“…Because the structure of the alkaloid dicytocarpine (5) (7,8) depends on correlation with lycoctonine via a long sequence involving dictyocarpinine, 6,10-dimethyldeltamine, deltamine, delatine, delpheline, 6-0-methyldelpheline, and deoxylycoctonine (9, 10), we have confirmed the structure and stereochemistry of dictyocarpine by an Xray analysis of its acetone complex. Both browniine and dictyocarpine possess a 1 otmethoxyl group.…”
Browniine perchlorate crystallizes in the monoclinic space group P2V The structure was solved by multisolution methods and refined to an R of 0.078 for 2766 observed reflections. Dictyocarpine crystallizes from acetone as an acetone complex. The crystals are orthorhombic, space group P212121. The structure was solved by multisolution methods and refined to an R of 0.085 for 2483 observed reflections. These structural results require the configuration of the C(l)-methoxyl group in all C19-diterpenoid alkaloids related to lycoctonine to be revised from ß to a.Recently, we described the methylation of delsoline (1) with methyl iodide and sodium hydride to give the known alkaloid dephatine (2) (1). Because the a-configuration of the C(7)-hydroxyl group in delsoline is well established by chemical (2) and spectral data (3), we pointed out that delphatine must also bear a C( 1 )-ot-methoxyl
“…Because the structure of the alkaloid dicytocarpine (5) (7,8) depends on correlation with lycoctonine via a long sequence involving dictyocarpinine, 6,10-dimethyldeltamine, deltamine, delatine, delpheline, 6-0-methyldelpheline, and deoxylycoctonine (9, 10), we have confirmed the structure and stereochemistry of dictyocarpine by an Xray analysis of its acetone complex. Both browniine and dictyocarpine possess a 1 otmethoxyl group.…”
Browniine perchlorate crystallizes in the monoclinic space group P2V The structure was solved by multisolution methods and refined to an R of 0.078 for 2766 observed reflections. Dictyocarpine crystallizes from acetone as an acetone complex. The crystals are orthorhombic, space group P212121. The structure was solved by multisolution methods and refined to an R of 0.085 for 2483 observed reflections. These structural results require the configuration of the C(l)-methoxyl group in all C19-diterpenoid alkaloids related to lycoctonine to be revised from ß to a.Recently, we described the methylation of delsoline (1) with methyl iodide and sodium hydride to give the known alkaloid dephatine (2) (1). Because the a-configuration of the C(7)-hydroxyl group in delsoline is well established by chemical (2) and spectral data (3), we pointed out that delphatine must also bear a C( 1 )-ot-methoxyl
“…Previous investigations on the phytochemistry of this plant by the Pelletiers research group resulted in the isolation of more than ten diterpenoid alkaloids [6 -10]. Our present study on the whole plants of Delphinium tatsienense led to the identification of three new diterpenoid alkaloids, designated as tatsienenseines A -C (1 -3), besides twentytwo known diterpenoid alkaloids, i.e., majusine C [11], delbonine [12], 6-acetyldepheline [13] [14], deltatsine [7], browniine [15], 14-acetyldelcosine [15], 14-acetylbrowniine [15], postanisine F [16], ajacine [15], delcosine [17], leroyine 14-O-acetate [18], 7-acetylbarbaline [19], acetyldelgrandine [20], deacetylambiguine [6], ajadelphine [21], 14-deacetylnudicauline [22], delsoline [23], barbaline [19], delsemine A [23], delsemine B [23], tatsinine [23], and delgrandine [20]. These known compounds were identified by comparing their spectroscopic data with those reported in the literature.…”
Three new C 20 -diterpenoid alkaloids, along with twenty-two known alkaloids, were isolated from the whole herbs of Delphinium tatsienense. The new alkaloids include a vakognavine-type C 20 -diterpenoid alkaloid, designated as tatsienenseine A (1), and two hetisine-type C 20 -diterpenoid alkaloids, designated as tatsienenseines B (2) and C (3). Their structures were elucidated by IR, HR-ESI-MS, 1D-and 2D-NMR analyses.Introduction. -Diterpenoid alkaloids are believed to be the major bioactive components of the genus Delphinium [1 -4], a large genus within the Ranunculaceae family. As a class of structurally complex compounds, they possess a broad range of chemical and pharmacological properties, and also demonstrated a characteristic merit for chemotaxonomic considerations [1 -4]. Delphinium tatsienense Franch grows mainly in southwest Sichuan and northwest Yunnan of China [5]. Previous investigations on the phytochemistry of this plant by the Pelletiers research group resulted in the isolation of more than ten diterpenoid alkaloids [6 -10]. Our present study on the whole plants of Delphinium tatsienense led to the identification of three new diterpenoid alkaloids, designated as tatsienenseines A -C (1 -3), besides twentytwo known diterpenoid alkaloids, i.e., majusine C [20]. These known compounds were identified by comparing their spectroscopic data with those reported in the literature. Herein, we described the separation and structural elucidation of the three new alkaloids 1 -3.
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