Indole alkaloids from Vinca major and V. minor growing in Turkey

A new indole alkaloid, 11-hydroxypolyneuridine, was isolated from Vinca major subsp. major L. and the known indole alkaloids vallesiachotamine and isovallesiachotamine from Vinca minor L. This is the first report on the alkaloids of both Vinca species growing in Turkey; vallesiachotamine and isovallesiachotamine were isolated from a Vinca species for the first time. V. minor may be considered as a new source for these two alkaloids due to their occurrence in high amount in the aerial parts of the plant. The alkaloid extracts of the two Vinca species were found to have high lipid peroxidation inhibitory and DPPH radical scavenging activities. Anticholinesterase activity of the extracts was also very strong.     

HPLC determination of majdine in Vinca herbacea

A reliable HPLC method coupled with DAD detection was developed and validated for determination of majdine in Vinca herbacea. The chromatographic separation was carried out on a Symmetry C18 column (250 mm x 4.6 mm, 5 microm, Waters) with an isocratic solvent system of 25 mM potassium phosphate buffer (pH = 3.0)-acetonitrile. UV detection was performed at 225 nm. Good linear behavior over the investigated concentration range was observed with the value of r2 > 0.9978. The method was reproducible with intra- and inter-day variations of less than 4.38%. The proposed method was linear, accurate, precise and specific. The validated method was successfully applied to quantify majdine in various parts of V. herbacea, which was collected during the flowering months of April and May. The results indicated that the developed HPLC method could be used for the quality control of V. herbacea and for the standardization of its extracts in majdine.     

On the elucidation of the mechanism of Vinca alkaloid fluorination in superacidic medium

Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20' activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments unambiguously revealed the involvement of a 1,2-hydride shift mechanism.     

Vinca alkaloids. XXXII. Microbiological conversions of vindoline, a major alkaloid from Vinca rosea L

Vindoline, a major alkaloid from Vinca rosea _L was subjected to microbiological conversion using Streptomyces cultures. Several new metabolites were isolated and their structures elucidated.     

Zur Kenntnis der Alkaloide aus Vinca minor L.

Zusammenfassung Aus Vinca minor L. wurde neben Vincamin das neue Alkaloid Isovincamin isoliert. Beide isomeren Alkaloide werden physikalisch charakterisiert.Mit 4 Abbildungen.     

Nachweis von Desacetylakuammilin und 10-Methoxy-desacetylakuammilin in Vinca minor L. 147. Mitteilung über Alkaloide

The two indole alkaloids desacetylakuammiline ( 2 ) and 10-methoxy-desacetylakuammiline ( 4 ) were shown to occure in the upper parts of the small periwinkel Vinca minor L. The structure of the hitherto unknown 10-methoxy-desacetylakuammiline was established on the bases of chemical, spectroscopic and o.r.d. evidence.     

Alkaloids of Vinca major

Summary 1. From the epigeal part ofVinca major have been isolated the known bases akuammicine, vincamajine, vincamajoridine, and ervine, and the new alkaloid majorinine with the composition C₂₂H₂₄N₂O₄, mp 195–196°C.2. On the basis of chemical transformations and IR, UV, mass, and PMR spectra using the methods of double resonance collapse and INDOR the structure of 21-hydroxy-10-methoxyvinorine and the stereochemistry (I) have been established for majorinine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 382–387, May–June, 1977.     

The Phytochemical Analysis of Vinca L. Species Leaf Extracts Is Correlated with the Antioxidant,Antibacterial, and Antitumor Effects

