European Journal of Chemistry

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

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Shahobiddin Adizov
Bakhodir Tashkhodjaev

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.


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Adizov, S.; Tashkhodjaev, B. Indole Type Akuammiline from Vinca Erecta: Crystal Structure of 10-OAc-Akuammine. Eur. J. Chem. 2019, 10, 345-349.

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References

[1]. Kurmukov, A. G.; Zakirov, U. B. Alkaloids and medicinal herb preparations, First edition, Ibn Sina Publ. , Tashkent, Uzbekistan, 1992.

[2]. Sadriddinov, F. S.; Kurmukov, A. G. Pharmacology of plant alkaloids and their use in medicine, Tashkent, Medicina, 1980.

[3]. Aripov, Kh. N., Results of the study of alkaloid plants, Edition FAN, Tashkent, 1993.

[4]. Azimova, S. S.; Yunusov, M. S. Natural Compounds: Alkaloids. Plant Sources, Structure and Properties; Springer, Science & Business Media: New York, NY, USA, 2013.
https://doi.org/10.1007/978-1-4614-0560-3

[5]. Mashkovskiy, M. D. Medical product. Abu Ali Ibn Sina Publ., Tashkent, Uzbekistan, 1998.

[6]. Le-Men J.; Taylor, W. I. J. Cellular Mol. Life Sci. Exp. 1965, 21, 508-510.
https://doi.org/10.1007/BF02138961

[7]. Rakhimov, D. A.; Il'yasova, Kh. T.; Malikov, V. M.; Yunusov, S. Yu. Chem. Nat. Comp. 1969, 5, 440-445.
https://doi.org/10.1007/BF00568586

[8]. Chatterjee, A.; Mukherjee, B.; Ray, A. Tetrahedron Lett. 1965, 41, 3633-3637.
https://doi.org/10.1016/S0040-4039(01)89147-4

[9]. Yagudaev, M. R. Chem. Nat. Comp. 1985, 21, 131-135.
https://doi.org/10.1080/10437797.1985.10671721

[10]. Il'yasova, Kh. T.; Malikov, V. M.; Yunusov, S. Y. Chem. Nat. Comp. 1968, 4, 278-278.
https://doi.org/10.1007/BF00568553

[11]. Il'yasova, Kh. T.; Malikov, V. M.; Yunusov, S. Y. Chem. Nat. Comp. 1971, 7, 155-156.
https://doi.org/10.1007/BF00568687

[12]. Abdurakhimova, N.; Yuldashev, P. Kh.; Yunusov, S. Y. Dan. UzSSR 1964, 4, 33-37.

[13]. Rakhimov, D. A.; Sharipov, M. R.; Malikov, V. M.; Yunusov, S. Y. Chem. Nat. Comp. 1971, 7, 663-663.
https://doi.org/10.1007/BF00568447

[14]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[15]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[16]. Ghosh, R.; Roychowdhury, P.; Chattopadhyay, D.; Iitaka, Y. Acta Crystallogr. C 1988, 44, 2151-2154.
https://doi.org/10.1107/S0108270188009114

[17]. Lim, S. H.; Low, Y. Y.; Sinniah, S. K.; Yong, K. T.; Sim, K. S.; Kam, T. S. Phytochemistry 2014, 98, 204-215.
https://doi.org/10.1016/j.phytochem.2013.11.014

[18]. Buckingham, J.; Baggaley, K. H.; Roberts, A. D.; Szabo L. F. Second Edition, Dictionary of alkaloids, CRC Press, London, UK, 2010.

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