The diterpene alkaloids: the structure and stereochemistry of heteratisine

Aneja, R.; Locke, David M.; Pelletier, S. W.

doi:10.1016/s0040-4020(01)93482-9

Cited by 23 publications

(2 citation statements)

References 20 publications

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“…Detailed studies by Pelletier on hetisine[ 30 ] atisine and heteratisine[ 31 32 33 ] in the years 1962–1964 helped in their structure elucidation. Further investigations on A. heterophyllum in 1967–1968 by Pelletier et al .…”

Section: Phytochemistrymentioning

confidence: 99%

Abhava pratinidhi dravya: A comparative phytochemistry of Ativisha, Musta and related species

Muthialu

Kuruvilla

Kumar

et al. 2015

J Ayurveda Integr Med

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Authentic Ativisha (Aconitum heterophyllum) is a rare, endangered Himalayan species. Ayurveda classical texts of c. 15th–16th century, introduced “abhava-pratinidhi dravya” concept, wherein Ativisha was categorized as an abhava dravya (unavailable drug) and Musta (Cyperus rotundus) was suggested as a pratinidhi dravya (substitute) for it. C. rotundus is a weed, abundantly available pan-India. Cryptocoryne spiralis (Naattu Athividayam) and Cyperus scariosus (Nagarmotha) are also traded as Ativisha and Musta, respectively. Yet, there are no scientific studies to validate the use of substitutes. A. heterophyllum bears no similarity in terms of botanical classification with the other candidates. This article reviews published literature with an emphasis to look for similar phytochemicals or groups of phytochemicals in the species that could contribute to similar pharmacological activities, thereby supporting the drug substitution from a bio-medical perspective. Alkaloids like atisine were found to be the main focus of studies on A. heterophyllum, whereas for the Cyperus spp., it was terpenoids like cyperene. Although alkaloids and terpenoids were reported from both species, alkaloids in C. rotundus and terpenoids in A. heterophyllum were minor constituents. Reports on phytochemicals on Cryptocoryne spiralis and C. scariosus were very limited. Despite no significant similarities in chemical profiles reported, the dravyaguna (Ayurvedic drug classification) of Ativisha and Musta was quite similar warranting further exploration into the bio-functional aspects of the drug materials.

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Section: Phytochemistrymentioning

confidence: 99%

Abhava pratinidhi dravya: A comparative phytochemistry of Ativisha, Musta and related species

Muthialu

Kuruvilla

Kumar

et al. 2015

J Ayurveda Integr Med

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“…For the isolation and idenfication of 6-benzoylheteratisine, see: Aneja et al (1973), Jacobs et al (1947), Nigmatullaev et al (2000). For antiarhythmic activity, see: Salimov et al (1996).…”

Section: Related Literaturementioning

confidence: 99%

(1α,8β)-6β-Benzoyloxy-6-dehydroxyheteratisine fromAconitum zeravschanicum

Tashkhodzhaev

Salimov

2009

Acta Cryst E

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The title compound, C29H37NO6, was isolated from Aconitum zeravschanicum and exhibits antiarhythmic activity. It is a derivative of the diterpenoid alkaloid heteratisine and as such the core framework of the molecule contains four six-membered, three seven-membered and one five-membered ring. The chair conformation of one of the methoxy-substituted six-membered rings is different from that observed in heteratisine hydrobromide monohydrate. In the latter case, this ring adopts a boat conformation due to a stabilizing intramolecular N—H⋯O hydrogen bond. In the crystal structure of the title compound, there is only one acidic H atom. This hydroxyl group forms an intermolecular O—H⋯O hydrogen bond that links molecules into infinite chains along the b axis.

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