A New Indole Alkaloid from Cleome droserifolia

The phytochemical investigations on Cleome droserifolia resulted in the isolation and characterization of a new indole alkaloid, 5‐hydroxy‐2‐methoxy‐1‐methyl‐1H‐indole‐3‐carbaldehyde ( 1 ). The structure elucidation was carried out on the basis of 1D‐ and 2D‐NMR techniques. In addition to 1 , two known aromatic derivatives, veratrol ( 2 ) and 2‐methoxy‐4‐methylacetophenone ( 3 ), were also obtained. All these compounds were purified by repeated column chromatography of the CH₂Cl₂ fraction obtained from MeOH extract of Cleome droserifolia. The structure of the new compound 1 was finally confirmed by the combined 1D (¹H‐ and ¹³C‐) and 2D (H? C correlations; HMBC and HSQC) NMR and IR spectroscopy, mass spectrometry (MS), and UV absorption spectroscopy techniques. The comparison of the physical and spectroscopic data with those in the literature provided evidence for the structure confirmation of known compounds. All the purified compounds were subjected to urease and α‐glucosidase enzymes inhibition. The results showed that compound 1 was more potent with an IC₅₀ value 11.97±2.067 μg/ml towards urease inhibition, while the activity of α‐glucosidase enzyme was marginal.     

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 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.     

Citropremide and Citropridone: A New Ceramide and a New Acridone Alkaloid from the Stem Bark of Citropsis gabunensis

The structure elucidation and complete ¹H‐ and ¹³C‐NMR assignments are reported for two new compounds: the ceramide citropremide ( 1 ), and the acridone alkaloid citropridone ( 2 ). Both of these secondary metabolites were isolated from the stem bark of Citropsis gabunensis. High‐resolution mass, IR and UV spectrometry, and NMR experiments including COSY, HMQC, and HMBC were used for the determination of the structures and NMR spectral assignments.     

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.     

Nepethalates A and B: Two New Phthalate Derivatives from Nepeta clarkei

The structure elucidation of two new phthalate derivatives named nepethalates A ( 1 ) and B ( 2 ) is reported. Both of these secondary metabolites were isolated from the MeOH extract of Nepeta clarkei. HR‐EI‐MS, IR and UV absorption spectrometry, and NMR experiments including COSY, HMQC, and HMBC were used for the determination of the structures and complete ¹H‐ and ¹³C‐NMR assignments.     

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.     

Two New Endiandric Acid Analogs,a New Benzopyran,and a New Benzenoid from the Root of Beilschmiedia erythrophloia

Phytochemical investigation of the root of Beilschmiedia erythrophloia led to the isolation and structural elucidation of two new endiandric acid analogs, endiandric acids I and J ( 1 and 2 , resp.), a new benzopyran, dehydrooligandrol methyl ether ( 3 ), and a new benzenoid, farnesylol ( 4 ), together with six known compounds. Their structures were established on the basis of extensive 1D‐ and 2D‐NMR analyses in combination with HR‐MS experiments.     

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.     

A New Diterpenoid Alkaloid from the Roots of a White‐Flowering Aconitum orientale Sample

From the roots of a white‐flowering Aconitum orientale Miller sample, collected in Artvin‐?av?at, Turkey, a new diterpenoid alkaloid named aconitorientaline ( 1 ) was isolated, along with the known diterpenoid alkaloids septentiriodine, lappaconitine, finaconitine, ranaconitine, puberanidine and delstaphinine (Fig.). The structure of 1 was established on the basis of ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, NOESY, HSQC, and HMBC studies. All the known compounds were identified by comparison of their ¹H‐ and ¹³C‐NMR data and co‐TLC behavior with those of authentic samples.     

Combretins A and B,New Cycloartane‐Type Triterpenes from Combretum fragrans

The phytochemical studies on the leaves of the traditionally used medicinal plant Combretum fragrans F. Hoffm (Combretaceae) from Cameroon have led to the isolation of combretins A and B ( 1 and 2 , resp.), two new cycloartane‐type triterpenes from the AcOEt‐soluble subfraction along with β‐sitosterol ( 3 ), oleanolic acid ( 4 ), ursolic acid ( 5 ), and pratensein ( 6 ). The compounds 4  –  6 are reported for the first time from this species. The structures of the new triterpenes were elucidated by spectroscopic techniques including ¹H‐ and ¹³C‐NMR (DEPT), and 2D‐NMR experiments.     

Two New Octulosonic Acid Derivatives and a New Cyclohexanecarboxylic Acid Derivative from Erigeron bonariensis L.

The AcOEt‐soluble part of a MeOH extract from the whole plant of Erigeron bonariensis yielded two new rare‐class octulosonic acid derivatives, rel‐methyl (1R,2S,3S,5R)‐3‐(trans‐caffeoyloxy)‐7‐[(trans‐caffeoyloxy)methyl]‐2‐hydroxy‐6,8‐dioxabicyclo[3.2.1]octane‐5‐carboxylate ( 1 ) and 5,8‐di[O‐trans‐caffeoyl]‐3‐deoxy‐β‐D ‐gluco‐oct‐2‐ulopyranosonosyl 4,8‐di[O‐trans‐caffeoyl]‐3‐deoxy‐β‐D ‐gluco‐oct‐2‐ulopyranosidonic acid ( 2 ) along with a cyclohexanecarboxylic acid derivative, (1α,3β,4β,5β)‐1,4‐di‐3,5‐dihydroxy‐bis(trans‐caffeoyloxy)cyclohexanecarboxylic acid ( 3 ). The structures of these compounds were elucidated through ESI‐MS, and 1D‐ and 2D‐NMR spectroscopic techniques including ¹H‐ and ¹³C‐NMR, HMQC or HSQC, and HMBC experiments.     

