N-oxides of homoaporphine alkaloids from Merendera raddeana

Yusupov, M. K.; Chommadov, B.; Aslanov, Kh. A.

doi:10.1007/bf00629836

Cited by 4 publications

(5 citation statements)

References 6 publications

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“…1). A key difference was an N-oxide moiety, consistent with a 16 amu difference in the HRMS data of compound 3 relative to 2, indicating oxidation of the tertiary nitrogen into N-oxide to give (+)-O-methylkreysigine-Noxide, which was reported previously as a semisynthetic product [31]. Inspection of the NMR data of 3 showed signals characteristic of two singlet aromatic protons (δ H /δ C 6.74/111.4, H-3 and 6.59/107.3, H-9), nine aliphatic protons (δ H 3.17, H 2 -4; 3.84 and 3.55, H 2 -5; 3.86, H-6a; 2.06 and 2.97, H 2 -7 and 2.22 and 2.58, H 2 -8), one N-methyl group (δ H /δ C S5, Supplementary Data).…”

Section: Resultssupporting

confidence: 82%

Phenethyisoquinoline alkaloids from the leaves of Androcymbium palaestinum

et al. 2020

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Thirteen compounds were isolated from the methanolic extract of the leaves of Androcymbium palaestinum Baker (Colchicaceae). Of these, three were new, two were new natural products, and eight were known. The new isolated compounds were (+)-1-demethylandrocine (5), (−)andropalaestine (8), and (+)-2-demethyl-β-lumicolchicone (10), while the new natural products were (+)-O-methylkreysigine-N-oxide (3) and (+)-O,O-dimethylautumnaline (9). Moreover, two known compounds are reported for the first time from this species, specifically (−)-colchicine ( 11) and (−)-3-demethyldemecolcine (13). The structures of the isolated compounds were elucidated using a series of spectroscopic and spectrometric techniques, principally HRESIMS, 1D-NMR ( 1 H and 13 C-NMR) and 2D-NMR (COSY, edited-HSQC, and HMBC). ECD spectroscopy was used for assigning the absolute configurations of compounds 3, 5, and 10. The cytotoxic activities of the isolated compounds were evaluated using the MDA-MB-435 (melanoma), MDA-MB-231 (breast), and OVCAR3 (ovary) cancer cell lines. Compound 11 was the most potent against all tested cell lines, with IC 50 values of 12, 95 and 23 nM, respectively.

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Section: Resultssupporting

confidence: 82%

Phenethyisoquinoline alkaloids from the leaves of Androcymbium palaestinum

et al. 2020

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“…b-lumicolchicine was found in different parts of M. raddeana grows in Uzbekistan [154]. Seasonal variation in M. raddeanea organ alkaloids was also given.…”

Section: Terrestrial Cyclobutane-containing Alkaloidsmentioning

confidence: 98%

“…Psychogenic effects are absent [235]. Compound (154) had hypotensive and uterotonic activity [236]. Structures of compounds (152)- (154) are shown in Fig.…”

Section: Synthetic Analogs Of Natural Alkaloids With Cyclobutane Ringmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

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“…Also aerial parts of M. raddeana afforded colchicine, -lumicolchicine, Ndeacetyl-N-formylcolchicine, merenderine (bechuanine), kreisigine, O-methyl-kereisigine, cornigerine, and 2-and 3-demethylcolchicines. Seasonal variation in M. raddeanea organ alkaloids was given (Yusupov et al 1991).…”

Section: Accepted Manuscriptmentioning

confidence: 99%