ent-Kaurenoids from the roots of Cacalia pilgeriana

Two new ent-kaurenoids,19-acetoxyl-ent-3beta,17-dihydroxykaur-15-ene (1), 19-acetoxyl-ent-3beta-hydroxykaur-15-en-17-al (2), together with seven known ent-kaurenoids: ent-kaur-16-en-19-al (3), ent-kaur-16-en-19-oic acid (4), ent-kauran-16beta,17-diol (5), ent-15beta, 16beta-epoxy-17-hydroxykauran-19-oic acid (6),19-acetyl-ent-3beta-hydroxyl-kaur-16-ene (7), ent-3beta,19-dihydroxykaur-16-ene (8), ent-17-hydroxykaur-15-ene (9), were isolated from Cacalia pilgeriana. Their structures were elucidated by spectroscopic methods including 2D NMR spectral analysis.     

Two new diterpenoid dimers,fritillebinide D and E,from bulbs of Fritillaria ebeiensis

Two new ent-kaurane diterpenoid dimers, fritillebinide D (1) and fritillebinide E (2), were isolated from bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Their structures have been determined to be ent-3β-acetoxy-kauran-16β, 17-acetal ent-3β-acetoxy-16β-kauran-17(R)-aldehyde (1) and ent-3β-acetoxy-kauran-16β,17-acetal ent-3β-acetoxy-16β-kauran-17(S)-aldehyde (2) by means of spectral analysis.     

Triterpenes from Campanula lactiflora

One new triterpene compound, 3β-acetoxylup-20(30)-en-29-al (1) and two known 3-acetylptiloepoxide (2) and 3β-acetoxylup-20(29)-ene (3) were isolated for the first time from the leaves of Campanula lactiflora and their structures were deduced by high field 1D and 2D 400 MHz NMR, EI-MS and (+) LC-MS/MS spectra.     

Structural elucidations of two ent-kaurane dimers from bulbs of Fritillaria ebeiensis var. purpurea

A novel ent-kaurane diterpenoid dimer, fritillebinide B (1) together with one known diterpenoid dimer fritillebinide A (2) were isolated from the bulbs of Fritillaria ebeiensis var. purpurea G.D. Yu et P. Li. Compound 1 has been established to be ent-3β-acetoxy-kauran-16β,17-acetal ent-16β-kauran-17(R)-aldehyde (1) by means of spectral analysis and chemical evidence.     

Structures of two diterpenoid dimers from bulbs of Fritillaria ebeiensis

A new ent-kaurane diterpenoid dimer, fritillebinide C (1) together with one known diterpenoid dimer fritillebinide B (2) were isolated from the bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Compound 1 has been determined to be ent-3β-acetoxy-kauran-16β, 17-acetal entβ-kauran-17(S)-aldehyde (1) by means of spectral analysis and chemical evidence.     

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.     

Chemical constituents of Pseudopterogorgia species of the Indian ocean

A new ceramide, (2S,3R,4E)-1,3-dihydroxy-2-[(hexadecanoyl)amino]-nonadeca-4-ene (1), cholest-5-en-3β,7β,19-triol (2), identified as its, peracetyl derivative (3), and batyl alcohol (4) were isolated from Pseudopterogorgia species. 1 exhibited antibacterial activity against Gram-positive and Gram-negative bacteria.     

A cyclic peroxide of clerodenoic acid from the Taiwanese liverwort Schistochila acuminata

Two minor diterpenoids, 15(16)-peroxy-3, 13-clerodadien-18-oic acid (4) and totarol (7), were isolated from the liverwort Schistochila acuminata. The former is a further oxidized cyclic peroxide from the major component. The latter is a rearranged abietane alcohol which skeleton was found in liverworts for the first time.     

Isolation and structure elucidation of novel gamma-lactones from Saccopetalum prolificum

Two novel γ-lactones, saccopetrin C (1) and saccopetrin D (2), were isolated from the roots of Saccopetalum prolificum. Their structures were established by spectroscopic and chemical methods.     

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.     

Labdane diterpenes from the seeds of Platycladus orientalis

Two new labdane diterpenes, 14(R),15-dihydroxy-8(17),12(E)-labdadien-19-oic acid (1) and 16-methyl-12,15-epoxy-8(17),13-labdadien-19-oic acid (2), together with four known compounds, were isolated from the seeds of Platycladus orientalis. Their structures were established by spectroscopic methods. The stereochemistry of compound 1 was defined by X-ray crystallographic analysis.     

A new dicoumarinoid glycoside from Daphne giraldii

A new dicoumarinoid glycoside, named giraldoid A (1), has been isolated from Daphne giraldii Nitsche. The structure of 1 was determined as 7-O-β-glucosyl-8-(7-hydroxy-2H-1-benzopyran-2-one-8-)yl-2H-1-benzopyran-2-one on the basis of chemical reactions and spectroscopic methods.     

