Dihydroindole Alkaloids Research Articles

Electro-Oligomerization of Vindoline

In a break from traditional oncolytic agents based on dimeric combinations [1] of catharanthine and vindoline [2] units, higher cytotoxicity of a designed dimeric vindoline is predicted [3] via its interfacial docking between α- and β-tubulins. Electrosynthesis potentially is a route to higher molecular weight analogs of vindoline. Out of the three dimers resulting from electrochemical oxidation of vindoline [4] only one was characterized; chemical formation of trimeric vindoline [5] has been reported.Even though vindoline is commonly referred to as a dihydro-indole alkaloid [6], its electrochemistry [7] is dominantly reflective of structurally related anilines. Like electro-polymerization of anilines, our work based on anodic cyclic voltammetry of vindoline suggests formation of vindoline oligomers that readily pass into solution.

Quick access to the core of mersicarpine through an SNAr strategy

A quick access to the core of dihydroindole alkaloid mersicarpine was developed based on straightforward transformations from readily available and inexpensive starting materials. The synthetic route features an aldol reaction, a Beckmann rearrangement for the synthesis of the δ-lactam, an intramolecular SNAr strategy for indoxyl heterocycle formation, and in situ autoxidation of indoxyl intermediate. The new strategy offered an alternative approach for the formation of an oxidized indoxyl moiety, which could potentially have a wider application in the total synthesis of indole alkaloids containing apparent or masked indoxyl moieties.

Mersicarpine, an Unusual Tetracyclic Dihydroindole Alkaloid Incorporating a Seven‐Membered Imine Ring.

A novel dihydroindole derivative, viz., mersicarpine, incorporating a novel tetracyclic carbon skeleton, containing a seven-membered imine ring, was obtained from a Malayan Kopsia species. The structure was established by spectroscopic analysis and a possible biogenetic pathway from a leuconolam precursor is presented.

Mersicarpine, an unusual tetracyclic dihydroindole alkaloid incorporating a seven-membered imine ring

A novel dihydroindole derivative, viz., mersicarpine, incorporating a novel tetracyclic carbon skeleton, containing a seven-membered imine ring, was obtained from a Malayan Kopsia species. The structure was established by spectroscopic analysis and a possible biogenetic pathway from a leuconolam precursor is presented.

Aspidospermidose: a new dihydroindole alkaloid from the leaves of Rhazya stricta

A new dihydroindole alkaloidal glycoside, aspidospermidose, has been isolated from the leaves of Rhazya stricta, and has been assigned structure (1) on the basis of spectral studies.

ChemInform Abstract: Bannucine (I), a New Dihydroindole Alkaloid from Catharanthus roseus (L) G.Don.

Chemischer InformationsdienstVolume 17, Issue 38 Natural Products ChemInform Abstract: Bannucine (I), a New Dihydroindole Alkaloid from Catharanthus roseus (L) G.Don. ATTA-UR-RAHMAN ATTA-UR-RAHMAN, ATTA-UR-RAHMAN ATTA-UR-RAHMANSearch for more papers by this authorI. ALI, I. ALISearch for more papers by this authorM. I. CHAUDHARY, M. I. CHAUDHARYSearch for more papers by this author ATTA-UR-RAHMAN ATTA-UR-RAHMAN, ATTA-UR-RAHMAN ATTA-UR-RAHMANSearch for more papers by this authorI. ALI, I. ALISearch for more papers by this authorM. I. CHAUDHARY, M. I. CHAUDHARYSearch for more papers by this author First published: September 23, 1986 https://doi.org/10.1002/chin.198638299AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume17, Issue38September 23, 1986 RelatedInformation

Bannucine ? a new dihydroindole alkaloid from Catharanthus roseus(L) G.Don

A new dihydroindole alkaloid, ‘bannucine,’ has been isolated from the leaves of Catharanthus roseus(L) G.Don, and has been found to have a five-membered lactam ring attached to the vindoline moiety.

Isolation and structure of a new alkaloid from rauwolfia serpentina benth

A new dihydroindole alkaloid sandwicolidine has been isolated from Rauwolfia serpentina and its structure elucidated through chemical and spectroscopic studies.

NMR investigation of alkaloids. III.13C NMR spectra and reconsideration of the stereochemistry of herbamine and herbadine

The stereochemistry previously proposed for herbamine (V) and herbadine (II) as C2-βH has been reconsidered on the basis of a comparative study of the13C NMR of these compounds and of vincamajine, quebrachidine, ajmaline, vincamajoreine, and majoridine, and it has been established unambiguously that herbamine and herbadine belong to the dihydroindole alkaloids with C2-αH, herbamine being C3-hydroxyvincamajine, and herbadine C6-hydroxyquebrachidine.

Les Alcaloïdes majoritaires duStrychnos scheffleridu Zaire

Leaves and stem barks of S. scheffleri GILG afforded eight dihydroindole alkaloids. Four tertiary monomers (O-methyl Na-acetylstrychnosplendine, Na-acetylstrychnosplendine, strychnobrasiline and strychnofendlerine) have been isolated from leaf material while stem barks yielded one tertiary monomer (desacetylisoretuline), one tertiary symmetrical dimer (bis-nordihydrotoxiferine) and two quaternary monomers (mavacurine and fluorocurine).

