Xanthone O‐Glycosides from the Roots of Pteris Multifida

Two new xanthone glycosides and six known compounds were isolated from the roots of Pteris multifida. Based on spectroscopic and chemical methods, the structures of the new compounds were elucidated as 1‐hydroxy‐4,7‐dimethoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 1 ), and 1,3‐dihydroxy‐7‐methoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1 →2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 2 ), respectively.     

Chemical Components of Seriphidium Santolium Poljak

A new biflavonoid glucoside, apigenin‐7‐O‐β‐D‐glucopyranoside‐(3′‐O‐7″)‐quercetin‐3″‐methyl ether ( 1 ) together with twenty known compounds, apigenin ( 2 ), luteolin ( 3 ), chrysoeriol ( 4 ), tricin ( 5 ), hispidulin ( 6 ), pectolinarigenin ( 7 ), eupatilin ( 8 ), 5,7‐dihydroxy‐6,3′,4′,5′‐tetramethoxyflavone ( 9 ), 5,7,4′‐trihydroxy‐6,3′,5′‐trimethoxyflavone ( 10 ), 3,6‐O‐dimethylquercetagetin‐7‐O‐β‐D‐glucoside ( 11 ), 6‐hydroxy‐5,7‐dimethoxy‐coumarin ( 12 ), taraxerol ( 13 ), taraxeryl acetate ( 14 ), a mixture of β‐sitosterol ( 15 ) and stigmasterol ( 16 ), a mixture of the n‐alkyl trans‐p‐coumarates ( 17 ), a mixture of the n‐alkyl trans‐ferulates ( 18 ), 2‐hydroxy‐4,6‐dimethoxyacetophenone ( 19 ), 4‐hydroxy‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 20 ), and 2‐hydroxycinnamoyl‐β‐D‐glucopyranoside ( 21 ), were isolated from the whole plant of Seriphidium santolium Poljak. The structures of these compounds were determined by means of spectral and chemical studies.     

1H, 13C and 15N NMR spectroscopic characterization of unexpected degradation products of the nifedipine analogue bis(2‐cyanoethyl) 2,6‐dimethyl‐4‐(2‐nitrophenyl)‐1,4‐dihydro‐3,5‐pyridinedicarboxylate

In the course of saponification experiments with bis(2‐cyanoethyl) 2,6‐dimethyl‐4‐(2‐nitrophenyl)‐1,4‐dihydro‐3,5‐pyridinedicarboxylate ( 1 ), an analogue of the calcium channel blocker nifedipine, three unexpected degradation products were isolated. The compounds were identified as 3‐(2‐acetamido‐1‐carboxy‐1‐propenyl)‐1‐hydroxy‐2‐indolecarboxylic acid ( 3 ), 9‐hydroxy‐1,3‐dimethyl‐β‐carboline‐4‐carboxylic acid ( 4 ) and 6‐hydroxy‐2,4‐dimethyl‐5‐oxo‐5,6‐dihydrobenzo[c][2,7]naphthyridine‐1‐carboxylic acid ( 6 ). The structures of these compounds were deduced from one‐ and two‐dimensional ¹H, ¹³C and natural abundance ¹⁵N NMR experiments (¹H,¹H‐COSY, gs‐HSQC, gs‐HMBC, ¹⁵N gs‐HMBC), and corroborated by comparison of their NMR data with the respective data for structurally similar compounds. Copyright © 2002 John Wiley & Sons, Ltd.     

Synthesis and isolation of nitro‐bT‐carbolines obtained by nitration of commercial β‐carboline alkaloids

Nitration of commercial full aromatic β‐carboline alkaloids nor‐harmane ( 1 ), harmane ( 2 ), harmine ( 3 ), harmol ( 4 ), and the 7‐acetylated derivative of harmol ( 5 ) is described. Advantages and disadvantages of different nitration reagents which involve acidic conditions (HNO₃/H⁺) and neutral conditions (Cu(NO₃)₂; ceric ammonium nitrate) are discussed. A complete ¹H and ¹³C‐nmr characterization including ms and also uv absorption spectra in neutral and acid media is presented. A detailed ei‐ms and ld‐tof‐ms study is enclosed because the nitro‐β‐carbolines constitute a new family of β‐carboline‐like chromophores with potential use as matrix in uv‐maldi‐tof‐ms.     

