Alkaloids from Stems of Ervatamia yunnanensis (II)

The non-alkaloid chemical constituents, which were isolated from the stems of Ervatamia yunnanensis Tsiang (Apocynaceae), have been reported in previous paper 1. As a part of our continuing research on the isolation of active compounds for anti-addictive …     

Two New Oxindole Alkaloids from Ervatamia yunnanensis

ErvalanIiaYunnanensiSTsianghasbeenusedasafolkmedicineinChinaforthetreatmentofhypertensi0n'.Aspart0fourc0ntinuingpr0gramonthestudyofplant-derivedbioactivecomp0unds,thechemicaIconstituents0fE.yunnanensI1vgrowinginYunnanwereinvestigated.Intheprevi0uspaper,werep0rtedthestructuresofind0lealkal0ids;l9S-hydr0xy-tacamine,tabernaemontanine,l7-demethoxy-c0rynoxineB,l7-demethoxy-hydr0c0rynoxineB,20-epi-ervatamine,19,2O-dehydroervatamine,includinganewone,l9S-hydroxy-16-epi-tacaminefr0mthisspecies'.T…     

Flabelliformides A and B,Two Novel Indole Alkaloids from Ervatamia flabelliformis

Flabelliformides A ( 1 ) and B ( 2 ), containing a novel C₂₀ indole core, have been isolated from the stems of Ervatamia flabelliformis. The structures of 1 and 2 were elucidated on the basis of spectral analysis and X‐ray crystallography.     

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.     

New Indole Alkaloids from Rauvolfia yunnanensis

Three new indole alkaloids, 10‐methoxy‐16‐de(methoxycarbonyl)pagicerine ( 1 ), (5β)‐17‐O‐deacetyl‐5,11‐dimethoxyakuammiline ( 2 ), and ((16S,19E)‐N¹‐(hydroxymethyl)isositsirikine ( 3 ) were isolated from the roots of Rauvolfia yunnanensis, together with seven known alkaloids. The structures of the new compounds were elucidated by in‐depth spectroscopic and mass‐spectrometric analyses.     

Alkaloids from Stems of Ervatamia yunnanensis （Ⅱ）

Six indole alkaloids were isolated from the stems of Ervatamia yunnanensis. Among them, 10-hydroxy-19, 20-dihydroisositsirikine （I） is new. The other five are known alkaloids, namely： matrine （Ⅱ）, 19, 20-dihydroisositsirikine （Ⅲ）, 19-s-voacangarine （Ⅳ）, 1 l＇-methoxyl-19s- heyneanine （Ⅴ）, conodurine （Ⅵ）. The structural elucidation of the alkaloids was based on spectral means.     

Two Novel Alkaloids from Zanthoxylum nitidum

Two novel alkaloids, 4,5‐dihydroxy‐1‐methyl‐3‐oxo‐2‐(trichloromethyl)‐3H‐indolium chloride ( 1 ) and 4‐(2‐methoxyethyl)‐N,N‐dimethylbenzenamine ( 2 ), were isolated from the EtOH extract of the roots of Zanthoxylum nitidum. Their structures were identified on the basis of spectroscopic and mass‐spectrometric analyses.     

Indole Alkaloids from the Roots of Ervatamia hainanensis

Evratamia hainanensis Tsiang, is distributed in the mountain and forest regions of 100-500 metres height in the southern part of China. Its root has been used for the treatment of stomachache, dysentery, rheumatic arthritis, hypertension and virus hepatit…     

Two New Indole Alkaloids from Emmenopterys henryi

Two new indole alkaloids, 5‐oxodolichantoside ( 1 ) and deglycocadambine ( 2 ), were isolated from the twigs and leaves of Emmenopterys henryi, together with four known indole alkaloids and five known iridoids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and confirmed by single‐crystal X‐ray diffraction studies. This is the first report on the isolation of indole alkaloids from this species. The indole alkaloids were evaluated for their cytotoxic activities against five human cancer lines.     