Beilschmiedic Acids F and G,Further Endiandric Acid Derivatives from Beilschmiedia anacardioides

Two new endiandric acid derivatives, beilschmiedic acid F ( 1 ) and beilschmiedic acid G ( 2 ), together with three known constituents, beilschmiedic acid A, beilschmiedic acid C, and sitosterol 3‐β‐D ‐glucopyranoside, were isolated from the stem bark of Beilschmiedia anacardioides. Their structures were elucidated mainly by using a combination of 1D‐ and 2D‐NMR techniques. The structure and relative configuration of beilschmiedic acid G ( 2 ) was also confirmed by X‐ray crystallographic analysis.     

Complete 1H and 13C NMR chemical shift assignment of N1‐ and N3‐alkylnitrohistidines and of 1,4,6,7‐tetrahydroimidazo[4,5‐b]pyridines

¹H and ¹³C NMR data for 13 nitrohistidine derivatives are reported, providing a diagnostic method for the elucidation of the N¹‐( 2 ) and the N³‐substituted ( 3 ) regioisomers. Spectral assignments of constrained surrogates of His ( 4 ) and of the His–Gly dipeptide ( 5 and 6 ) are also described. The structure of the compounds was confirmed by NOESY and heteronuclear (¹³C, ¹H) short‐ and long‐range correlation experiments. Copyright © 2003 John Wiley & Sons, Ltd.     

New Tryptophan Metabolites from Cultures of the Lipophilic Yeast Malassezia furfur

Eleven new indole alkaloids were isolated from cultures of the human pathogenic yeast Malassezia furfur after addition of L ‐tryptophan as the sole N‐source: pityriacitrin B ( 2 ), the malassezindoles A ( 3 ) and B ( 4 ), malassezialactic acid ( 6 ), the malasseziazoles A ( 7 ), B ( 8 ), and C ( 9 ), pityriazole ( 10 ), malasseziacitrin ( 11 ), and malassezione ( 12 ), along with the known d‐ indole‐3‐lactic acid (=(αR)‐α‐hydroxy‐1H‐indole‐3‐propanoic acid 5 ), and 2‐hydroxy‐1‐(1H‐indol‐3‐yl)ethanone ( 13 ). The structural elucidation of these compounds was performed by spectroscopic methods (MS as well as 1D‐ and 2D‐NMR). The biogenetic relationships (Scheme) and biological activities of the new metabolites are discussed.     

Polyoxygenated Sterols from Freshwater Clam

Two new biologically active polyoxygenated sterols, 3,5,9‐trihydroxycholest‐7‐en‐6‐one ( 1 ) and cholest‐7‐ene‐3,6,9‐triol ( 3 ), together with one known sterone, topsentisterol D3 ( 2 ), were isolated from freshwater clam (Corbicula fluminea Muller ; an important cultured edible shellfish in Taiwan). The structure elucidation of sterols 1 – 3 were accomplished by ¹H‐ and ¹³C‐NMR, HMQC, and HMBC, and MS analyses. The sterols 1 – 3 displayed cytotoxicities against the human hepatoma Hep G2 cells (IC₅₀: 6.04±0.07, 40.78±4.28, and 10.57±0.51 μg/ml, resp.).     

Synthesis and structure elucidation of five new conjugates of oleanolic acid derivatives and chalcones using 1D and 2D NMR spectroscopy

Five new conjugates of oleanolic acid derivatives and chalcones have been designed and synthesized. The structure elucidation of these conjugates was accomplished by using extensive 1D (¹H, ¹³C) and 2D NMR spectroscopic studies (COSY, HSQC and HMBC); and α‐glucosidase inhibitory activity is reported for these conjugates. Compound 2b (IC₅₀ = 47.5 µm ) displayed much stronger activity than oleanolic acid and acarbose. Copyright © 2012 John Wiley & Sons, Ltd.     

Synthesis of Some Bromomethyl‐ and (4‐Bromomethyl)phenyl‐Derivatives of 1,4,8,11 Tetraaza[14] annulene and Their Corresponding Sulfanylmethylene‐Derivatives Using 3‐Substituted Trimethinium Salts

Four new 6,13‐di(bromomethyl)‐ and di[(4‐bromomethyl)phenyl]1,4,8,11‐tetraaza[14]annulene derivatives C , D , E , F were synthesized using the condensation reaction of the correspondingly substituted vinamidinium salts with aromatic amines in acetonitrile/acetic acid. The reaction of these annulenes with thiourea leads to the corresponding thiol derivatives G and H . The UV/vis spectral behavior of compounds C , D , E , F , G , H was examined in DMSO. Elemental analysis, IR, ¹H‐NMR, ¹³C‐NMR, and mass spectral data confirm the molecular structure of the newly synthesized compounds.     

Two New Sesquiterpenoids from the Rhizomes of Curcuma xanthorrhiza

Zedoardiol ( 1 ), a new furanoguaiane sesquiterpenoid, and 3,4‐dihydroxybisabola‐1,10‐diene ( 2 ), a new naturally occurring bisabolane sesquiterpenoid, together with six known compounds, were isolated from Curcuma xanthorrhiza Roxb . Their structures were determined on the basis of comprehensive spectroscopic analyses, mainly 1D‐ and 2D‐NMR, MS, IR and X‐ray single‐crystal diffraction. Herein, the isolation and structure elucidation of the compounds are described.     

Three New Diterpenoids from Euphorbia sororia L.

Three new diterpenoids with jatrophane‐type skeleton, sororianolides A–C ( 1 – 3 , resp.), were isolated from Euphorbia sororia. The identification and structure elucidation of these compounds were based on 1D‐ and 2D‐NMR‐spectral data analysis. It was the first time to isolate diterpenoids in this species.