Synthesis of some fused β‐carbolines including the first example of the pyrrolo[3,2‐c]‐β‐carboline system

Condensation of 1‐methyl‐β‐carboline‐3‐carbaldehyde with ethyl azidoacetate and subsequent thermolysis of the resulting azidopropenoate was used to [c] annulate a pyrrole ring onto the β‐carboline moiety, thus producing the first example of the pyrrolo[3,2‐c]‐β‐carboline ring system. The latter ring system results from cyclization at the C‐4 carbon, whereas cyclization at the N‐2 nitrogen atom also occurs to form a pyrazolo[3,2‐c]‐β‐carboline ring system. Condensation of β‐carboline‐1‐carbaldehyde with ethyl azidoacetate produced a non‐isolable intermediate, which immediately underwent cyclization, however in this case cyclization occurred via attack at the ester and the azide remained intact. The resulting 5‐azidocanthin‐6‐one was transformed to the first examples of 5‐aminocanthin‐6‐ones. β‐Carboline‐1,3‐dicarbaldehyde failed to give an acceptable reaction with ethyl azidoacetate, but did undergo selective condensation with dimethyl acetylene dicarboxylate at the C‐1 carbaldehyde with concomitant cyclization to form a highly functionalized 2‐formyl‐canthine derivative.     

The Constituents of Lindera Glauca

Twenty‐eight compounds including seven alkaloids, (+)‐3‐chloro‐N‐formylnornantenine ( 1 ), (+)‐N‐formylnornantenine ( 2 ), (+)‐boldine ( 3 ), (+)‐norboldine ( 4 ), (‐)‐norboldine ( 5 ), lycicamine ( 6 ), and tetrahydroberberine ( 7 ); four flavonoids, kaempferol ( 8 ), kaempferol‐3‐O‐arabinoside ( 9 ), quercetin ( 10 ), and quercetin‐3‐O‐rhamnoside ( 11 ); one butanolide, akolactone A ( 12 ); one p‐quinone, 2,6‐dimethoxy‐p‐quinone ( 13 ); one cyclohex‐2‐en‐1‐one, blumenol A ( 14 ); six benzenoids, methylparaben ( 15 ), p‐hydroxybenzoic acid ( 16 ), vanillic acid ( 17 ), syringic acid ( 18 ), 3,4,5‐trimethoxybenzoic acid ( 19 ), and 3‐(3,4‐dihydroxyphenyl) propionic acid ( 20 ); one diterpene, phytol ( 21 ); one triterpene, squalene ( 22 ); six steroids, (3‐sitosterol ( 23 ), β‐sitostenone ( 24 ), stigmasta‐4,22‐dien‐3‐one ( 25 ), 6β‐hydroxy‐β‐sitostenone ( 26 ), 6β‐hydroxystigmasterone ( 27 ), and β‐sitosteryl‐D‐glucoside ( 28 ) were isolated from the aerial part of Lindera glauca. These compounds were characterized and identified by physical and spectral method. All compounds were isolated for the first time from this plant. Among them, (+)‐3‐chloro‐N‐formylnornantenine ( 1 ) is a new one.     

