A New 30‐Noroleanane Saponin from Wedelia chinensis

A novel 30‐nortriterpenoid saponin, (3β)‐3‐hydroxy‐30‐noroleana‐12,20(29)‐dien‐28‐oic acid 3‐(β‐D ‐glucopyranosiduronic acid 6‐methyl ester) ( 1 ), and a known compound, (3β)‐oleanolic acid 3‐(β‐D ‐glucopyranosiduronic acid 6‐methyl ester) ( 2 ), were isolated from the aerial parts of Wedelia chinensis. The structures were established by their spectral data including ¹H‐ and ¹³C‐NMR, ¹H,¹H‐COSY, HMBC, HSQC, NOESY, and HR‐FAB‐MS data.     

A New Cyclopropyl‐Triterpenoid from Ochradenus arabicus

One new cyclopropyl‐triterpenoid ( 1 ), along with four known constituents including octacosan‐1‐ol ( 2 ), pentacosanoic acid ( 3 ), β‐sitosterol ( 4 ), and β‐sitosterol 3‐O‐β‐D ‐glucopyranoside ( 5 ) were isolated from the aerial parts of Ochradenus arabicus for the first time. These compounds were isolated by repeated column chromatography followed by further purification through recycling HPLC. The structure of the new secondary metabolite 1 was established on the basis of UV, IR, 1D‐ (¹H‐ and ¹³C‐) and 2D‐NMR (HMBC and HSQC), and MS spectral data. The molecular mass was determined by HR‐MS, and hence the molecular formula was deduced. The configurations of stereogenic centers in the molecule were assigned by NOESY experiments, along with biogenetic considerations. The structures of the known compounds were confirmed by comparison of their physical and spectroscopic data with those reported in literature.     

New Limonoids from the Seeds of Xylocarpus granatum

Three novel limonoids, 2,3‐dideacetylxyloccensin S ( 1 ), 30‐deacetylxyloccensin W ( 2 ), and 7‐hydroxy‐21β‐methoxy‐3‐oxo‐24,25,26,27‐tetranortirucalla‐1,14‐diene‐23(21)‐lactone ( 3 ), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. The structures were elucidated on the basis of 1D‐ and 2D‐NMR (including ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and NOESY) data and confirmed by HR‐MS.     

Two Glycosides and Other Constituents from Anemone tomentosa Roots

Two new natural products, i.e., 1‐O,2‐O‐[(1S,2S)‐1‐(3‐acetyl‐2,4,6‐trihydroxyphenyl)‐3‐hydroxypropane‐1,3‐diyl]‐β‐D ‐glucopyranose (=tomentoside I; 1 ) and (3β)‐3‐(acetyloxy)ferruginol 12‐[6‐O‐(4‐hydroxy‐3,5‐dimethoxybenzoyl)‐β‐D ‐glucopyranoside] (=tomentoside II; 2 ), were isolated from the EtOH extract of the root of Anemone tomentosa, together with five known compounds. Their structures were characterized by means of spectroscopic methods, especially by ¹H‐, ¹³C‐, and 2D‐NMR and HR‐MS, as well as by chemical methods and comparison with literature data.     

Triterpene Esters Isolated from Leaves of Maytenus salicifolia Reissek

The triterpene ester (3β)‐olean‐18‐en‐3‐yl stearate ( 1 ), together with (3β)‐urs‐12‐en‐3‐yl stearate ( 2 ), and (3β)‐lup‐20(29)‐en‐3‐yl stearate ( 3 ) were isolated from leaves of Maytenus salicifolia Reissek (Celastraceae). The structure of 1 , a new compound, including its configuration, was established by ¹H, ¹³C, and DEPT‐135 NMR data, including 2D experiments (HSQC, HMBC, COSY, and NOESY). The molecular mass (692 Da) was confirmed by gas chromatography coupled with mass spectrometry (CG/MS).     

