Three New Peroxy Triterpene Lactones from Pseudolarix kaempferi

Three new 3(4),9(10)‐disecocycloartane peroxy triterpene lactones, named as pseudolarolides Q₂, T₁, and T₂ ( 1 – 3 , resp.), along with five known triterpenoids, were isolated from the seeds of Pseudolarix kaempferi Gord . Their structures were elucidated to be (9R,10R,16R,23R,25R)‐16,23‐epoxy‐9,10‐epidioxy‐3,4:9,10‐disecocycloart‐1(2)‐ene‐3,4:26,23‐diolide ( 1 ), (1R,9R,10S,16R,23S,25R)‐1,4:16,23‐diepoxy‐9,10‐epidioxy‐3,4;9,10‐disecocycloartan‐26(23)‐olid‐3‐oic acid methyl ester ( 2 ), and (1R,9R,10S,16R,23R,25R)‐1,4:16,23‐diepoxy‐9,10‐epidioxy‐3,4;9,10‐disecocycloartan‐26(23)‐olid‐3‐oic acid methyl ester ( 3 ) on the basis of spectroscopic analysis.     

Chemical constituents from Pseudolarix kaempferi

A novel degraded triterpenoid isopseudolaritone A (1) and one new oligosaccharide, 1-O-isopropyl-6-O-[2-O-methyl-alpha-L-rhamnopyranosyl(1 --> 6)]-beta-D-glucopyranose (2), two new artefacts, 9-O-formacyl cedrusin (5) and 9,9'-O-diformacyl cedrusin (6), as well as 12 known phenolic Compounds (3-4, 7 16), were isolated from the root bark of Pseudolarix kaempferi. Their structures were elucidated mainly by spectroscopic methods.     

Novel Triterpene Saponins from Zizyphus joazeiro

Two dammarane‐type saponins with a novel aglycone derived from the parent 16,22‐epoxy‐24‐methylidenedammarane and lotoside A, a new lotogenin derivative, were isolated from the MeOH extract of the stem bark of the Brazilian medicinal plant Zizyphus joazeiro, in addition to the known saponin 3β‐{{O‐[O‐[α‐L ‐arabinofuranosyl‐(1→2)]‐O‐[β‐D ‐glucopyranosyl‐(1→3)]]‐α‐L ‐arabinopyranosyl}oxy}jujubogenin ( 1 ). The structures of the new compounds were determined as 16,22‐epoxy‐3β‐[(β‐D ‐glucopyranosyl)oxy]‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 2 ), 16,22‐epoxy‐3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 3 ), and 3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}lotogenin ( 4 ) by means of 1D‐ and 2D‐NMR spectroscopy, as well as FAB mass spectrometry. For the novel aglycone, we propose the name joazeirogenin and, for the new saponins, joazeiroside A ( 2 ) and B ( 3 ). Joazeirogenin was found to be 16,22‐epoxy‐24‐methylidenedammarane‐3β,15α,16α,20β‐tetrol.     

A Novel Ursane Triterpene from Rubus swinhoei

As a part of investigation on the plant of Rubus, we studied the chemical constituents of the roots of R. swinhoei. A novel ursane triterpene, named swinhoeic acid, was isolated and converted into its methyl-ester with CH2N2. This paper deals with its structure elucidation.Figure 1 The structure of 1 and 1a Figure 2 The key HMBC correlationsCompound 1a, was obtained as white powder, [?] - 66 (c 0.1, CHCl3). Its molecular formula was assigned as C31H48O5 by HR-EIMS ([M]+ m/z 500.3487…     

Two New Triterpene Esters from Daphniphyllum oldhami

Two new triterpene esters,2-O-eaffeoylalphitolic acid(1)and methyl 2-O-eaffeoyl-alphitolate(2),together with two known triterpenes were isolated from the shrub Daphniphyllum oldnami.The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis and compared with related compound.     

Two New Triterpene Saponins from Acanthophyllum laxiusculum

Two new triterpene glycosides, 1 and 2 , together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman ‐Czeika . The structures of the new compounds were established by extensive 1D‐ and 2D‐NMR spectroscopic experiments and MS analyses as 23‐O‐β‐D ‐galactopyranosylgypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 1 ) and gypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 2 ).     

Two New Triterpene and a New Nortriterpene Glycosides from Phlomis viscosa

The isolation and structure elucidation of two new oleanane‐type triterpene glycosides, 29‐(β‐D ‐glucopyranosyloxy)‐2α,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2α,3β,4α,29α)‐29‐(β‐D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 1 ) and its C(20)‐epimer, 30‐(β‐D ‐glucopyranosyloxy)‐2α,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2α,3β,4α,29β)‐29‐β‐D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 2 ), and a novel nortriterpene glycoside, (17S)‐2α,18β,23‐trihydroxy‐3,19‐dioxo‐19(18→17)‐ abeo‐28‐norolean‐12‐en‐25‐oic acid β‐D ‐glucopyranosyl ester (=(1R,2S,4aS,4bR,6aR,7R,9R,10aS,10bS)‐3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11‐tetradecahydro‐1‐hydroxy‐7‐(hydroxymethyl)‐3′,4′,4a,4b,7‐pentamethyl‐2′,8‐ dioxospiro[chrysene‐2(1H),1′‐cyclopentane]‐10a‐carboxylic acid β‐D ‐glucopyranosyl ester; 3 ) from Phlomis viscosa (Lamiaceae) are reported. The structures of the compounds were asigned by means of spectroscopic (IR, 1D‐ and 2D‐NMR, and LC‐ESI‐MS) and chemical (acetylation) methods.     

