'-hydroxytigloyloxy)-14-hydroxycostunolide (6), were isolated from Eupatorium lindleyanum. They were tested for cytotoxicity against A-549, BGC-823, SMMC-7721, and HL-60 tumour cell lines. The results showed that these compounds demonstrated potent cytotoxicity. The structures of the compounds were elucidated by means of ¹H and ¹³C NMR spectroscopic analysis, including 2D NMR experiments.     

Stilbenoids from Stemona sessilifolia

Two new dihydrostilbenes, stilbostemins H (1), I (2), and a new dihydrophenanthrene, stemanthrene E (3), were isolated and identified from the roots of Stemona sessilifolia, together with known stilbostemins B, D and G, and stemanthrenes A and C (4-8). Structures of new stilbenoids were established by 1D and 2D ¹H NMR and ¹³C NMR spectroscopic analyses.     

Stilbenoids from Stemona japonica

Three new dihydrostilbenes, stilbostemins J-L (1-3), and a new dihydrophenanthrene, stemanthrene F (4), were isolated from the roots of Stemona japonica together with two known bibenzyls, 3,5-dihydroxy-4-methylbibenzyl (5) and 3,5-dihydroxy-2'-methoxy-4-methylbibenzyl (6). Their structures were elucidated by spectroscopic analyses. Compounds 3-6 exhibited strong antibacterial activities against Staphylococcus aureus and Staphylococcus epidermidis.     

Three new isoprenylated flavonoids from the roots of Sophora flavescens

Three new flavonoids isoprenylated as 2,2-dimethyl-dihydropyran groups, named sophoranodichromanes A-C (1-3), have been isolated from the roots of Sophora flavescens, together with the known compounds, chrysophanol (4), soyasapogenol B (5) and β-sitosterol (6). Their structures have been elucidated by spectroscopic methods.     

A new anti-HIV lupane acid from Gleditsia sinensis Lam.

A new lupane acid, 2β-carboxyl,3β-hydroxyl-norlupA (1)-20 (29)-en-28-oic acid (1), together with five known lupane acid derivatives (2-6), were isolated from the stings of Gleditsia sinensis Lam.. Their structures were elucidated on the basis of 1D and 2D NMR techniques. All these known compounds were isolated from this genus for the first time. The new compound 1 showed strong anti-HIV activity.     

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.     

Two new phenylpropanoid esters of rhamnose from Lagotis yunnanensis

Two new phenylpropanoid esters of rhamnose, lagotoside B (1) and lagotoside C (2), together with three known compounds (3-5), were isolated from Lagotis yunnanensis. The structures of 1 and 2 were elucidated by spectroscopic methods. Compounds 3-5 have been obtained from this species for the first time.     

Immunosuppressive terpenes from Prinsepia utilis

Two new hemiterpenes, utililactone (1) and epiutililactone (2), along with nine known compounds (3-11), were isolated from the leaves of Prinsepia utilis. Their structures were elucidated on the basis of spectroscopic data. The isolated compounds showed significant immunosuppressive activities.     

Two new 18-carbon norditerpenoid alkaloids from Aconitum sinomontanum

Two new 18-carbon norditerpenoid alkaloids, sinaconitines A (1) and B (2), together with two known alkaloids, ranaconitine (3) and lappaconitine (4), were isolated from the roots of Aconitum sinomontanum. Their structures were elucidated on the basis of spectral evidences and X-ray crystallographic analysis for 1. Furthermore, the reversed ¹³C NMR assignments for C-10 and C-13 of 3, 4, puberanine, puberanidine and demethyllappaconitine were revised. Compounds 1-4 were evaluated for cyclooxygenase-2 (COX-2) enzyme inhibitory activity. However, they did not show any inhibition at 10 μM.     

Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia

A novel diterpenoid ester, fritillahupehin (1) and three known fatty acids, palmitic acid (2), lignoceric acid (3) and azelaric acid (4), have been isolated from the bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16β-yl lignocerate by means of spectroscopic and chemical evidence. Compounds 2-4 were isolated from Fritillaria sp. for the first time.     

Bromophenols from the brown alga Leathesia nana

Two new bromophenols, (E)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-methylpropenal (1) and 3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-methyl-1-propanol (2), together with 11 known bromophenols (3-13), were isolated from the ethanolic extract of the brown alga Leathesia nana S. et G. Their structures have been elucidated by spectroscopic methods, including IR, MS, HRMS, 1D and 2D NMR techniques.     

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.     

A new lignan from the seeds of Sphaerophysa salsula

A new compound, sphaerophysin A (1), together with 16 known compounds (2-17) were obtained from the ethanolic extract of the seeds of Sphaerophysa salsula. The structure of 1 was elucidated on the basis of spectral and chemical evidence. Compounds 2-17 were isolated from the plant for the first time.     

A new diterpenoid and active stilbenes from Pinus armandii heartwood

8(17),13-Labdadien-16,14-olid-18-oic acid (1), a new diterpenoid, has been isolated from the heartwood of Pinus armandii Francher, along with seven known diterpenoids (2-8) and four known stilbenes (9-12). Their structures have been elucidated by spectral evidence. (E)-3-Hydroxy-5-methoxystilbene (9) showed significant inhibition against white-rot fungi.     

Three new triterpenoid saponins from the rhizomes of Impatiens pritzellii var. hupehensis

Three new triterpenoid saponins, impatiprins A-C (1-3), together with a known triterpenoid (4) and two known triterpenoid saponins (5, 6), were isolated from the rhizomes of Impatiens pritzellii Hook. f. var. hupehensis Hook. f. The structures of 1-3 were determined by 1D and 2D NMR, FAB-MS techniques and chemical methods. Compounds 1 and 2 showed weak cytotoxicities against S-180, HeLa and HepG2 cell lines.     

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, ¹H, ¹³C and 2D NMR). Compounds 1-5 were isolated from the Cercis genus for the first time.     

Three new C21-steroidal glycosides from the roots of Cynanchum inamoenum

Three new C₂₁-steroidal glycosides presenting an unusual 13,14:14,15-disecopregnane-type skeleton, named inamosides A-C (1-3), together with two known C₂₁-steroidal glycosides, were isolated from the MeOH extract of the roots of Cynanchum inamoeum (Maxim.) Loes (Asclepiadaceae). The aglycone of compounds 1, 2, and 3 has a 2β-hydroxyl, which has not yet been reported in the literature. The structure and relative configuration of the aglycone of compounds 1, 2, and 3 were established by X-ray crystallographic analysis.