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.     

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.     

Triterpenoidal Secondary Metabolites from Lantana Camara Linn.

Three new pentacyclic triterpenoids, camarin ( 1 ), lantacin ( 2 ), and camarinin ( 3 ) were isolated from the aerial parts of Lantana camara Linn ., together with seven known compounds. The structures of the new constituents were elucidated by chemical transformation, HR‐EI mass spectrometry, and NMR spectroscopy, including 1D (¹H‐ and ¹³C‐NMR) and 2D (¹H,¹H‐COSY, NOESY, ¹H,¹H‐TOCSY, J‐resolved, HMQC, and HMBC) 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.     

Lyciumaside and Lyciumate: A New Diacylglycoside and Sesquiterpene Lactone from Lycium shawii

One new diacylglycoside named lyciumaside ( 1 ) and a new sesquiterpene lactone named lyciumate ( 2 ) were isolated from Lycium shawii Roem . & Schult . The structures of the two new compounds were elucidated based on 1D‐ (¹H‐ and ¹³C‐NMR and NOE) and 2D‐NMR (COSY, HSQC, and HMBC) spectroscopic techniques, and mass spectrometry (ESI‐MS). Preliminary evaluations demonstrated lyciumaside ( 1 ) possesses strong antioxidant activity with an IC₅₀ = 30 μg/ml (80% inhibition) while it was inactive in α‐glucosidase and urease enzymes assays.     

Petrorhagiosides A – D,New γ‐Pyrone Derivatives from Petrorhagia saxifraga Link

Four novel γ‐pyrone (=4H‐pyran‐4‐one) metabolites, petrorhagiosides A–D, along with four known analogs, have been isolated from the MeOH extract of Petrorhagia saxifraga, a perennial herbaceous plant typical of Mediterranean vegetation. The structures of the new compounds were established on the basis of extensive spectroscopic analyses including 1D‐ an 2D‐NMR (¹H,¹H‐DQ‐COSY, TOCSY, HSQC, CIGAR‐HMBC, and HSQC‐TOCSY) experiments.     

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.     

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 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.     

A New Irregular Trihydroxy Sesquiterpene from Teucrium mascatense

A new trihydroxy sesquiterpene, rel‐(1R,4aR,5S,6S,7S,8aR)‐decahydro‐6,8a‐dimethyl‐5‐(propan‐2‐yl)naphthalene‐1,6,7‐triol ( 1 ), has been isolated as a result of the phytochemical investigation on the CH₂Cl₂ extract of Teucrium mascatense. The structure elucidation of the new constituent was carried out by the combined use of 1D‐ (¹H‐ and ¹³C‐NMR) and 2D‐NMR (HMBC and HSQC) spectroscopic analysis, along with mass spectrometric techniques. In addition to the new constituent 1 , the known metabolite 2 , previously isolated from Crataegus pinnatifida, was also identified.     

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 Antifungal `Quinone Methide' Diterpenes from Bobgunnia madagascariensis and Study of Their Interconversion by LC/NMR

Two new `quinone methide' diterpenes with a cassane skeleton were isolated from the root bark of Bobgunnia madagascariensis (Desv. ) J. H. Kirkbr. & Wiersema (Leguminosae). The two compounds occurred as a diastereoisomer mixture 1 / 2 . Their structure was established as (4R,6aS,10aS)‐ and (4S,6aS,10aS)‐ 1,4,6a,7,8,9,10,10a‐octahydro‐4,11‐dihydroxy‐7,7,10a‐trimethyl‐2H‐phenanthro[1,2‐c]pyran‐6,12‐dione by spectroscopic methods and by comparison with the data obtained for another `quinone methide' diterpene isolated previously from the same plant and identified by single‐crystal X‐ray analysis. ¹H‐ and ¹³C‐NMR signals were assigned by extensive in‐mixture 2D correlation experiments, and ¹H‐NMR spectra of the separated diastereoisomers 1 and 2 were recorded by on‐flow LC/NMR. The interconversion of 1 and 2 was followed by repeated stop‐flow LC/NMR experiments over a two‐hour period. Compounds 1 and 2 showed moderate antifungal properties towards human pathogenic fungi, in particular the yeast Candida albicans.     

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.     

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.     

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.     

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.     

Four New 13,28‐Epoxyoleanane Saponins from Lysimachia lobelioides

Four new oleanane saponins, lobelioidosides A–D ( 1 – 4 , resp.), all endowed with 16‐oxo and a 23‐OH group, as well as with a 13,28‐epoxy bridge as a common moiety, have been isolated from the 75% EtOH extract of the whole plant of Lysimachia lobelioides. Their structures were elucidated on the bases of MS, ¹H‐ and ¹³C‐NMR, HMQC, HMBC, and ¹H,¹H‐COSY data analysis.     

A Novel Alkaloid from Aspidosperma pyricollum (Apocynaceae) and Complete 1H and 13C Chemical Shift Assignments

A novel natural product indole, alkaloid, named rel‐pyricolluminol ( 1 ), was isolated from Aspidosperma pyricollum Müll .Arg . together with six known metabolites sitsirikine ( 2 ), aparicin ( 3 ), ulein ( 4 ), stemmadenine ( 5 ), lupeol ( 6 ), and (3β)‐sitoster‐3‐yl β‐D ‐glucopyranoside ( 7 ). These compounds were characterized on the basis of their spectral data, mainly 1D‐ (¹H,¹³C‐DEPTQ) and 2D‐NMR (¹H,¹H‐COSY, NOESY, HSQC, and HMBC), and mass spectra (EI‐MS and HR‐ES‐MS), involving also comparison with data from the literature.     

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.     

Spectral study of a new dihydroisocoumarin

A novel dihydroisocoumarin, 3,4‐dihydro‐6,8‐dihydroxy‐3‐(2′‐acetyl‐3′‐hydroxy‐5′‐methoxy)methyl‐1H‐[2]benzopyran‐1‐one, was isolated from the chloroform extract of the sap of the traditional herb Aloe vera. Its structure was determined by high‐resolution negative fast atom bombardment mass spectrometry (MS), 2D NMR spectroscopy and x‐ray crystallography. The molecular structure was elucidated by 2D NMR analysis. The complete assignment of the ¹H and ¹³C NMR spectra of this compound was performed by using ¹H detected one‐bond heteronuclear multiple quantum correlation (HMQC) and long‐range (two and three bonds) heteronuclear multiple quantum bond correlation (HMBC) experiments. Detailed analyses of the one‐ and two‐dimensional NMR techniques are presented in additional to the spectral properties (MS, IR and UV). Copyright © 2003 John Wiley & Sons, Ltd.