Phlomisamide and Phlomisteriod: A New Ceramide and a New Stigmasterol Derivative from Phlomis cashmeriana

Phlomisamide ( 1 ), a new ceramide, and a new stigmasterol derivative, phlomisteriod ( 2 ), have been isolated from Phlomis cashmeriana. Their structures were elucidated by comprehensive analysis of their 1D‐ (¹H‐ and ¹³C‐NMR) and 2D‐NMR (COSY, HMQC, HMBC), and HR‐EI‐MS data.     

Two New Withanolides from Physalis peruviana

Two new perulactone‐type withanolides, named perulactone C ( 1 ) and perulactone D ( 2 ), together with four known compounds, perulactone ( 3 ), perulactone B ( 4 ), blumenol A, and (+)‐(S)‐dehydrovomifoliol, were isolated from the aerial parts of Physalis peruviana. The structures of the new compounds were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS.     

New Diterpene Alkaloids from Aconitum sungpanense var. leucanthum

Five new C₁₉ diterpene alkaloids, leucanthumsines A ( 1 ), B ( 2 ), C ( 3 ), D ( 4 ), and E ( 5 ), were isolated from the Chinese medicinal herb Aconitum sungpanense var. leucanthum, together with the known C₁₉ diterpene alkaloids pseudaconine, neoline, 1‐O‐methyldelphisine, crassicaudine, chasmanine, talatisamine, indaconitine, ezochansmanine, and leueantine D. The structures of these new alkaloids were elucidated by HR‐MS and advanced NMR methods, including ¹H‐ and ¹³C‐NMR (DEPT), ¹H,¹H‐COSY, HMQC, and HMBC experiments.     

Two New 3,4‐seco‐Cycloartane Triterpenes from Gardenia sootepensis

Two new 3,4‐seco‐cycloartane triterpenes, named sootepin F ( 1 ) and sootepin G ( 2 ), together with two known compounds, coronalolide methyl ester ( 3 ) and sootepin D ( 4 ), were isolated from the leaves and twigs of Gardenia sootepensis. Their structures were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS.     

Three New Pentacyclic Triterpenoids from Lantana camara

Three new pentacyclic triterpenes ursoxy acid ( 1 ), methyl ursoxylate ( 2 ), and ursangilic acid ( 3 ), along with three known compounds dotriacontanoic acid, oleanolic acid acetate, and tetracosanoic acid, were isolated from the aerial parts of Lantana camara Linn . Structures of the new compounds were elucidated by chemical transformation and spectral studies including 1D (¹H‐ and ¹³C‐NMR) and 2D (COSY‐45, NOESY, J‐resolved, HMQC, and HMBC) NMR spectroscopy.     

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.     

Complete assignments of 1H and 13C NMR data for two new sesquiterpenes from Cyperus rotundus L.

Two new sesquiterpenes, epi‐guaidiol A (1) and sugebiol (3), together with four known sesquiterpenes, guaidiol A(2), sugetriol triacetate (4), cyperenoic acid (5), and cyperotundone (6) were isolated from the rhizomes of Cyperus rotundus L. Their structures were identified by MS and NMR experiments, and the complete assignments of ¹H and ¹³C NMR data for two new sesquiterpenes were obtained by the aid of two‐dimensional (2D) NMR techniques, including HSQC, HMBC, ¹H‐¹HCOSY and nuclear overhauser enhancement spectroscopy(NOESY). Copyright © 2009 John Wiley & Sons, Ltd.     

Three New Caged Prenylxanthones from Garcinia bracteata

Three new caged prenylxanthones (xanthone=9H‐xanthen‐9‐one), named neobractatin ( 1 ), 3‐O‐methylneobractatin ( 2 ), and 3‐O‐methylbractatin ( 3 ), along with eight known compounds, were isolated from the twig of Garcinia bracteata. The structures of the new compounds were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS analysis.     

Dimeric Coumarin and Phenylpropanoids from Clausena lenis

A new dimeric coumarin, diseselin B ( 1 ), and three new phenylpropanoids, lenisin A–C ( 2 – 4 ), together with eight known O‐terpenoidal coumarins, were isolated from the aerial part of Clausena lenis. Lenisin A ( 2 ) was also isolated from the aerial part of C. excavata. The structures were elucidated on the basis of 1D‐ and 2D‐NMR experiments (HMQC, HMBC, and ¹H,¹H‐COSY).     

Two new acylated flavonoid glycosides from Morina nepalensis var. alba Hand.‐Mazz.

From the whole plant of Morina nepalensis var. alba Hand.‐Mazz., two new acylated flavonoid glycosides ( 1 and 2 ), together with four known flavonoid glycosides ( 3–6 ), were isolated. Their structures were determined to be quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (monepalin A, 1 ), quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranoside (monepalin B, 2 ), quercetin 3‐O‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (rumarin, 3 ), quercetin 3‐O‐β‐D ‐galactopyranoside ( 4 ), quercetin 3‐O‐β‐D ‐glucopyranoside ( 5 ) and apigenin 4^′‐O‐β‐D ‐glucopyranoside ( 6 ). Their structures were determined on the basis of chemical and spectroscopic evidence. Complete assignments of the ¹H and ¹³C NMR spectra of all compounds were achieved from the 2D NMR spectra, including H–H COSY, HMQC, HMBC and 2D HMQC‐TOCSY spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

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.     

