European Journal of Chemistry 2019, 10(4), 345-349 | doi: https://doi.org/10.5155/eurjchem.10.4.345-349.1898 | Get rights and content






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Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine


Shahobiddin Adizov (1,*) orcid , Bakhodir Tashkhodjaev (2) orcid

(1) Laboratory of High-Molecular Plant Substances and Physical Methods of Research, Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Uzbekistan
(2) Physical methods of research, Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, Uzbekistan
(*) Corresponding Author

Received: 24 May 2019 | Revised: 21 Aug 2019 | Accepted: 24 Aug 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

Abstract


Single crystal X-ray diffraction has established the absolute configuration of the indole alkaloids from Vinca erecta such as akuammiline-o-acyl derivative of akuammine with a 3D stable polycyclic framework. Crystal data for C24H28N2O5: orthorhombic, space group P212121 (no. 19), a = 7.349(3) Å, b = 16.099(5) Å, c = 17.323(5) Å, = 2049.5(12) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 0.789 mm-1, Dcalc = 1.376 g/cm3, 1742 reflections measured (7.496° ≤ 2Θ ≤ 119.792°), 1742 unique (Rsigma = 0.0374) which were used in all calculations. The final R1 was 0.0608 (I > 2σ(I)) and wR2 was 0.1680 (all data). The polycyclic framework of the well-known picrinine and akuammine is compared. The ether bridges located in different positions of the framework and forming five-membered cycles do not change the conformation of the polycyclic akuammiline framework. In V. erecta alkaloids, the exomethylene fragment (C18-C19=C20-C21) of the polycyclic backbone always takes on the E-condition.


Keywords


Chirality; Akuammine; Akuammiline; Indole alkaloids; Absolute configuration; Single crystal structure

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DOI: 10.5155/eurjchem.10.4.345-349.1898

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Funding information


The work was carried out according to the fundamental research projects №PZ-20170929764, №Т.4-18 and ВА-ФА-Ф6-010 S. Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences Republic of Uzbekistan.

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Adizov, S.; Tashkhodjaev, B. Eur. J. Chem. 2019, 10(4), 345-349. doi:10.5155/eurjchem.10.4.345-349.1898
Adizov, S.; Tashkhodjaev, B. Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine. Eur. J. Chem. 2019, 10(4), 345-349. doi:10.5155/eurjchem.10.4.345-349.1898
Adizov, S., & Tashkhodjaev, B. (2019). Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine. European Journal of Chemistry, 10(4), 345-349. doi:10.5155/eurjchem.10.4.345-349.1898
Adizov, Shahobiddin, & Bakhodir Tashkhodjaev. "Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine." European Journal of Chemistry [Online], 10.4 (2019): 345-349. Web. 10 Apr. 2020
Adizov, Shahobiddin, AND Tashkhodjaev, Bakhodir. "Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.4.345-349.1898

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