Five New C19‐Diterpenoid Alkaloids from Aconitum hemsleyanum

Five new C₁₉‐diterpenoid alkaloids, named hemsleyaconitines A–E ( 1 – 5 , resp.), were isolated from Aconitum hemsleyanum Pritz. By UV, IR, MS, 1D‐ and 2D‐NMR analyses, their structures were elucidated as 18‐dehydroxygeniculatine D ( 1 ), 6‐hydroxy‐14‐O‐veratroylneoline ( 2 ), 14‐O‐acetyl‐8‐ethoxysachaconitine ( 3 ), 18‐veratroylkaracoline ( 4 ) and 8‐O‐ethylaustroconitine B ( 5 ).     

New Diterpenoid Alkaloids from Aconitum liangshanicum

One new C₁₉‐diterpenoid alkaloid, named liangshantine ( 1 ), and three new C₂₀‐diterpenoid alkaloids, liangshansines A–C ( 2 – 4 , resp.), as well as eight known compounds, were isolated from the roots of Aconitum liangshanicum. The structures of these new alkaloids were elucidated by spectroscopic methods.     

Four New Nor‐Diterpenoid Alkaloids from Aconitum brachypodum

Four new C₁₉‐nor‐diterpenoid alkaloids, named brachyaconitines A–D ( 1 – 4 ), were isolated from the roots of Aconitum brachypodum Diels. Their structures were elucidated as 3‐O‐acetyl‐20‐deethyl‐20‐formylaconitine ( 1 ), 3‐O‐acetyl‐19,20‐didehydro‐20‐deethylaconitine ( 2 ), 3‐O‐acetyl‐8‐de(acetyloxy)‐7,8,17,20‐tetradehydro‐20‐deethyl‐7,17‐secoaconitine ( 3 ), and 1‐O‐methylflavaconitine ( 4 ) by means of MS, IR, 1D‐ and 2D‐NMR analyses. The structure of compound 1 was confirmed by an X‐ray diffraction experiment.     

Further Alkaloids from the Leaves of Trigonostemon lii

Four new indole alkaloids, trigonoliimines D–G ( 1 – 4 , resp.), were isolated from Trigonostemon lii. Their structures were elucidated by spectroscopic methods, including extensive 1D‐ and 2D‐NMR experiments.     

Three New Monoterpene Alkaloids and a New Caffeic Acid Ester from Incarvillea mairei var. multifoliolata

Three new monoterpene alkaloids, mairine A ( 1 ), mairine B ( 2 ), and mairine C ( 3 ), and a new caffeic acid ester, 2‐(1‐hydroxy‐4,4‐dimethoxycyclohexyl)ethyl caffeate ( 4 ), were isolated from the EtOH extract of the whole plants of Incarvillea mairei var. multifoliolata. The structures of these compounds were established on the basis of 1D‐ and 2D‐NMR and HR‐ESI‐MS analysis.     

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.     

Diterpenoid Alkaloids from Delphinium tatsienense

Three new C₂₀‐diterpenoid alkaloids, along with twenty‐two known alkaloids, were isolated from the whole herbs of Delphinium tatsienense. The new alkaloids include a vakognavine‐type C₂₀‐diterpenoid alkaloid, designated as tatsienenseine A ( 1 ), and two hetisine‐type C₂₀‐diterpenoid alkaloids, designated as tatsienenseines B ( 2 ) and C ( 3 ). Their structures were elucidated by IR, HR‐ESI‐MS, 1D‐ and 2D‐NMR analyses.     

Diterpenoid Alkaloids from Delphinium yunnanense

Three new diterpenoid alkaloids, along with eleven known alkaloids, were isolated from the whole herbs of Delphinium yunnanense. The new alkaloids include a rearranged‐type C₁₉‐diterpenoid alkaloid, named yunnanenseine A ( 1 ), and two hetisine‐type C₂₀‐diterpenoid alkaloids, named yunnanenseine B and C ( 2 and 3 , resp.). Their structures were elucidated by detailed NMR‐spectroscopic studies.     

Evollionines A–C,Three New Alkaloids Isolated from the Fruits of Evodia rutaecarpa

A phytochemical study of the CHCl₃ extract of the dried unripe fruits of Evodia rutaecarpa (Juss. ) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C ( 1 – 3 , resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single‐crystal X‐ray analysis.     

Dapholidins A – C,New Isomeric Biisoflavonoids From Daphne oleoides

Three new isomeric biisoflavonoids, dapholidins A–C ( 1 – 3 , resp.), have been isolated from the AcOEt‐soluble fraction of the MeOH‐soluble extract of the roots of Daphne oleoides, along with the known compounds daphwazirin ( 4 ), daphnetin 8‐O‐β‐D ‐glucopyranoside ( 5 ), daphnin ( 6 ), daphneticin 4″‐O‐β‐D ‐glucopyranoside ( 7 ), and 6,7‐dihydroxy‐3‐methoxy‐8‐[2‐oxo‐2H‐1‐benzopyran‐7‐(O‐β‐D ‐glucopyranosyl)‐8‐yl]‐2H‐1‐benzopyran‐2‐one ( 8 ). The structures of the new compounds were determined by spectroscopic analyses, including 1D‐ and 2D‐NMR.     