Indole Alkaloids from the Leaves of Anthocephalus chinensis

Anthocephalusine A ( 1 ) and 3β‐isodihydrocadambine 4‐oxide ( 2 ) were isolated from the leaves of Anthocephalus chinensis (Rubiaceae), together with five known compounds. The structures were established by spectroscopic methods including 2D‐NMR analyses.     

Two New Indole Alkaloids from Tabernaemontana hystrix Steud. (Apocynaceae)

Two new monoterpene indole alkaloids named ibogamine‐7,8‐dione ( 1 ) and 12‐methoxyvoachalotine ( 2 ), and eight known ones, coronaridine ( 3 ), coronaridine hydroxyindolenine ( 4 ), 5‐oxocoronaridine ( 5 ), 3‐oxocoronaridine hydroxyindolenine ( 6 ), 3‐oxocoronaridine ( 7 ), vobasine ( 8 ), ibogamine ( 9 ), and olivacine ( 10 ), were isolated from a CH₂Cl₂ extract of the root bark from Tabernaemontana hystrix. The structures of the compounds were elucidated on the basis of spectroscopic data analyses, mainly ¹H‐ and ¹³C‐NMR, including 2D experiments (¹H,¹H‐COSY, HMBC, and HMQC).     

云南萝芙木花新吲哚生物碱

从云南萝芙木(Rauvolfia yunnanensis Tsiang)花乙酸乙酯提取物中分离得到9个化合物(其中4个为吲哚类生物碱), 即(18Z)-11-methoxypicrinine(1), caberoline(2), 11-methoxystrictamine(3)和strictamine(4), 以及russulamide(5), ursolic acid(6), urs-12(13)-en-3α-yl acetate(7), β-amyryl nonanoate(8)和β-sitosterol(9); 采用UV, IR, MS和1D, 2D NMR方法对化合物的结构进行了鉴定, 其中化合物1为新吲哚生物碱, 化合物5, 7和8系首次从该植物中分离得到, 但未得到利血平和育亨宾.     

Alkaloids from Ochrosia borbonica

Ten new monoterpenoid indole alkaloids, ochroborines A and B ( 1 and 2 , resp.), 10‐hydroxyisovallesiachotamine ( 3 ), 10‐hydroxyisositsirikine ( 4 ), 10,11‐dimethoxysitsirikine ( 5 ), 10‐methoxyapoyohimbine ( 6 ), 10‐hydroxyakuammidine ( 7 ), akuammidine 17‐O‐β‐D ‐glucoside ( 8 ), 15α‐hydroxyapparicine ( 9 ), and 15α‐hydroxy‐10‐methoxyapparicine ( 10 ), and 24 known alkaloids were isolated from leaves and twigs of Ochrosia borbonica J. F.Gmel . These structures were elucidated based on 1D‐ and 2D‐NMR, FT‐IR, UV, and MS data. 10‐Hydroxyisovallesiachotamine ( 3 ), ellipticine, and 10‐methoxyellipticine showed cytotoxic activities against five human cancer cell lines.     

Three New Indole Alkaloids from the Leaves of Kopsia officinalis

Three new indole alkaloids, 11,12‐de(methylenedioxy)danuphylline ( 1 ), methyl (2β,11β,12β,19α)‐6,7‐didehydro‐8,21‐dioxo‐11,21‐cycloaspidospermidine‐2‐carboxylate ( 2 ), and (2β,5β)‐aspidofractinin‐16‐ol ( 3 ) were isolated from Kopsia officinalis, together with 16 known compounds. Their structures were determined by spectroscopic methods. The isolated known compound (?)‐12‐methoxykopsinaline displayed antimanic effects in Drosophila, with an IC₅₀ value of 12.5 μg/ml.     