Chemical Components of Anaphalis Sinica Hance

Twenty components (including a new flavanone) were isolated and identified from the whole plant of Anaphalis sinica Hance. Their structures were determined on the basis of spectral analysis and chemical transformation. These components are 6‐[(5‐methyl‐6‐ethyl‐4‐hydroxy‐pyrone‐3‐yl)‐methylene]glabranine ( 1 ), kaempferol ( 2 ), tiliroside ( 3 ), quercetin ( 4 ), quercetin‐3‐O‐β‐D‐glucoside ( 5 ), scutellarin ( 6 ), 5,7‐dihydroxy‐8‐methoxyflavone ( 7 ), 5,7‐dihydroxy‐4′‐methoxy‐flavone‐7‐O‐α‐L‐rhamnopyranosyl(1→6)‐β‐D‐glucopyranoside ( 8 ), helipyrone ( 9 ), 4′‐hydroxydehydrokawain ( 10 ), panamin ( 11 ), ursolic acid ( 12 ), pomolic acid ( 13 ), 3‐acetyloleanolic acid ( 14 ), a mixture of N‐(2‐hydroxy‐acyl)‐4‐hydroxy‐8(E)‐ene‐sphingenine ( 15 ), O‐methyl‐D‐inositol ( 16 ), a mixture of β‐sitosterol ( 17 ) and stigmasterol ( 18 ) and a mixture of daucosterol ( 19 ) and stigmasterol‐β‐D‐glucoside ( 20 ). Among them, 6‐[(5‐methyl‐6‐ethyl‐4‐hydroxy‐pyrone‐3‐yl)‐methylene]glabranine ( 1 ) is a new compound, and ¹³C NMR data of panamin ( 11 ) is reported for the first time.     

The Chemical Constituents from the Heartwood of Eucalyptus Citriodora

Nineteen compounds were isolated from the CHCl₃ soluble portion of the heartwood of Eucalyptus citriodora. These compounds included trans‐calamenene (1), T‐muurolol (2), α‐cadinol (3), 2β‐hydroxy‐α‐cadinol (4), 4‐hydroxy‐3,5‐dimethoxybenzaldehyde (5), 4‐hydroxy‐3,5‐dimethoxybenzoic acid (6), linoleic acid (7), squalene (8), α‐tocopherol (9), erythrodiol (10), morolic acid (11), betulonic acid (12), cycloeucalenol (13), cycloeucalenol vernolitate (14), β‐sitosterol (15), β‐sitosteryl‐β‐D‐glucopyranoside (16), β‐sitostenone (17), yangambin (18), sesamin (19). Among them, 14 is a new compound. The structures of these compounds were elucidated on the basis of spectroscopic evidence.     

Xanthones from the stems of Cratoxylum cochinchinense

Four new xanthones, 1‐methoxy‐3,7,8‐trihydroxyxanthone (1), 1‐methoxy‐4,7,8‐trihydroxyxanthone (2), 1‐methoxy‐4,7‐dihydroxyxanthone (3), and 1,4‐dimethoxy‐2,7‐dihydroxyxanthone (4) were isolated from the stems of Cratoxylum cochinchinense along with four known xanthones (5–8). The structures of new compounds were determined by extensive spectroscopic analyses, mainly 1D and 2D NMR and HRESIMS data. Copyright © 2012 John Wiley & Sons, Ltd.     

Flavone Glycosides from Strobilanthes Formosanus

Two new flavone glycosides, 3′‐hydroxy‐5,7‐dimethoxyflavone 4′‐O‐β‐D‐apiofuranoside ( 1 ), and 5,7‐dimethoxyflavone 4′‐O‐[β‐D‐apiofuranosyl(1→5)‐ β‐D‐glucopyranoside] ( 2 ) along with four known compounds, 4′‐hydroxy‐5,7‐dimethoxyflavone ( 3 ), 2,6‐dimethoxy‐1,4‐benzoquinone ( 4 ), lupeol ( 5 ) and betulin ( 6 ) were isolated from the stem and roots of Strobilanthes formosanus. Their structures were elucidated on the basis of their spectroscopic evidence.     

Synthesis of acrimarins from 1,3,5‐trioxygenated‐9‐acridone derivatives

1,3,5‐Trihydroxy‐9(10H)‐acridinone (1) was prepared from 3‐hydroxyanthranillic acid with phloroglucinol. 1,3‐Dihydroxy‐5‐methoxy‐9(10H)‐acridinone (2) was prepared from 3‐methoxyanthranillic acid and phloroglucinol. Methylation of 1 under different conditions gave 1‐hydroxy‐3,5‐dimethoxy (3), 1‐hydroxy‐3,5‐dimethoxy‐10‐methyl (4), 1‐hydroxy‐3,5‐dimethoxy‐4‐methyl (5), 1,3,5‐trimethoxy‐10‐methyl (6) and 1,3,5‐trimethoxy‐4,10‐dimethyl (7) analogues. Demethylation of 4 afforded the 1,3,5‐trihydroxy‐10‐methyl analogue 8. Condensation of acridones 1, 2, 3 and 4 individually with E‐suberenol (9) gave four novel acrimarins (acridone‐coumarin dimers) 10, 11, 12 and 13 respectively, while the acridone 8 gave previously reported acrimarin‐G (14).     

