The Diterpenoid Alkaloids of Consolida ambigua

Pelletier, S. William; Sawhney, Rajinder S.; Desai, H. K.; Mody, Naresh V.

doi:10.1021/np50009a011

Cited by 43 publications

(43 citation statements)

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“…The known alkaloids, delphatine (Pelletier et al, 1980), lappaconitine (Ulubelen et al, 2002), puberanine (Yu quan De and Das, 1983), N-acetylsepaconitine (TelÕnov et al, 1988), a new lycoctonine-type norditerpenoid alkaloid swatinine (1) and a benzene derivative 4-[2-(methoxycarbonyl)anilino]-4-oxobutanoic acid (2) have been isolated from this plant.…”

Section: Resultsmentioning

confidence: 99%

Alkaloids of Aconitum laeve and their anti-inflammatory, antioxidant and tyrosinase inhibition activities

et al. 2005

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Section: Resultsmentioning

confidence: 99%

Alkaloids of Aconitum laeve and their anti-inflammatory, antioxidant and tyrosinase inhibition activities

et al. 2005

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“…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.…”

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confidence: 76%

Diterpenoid Alkaloids from Delphinium tatsienense

Chen

Liu

et al. 2011

Helvetica Chimica Acta

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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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“…8,9) The NMR spectra of compound 4 lacked an N-ethyl group when compared with anthranoyl-lycoctonine (5). 12) Except for this point, the 1 H-NMR spectra of the two alkaloids are very similar. Comparison of the 13 C-NMR data of 4 and 5 led to the structure of jiufengtine as 4, an N-deethyl derivative of anthranoyl-lycoctonine (5) and revision of the assignments (Table 2) for C-5, C-9, C-10, C-13 of the 13 C-NMR spectrum of 4.…”

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confidence: 87%

New C 19-Diterpenoid Alkaloids from the Roots of Delphinium potaninii var. jiufengshanense.

Shen

Zhou

Chen

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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The plants Delphinium potaninii W. T. WANG and its variety D. potaninii var. jiufengshanense W. J. ZHANG et G. H. CHEN 1) grow in Sichuan province, China. Their roots are used as a folk medicine for rheumatism and neuralgia. Our investigations showed that these two plants contain mainly lycoctonine-type alkaloids.2-7) In a continuing search for new active alkaloids two new C 19 -diterpenoid alkaloids, jiufengdine (1) and jiufengtine (4), were isolated from the roots of D. potaninii var. jiufengshanense. We report here the isolation and structures of these new alkaloids. Results and DiscussionJiufengdine (1) [d H 6.67, 6.67, 7.29, each 1H, m, 7.79 (1H, dd, Jϭ8.2, 1.6 Hz); d C see Table 1] Since a proton-triplet at d 4.79 (Jϭ5.0 Hz) was attributable to 14b-H, this is true in many C 19 -diterpenoid alkaloids bearing an ester group at C-14, 8,9) especially in the presence of long-range 1 H-13 C correlations HMBC of the 14-H with the carbonyl carbon (d 176.8) in the isopentanoate moiety, indicating the presence of the 14-isopentanoyl group. Similarly, the remaining anthranoyl group could be located at C-18 due to the 1 H- 13C long-range correlations (HMBC) between H 2 -18 (d H 4.10, 4.15) and the anthranoyl carbonyl carbon (d C 167.7). Compared with elanine (2), 10) the 1 H-NMR spectrum of jiufengdine (1) gave an additional NH 2 group. Except for those differences, the 13 C-NMR data (Table 1) of (1) and elanine (2) are very similar, thus leading to the structure of jiufengdine as 1. Meanwhile, the stereochemistry of C-2Ј in 1 could be deduced temporarily as S only based on comparison of the 13 C-NMR data with glaucedine (3). 11)Assignments of 1 H-and 13 C-NMR data were made by careful analysis of the spectra, including 1 H-1 H COSY, HMQC and HMBC, in meanwhile, also leading to suggestion of revision of the assignments (Table 1) for C-5, C-9, C-10, and C-13 of the 13 C-NMR spectrum of elanine (2). Jiufengtine (4) ). The NMR spectra of 4 revealed the presence of four methoxyls (d H 3.31, 3.34, 3.37, 3.42; d C 55.7, 56.2, 57.7, 58.0), and an anthranoyl [d H 6.64, 6.69, 7.29, 7.76 (each 1H); d C see Table 2] group. Compound 4 was considered to be a lycoctonine-type alkaloid by comparison of the NMR properities with many known C 19 -diterpenoid alkaloids.8,9) The 1H-triplet signal at d 3.62 (Jϭ4.8 Hz) could be assigned to 14b-H based on comparison with many alkaloids bearing a methoxyl at C-14.8,9) The NMR spectra of compound 4 lacked an N-ethyl group when compared with anthranoyl-lycoctonine (5).12) Except for this point, the 1 H-NMR spectra of the two alkaloids are very similar. Comparison of the 13 C-NMR data of 4 and 5 led to the structure of jiufengtine as 4, an N-deethyl derivative of anthranoyl-lycoctonine (5) and revision of the assignments (Table 2) for C-5, C-9, C-10, C-13 of the 13 C-NMR spectrum of 4. In addition, as compared with 5, the 13 C-NMR spectrum of 4 clearly showed changes in the chemical shifts of C-1, C-2, C-3, C-5, C-7, C-10, C-17, and C-19 caused by N-deethylation, as in N-deethyldelphatine...

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The Diterpenoid Alkaloids of Consolida ambigua

Cited by 43 publications

References 7 publications

Alkaloids of Aconitum laeve and their anti-inflammatory, antioxidant and tyrosinase inhibition activities

Alkaloids of Aconitum laeve and their anti-inflammatory, antioxidant and tyrosinase inhibition activities

Diterpenoid Alkaloids from Delphinium tatsienense

New C 19-Diterpenoid Alkaloids from the Roots of Delphinium potaninii var. jiufengshanense.

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