Phenylpropanoid Esters of Rhamnose from Buddleja asiatica

Four new phenylpropanoid esters of rhamnose, asiatisides A–D, along with the known compounds, buergeriside C₁ ( 5 ), p‐methoxycinnamic acid, ferulic acid, and O‐methylferulic acid were obtained from the aerial parts of Buddleja asiatica Lour by chromatographic methods. The new compounds were elucidated as 3‐O‐acetyl‐4‐O‐(p‐methoxycinnamoyl)‐α‐L ‐rhamnopyranose ( 1 ), 3‐O‐acetyl‐4‐O‐feruloyl‐α‐L ‐rhamnopyranose ( 2 ), 2‐O‐acetyl‐4‐O‐(O‐methylferuloyl)‐α‐L ‐rhamnopyranose ( 3 ), 2‐O‐acetyl‐4‐O‐(p‐methoxycinnamoyl)‐α‐L ‐rhamnopyranose ( 4 ) by spectral data (1D‐, 2D‐NMR, and MS), respectively.     

Itosides A – I,New Phenolic Glycosides from Itoa orientalis

Eight new benzoylated gentisyl alcohol (=2‐(hydroxymethyl)benzene‐1,4‐diol) glucosides, itosides A–H ( 1 – 8 ), together with the new pyrocatechol (=benzene‐1,2‐diol) glycoside itoside I ( 9 ) were isolated from the bark and twigs of Itoa orientalis (Flacourtiaceae). In itosides B–D ( 2 – 4 ), the gentisyl alcohol moiety was esterified by 1‐hydroxy‐6‐oxocyclohex‐2‐ene‐1‐carboxylic acid, while itosides E–H ( 5 – 8 ) contained instead an additional 2‐hydroxybenzoic acid moiety. The compounds were accompanied by the known derivatives 4‐hydroxytremulacin ( 10 ), poliothyrsoside ( 11 ), poliothyrsin ( 12 ), homaloside D ( 13 ), tremulacin, and pyrocatechol β‐D ‐glucopyranoside. The structures of the new compounds were elucidated by spectral and chemical methods.     

Five New β‐Carboline‐Type Alkaloids from Stellaria dichotoma var. lanceolata

Five new β‐carboline‐type alkaloids, dichotomines F–J ( 1 – 5 , resp.), along with nine known compounds, dichotomides I, III, V, and VII ( 6 – 9 , resp.), stellarines A and C ( 10 – 11 , resp.), dichotomine B ( 12 ), glucodichotomine B ( 13 ), and 1‐acetyl‐3‐carboxy‐β‐carboline ( 14 ), were isolated from the roots of Chinese medicinal plant Stellaria dichotoma L. var. lanceolata. Their structures were determined by chemical and spectroscopic means. Compounds 12 and 13 exhibited moderate cytotoxicity.     

Norlignans and Phenylpropanoids from Metasequoia glyptostroboides Hu et Cheng

Five new compounds, i.e., the three new norlignans metasequirins G–I ( 1 – 3 ) and the two new phenylpropanoids 7‐(3‐ethoxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐ethoxy‐5‐methoxyphenyl)propane‐1,2,3‐triol; 4 ) and 7‐(3‐hydroxy‐5‐methoxyphenyl)propane‐7,8,9‐triol (=1‐(3‐hydroxy‐5‐methoxy‐phenyl)propane‐1,2,3‐triol; 5 ), were isolated from the branches and stems of Metasequoia glyptostroboides Hu et Cheng . Their structures were elucidated by physical, chemical, and spectroscopic methods, including 1D‐ and 2D‐NMR and HR‐ESI‐MS. The cytotoxicites of the five compounds were tested against A549 and Colo 205 cell lines by the MTT method.     

New Polyketides Isolated from Botryosphaeria australis Strain ZJ12‐1A

Four new polyketides, botryosphaerones A–D ( 1 – 4 , resp.), were obtained from the fermentation culture of Botryosphaeria australis strain ZJ12‐1A, together with four known compounds, O‐methylasparvenone ( 5 ), 6‐ethyl‐2,7‐dimethoxyjuglon ( 6 ) and its monoacetyl derivative 7 , and O‐methylaspmenone ( 8 ). Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF mass spectrometry, and by comparison with reported data. All compounds were evaluated for their cytotoxic and antimicrobial activities in vitro. Only compounds 6 and 7 showed cytotoxic and antimicrobial activities, as already reported.     