The phytochemical analysis of Vinca minor, V. herbacea, V. major, and V. major var. variegata leaf extracts showed species-dependent antioxidant, antibacterial, and cytotoxic effects correlated with the identified phytoconstituents. Vincamine was present in V. minor, V. major, and V. major var. variegata, while V. minor had the richest alkaloid content, followed by V. herbacea. V. major var. variegata was richest in flavonoids and the highest total phenolic content was found in V. herbacea which also had elevated levels of rutin. Consequently, V. herbacea had the highest antioxidant activity followed by V. major var. variegata. Whereas, the lowest one was of V. major. The V. minor extract showed the most efficient inhibitory effect against both Staphylococcus aureus and E. coli. On the other hand, V. herbacea had a good anti-bacterial potential only against S. aureus, which was most affected at morphological levels, as indicated by scanning electron microscopy. The Vinca extracts acted in a dose-depended manner against HaCaT keratinocytes and A375 melanoma cells and moreover, with effects on the ultrastructure, nitric oxide concentration, and lactate dehydrogenase release. Therefore, the Vinca species could be exploited further for the development of alternative treatments in bacterial infections or as anticancer adjuvants.     

A method for the quantitative determination of vincamine in the epigeal part of Vinca erecta

Summary An extraction-photometric method for the determination of vincamine in its raw material — the epigeal part ofVinca erecta — has been developed.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 65–66, January, 1971.     

Optimization of the separation of Vinca alkaloids by nonaqueous capillary electrophoresis

A rapid method for the determination of Vinca alkaloids by nonaqueous capillary electrophoresis with diode array detection has been developed. A group of 11 alkaloids (catharanthine, vinorelbine, anhydrovinblastine, vinflunine, vindoline, 4-O-deacetylvinorelbine, 4-O-deacetylvinflunine, vindesine, vinblastine, 4'-deoxy-20',20'-difluorovinblastine, vincristine) could be readily separated within 10 min. The compounds were separated using a capillary of 38 cm effective length, a running buffer composed of 50 mM ammonium acetate and 0.6 M acetic acid in a methanol-acetonitrile (75:25, v/v) mixture. A constant voltage of 25 kV with a ramp time of 1 min and a 344.7 x 10(3) Pa pressure, applied simultaneously to inlet and outlet buffer vials, were used during sample analysis. Five of these alkaloids were selected for optimization of the separation and for validation studies with respect to specificity, linearity, range, limits of quantification and detection and then accuracy. The feasibility of the assay was demonstrated by analyzing a commercial sample of vinorelbine (Navelbine, ampoule at 10 mg/ml of vinorelbine base). The results were compared with a high-performance liquid chromatography method.     

The structure of majdine, pseudokopsinine, and vinervinine

Summary Three new bases have been isolated fromVinca erecta andV. major. The structures of majdine, pseudokopsinine, and vinervinine have been established.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 5, pp. 310–315, 1967     

Indole alkaloids from cultivated Vinca major

Nine new indole alkaloids, vinmajines A–I (1–9), and 43 known indole alkaloids were isolated from cultivated Vinca major in Kunming. The new structures were elucidated by extensive spectroscopic and quantum theory analysis. In addition, the results also supported that types of indole alkaloids from V. major might be influenced significantly by the ecological environment.     

Vinmajorines C – E,Monoterpenoid Indole Alkaloids from Vinca major

Three new monoterpenoid indole alkaloids, vinmajorines C–E ( 1 – 3 ), along with 18 known analogues ( 4 – 21 ), were isolated from the whole plants of Vinca major. The new structures were elucidated as (5α,15β,16R,17α,19β,20α,21β)‐10,17‐dimethoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐19‐ol ( 1 ), (5α,15β,16R,17α,20α,21β)‐10‐methoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐17‐ol ( 2 ), and (5α,15β,16R,17α,20α,21β)‐10‐methoxy‐21‐methyl‐18‐oxa‐5,16‐cycloyohimban‐17‐yl acetate ( 3 ), respectively, by extensive NMR and MS analysis and comparison with known compounds. Compounds 1 – 3 were evaluated for their cytotoxic activities against five human cancer cell lines, compounds 1 and 3 showing moderate cytotoxic activities.     

Untersuchungen über die Biosynthese der Cyclite, 20. Mitt.: Über die Bildung vonl-Bornesit inVinca-Arten

Incorporation experiments with radioactively labelledmyo-inositol andd-glucose inVinca minor andVinca rosea make it very probable that in these plantsl-bornesitol is formed through direct methylation ofmyo-inositol.     