Physical properties of diblock methylcellulose derivatives with regioselective functionalization patterns: First direct evidence that a sequence of 2,3,6‐tri‐O‐methyl‐glucopyranosyl units causes thermoreversible gelation of methylcellulose

This article describes detailed structure‐property relationships of 5 regioselectively methylated celluloses and 10 diblock cellulose derivatives with regioselective functionalization patterns: methyl 2,3,6‐tri‐O‐ ( 1 , 236MC), methyl 2,3‐di‐O‐ ( 2 , 23MC), methyl 2,6‐di‐O‐ ( 3 , 26MC), methyl 3‐O‐ ( 4 , 3MC), methyl 6‐O‐methyl‐cellulosides ( 5 , 6MC), methyl β‐D‐glucopyranosyl‐(1→4)‐2,3,6‐tri‐O‐methyl‐ ( 6 , G‐236MC), methyl β‐D‐glucopyranosyl‐(1→4)‐2,3‐di‐O‐methyl‐ ( 7 , G‐23MC), methyl β‐D‐glucopyranosyl‐(1→4)‐2,6‐di‐O‐methyl‐ ( 8 , G‐26MC), methyl β‐D‐glucopyranosyl‐(1→4)‐3‐O‐methyl‐ ( 9 , G‐3MC), methyl β‐D‐glucopyranosyl‐(1→4)‐6‐O‐methyl‐ ( 10 , G‐6MC), methyl β‐D‐glucopyranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐2,3,6‐tri‐O‐methyl‐ ( 11 , GG‐236MC), methyl β‐D‐glucopyranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐2,3‐di‐O‐methyl‐ ( 12 , GG‐23MC), methyl β‐D‐glucopy‐ranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐2,6‐di‐O‐methyl‐ ( 13 , GG‐26MC), methyl β‐D‐glucopyranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐3‐O‐methyl‐ ( 14 , GG‐3MC), and methyl β‐D‐glucopyranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐6‐O‐methyl‐cellulosides ( 15 , GG‐6MC). Surface tension, differential scanning calorimetry, fluorescence, and dynamic light scattering measurements of aqueous solutions of compounds 1 – 15 revealed that there was no relationship between aggregation behaviors and gel formation, gelation occurred only when the hydrophobic environments formed by hydrophobic interactions between the sequences of 2,3,6‐tri‐O‐methyl‐glucopyranosyl units upon heating. The diblock structure consisting of cellobiosyl block and approx. ten 2,3,6‐tri‐O‐methyl‐glucopyranosyl units was of crucial importance for thermoreversible gelation of methylcellulose. © 2011 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 49: 1539–1546, 2011     

New saponins from Sechium mexicanum

The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (1) and {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐[β‐D ‐apiosyl‐(1 → 3)]‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (2), together with the known compounds {3‐O‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,6β,16α,23‐pentahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (3), tacacosides A₁ (4) and B₃ (5). The structures of saponins 1 and 2 were elucidated using a combination of ¹H and ¹³C 1D‐NMR, COSY, TOCSY, gHMBC and gHSQC 2D‐NMR, and FABMS of the natural compounds and their peracetylated derivates, as well as by chemical degradation. Compounds 1–3 are the first examples of saponins containing polygalacic and 16‐hydroxyprotobasic acids found in the genus Sechium, while 4 and 5, which had been characterized partially by NMR, are now characterized in detail. Copyright © 2009 John Wiley & Sons, Ltd.     