Five New Aromatic Glycosides from Carthamus tinctorius

Five new aromatic glycosides, 1 – 5 , named as carthamosides B₄–B₈, together with three known compounds, 4′‐(hydroxyphenacyl)‐β‐D ‐glucopyranoside ( 6 ), benzyl‐O‐α‐L ‐rhamnopyranosyl‐(1→6)‐β‐D ‐glucopyranoside ( 7 ), and 4‐(methoxybenzyl)‐O‐β‐D ‐glucopyranoside ( 8 ), have been isolated from the air‐dried flower of Carthamus tinctorius. Their structures were identified on the basis of chemical and spectroscopic methods.     

Three New C19‐Diterpenoid Alkaloids from Aconitum hemsleyanum var. circinatum

Further phytochemical investigation of the roots of Aconitum hemsleyanum var. circinatum resulted in the isolation of three new aconitine‐type C₁₉‐diterpenoid alkaloids, hemsleyanines E–G ( 1 – 3 , resp.). The structures of these new alkaloids were elucidated on the basis of spectral data including 2D‐NMR.     

Three New Phthalides from Gnaphalium adnatum

Three new phthalides, gnaphalides A–C ( 1 – 3 , resp.), together with three known phthalides, were isolated from the aerial part of Gnaphalium adnatum. The structures of the new compounds were elucidated as 6‐(1,1‐dimethylprop‐2‐en‐1‐yl)‐5,7‐dihydroxy‐2‐benzofuran‐1(3H)‐one ( 1 ), 5‐hydroxy‐7‐[(2‐hydroxy‐3‐methylbut‐3‐en‐1‐yl)oxy]‐2‐benzofuran‐1(3H)‐one ( 2 ), and 1,3‐dihydro‐7‐[(3‐methylbut‐2‐en‐1‐yl)oxy]‐1‐oxo‐2‐benzofuran‐5‐yl β‐D ‐glucopyranoside ( 3 ) on the basis of spectral analyses. The structure of 1 was also confirmed by X‐ray crystallographic analysis. The three known phthalides, identified as 5,7‐dihydroxyisobenzofuran‐1(3H)‐one ( 4 ), anaphatol ( 5 ), and 7‐O‐(β‐glucopyranosyl)‐5‐hydroxyisobenzofuran‐1(3H)‐one ( 6 ), were isolated from the genus Gnaphalium for the first time.     

Further Withaphysalin Derivatives from Acnistus arborescens

Two new epimeric chlorinated withaphysalins, rel‐(4β,5β,6α,18S,22R)‐ and rel‐(4β,5β,6α,18R,22R)‐6‐chloro‐18,20‐epoxy‐18‐ethoxy‐4,5‐dihydroxy‐1‐oxowitha‐2,24‐diene‐26,22‐lactone ( 1 and 2 resp.), together with the new rel‐(4β,5β,6α,18R,22R)‐6‐chloro‐18,20‐epoxy‐4,5‐dihydroxy‐18‐methoxy‐1‐oxowitha‐2,24‐diene‐26,22‐lactone ( 3 ) and rel‐(3β,4β,5β,6β,18R,22R)‐5,6:18,20‐diepoxy‐3,18‐diethoxy‐4‐hydroxy‐1‐oxowith‐24‐ene‐26,22‐lactone ( 4 ) were isolated from the leaves of Acnistus arborescens and named withaphysalins T–W, respectively. The final structures and the complete ¹H‐ and ¹³C‐NMR assignments of the three chlorowithaphysalins 1 – 3 were performed by means of HR‐ESI‐MS and 1D‐ and 2D‐NMR experiments, including COSY, HSQC, and HMBC, beside comparison with spectral data of analogous compounds from the literature. The structure of 4 was also confirmed by means of a single‐crystal X‐ray diffraction analysis.     

Curcumaromins A,B, and C,Three Novel Curcuminoids from Curcuma aromatica

Three novel curcuminoids, curcumaromins A–C ( 1 – 3 , resp.), along with a known compound, longiferone B ( 4 ) were isolated from Curcuma aromatica Salisb . The structures of the new compounds were elucidated as (1E,4Z,6E)‐5‐hydroxy‐7‐{4‐hydroxy‐3‐[(1R*,6R*)‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl)phenyl}‐1‐(4‐hydroxyphenyl)hepta‐1,4,6‐trien‐3‐one ( 1 ), 2,3‐dihydro‐2‐(4‐hydroxyphenyl)‐6‐[(E)‐2‐(4‐hydroxyphenyl)ethenyl]‐5‐[(1R*,6R*)‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl]‐4H‐pyran‐4‐one ( 2 ), and (1E,6E)‐1,7‐bis(4‐hydroxyphenyl)‐4‐[(1R*,6R*)‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl]hepta‐1,6‐diene‐3,5‐dione ( 3 ) on the basis of spectroscopic analysis. Curcumaromins A–C ( 1 – 3 ) represented the first examples of menthane monoterpene‐coupled curcuminoids. The known compound, longiferone B ( 4 ), was the first daucane sesquiterpene isolated from the genus Curcuma.