Modifications on the basic skeletons of vinblastine and vincristine

The synthetic investigation of biologically active natural compounds serves two main purposes: (i) the total synthesis of alkaloids and their analogues; (ii) modification of the structures for producing more selective, more effective, or less toxic derivatives. In the chemistry of dimeric Vinca alkaloids enormous efforts have been directed towards synthesizing new derivatives of the antitumor agents vinblastine and vincristine so as to obtain novel compounds with improved therapeutic properties.     

Regulation of vincamine biosynthesis and associated growth promoting effects through abiotic elicitation,cyclooxygenase inhibition,and precursor feeding of bioreactor grown Vinca minor hairy roots

Hydroxylase/acetyltransferase elicitors and cyclooxygenase inhibitor along with various precursors from primary shikimate and secoiridoid pools have been fortified to vincamine less hairy root clone of Vinca minor to determine the regulatory factors associated with vincamine biosynthesis. Growth kinetic studies revealed that acetyltransferase elicitor acetic anhydride and terpenoid precursor loganin significantly reduce the growth either supplemented alone or in combination (GI?=?140.6?±?18.5 to 246.7?±?24.3), while shikimate and tryptophan trigger biomass accumulation (GI?=?440.2?±?31.5 to 540.5?±?40.3). Loganin also downregulates total alkaloid biosynthesis. Maximum flux towards vincamine production (0.017?±?0.001 % dry wt.) was obtained when 20-day-old hairy roots were fortified with secologanin (10 mg/l) along with tryptophan (100 mg/l), naproxen (8.4 mg/l), hydrogen peroxide (20 μg/l), and acetic anhydride (32.4 mg/l). This was supported by RT PCR (qPCR) analysis where 2- and 3-fold increase in tryptophan decarboxylase (TDC; RQ?=?2.0?±?0.09) and strictosidine synthase (STR; RQ?=?3.3?±?0.36) activity, respectively, was recorded. The analysis of variance (ANOVA) for growth kinetics, total alkaloid content, and gene expression studies favored highly significant data (P?<?0.05–0.01). Above treated hairy roots were also up-scaled in a 5-l stirred-tank bioreactor where a 40-day cycle yielded 8-fold increase in fresh root mass.     

Total synthesis of indole and dihydroindole alkaloids. VI. The total synthesis of some monomeric vinca alkaloids: dl-vincadine, dl-vincaminoreine, dl-vincaminorine, dl-vincadifformine, dl-minovine and dl-vincaminoridine.

A synthetic approach to a variety of monomeric Vinca alkaloids is described. The sequence involves, among its crucial phases, the generation of appropriate nine-membered ring intermediates which are then elaborated via a transannular cyclization approach to the desired natural products.     

Vinervine — A new alkaloid from the aboveground part of Vinca erecta RGL. ET schmalh

Summary From the aboveground part ofV. erecta gathered in the Shargun' settlement in the Surkhan-Darya region 1% of total alkaloids was isolated, and in the separation of these the bases vincanidine and a new phenolic base vinervine (C₂₀H₂₂O₃N₂) were obtained. Vinervine is an alkaloid of the 2-methyleneindoline group.Translated from Izvestiya Akademii Nauk SSSR, Khimicheskaya, No. 12, pp. 2152–2155, December, 1965     

Difference in the signals of the N-H proton in the NMR spectra of the indole,indoline, and hydroxyindole alkaloids

Chemistry of Natural Compounds - On the basis of the results of measurements of the chemical shifts of the signal of the NH proton in Vinca alkaloids, it has been established that the CS of the NH...     

Difforlemenine,alcaloide nouveau de vinca difformis pourr., determination de structure par RMN du 1H à 400 MHz.

The structure of a new alkaloïd of 2-acylindole type from leaves of $\text{Vinca difformis}$ Pourr. (Apocynacées) has been determinated.