Two New Triterpene Lactones from the Stems of Kadsura polysperma

Two new triterpene lactones, polysperlactones A ( 2 ) and B ( 3 ), were isolated from the stems of Kadsura polysperma, together with the known compounds heteroclitalactone D ( 1 ) and schisanlactone E ( 4 ). Their structures were elucidated by spectroscopic methods, including 2D‐NMR and HR‐MS techniques. The configuration of 1 was confirmed by X‐ray analysis. Compounds 2 and 3 are members of a rare class of 3,4‐secolanostane metabolites with ring‐expanded or cyclized structures, respectively.     

Philinopsides A and B,Two New Sulfated Triterpene Glycosides from the Sea Cucumber Pentacta quadrangularis

Two new sulfated triterpene glycosides, philinopsides A ( 1 ) and B ( 2 ), were isolated from the sea cucumber Pentacta quadrangularis. Their structures were established by extensive spectral analysis (2D‐NMR and MS) and chemical evidence. Philinopside A ( 1 ) and B ( 2 ) showed significant cytotoxicity (ED₅₀ 0.75–3.50 μg/ml) against ten tumor cell lines. Compound 1 also significantly inhibited the proliferation, migration, and tube formation of human microvascular endothelial cells.     

Two New Triterpene Saponins from Cyclamen africanum Boiss. & Reuter

Two new oleanane‐type triterpene saponins, afrocyclamins A and B ( 1 and 2 , resp.), were isolated from a MeOH extract of the roots of Cyclamen africanum Boiss . & Reuter , together with three known triterpenoid saponins, lysikokianoside, deglucocyclamin I, and its dicrotalic acid derivative. The structures were elucidated, on the basis of 1D‐ and 2D‐NMR experiments and mass spectrometry as (3β,20β)‐13,28‐epoxy‐16‐oxo‐3‐{O‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}oxy}oleanan‐29‐al ( 1 ) and (3β,16α,20β)‐16,28,29‐trihydroxy‐olean‐12‐en‐3‐yl O‐4‐O‐(4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl)‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranoside ( 2 ).     

Preparative isolation of pseudolaric acids A and B,and their glucosides from the root bark of Pseudolarix kaempferi using high‐speed counter‐current chromatography

In order to provide the chemical markers for the quality control of herbal medicines, four diterpenoids, pseudolaric acids A and B (PAA and PAB), and their glucosides were isolated from the methanol extract of the Chinese herb Pseudolarix kaempferi using high‐speed counter‐current chromatography (HSCCC). The diphase solvent system was n‐hexane/EtOAc/MeOH/H₂O which was used at two ratios (5:5:5:5 and 1:9:4:6 by volume) in the separation of pseudolaric acids and their glycosides, respectively. As a result, PAA (14 mg), PAB (129 mg), PAA‐O‐β‐D ‐glucopyranoside (8 mg, PAAG), and PAB‐O‐β‐D ‐glucopyranoside (42 mg, PABG) were obtained from 0.5 g of the crude extract. Their purities were determined to be above 97% by HPLC analysis. Their chemical structures were confirmed by ¹H and ¹³C NMR analysis or HPLC comparison with the reference compounds.     

Cimicifine A: A Novel Triterpene Alkaloid from the Rhizomes of Cimicifuga foetida

Cimicifine A ( 1 ), the first cycloartane triterpene alkaloid, was isolated from the rhizomes of Cimicifuga foetida, together with the known compound cimicifugoside H‐1 ( 2 ). Their chemical structures were established by extensive NMR and MS analyses and by comparison with literature.     

Gnetifolin L and O, Two Dimeric Stilbenes from Gnetum Montanum

GnetuI)1monlanlImgr0wsinthes0uthernpart0fChinaandhasbeenusedf0rthetreatment0fbronchitisandarthritisinf0lkmedicinel.Previously,aninvestigationofthisspeciesledt0theis0lationofs0meaIkal0idsanddibenzyletherderivatives2.lnourstudies,tenc0mp0nentsincludingresveratr0l,is0rhapontigenin,daucoster0l,O-sitosterol,stearicacid,gnetif0linE,gnet0l,is0rhapontigenin-3-O-6-gluc0pyra(-)8-viniferinandgnetifolinCwere0btainedfromthisplant'.Inthefurtherstudy,f0urnewdimericstilbenesnamedgnetif0IinMandN',gnetifoli…     

Two Novel Saponins from Lysimachia capillipes

We have isolated some flavones, lactone and two new saponins from Lysimachia capillipes1-3, now we continue to report the isolation and structural elucidation of two novel saponins, capilliposide C 1 and capilliposide D 2. Capilliposide C showed significant cytotoxic activity against human A2780 cells. The whole plant of Lysimachia capillipes was extracted with 95% and 50% EtOH, successively, and the extracts were combined and concentrated. The residue was chromatographed on silica gel res…     

Two Novel Nortriterpenoids from Gomphostemma parviflorum

Two new nortriterpenoids, gomphoparvin A ( 1 ) and B ( 2 ), together with five known compounds, were isolated from the AcOEt‐soluble MeOH extract of Gomphostemma parviflorum (whole plant). Their structures and relative configurations were elucidated mainly on the basis of 1D‐ and 2D‐NMR as well as MS analyses.     

Two Novel Alkaloids from Zanthoxylum nitidum

Two novel alkaloids, 4,5‐dihydroxy‐1‐methyl‐3‐oxo‐2‐(trichloromethyl)‐3H‐indolium chloride ( 1 ) and 4‐(2‐methoxyethyl)‐N,N‐dimethylbenzenamine ( 2 ), were isolated from the EtOH extract of the roots of Zanthoxylum nitidum. Their structures were identified on the basis of spectroscopic and mass‐spectrometric analyses.