Synthesis,crystal structure and activity evaluation of novel 3,4‐dihydro‐1‐benzoxepin‐5(2H)‐one derivatives as protein–tyrosine kinase (PTK) inhibitors

Four new 3,4‐dihydro‐1‐benzoxepin‐5(2H )‐one derivatives, namely (E )‐4‐(5‐bromo‐2‐hydroxybenzylidene)‐6,8‐dimethoxy‐3,4‐dihydrobenzo[b ]oxepin‐5(2H )‐one, ( 7 ), (E )‐4‐[(E )‐3‐(5‐bromo‐2‐hydroxyphenyl)allylidene]‐6,8‐dimethoxy‐3,4‐dihydrobenzo[b ]oxepin‐5(2H )‐one, ( 8 ), (E )‐4‐(5‐bromo‐2‐hydroxybenzylidene)‐6‐hydroxy‐8‐methoxy‐3,4‐dihydrobenzo[b ]oxepin‐5(2H )‐one, C₁₈H₁₅BrO₅, ( 9 ), and (E )‐4‐[(E )‐3‐(5‐bromo‐2‐hydroxyphenyl)allylidene]‐6‐hydroxy‐8‐methoxy‐3,4‐dihydrobenzo[b ]oxepin‐5(2H )‐one, ( 10 ), have been synthesized and characterized by FT–IR, NMR and MS. The structure of ( 9 ) was confirmed by single‐crystal X‐ray diffraction. Crystal structure analysis shows that molecules of ( 9 ) are connected into a one‐dimensional chain in the [010] direction through classical hydrogen bonds and these chains are further extended into a three‐dimensional network via C—H…O interactions. The inhibitory activities of these compounds against protein–tyrosine kinases (PTKs) show that 6‐hydroxy‐substituted compounds ( 9 ) and ( 10 ) are more effective for inhibiting ErbB1 and ErbB2 than are 6‐methoxy‐substituted compounds ( 7 ) and ( 8 ). This may be because ( 9 ) and ( 10 ) could effectively bind to the active pockets of the protein through intermolecular interactions.     

Structural elucidation and NMR assignments of four aromatic lactones from a mangrove endophytic fungus (No. GX4‐1B)

Two new aromatic lactones, 6‐hydroxy‐4‐hydroxymethyl‐8‐methoxy‐3‐ methylisocoumarin (1) and 1,10‐dihydroxy‐8‐methyl‐dibenz[b, e]oxepin‐6,11‐dione (2), together with two known compounds, 1,10‐dihydroxy‐dibenz[b, e]oxepin‐6,11‐dione (3) and 3‐hydroxymethyl‐6,8‐dimethoxycoumarin (4), were isolated from a mangrove endophytic fungus (No. GX4‐1B) collected from the South China Sea. Their structures were elucidated and the data of ¹H and ¹³C NMR were assigned completely by HREIMS, 1D and 2D NMR experiments including HMQC, HMBC and NOESY. Copyright © 2010 John Wiley & Sons, Ltd.     

Diversity of Chemical Constituents from Saxifraga Montana H.

A thorough phytochemical investigation of the whole plant of Saxifraga montana H. afforded a new glucoside, methyl 6″‐O‐(E)‐p‐hydroxycinnamoxyl‐glucosyringate ( 1 ), and seventeen known natural products, 3‐methyl‐6‐methoxy‐3,4‐dihydroisocoumarin‐8‐O‐β‐D‐glucospyranoside ( 2 ), gallic acid ( 3 ), glucosyringic acid ( 4 ), daphnoretin ( 5 ), chamaejasmoside ( 6 ), myricetin ( 7 ), quercetin ( 8 ), quercetin‐3‐O‐β‐D‐galactopyranoside ( 9 ), quercetin‐3‐O‐α‐L‐arabinoside ( 10 ), quercetin‐3‐O‐β‐D‐glucospyranoside ( 11 ), rutin ( 12 ), quercetin‐3‐O‐β‐D‐glucopyranosyl (6‐1) glucopyranoside ( 13 ), ursolic acid ( 14 ), 5,28‐stigmastadien‐3β‐ol ( 15 ), β‐sitosterol ( 16 ), β‐daucosterin ( 17 ), 6′‐palmitoxyl‐β‐daucosterin ( 18 ). On the basis of various spectroscopic methods, especially intensive 2D‐NMR (COSY, HMQC and HMBC), FAB‐MS and HR‐ESI‐MS techniques, their structures were elucidated.     