New Pyrrole Alkaloids with Bulky N‐Alkyl Side Chains Containing Stereogenic Centers from Lycium chinense

Four new pyrrole alkaloids, methyl 2‐[2‐formyl‐5‐(methoxymethyl)‐1H‐pyrrol‐1‐yl]propanoate ( 1 ), methyl 2‐[2‐formyl‐5‐(methoxymethyl)‐1H‐pyrrol‐1‐yl]‐3‐(4‐hydroxyphenyl)propanoate ( 2 ), dimethyl 2‐[2‐formyl‐5‐(methoxymethyl)‐1H‐pyrrol‐1‐yl]butanedioate ( 3 ), and dimethyl 2‐[2‐formyl‐5‐(methoxymethyl)‐1H‐pyrrol‐1‐yl]pentanedioate ( 4 ), were isolated from the AcOEt extract of the fruits of Lycium chinense Miller (Solanaceae). The stereogenic center C(2) in the bulky N‐alkyl side chain in each of 1 – 4 seems to hold the H‐atoms of nearby CH₂ groups, CH₂(7′) and CH₂(3) (if R≠H), leading to two different chemical shifts in the ¹H‐NMR spectrum due to their diastereotopic characteristics. In the ¹H‐NMR data of each of 2 – 4 , the enhancement of H? C(2) signal was inhibited by the R group, probably due to steric hindrance, and its chemical shift was influenced by the anisotropy effect. The structures of 1 – 4 were elucidated by analysis of various spectroscopic data, including 1D‐ and 2D‐NMR.     

New Epoxydammarane Triterpenes from Salvia santolinifolia

Three new 20,24‐epoxydammarane triterpenes, santolins A–C ( 1 – 3 ), were isolated from the AcOEt‐soluble fraction of the MeOH extract of Salvia santolinifolia (whole plant). Their structures were assigned based on ¹H‐NMR, ¹³C‐NMR (DEPT), and 2D‐NMR analyses, in combination with HR‐MS experiments and comparison with literature data of related compounds.     

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.     

Structure elucidation and total assignment of 1H and 13C NMR data for a new bisdesmoside saponin from Cordia piauhiensis

Extensive 1D (¹H NMR, HBBD‐¹³C NMR, DEPT‐¹³C NMR) and 2D (COSY, TOCSY, NOESY, HMQC and HMBC) NMR analysis was used to characterize the structure of a new bisdesmoside saponin isolated from the methanol extract of stems of Cordia piauhiensis Fresen as 3β‐O‐[α‐L ‐rhamnopyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl]ursolic acid 28‐O‐[β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranosyl] ester. Copyright © 2003 John Wiley & Sons, Ltd.     

New Glycosidic Constituents of Abutilon pakistanicum

Pakisides A and B ( 1 and 2 , resp.), new catalpol‐type iridoid glycosides, and a new glycoside, 3 , of scutellarein have been isolated from the AcOEt‐soluble fraction of the whole plant of Abutilon pakistanicum, along with buddlejoside and lapachol. The structures of new compounds were elucidated by spectroscopic techniques including ¹H‐and ¹³C‐NMR (DEPT), and 2D‐NMR experiments.     

Floccosic Acid,a New Triterpenic Acid from Nepeta floccosa

The isolation and structure elucidation of a new triterpenic acid named floccosic acid ( 1 ) is reported on the basis of the 1D‐ and 2D‐NMR assignments. This secondary metabolite was isolated as a new constituent, along with the known triterpenoids, betulinic acid and β‐amyrin. All these compounds were purified by repeated column chromatography of the MeOH extract of Nepeta floccosa. The structure elucidation of the new compound was accomplished by the combined mass spectrometry (MS), infrared (IR) and ultraviolet (UV) absorption spectroscopy, one‐ (¹H‐ and ¹³C‐) and two‐dimensional (H? C correlations; HMBC and HSQC) NMR techniques. The known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature.     

Four new ursane‐type saponins from Morina nepalensis var. alba

Four new ursane‐type saponins, monepalosides C–F, together with a known saponin, mazusaponin II, were isolated from Morina nepalensis var. alba Hand.‐Mazz. Their structures were determined to be 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[alpha;‐L ‐rhamnopyranosyl‐(1 → 2)]‐α‐L ‐arabinopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside C, 1 ), 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[alpha;‐L ‐rhamnopyranosyl‐(1 → 2)]‐β‐D ‐xylopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside D, 2 ), 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[beta;‐D ‐glucopyranosy‐(1 → 2)]‐α‐L ‐arabinopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside E, 3 ) and 3‐O‐β‐D ‐xylopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranoside (monepaloside F, 4 ) on the basis of chemical and spectroscopic evidence. 2D NMR techniques, including ¹H–¹H COSY, HMQC, 2D HMQC‐TOCSY, HMBC and ROESY, and selective excitation experiments, including SELTOCSY and SELNOESY, were utilized in the structure elucidation and complete assignments of ¹H and ¹³C NMR spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

A New Dimeric Secoiridoid Glycoside from the Leaves of Olea ferruginea Royle

A new dimeric secoiridoid glycoside, trivially named oleferrugine B ( 1 ), has been isolated from the AcOEt‐soluble part of the MeOH extract of leaves of Olea ferruginea Royle . The structure of the isolated compound was established on the basis of ESI‐MS fragmentation patterns, and 1D‐ and 2D‐NMR techniques, including ¹H‐ and ¹³C‐NMR, HSQC, ¹H,¹H‐COSY, HMBC, and NOESY experiments, and by comparison with literature data.     

Four New Germine Esters from Veratrum dahuricum

Four new alkaloids, compounds 1 – 4 , based on the germine (=4,9‐epoxycevane‐3,4,7,14,15,16,20‐heptol; 5 ) framework, were isolated from the rhizomes of V. dahuricum, together with germine proper. The X‐ray crystal structure of germine ( 5 ) was solved, and all compounds were characterized by circular dichroism, 1D‐ and 2D‐NMR (¹H,¹H‐COSY, DEPT, HSQC, HMBC), as well as HR‐MS analyses.