Structure elucidation and complete NMR spectral assignments of two new oleanane‐type pentacyclic triterpenoid saponins from the husks of Xanthoceras sorbifolia Bunge

Two new saponins were isolated from husks of Xanthoceras sorbifolia Bunge and their structures were elucidated as 3‐O‐[β‐D‐galactopyranosyl(1→2)]‐α‐L‐arabinofuranosyl(1→3)‐β‐D‐methyl glucuronic acid‐21‐O‐(3,4‐diangeloyl)‐α‐L‐rhamnose‐3β, 16α, 21β, 22α, 28β‐pentahydroxyl‐22‐acetoxy‐olean‐12‐ene(1) and 3‐O‐[β‐D‐galactopyranosyl(1→2)]‐α‐L‐arabinofuranosyl(1→3)‐β‐D‐methyl glucuronic acid‐21,22‐O‐diangeloyl‐3β,15α,16α,21β,22α,28β‐hexahydroxyl‐olean‐12‐ene(2) on the basis of 1D and 2D NMR (including ¹H, ¹³C‐NMR, ¹H? ¹H COSY, HSQC, HMBC and DEPT), ESI‐MS spectrometry and chemical methods. Copyright © 2009 John Wiley & Sons, Ltd.     

Three New Lanostane Triterpenoids,Inonotsutriols A,B, and C,from Inonotus obliquus

Three new lanostane‐type triterpenoids, inonotsutriols A ( 1 ), B ( 2 ), and C ( 3 ) were isolated from the sclerotia of Inonotus obliquus (Pers .: Fr.) (Japanese name: kabanoanatake; Russian name: chaga). Their structures were determined to be (3β,21R,24S)‐21,24‐cyclolanost‐8‐ene‐3,21,25‐triol ( 1 ), (3β,21R,24R)‐21,24‐cyclolanost‐8‐ene‐3,21,25‐triol ( 2 ), and (3β,21R,24S)‐21,24‐cyclolanosta‐7,9(11)‐diene‐3,21,25‐triol ( 3 ) on the basis of NMR spectroscopy including 1D and 2D experiments (¹H,¹H‐COSY, NOESY, HMQC, and HMBC) and EI‐MS.     

Two New Lycopodine Alkaloids from Huperzia serrata

Two new lycopodine alkaloids, (12β)‐12‐hydroxyhuperzine G ( 1 ) and (5β,6β,15α)‐15‐methyllycopodane‐5,6‐diol ( 2 ), were isolated from the whole plants of Huperzia serrata, together with six known compounds, huperzines A, B, and G, phlegmariurine B, (8β)‐8‐hydroxyphlegmariurine B, and lycoposerramine D. Their structures were elucidated on the basis of spectroscopic analysis, including HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and NOESY data.     

Three Novel Triterpenoids from the Aerial Part of Helwingia chinensis

Three novel triterpenoids named chinenols A – C ( 1 – 3 ), together with two known compounds, glutin‐5‐en‐3β‐ol ( 4 ) and daucosterol ( 5 ), were isolated from the aerial part of Helwingia chinensis Batal . The structures of 1 – 3 were determined on the basis of their HR‐EI‐MS, IR, ¹H‐ and ¹³C‐NMR (DEPT), and 2D (HMQC, HMBC, NOESY) data. Compounds 1 – 3 and 5 showed inhibition activity in an antibacterial assay.     

A New Megastigmane Palmitate and a New Oleanane Triterpenoid from Aster yomena Makino

A new megastigmane palmitate, 9‐oxomegastigm‐5(13)‐ene‐2β‐palmitate ( 1 ), and a new oleanane triterpenoid, (3β)‐3,23,28‐trihydroxyolean‐12‐en‐11‐one ( 2 ), together with three known oleanane‐type triterpenoids, β‐amyrin ( 3 ), erythrodiol ( 4 ), and (3β)‐olean‐12‐ene‐3,23,28‐triol ( 5 ), were isolated from the aerial parts of Aster yomena (Asteraceae). Their structures were identified based on 1D‐ and 2D‐NMR analysis, including ¹H,¹H‐COSY, HSQC, HMBC, and NOESY techniques.     

Two New Tetracyclic Triterpenoids and Other Constituents from Aster Ageratoides var. Oophyllus

Two new tetracyclic triterpenoids shiona‐19(E),21‐dien‐3β‐ol ( 1 ), and shiona‐22(29)‐en‐3β,21‐diol ( 2 ), together with four known compounds shiona‐21‐en‐3β‐ol ( 3 ), friedelinol ( 4 ), β‐sitosterol ( 5 ), and (24R)‐stigmast‐7,22(E)‐dien‐3a‐ol ( 6 ) were isolated from Aster ageratoides var. oophyllus. The structures of two new compounds were established on the basis of IR, MS, ¹H, ¹³C and 2D NMR spectroscopic methods.     

