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.     

Two New Compounds from Lindera chunii Merr.

The root of Lindera chunii Merr. is a noble traditional Chinese medicine and frequently used as a substitute for L. aggregata to cure the chronic disease of rheumatoid arthritis1. In our previous paper, we have reported some components from the roots of L…     

Norditerpenoid Alkaloids from the Aerial Parts of Aconitum cochleare Woroschin

From the aerial parts of Aconitum cochleare Woroschin, two new norditerpenoid alkaloids named aconitilearine ( 1 ) and N‐deethylmethyllycaconitine ( 2 ) were isolated along with the eight known norditerpenoid alkaloids 3 – 10 . The structures for the new compounds were established on the basis of ¹H, ¹³C, DEPT, homonuclear ¹H,¹H‐COSY, NOESY, HSQC, and HMBC NMR studies.     

Two New Alkaloids from the Roots of Aconitum sinomontanum Nakai

Two new alkaloids, ranaconidine (=20‐ethyl‐1α,14α,16β‐trimethoxyaconitane‐4,7,8,10‐tetrol; 1 ) and N‐(chloromethyl)taspine (=1‐[2‐(N‐(chloromethyl)‐N,N‐dimethylaminium)ethyl]‐3,8‐dimethoxybenzopyrano[5,4,3‐cde]benzopyran‐5,10‐dione; 2 ), together with two known compounds, i.e., benzethonium chloride ( 3 ) and ranaconine ( 4 ) were isolated from the roots of Aconitum sinomontanum Nakai . The structures of the compounds were elucidated on the basis of spectral evidences and in the comparison with previously published data.     

New Alkaloids from Daphniphyllum longeracemosum Rosenth.

Two new pentacyclic alkaloids, daphnilongertone ( 1 ) and 11‐hydroxydaphnigracine ( 2 ), together with the known congener dehydrodaphnigracine ( 3 ), were isolated from the fruits of Daphniphyllum longeracemosum. Their structures were elucidated spectroscopically. Compound 3 was isolated for the first time as a natural product.     

Three New Alkaloids from the Leaves of Uncaria rhynchophylla

Three new alkaloids, 2′‐O‐β‐D ‐glucopyranosyl‐11‐hydroxyvincoside lactam ( 1 ), 22‐O‐demethyl‐22‐O‐β‐D ‐glucopyranosylisocorynoxeine ( 2 ), and (4S)‐corynoxeine N‐oxide ( 3 ) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynoxeine N‐oxide ( 4 ), rhynchophylline N‐oxide ( 5 ), isorhynchophylline N‐oxide ( 6 ), and dihydrocorynantheine ( 7 ), and an indole alkaloid glycoside, strictosidine ( 8 ). The structures of 1 – 3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC₅₀=8.3 μM ) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1 – 7 (IC₅₀>100 μM for 1 – 6 or >30 μM for 7 ).     

Three New Lignan Derivatives from Lindera glauca (Siebold et Zucc.) Blume

Two new aryl‐tetralin lignan glycosides, linderanosides A and B ( 1 and 2 , resp.), and a new dihydrobenzofuran neolignan glycoside, linderanoside C ( 3 ), together with five known lignan derivatives ( 4 – 8 ) were isolated from the trunk of Lindera glauca. The structures of these new compounds were determined through spectroscopic analyses, including extensive 2D‐NMR data and acid hydrolysis. The absolute configurations of the compounds were clarified by circular dichroism (CD) spectroscopic studies. Compounds 1 – 8 were evaluated for their cytotoxicity against A549 (non‐small cell lung adenocarcinoma), SK‐OV‐3 (ovarian cancer cells), A498 (human kidney epithelial cells), and HCT‐15 (colon cancer cells) human tumor cell lines using sulforhodamine B assays in vitro.     

Lycodine‐Type Alkaloids from Lycopodium casuarinoides

Two new lycodine‐type alkaloids, huperzinine N‐oxide ( 1 ) and 8,15‐dihydrohuperzinine ( 2 ) as well as five known compounds, huperzinine ( 3 ), huperzine B ( 4 ), huperzine D ( 5 ), N‐demethylhuperzinine ( 6 ), and β‐obscurine ( 7 ), were isolated from the club moss Lycopodium casuarinoides. The structures of 1 and 2 were elucidated by spectroscopic methods and chemical transformation. The absolute configuration of 1 was established by chemical correlation with 3 , and that of 2 was determined by its CD spectrum.     

Two New Benzophenanthridine Alkaloids from Zanthoxylum nitidum

Two new benzophenanthridine alkaloids, named 8‐methoxysanguinarine ( 1 ) and 8‐methoxyisodecarine ( 2 ), were isolated from the EtOH extract of the rhizoma of Zanthoxylum nitidum. Their structures were determined on the basis of spectroscopic analysis.     

Two New Lycopodium Alkaloids from Lycopodium obscurum

Two new Lycopodium alkaloids, (+)‐cermizine D N‐oxide ( 1 ) and (8β)‐8‐(acetyloxy)obscurumine A ( 2 ), along with five known compounds, were isolated from the crude alkaloid portion of Lycopodium obscurum. Their structures were elucidated on the basis of spectroscopic data and chemical correlation. All of these alkaloids were tested in an assay for acetylcholine esterase (AChE) inhibitory activity.     

