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The molecular structures of two new C19 norditerpenoid alkaloids, 14-O-benzoyl-8-methoxybikhaconine [(1α,6α,14α,16β)-20-ethyl-13-hydroxy-1,6,8,16-tetramethoxy-4-methoxymethylaconitan-14-yl benzoate, C33H47NO8, (1)] and 14-O-benzoyl-8-ethoxybikhaconine [(1α,6α,14α,16β)-8-ethoxy-20-ethyl-13-hydroxy-1,6,16-trimethoxy-4-methoxymethylaconitan-14-yl benzoate, C34H49NO8, (2)], isolated for the first time from the roots of Aconitum chasmanthum Stapf ex Holmes of Pakistani origin, have been determined. The two alkaloids differ by one CH2 moiety in a side chain (8-methoxy versus 8-ethoxy), co-crystallize in a 65 (2):35 (2) ratio, i.e. 0.65C33H47NO8.0.35C34H49NO8, and are inseparable by thin-layer and column chromatography. The conformations of the rings in the two alkaloids are: A and E, chairs; D, half-chair; C and F, envelopes; and B, boat. The molecular dimensions are normal; the mean bond distances are Csp3—N 1.463 (6), Csp3—Csp3 1.54 (2), Csp3—O 1.41 (2), Csp2—O 1.342 (3) and C=O 1.204 (4) Å. There is a short intramolecular hydrogen bond with O...O and H...O distances of 2.556 (3) and 2.01 Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, 1

fcf

Structure factor file (CIF format)
Contains datablock c

CCDC reference: 130081

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