Two Novel Plumeran Indole Alkaloids Isolated from Aspidosperma cylindrocarpon (Apocynaceae)

Two novel indole alkaloids with plumeran skeleton, N‐benzoyl‐12‐demethoxycylindrocarine and N‐cinnamoyl‐12‐demethoxycylindrocarine ( 1 and 2 , resp.), were isolated from the MeOH extract of the stem bark of Aspidosperma cylindrocarpon Müll .Arg . These compounds were obtained by high‐speed counter‐current chromatography, and their structures were elucidated on the basis of their NMR (1D and 2D) data. They were tested in vitro against chloroquine‐resistant strains of Plasmodium falciparum, and only 2 showed a weak activity (IC₅₀ 127.97 ng/ml with respect to the standard drug). Several other known compounds, comprising steroids, flavonoids, the rarely found atraric acid, as well as the previously reported alkaloid 3 , were also isolated by conventional chromatographic techniques.     

A New Lycopodine Alkaloid from Phlegmariurus yunnanensis Ching

A new lycopodine alkaloid, 15α‐methyllycopodane‐5β,6β‐diol N‐oxide ( 1 ), was isolated from the whole plants of Phlegmariurus yunnanensis Ching , together with the two known alkaloids 15α‐methyllycopodane‐5β,6β‐diol ( 2 ) and lycoposerramine H ( 3 ), and four serratene‐type triterpenoids, serratenediol‐3‐acetate ( 4 ), serratenediol ( 5 ), lycocryptol ( 6 ), and serratriol ( 7 ). Their structures were elucidated on the basis of spectroscopic analyses, including HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and NOESY.     

Structure and Dynamic of Three Indole Alkaloids from the Campylospermum Genus (Ochnaceae)

A new indole alkaloid, calanthumindole ( 4 ), and three known biflavonoids, amentoflavone, sequoiaflavone, and podoscarpusflavone B, were isolated from Campylospermum calanthum (Ochnaceae). Calanthumindole is a new indole alkaloid of the serotobenine family characterized by the presence of a C?C bond between atoms C(7′) and C(8′) of the furan ring. This is the first compound to have a fully unsaturated furan ring among the members of this family. The combination of NMR and DFT allowed the determination and comparison of the 3D structures and relevant conformational characteristics of serotobenine ( 1 ), flavumindole ( 2 ), and calanthumindole ( 4 ).     

Alkaloids of NIRAM,natural dye from Polygonum tinctorium,and their anti-inflammatory activities

Phytochemical investigation of EtOH extract of NIRAM, natural dye from Polygonum tinctorium, resulted in the purification of nine alkaloid compounds (1–9) including four new compounds (1–4). Structures of these new compounds were elucidated by 1D and 2D NMR (¹H and ¹³C NMR, ¹H–¹H COSY, ¹H–¹³C HSQC, ¹H–¹³C HMBC), IR, UV, HR-ESI-MS, and ECD spectra. Isolated compounds (1–9) were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells. Compounds 1–3, 5, and 7 showed potent NO production inhibitory activities, with IC₅₀ values of 3.88–22.87 μM.     

Flavonoid Aglycones and Indole Alkaloids from the Roots of Acacia Confusa

From the methanolic extract of the roots of Acacia confusa Merr. (Leguminosae), (‐)‐2,3‐cis‐3,4‐cis‐4′‐methoxy‐3,3′,4,7,8‐pentahydroxyflavan ( 1 ), (‐)‐2,3‐cis‐3,4‐cis‐3,3′,4,4′,7,8‐hexahydroxyflavan ( 2 ), (‐)‐2,3‐trans‐3′,4′,7,8‐tetrahydroxydihydroflavonol ( 3 ), (+)‐catechin ( 4 ), (‐)‐epicatechin ( 5 ), 3′,4′,7,8‐tetrahydroxyflavonol ( 6 ) together with N‐methyltryptamine ( 7 ) and N,N‐dimethyltryptamine ( 8 ) were isolated, and their structures were established by analysis of their spectroscopic data. Among them, compound 1 was a new flavonoid. Additionally, the results of chromatographic bioassay on lettuce seeds indicated that compounds 7 and 8 exhibited significant phytotoxicity at a concentration lower than 14 mM.