Two New Daphniphyllum Alkaloids from Daphniphyllum calycinum

Two new daphniphyllum alkaloids named 2‐hydroxyyunnandaphnine D ( 1 ) and methyl 7‐hydroxyhomodaphniphyllate ( 2 ), together with eight known alkaloids, daphnioldhanin D, calyciphylline F, calyciphylline B, deoxycalyciphylline B, daphnicyclidin H, macropodumine C, 9,10‐epoxycalycine A, and yunnandaphnine A, were isolated from the stems and leaves of Daphniphyllum calycinum. Their structures and relative configurations were established on the basis of spectral evidence (including 2D‐NMR) and subsequently confirmed by a single‐crystal X‐ray crystallographic diffraction analysis.     

Two New Steroidal Alkaloids from Veratrum nigrum L.

Phytochemical studies on Veratrum nigrum L., collected in Shanxi, P. R. China, resulted in the isolation of two new steroidal alkaloids, 23‐methoxycyclopamine ( 1 ) and 15‐O‐(2‐methylbutanoyl)‐3‐O‐veratroylprotoverine ( 2 ). The structures of the two new compounds were established by means of extensive NMR spectroscopic studies.     

Optical Resolution and Structure Determination of New Indolizidine Alkaloids from Elaeocarpus sphaericus

Two new indolizidine alkaloids, (±)‐3‐oxoisoelaeocarpine ( 1 ) and (±)‐elaeocarpine N‐oxide ( 2 ), along with three known alkaloids, (±)‐isoelaeocarpine ( 3 ), (±)‐elaeocarpine ( 4 ), and (?)‐isoelaeocarpiline ( 5 ), were isolated from an EtOH extract of the branches and leaves of Elaeocarpus sphaericus. The structures of these compounds were determined by spectroscopic and chemical methods. Furthermore, enantiomers of compounds 1 and 3 were separated on a chiral CD‐Ph column, and their absolute configurations were determined by TD‐DFT (=time‐dependent density‐functional theory) quantum‐chemical calculations of their electronic circular dichroism (ECD) spectra.     

Novel Alkaloids from Stemona sessilifolia

Two new alkaloids, sessilifolines A ( 1 ) and B ( 2a ), were isolated from the stems of Stemona sessilifolia, together with three known alkaloids, tuberstemonine ( 3 ), sessilifoliamide A ( 4 ), and stemoninoamide ( 5 ). Their structures were established by mass‐spectrometric and spectroscopic methods, especially 2D‐NMR techniques.     

A New Sesquiterpene from the Roots of Lindera strychnifolia

The root of Lindera strychnifolia is used as a palliative and an antispasmodic in traditional chinese medicine. In previous studies of chemical constituents from this plant, more than 20 sesquiterpene lactones have been isolated and their structures were established1-7. In order to compare the difference of chemical constituents extracted by Supercritical Fluid Extraction (SFE) method and by organic solvent, the SFE extract from Lindera strychnifolia was investigated. A novel sesquiterp…     

Three New C19‐Diterpenoid Alkaloids from Aconitum forrestii

A further study of the alkaloid constituents of Aconitum forrestii led to the isolation of three new C₁₉‐diterpenoid alkaloids, named 14‐acetoxy‐8‐O‐methylsachaconitine ( 1 ), 14‐acetoxyscaconine ( 2 ), and 8‐O‐ethylcammaconine ( 3 ). Their structures were determined by UV, IR, and MS, 1D‐ and 2D‐NMR analyses.     

Three New Pregnane Alkaloids from Veratrum taliense

Three new alkaloids, 3‐O‐acetylveralkamine ( 1 ), veralkamine 3‐(β‐D ‐glucopyranoside) ( 2 ), and 6,7‐epoxyverdine ( 3 ), together with five known alkaloids, veramitaline, veralkamine ( 4 ), angeloylzygadenine, veratroylzygadenine, and veramiline 3‐(β‐D ‐glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine ( 4 ) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.     

Two New Alkaloids from Flueggea virosa

Two new securinega‐type alkaloids and four known ones were isolated from the twigs and leaves of Flueggea virosa. The structures of the new compounds were elucidated by means of spectroscopic methods (UV, IR, HR‐ESI‐MS, and 1D‐ and 2D‐NMR), and the absolute configurations were assigned by CD spectra. The structures of the known compounds were identified by comparison of their physical and spectroscopic data with those reported in the literature.     

Three New Monoterpenoid Indole Alkaloids from Ervatamia flabelliformis

The three new monoterpenoid indole alkaloids 1 – 3 were isolated from the stems of Ervatamia flabelliformis. The structures were elucidated on the basis of spectral analysis and chemical derivatization.     

Two New Nitrone Alkaloids from Huperzia serrata

Two new nitrone alkaloids were isolated from the whole plant of Huperzia serrata (Thunb .) Trev . They are both phlegmarine‐type lycopodium alkaloids with a nitrone moiety. Their structures were elucidated on the basis of spectral evidences, and their configurations were established on the basis of optical rotation, CD, and NOESY‐NMR data.