Anthraquinones and Lignans from Cassia occidentalis

One new anthraquinone glycoside, 6‐O‐(α‐L ‐rhamnopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl)emodin ( 1 ), and two new sesquilignans, seslignanoccidentaliols A ( 2 ) and B ( 3 ), were isolated from the whole plant of Cassia occidentalis. The structures of the new compounds were established by means of spectroscopic methods, especially 2D‐NMR data (¹H,¹H‐COSY, HMQC, HMBC, and ROESY), as well as HR‐ESI‐MS analysis. One previously reported sesquilignan, erythro‐guaiacylglycerol‐β‐O‐4′‐(5′)‐methoxylariciresinol, was revised to be seslignanoccidentaliol A ( 2 ). The 6‐O‐(α‐L ‐rhamnopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl)emodin ( 1 ) exhibited moderate anti‐HIV‐1 activity with an EC₅₀ value of 2.90 μg/ml and a therapeutic‐index (TI) value of 260.     

New Triterpenoid Glycosides from Centella asiatica

Four new triterpenoid glycosides named asiaticoside C ( 1 ), D ( 2 ), E ( 3 ), and F ( 4 ) were isolated from the BuOH fraction of the EtOH extract of whole plants of Centella asiatica, together with three known compounds, asiaticoside ( 5 ), madecassoside ( 6 ), and scheffuroside B ( 7 ). Based on FAB‐MS, IR, ¹H‐ and ¹³C‐NMR, and 2D‐NMR data (HMQC, HMBC, COSY), the structures of the new compounds were determined as (2α,3β,4α)‐23‐(acetyloxy)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 1 ), (2α,3β)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 2 ), asiatic acid 6‐O‐β‐D ‐glycopyranosyl‐β‐D ‐glucopyranosyl ester ( 3 ), (3β,4α)‐3,23‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 4 ).     

Three New Clerodane Diterpenoids from the Bulbils of Dioscorea bulbifera L. var. sativa

From the bulbils of Dioscorea bulbifera L. var. sativa, three new clerodane diterpenoids, bafoudiosbulbin C (=methyl (2β,8α,12S)‐17‐oxo‐2,19 : 8,19 : 12,17 : 15,16‐tetraepoxycleroda‐3,13(16), 14‐triene‐18‐carboxylate; 1 ), bafoudiosbulbin D (=methyl (2β,6β,12R)‐17,19‐dioxo‐2,19 : 6,17 : 8,12 : 15,16‐tetraepoxycleroda‐13(16),14‐diene‐18‐carboxylate; 2 ), and bafoudiosbulbin E (=methyl (2β,3α,4α,6β,12R)‐17,19‐dioxo‐2,19 : 3,4 : 6,17 : 8,12 : 15,16‐pentaepoxycleroda‐13(16),14‐diene‐18‐carboxylate; 3 ) were isolated, together with the known compounds bafoudiosbulbins A and B, 3‐O‐β‐D ‐glucopyranosyl‐β‐sitosterol, and 6′‐stearoyl‐3‐O‐β‐D ‐glucopyranosyl‐β‐sitosterol. Their structures were established by high‐field NMR techniques (¹H,¹H‐COSY, ¹³C‐DEPT, HSQC, HMBC, and NOESY), MS analyses, as well as by comparison of their spectral data with those of related compounds.     

Acovulparine,a New Norditerpene Alkaloid from Aconitum vulparia

Acovulparine (=1α,6β,7R,8β,14α,16β)‐4‐(hydroxymethyl)‐1,6,14,16‐tetramethoxyaconit‐19‐ene‐7,8‐diol; 1 ), a new norditerpene alkaloid, was isolated from the MeOH extract of the whole plants of Aconitum vulparia Reichenb ., together with the known compounds lycoctonine ( 2 ) and delcosine ( 3 ). The structures were established by HR‐EI‐MS and advanced 2D‐NMR, including ¹H‐NMR, JMOD, ¹H,¹H‐COSY, HSQC, and HMBC experiments. Acovulparine was found to contain the rare C(19)?N azomethine group.     

Chemical Constituents from Cynoglossum gansuense

Two new alkaloids, i.e., (2,3‐dihydro‐1‐oxo‐1H‐pyrrolo[1,2‐a]pyrrol‐7‐yl)methyl (2S*,3S*)‐3‐[(β‐D ‐glucopyranosyl)oxy]‐2‐hydroxy‐2‐(1‐methylethyl)butanoate ( 1 ) and 1,2‐dihydro‐8‐methoxy‐2‐oxoquinoline‐4‐carboxylic acid ( 2 ), were isolated from the alcoholic extract of the whole plant of Cynoglossum gansuense, together with twelve known compounds Their structures were characterized by means of spectroscopic methods, especially by ¹H‐, ¹³C‐, and 2D‐NMR, as well as by HR‐MS experiments and comparison with literature data.     