The alkaloids of Rauwolfia volkensii

The roots of Rauwolfia volkensii yielded 26 alkaloids comprising five main groups 3- sarpagan, akuammicine, heteroyohimbine with derived oxindole and anhydronium bases, yohimbine with 18-hydroxy-yohimbine and its derived esters, and dihydroindole alkaloids. The principal alkaloids were ajmaline (0.08 per cent) and reserpiline (0.15 per cent), and the reserpine yield (0.0007 per cent) was very low

Total Synthesis of Indole and Dihydroindole Alkaloids. XVIII. Isomers and analogues of vinblastine

AbstractThe synthesis and conformational analysis of (3′R)‐3‐hydroxyleurosidine (5), (3′S)‐3‐hydroxyleurosidine (10), (3′S)‐3‐acetoxy‐4′‐deoxyleurosidine (15), (3′R)‐3‐acetoxy‐4′‐deoxyleurosidine (23), (3′R)‐3‐acetoxy‐4′‐deoxyvinblastine (16), (3′S)‐3‐acetoxy‐4′‐deoxyleurosidine (28) is discussed.

Chromogenic reactions of Rauwolfia alkaloids after separation by thin-layer chromatography

Forty-one Rauwolfia alkaloids were tested using 11 chromogenic reagents. Ferric chlorid-perchloric acid reagent was preferred for general use. The dihydroindole alkaloids comprised the most readily definable group but aricine, 10, 11-dimethoxyheteroyohimbines, sarpagine and ar-substituted 18-hydroxy-yohimbines and their esters could be distinguished using various reagents.

Total synthesis of indole and dihydroindole alkaloids. XVII. The total synthesis of catharine and vinamidine (catharinine)

Oxidation of 16,18-dicarbomethoxycleavamine gave the epoxide (6) and the enamide (9). Similar oxidation of 3′,4′-dehydrovinblastine (8) or leurosine (7) gave the natural product catharine (3). Potassium permanganate oxidation of 7 or 8 gave 3R-hydroxyvinamidine (19) whereas similar oxidation of 4′-deoxyleurosidine (29) gave the alkaloid vinamidine (4).

Total synthesis of indole and dihydroindole alkaloids. XVI. Derivatives of vinblastine and vincristine: change of functionality in the vindoline unit

Studies describing the preparation of various derivatives of vinblastine and vincristine are presented. Vindoline (3) is transformed into a series of derivatives and the latter via Polonovski-type coupling with catharanthine (2) provide the bisindole alkaloid derivatives of the vinblastine series. Selective Jones' oxidation transforms the vinblastine family into the corresponding vincristine derivatives.

Total Synthesis of Indole and Dihydroindole Alkaloids. XV. Further Chemistry of Vindoline

AbstractThe general reactivity of various sites in the vindoline series has been investigated. The facility of electrophilic substitution at C(15) and the effect of steric crowding on reactions at C(4) are discussed. At the basic nitrogen sites, oxidations with mercuric acetate and potassium permanganate are also discussed.

Total synthesis of indole and dihydroindole alkaloids. 14. A total synthesis of vindoline

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of indole and dihydroindole alkaloids. 14. A total synthesis of vindolineJames P. Kutney, Ursula Bunzli-Trepp, Ka Kong Chan, Joao P. De Souza, Yutaka Fujise, Toshio Honda, Junki Katsube, Frederick K. Klein, Albert Leutwiler, and Cite this: J. Am. Chem. Soc. 1978, 100, 13, 4220–4224Publication Date (Print):June 1, 1978Publication History Published online1 May 2002Published inissue 1 June 1978https://doi.org/10.1021/ja00481a035RIGHTS & PERMISSIONSArticle Views505Altmetric-Citations41LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (660 KB) Get e-Alerts Get e-Alerts

Leaf Alkaloids of Rauwolfia cumminsii Stapf.

The leaves of Rauwolfia cumminsii Stapf yield at least 12 indole alkaloids. Two E–seco indole alkaloids (corynantheol and corynantheal), seven ajmalantype dihydroindole alkaloids (endolobine, norpurpeline, dihydronorpurpeline, normitoridine, norseredamine, nortetraphyllicine and seredamine–17–O–(3', 4', 5') trimethoxybenzoate), two sarpagan alkaloids (normacusine B–O–methyl and an incompletely characterised compound) and the indoline alkaloid picrinine were isolated. The apparent scarcity of Namethylated indoline alkaloids in the plant may prove to be significant.

Total Synthesis of Indole and Dihydroindole Alkaloids. XIII. Further Chemistry of Catharanthine

AbstractFurther investigations on the chemistry of catharanthine have provided information, valuable in the estimation of reactivity and steric requirements of the skeleton. Specific hydroxylations at C(3), C(4) and C(18) have allowed the preparation of several derivatives including (3R, 4 R)‐3‐hydroxy‐3, 4‐dihydrocatharanthine (7); (3R,4 R)‐3, 4‐dihydroxycatharanthinic acid lactone (15); 18‐decarbomethoxy‐18‐hydroxycatharanthine (40).

Inhibition of energy-transducing functions of chloroplasts by spegazzinine

The effects of spegazzinine, a dihydroindole alkaloid, on various energy-transducing functions of chloroplasts were studied. The following observations were made, (i) Spegazzinine inhibited both cyclic and noncyclic photophosphorylation in isolated spinach chloroplast. The I 50 value was about 80 μ m. Over a concentration range which gave marked inhibition of ÀTP synthesis, there was no effect on basal or uncoupled electron flow or light-induced proton accumulation by isolated thylakoids, while the fraction of electron transport stimulated by coupled phosphorylation was reduced to the basal level by spegazzinine. (ii) The regulatory effect of low concentrations of ATP on proton movements and electron transport was diminished by the alkaloid, (iii) Spegazzinine also inhibited with similar efficiency the ATPase activities of membrane-bound coupling factor 1 (CF 1) and of purified CF 1. One mole of spegazzinine per mole of CF 1 seemed to be required to inhibit the ATPase activity, (iv) The allosteric effect of ADP on ATPase activity was not affected by spegazzinine. (v) On the basis of these results it is concluded that spegazzinine acts as an energy transfer inhibitor of hotophosphorylation and that its site of action may be at or near the catalytic site of ATPase.