Rearranged abietane diterpenoids from Clerodendrum mandarinorum

Five new abietane derivatives which have a commonly rearranged abietane skeleton contained a 17(15 → 16),18(4 → 3)-diabeo-abietane framework, mandarones D-H, were isolated from the stem of Clerodendrum mandarinorum Diels (Verbenaceae). The structures were characterized as (16S)-12,16-epoxy-11-hydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13-pentaene-7-one (mandarone D, 1), 12,16-epoxy-11,14-dihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-7-one (mandarone E, 2), 12,16-epoxy-6,11,14-trihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-7-one (mandarone F, 3), 12,16-epoxy-11,14-dihydroxy-6-methoxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-2,7-dione (mandarone G, 4) and 12,16-epoxy-11,14-dihydroxy-17(15 → 16),18(4 → 3)-diabeo-abieta-3,5,8,11,13,15-hexaene-1,7-dione (mandarone H, 5) respectively, mainly based on the spectral analysis and by comparison with those of closely related compounds.     

Two new and four known polyphenolics obtained as new cell-cycle inhibitors from Rubus aleaefolius Poir

Two new polyphenolics, rubuphenol (1) and sanguiin H-2 ethyl ester (2), were isolated together with ellagic acid (3), ethyl gallate (4), 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (5) and 1,2,3,6-tetra-O-galloyl-β-D-glucopyranose (6) as new cell-cycle inhibitors from Rubus aleaefolius by bioassay-guided separation procedure and the structures of 1 and 2 were elucidated by spectroscopic method. Compounds 1 - 6 inhibited the cell cycle progression of tsFT210 cells at the G₀/G₁ phase with the MIC values of 14.6 μM (1), 22.1 μM (2), 10.3 μM (3), 7.8 μM (4), 7.9 μM (5) and 6.6 μM (6).     

Stilbene C-glucosides from Cissus repens

Four new stilbene C-glucosides, namely trans-3-O-methyl-resveratrol-2-C-β-glucoside (1), cis-3-O-methyl-resveratrol-2-C-β-glucoside (2), trans-3-O-methyl-resveratrol-2-(2-p-coumaric)-C-β-glucoside (cissuside A) (3), and trans-3-O-methyl-resveratrol-2-(3-p-coumaric)-C-β-glucoside (cissuside B) (4), were isolated from the aerial parts of Cissus repens, along with known trans-resveratrol (5), trans-resveratrol-2-C-β-glucoside (6) and cis-resveratrol-2-C-β-glucoside (7). Their structures were established by spectroscopic methods. Stilbene C-glucosides were found in the genus Cissus for the first time.     

A new saponin from the leaves and stems of Panax quinquefolium L. collected in Canada

A new dammarane-type saponin named quinquenoside L3 (1) together with vina-ginsenoside R3 (2) were isolated from the leaves and stems of Panax quinquefolium L. collected in Canada. On the basis of physicochemical and spectral evidences, 1 was established as 3-O-β-D-glucopyranosyl-20-O-[β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosyl] 20(S)-dammar-23-ene-3β, 12β,20,25-tetryol.     

Inhibition of Na+,K+-ATPase activity by (-)-ent-Kaur-16-en-19-oic acid and its derivatives

The diterpene, (-)- ent-kaur-16-en-19-oic acid, from Croton oblongifolius was identified as an Na +,K +-ATPase inhibitor. This compound exhibits an IC 50 of 2.2 x 10( -5 )M against crude enzyme Na +,K +-ATPase from rat brain. The semi-synthetic derivatives, (-)-methyl kaur-16-en-19-oate, (-)-kaur-16-en-19-ol, (-)-16beta,17-epoxykauran-19-oic acid and (-)-17-hydroxykaur-15-en-19-oic acid were also tested and their IC 50 were 5.5 x 10 (-4), 5.0 x 10( -4), 4.8 x 10( -4) and 6.0 x 10 (-4) M, respectively.     

A new triterpenoid, madhunolic acid, from the seeds of Madhuca latifolia

A new triterpenoid, madhunolic acid, along with the three known constituents stigmasterol, 4-hydroxymethyl benzoate, and hydroquinone were isolated from the fruit seeds of Madhuca latifolia. The structure of the new compound was elucidated as 2β,3β,23-trihydroxyurs-5,12,20-trien-28-oic acid (1) on the basis of spectral data and chemical evidence.     

Triterpenoid Saponins from Leaves and Stems of Panax Quinquefolium L

In the chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L., two new minor dammarane saponins, quinquenoside L₁ (1) and L₂ (2) have been isolated. By means of physico-chemical evidences and spectral analysis their structures were established as 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosy-dammara-23,25-diene-3β, 12β, 20(S)-triol (1) and 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-D-glucopyranosyl-(24Z)-dammar-24-ene-3β, 12β, 20(S), 26-tetraol (2).     

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.