Three New Lanostane Triterpenoids from Inonotus obliquus

Three new lanostane‐type triterpenoids, inonotsulides A, B, and C ( 1 – 3 , resp.) were isolated from the sclerotia of Inonotus obliquus (Pers .: Fr.) (Japanese name: Kabanoanatake; Russian name: Chaga). Their structures were determined to be (20R,24S)‐3β,25‐dihydroxylanost‐8‐en‐20,24‐olide ( 1 ), (20R,24R)‐3β,25‐dihydroxylanost‐8‐en‐20,24‐olide ( 2 ), and (20R,24S)‐3β,25‐dihydroxylanosta‐7,9(11)‐dien‐20,24‐olide ( 3 ) on the basis of chemical transformation, NMR spectroscopy including 1D and 2D (¹H,¹H‐COSY, NOESY, HMQC, HMBC), EI‐MS, and single‐crystal X‐ray analysis.     

Flavonol Glycosides with α‐Glucosidase Inhibitory Activities and New Flavone C‐Diosides from the Leaves of Machilus konishii

Seventeen flavonoids, five of which are flavone C‐diosides, 1 – 5 , were isolated from the BuOH‐ and AcOEt‐soluble fractions of the leaf extract of Machilus konishii. Among 1 – 5 , apigenin 6‐C‐β‐D ‐xylopyranosyl‐2″‐O‐β‐D ‐glucopyranoside ( 2 ), apigenin 8‐C‐α‐L ‐arabinopyranosyl‐2″‐O‐β‐D ‐glucopyranoside ( 4 ), and apigenin 8‐C‐β‐D ‐xylopyranosyl‐2″‐O‐β‐D ‐glucopyranoside ( 5 ) are new. Both 4 and 5 are present as rotamer pairs. The structures of the new compounds were elucidated on the basis of NMR‐spectroscopic analyses and MS data. In addition, the ¹H‐ and ¹³C‐NMR data of apigenin 6‐C‐α‐L ‐arabinopyranosyl‐2″‐O‐β‐D ‐glucopyranoside ( 3 ) were assigned for the first time. The isolated compounds were assayed against α‐glucosidase (type IV from Bacillus stearothermophilus). Kaempferol 3‐O‐(2‐β‐D ‐apiofuranosyl)‐α‐L ‐rhamnopyranoside ( 12 ) was found to possess the best inhibitory activity with an IC₅₀ value of 29.3 μM .     

Sesquiterpenes from Rhizomes of Cyperus rotundus with Cytotoxic Activities on Human Cancer Cells in vitro

Two new sesquiterpenes, cyperusol A₃ ( 1 ) and 3β‐hydroxycyperenoic acid ( 2 ), along with three known sesquiterpenes, britanlin E ( 3 ), 1β,4α‐dihydroxyeudesm‐11‐ene ( 4 ), and 11,12‐dihydroxyeudesm‐4‐en‐3‐one ( 5 ), were isolated from the AcOEt‐soluble fraction of rhizomes of Cyperus rotundus L. The structures of 1 and 2 were elucidated by physical and spectroscopic methods (¹H‐ and ¹³C‐NMR, 2D‐NMR, and MS). All of the isolates, 1 – 5 , were evaluated for their cytotoxic activities against human ovarian cancer cells (A2780) and endometrial adenocarcinoma cells (Ishikawa) using MTT assays.     

A New Lycopodine Alkaloid from Phlegmariurus yunnanensis Ching

A new lycopodine alkaloid, 15α‐methyllycopodane‐5β,6β‐diol N‐oxide ( 1 ), was isolated from the whole plants of Phlegmariurus yunnanensis Ching , together with the two known alkaloids 15α‐methyllycopodane‐5β,6β‐diol ( 2 ) and lycoposerramine H ( 3 ), and four serratene‐type triterpenoids, serratenediol‐3‐acetate ( 4 ), serratenediol ( 5 ), lycocryptol ( 6 ), and serratriol ( 7 ). Their structures were elucidated on the basis of spectroscopic analyses, including HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and NOESY.