Semi-synthesis and structural elucidation of brevicanines A–D, four new C19-diterpenoid alkaloids with rotameric phenomenon from Aconitum brevicalcaratum

Wang, Zhongsheng; Chen, Wei; Jiang, Haiyue; Gao, Feng; Zhou, Xian‐Li

doi:10.1016/j.fitote.2019.03.012

Cited by 9 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…When ester groups are present at C-8 and C-14, they exhibit acute toxicity [8]. In the past five years, 70 new compounds were discovered, with 65 obtained from Aconitum and 5 from Delphinium [32,34,38,[40][41][42][43][44][45][46][47][48][49][50][51][52][53][54]. The compounds were further discussed according to the presence of oxygen-containing groups connected at C-3, C-6, or C-15 positions.…”

Section: C18-dasmentioning

confidence: 99%

“…Notably, compounds 50-57, featuring a double bond between the N and C-19, were isolated from Aconitum [38,40,50]. Compounds 58-64 are linked to a 2-(2-methyl-4oxoquinazolin-3-yl) benzoate moiety at C-18 [49,54]. Compounds 58-63 exhibit rotational isomerism due to an unusual axial chiral phenyl-quinoline side chain at C-18, with the stereoisomerism studied by temperature-varying NMR techniques [49,54].…”

Section: C18-dasmentioning

confidence: 99%

See 1 more Smart Citation

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Wang,

Xin,

Sun

et al. 2024

Molecules

View full text Add to dashboard Cite

Terpenoid alkaloids are recognized as a class of compounds with limited numbers but potent biological activities, primarily derived from plants, with a minor proportion originating from animals and microorganisms. These alkaloids are synthesized from the same prenyl unit that forms the terpene skeleton, with the nitrogen atom introduced through β-aminoethanol, ethylamine, or methylamine, leading to a range of complex and diverse structures. Based on their skeleton type, they can be categorized into monoterpenes, sesquiterpenes, diterpenes, and triterpene alkaloids. To date, 289 natural terpenoid alkaloids, excluding triterpene alkaloids, have been identified in studies published between 2019 and 2024. These compounds demonstrate a spectrum of biological activities, including anti-inflammatory, antitumor, antibacterial, analgesic, and cardioprotective effects, making them promising candidates for further development. This review provides an overview of the sources, chemical structures, and biological activities of natural terpenoid alkaloids, serving as a reference for future research and applications in this area.

show abstract

Section: C18-dasmentioning

confidence: 99%

Section: C18-dasmentioning

confidence: 99%

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Wang,

Xin,

Sun

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

“…Wang and co‐workers isolated four new C 19 ‐diterpenoid alkaloids brevicanines A–D from the roots of Aconitum brevicalcaratum [50] and the semisynthesis of brevicanine A ( 95 ) was also accomplished by the same group in 2019 using parent diterpenoid scaconine ( 94 ) as a starting material [50] . At first, 2‐methyl‐4‐oxoquinazolin‐3‐yl)benzoic acid ( 93 ) was prepared according to the literature method use anthranilic acid ( 92 ), the pheromone of the black chafer Holotrichia as a starting material [51] .…”

Section: Semisynthesis At Room Temperature and Pharmacological Aspectsmentioning

confidence: 99%

“…The cytotoxic activity against two cell lines was also evaluated. However, it has been found that none of them showed potent inhibition against Michigan Cancer Foundation‐7 (MCF‐7) and HepG2 ( liver cancer cell line) in vitro [50] …”

Section: Semisynthesis At Room Temperature and Pharmacological Aspectsmentioning

confidence: 99%

Diterpenoids: Natural Distribution, Semisynthesis at Room Temperature and Pharmacological Aspects‐A Decade Update

Majhi¹

2020

ChemistrySelect

View full text Add to dashboard Cite

Diterpenoids are a wide and structurally diverse class of natural products and secondary metabolites obtained from four isoprene units joined in a head‐tail fashion. It has been extensively investigated that a semisynthesis is an essential tool for enhancing the biological activity of starting natural products. Different diterpenoids have been employed as starting materials for the synthesis of bioactive semisynthetic derivatives at room temperature in this review. Energy plays a profound role in chemical transformations. However, according to the sixth principle of green chemistry, the most successful route to save energy is to develop strategies/protocols that are able enough to perform the reactions at ambient temperature. This review is aimed to offer an overview of natural distributions of diterpenoids, design, and semisynthesis of diterpenoids at room temperature, and highlights biological activities of semisynthetic derivatives for the first time from 2010–2019.

show abstract

“…Our continued studies on the roots of A. novoluridum have resulted in the isolation of four new diterpenoid alkaloids, which were identified as novolunines D-F (1-3), 8-O-ethylbrevicanine C (4) (Figure 1). In addition, three known ones were isolated and identified as scaconine (5), 4 8-O-ethylscaconine (6) 5 and 14-O-acetyl-8-Omethyl-18-O-2-(2-metyl-4-oxo-4H-quinazolin-3-yl)benzoylcammaconine (7). 6 Herein, we report the isolation and structural elucidation of these compounds, as well as their cytotoxicity and inhibitory effect on NO production of RAW264.7 cells induced by LPS.…”

mentioning

confidence: 99%

New C19-Diterpeniod Alkaloids from Aconitum novoluridum

Zhou¹,

Huang²,

Deng³

et al. 2023

HETEROCYCLES

View full text Add to dashboard Cite

Four new C19-diterpenoid alkaloids novolunines D-F (1-3) and 8-Oethylbrevicanine C (4), were isolated from the root of Aconitum novoluridum. The structures of four new alkaloids were established on the basis of spectra data (HR-ESI-MS, 1D-and 2D-NMR). The anti-inflammatory activity of isolated alkaloids was also carried out. The Aconitum genus plants are known to contain a number of norditerpenoid and diterpenoid alkaloids. 1

show abstract

Semi-synthesis and structural elucidation of brevicanines A–D, four new C19-diterpenoid alkaloids with rotameric phenomenon from Aconitum brevicalcaratum

Cited by 9 publications

References 14 publications

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Exploring the Biomedical Potential of Terpenoid Alkaloids: Sources, Structures, and Activities

Diterpenoids: Natural Distribution, Semisynthesis at Room Temperature and Pharmacological Aspects‐A Decade Update

New C19-Diterpeniod Alkaloids from Aconitum novoluridum

Contact Info

Product

Resources

About