A Short Synthesis of Natural Isocoumarin Glucoside Delphoside

A simple synthesis of delphoside, 3-methyl-6-hydroxy-8-O-β-D-glucopyranosyloxy isocoumarin (1), isolated from Delphinium spp. is described. 3,5-Dimethoxyhomophthalic anhydride (2) on treatment with acetyl chloride in the presence of 1,1,3,3-tetramethylguanidine (TMG) and triethyl amine afforded the 6,8-dimethoxy-3-methylisocoumarin (3). Regioselective demethylation of the latter furnished 8-hydroxy-6-methoxy-3-methylisocoumarin (4). Glycosylation with O-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)trichloroacetimidate in presence of catalytic amount of boron trifluoride etherate followed by deacetylation using 5% potassium carbonate afforded 3-methyl-6-methoxy-8-O-β-D-glucopyranosyloxyisocoumarin (6) that was finally demethylated to yield delphoside 1.     

Preparation and purification of canthinone and β‐carboline alkaloids from Picrasma quassioides based on bioautography and mass‐spectrometry‐directed autopurification system

Picrasma quassioides (D. Don) Benn. is a widely used traditional Chinese medicine for anti‐inflammation and antibiosis. Canthinone and β‐carboline alkaloids are the main characteristic constituents that possess diverse pharmacological effects, such as anti‐inflammatory and anti‐infectious properties. In this study, bioautography in thin‐layer chromatography indicated that the antiradical activity compound may be alkaloids. Then, a simple, fast, and efficient method was established for the separation and purification of two types of alkaloids from P. quassioides by mass‐spectrometry‐directed autopurification system. Eight alkaloids were isolated and purified in this one‐step methodology. Among them, five compounds ( 3 , 95.1%, 58.8 mg; 4 , 98.4%, 71.7 mg; 6 , 97.8%, 365.4 mg; 7 , 97.7%, 172.7 mg; 8 , 98.2%, 180.3 mg) were obtained in large amounts with extremely high purities. Then, the antiradical activities of the isolates showed that 4‐methoxy‐5‐hydroxycanthin‐6‐one ( 6 ) exhibited obvious 1,1‐diphenyl‐2‐picryl‐hydrazyl free radical scavenging activity with an IC₅₀ value of 84.037 μM. This study offers a new method for the preparation of targeted bioactive alkaloids in P. quassioides. This work also provides a reference for the separation of other targeted chemical components with potential activities from traditional Chinese herbal medicines.     

Tetrapterosides A and B,two new oleanane‐type saponins from Tetrapleura tetraptera

From the stem bark of Tetrapleura tetraptera, two new oleanane‐type saponins, tetrapteroside A 3‐O‐{6‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐hydroxyocta‐2,7‐dienoyl]‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (1), and tetrapteroside B 3‐O‐{ β‐D ‐glucopyranosyl‐(1 → 2)‐6‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane‐type saponins. Their structures were elucidated by the combination of mass spectrometry (MS), one and two‐dimensional NMR experiments. Copyright © 2009 John Wiley & Sons, Ltd.     

Bioactive Components from the Mycelium of Antrodia Salmonea

Three new compounds, 2,4‐dimethoxy‐6‐methylbenzene‐1,3‐diol ( 1 ), salmoquinone ( 2 ), and 3‐(4‐hydroxyphenyl)‐4‐isobutyl‐1H‐pyrrole‐2,5‐dione ( 3 ), together with six known compounds, 2‐methoxy‐6‐methyl‐p‐benzoquinone ( 4 ), 2,3‐dimethoxy‐5‐methyl‐p‐benzoquinone ( 5 ), 2‐hydroxy‐5‐methoxy‐3‐methyl‐p‐benzoquinone ( 6 ), eburcoic acid ( 7 ), fomefficinic acid C ( 8 ), and a pyrroledione ( 9 ), were isolated from the mycelium of Antrodia salmonea. The structures of these compounds were elucidated by spectrometric analyses including IR, NMR, and MS. Among these compounds, 4 and 5 exhibited cytotoxicity against KB, HepG2, and H2058 cell lines.