Four New Diterpenoid Alkaloids from the Roots of <i>Aconitum carmichaelii</i>

Li, Yu; Gao, Feng; Zhang, Ji-Fa; Zhou, Xian‐Li

doi:10.1002/cbdv.201800147

Cited by 11 publications

(9 citation statements)

References 23 publications

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“…Based on these data, we have already isolated and purified some of these compounds from their corresponding raw plant materials, including 8-dehydroxybikhaconine ( 13) and (19R)-acetonyltalatisamine (23) as new compounds from the roots of A. ouvrardianum. 10 Also, we reported nagaconitines A (36), B (34), C (20), and D (18) as new compounds from the roots of A. nagarum var. heterotrichum 11 and 14-anisoylliljestrandisine (32) from the roots of A. tsaii.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

Aconitum Diterpenoid Alkaloid Profiling to Distinguish between the Official Traditional Chinese Medicine (TCM) Fuzi and Adulterant Species Using LC-qToF-MS with Chemometrics

et al. 2021

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The lateral roots of Aconitum carmichaelii, known in Chinese as fuzi, are officially recognized as a materia medica in the Chinese Pharmacopoeia and used culinarily to prepare herbal soups. A strategy combining UPLC-qToF-MS analysis of A. carmichaelii and its intraspecies and interspecies chemometrics study was developed to examine the distribution of Aconitum marker metabolites. Four diterpenoid alkaloids were recognized to be important markers in fuzi, and another 15 markers were identified to differentiate A. carmichaelii from adulterant species. The detected fuzi markers, mesaconitine (47) and hypaconitine (51), are known to be the principal toxins in this herb, while fuziline (6) and benzoylmesaconine (25) are associated with its medicinal properties. Additional marker compounds have been detected in other Aconitum species that are useful for identifying adulteration. This study provides a useful resource for detecting traditional Chinese medicine (TCM) adulterants and assisting in the quality control of botanical products in TCM and beyond.

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Section: ■ Results and Discussionmentioning

confidence: 98%

Aconitum Diterpenoid Alkaloid Profiling to Distinguish between the Official Traditional Chinese Medicine (TCM) Fuzi and Adulterant Species Using LC-qToF-MS with Chemometrics

et al. 2021

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“…Talatisamine (purity > 98%) was isolated from the Roots of Aconitum carmichaelii by our research group as described [7]. UPLC grade methanol, acetonitrile, and acetic acid were purchased from Thermo Fisher Scientific.…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

Metabolite Profiling of Talatisamine in Heart Tissue After Oral Administration and Analysis of Cardiac Bioactivities

et al. 2022

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The lateral roots of the Aconitum carmichaelii (“Fuzi”) have been used for centuries as a cardiotonic in China. The diterpenoid alkaloid talatisamine (TA) is a major bioactive component of Fuzi, but the identity and bioactivities of TA metabolites have not been examined in detail. In this study, metabolite profiling of TA was performed in rat heart by UPLC-MS following oral administration. Metabolites were identified by comparing protonated molecules, fragmentation patterns, and chromatographic behaviors with those of standard compounds. Metabolites of TA were then prepared and tested for cardiotonic activity on isolated frog hearts. The metabolite cammaconine, a C19 diterpenoid alkaloid with a hydroxyl group at C-18, exhibited substantial cardiotonic activity during frog heart perfusion. To further investigate the structure–cardiac effect relationships, a series of C19-diterpenoid alkaloids with 18-OH were prepared. Eight tested compounds (5–12) demonstrated measurable cardioactivity, of which compound 5 with an N-methyl group and compound 7 with a methoxy at C-16 showed stronger effects on ventricular contraction than the other compounds. Thus, 18-OH is a critical structural feature determining cardiotonic activity, and efficacy is improved by the presence of an N-methyl or methoxy at C-16. Preliminary mechanistic studies suggested that the cardiotonic effect of compound 5 is mediated by enhanced cellular calcium influx. Metabolites of TA with these structural features may be useful therapeutics to prevent heart failure.

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“…Li et al isolated four new C-19 NDAs, carmichasines A–D 103 – 106 from A. carmichaelii Debeaux ( Figure 15 ) [ 92 ]. Extraction of the roots of A. taronense Fletcher et Lauener, which has been used in traditional Chinese medicine (TCM) to treat rheumatism and arthritis, yielded four new C-19 NDAs, taronenines A–D 107 – 110 ( Figure 16 ) [ 93 ]; NDAs 107 , 108 , and 110 exhibited anti-inflammatory activity when tested in mice cells.…”

Section: Norditerpenoid Alkaloid (Nda) Biodiversitymentioning

confidence: 99%

Poisonous Piperidine Plants and the Biodiversity of Norditerpenoid Alkaloids for Leads in Drug Discovery: Experimental Aspects

Qasem

Rowan

Blagbrough

2022

IJMS

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There are famous examples of simple (e.g., hemlock, Conium maculatum L.) and complex (e.g., opium poppy, Papaver somniferum L., Papaveraceae) piperidine-alkaloid-containing plants. Many of these are highly poisonous, whilst pepper is well-known gastronomically, and several substituted piperidine alkaloids are therapeutically beneficial as a function of dose and mode of action. This review covers the taxonomy of the genera Aconitum, Delphinium, and the controversial Consolida. As part of studying the biodiversity of norditerpenoid alkaloids (NDAS), the majority of which possess an N-ethyl group, we also quantified the fragment occurrence count in the SciFinder database for NDA skeletons. The wide range of NDA biodiversity is also captured in a review of over 100 recently reported isolated alkaloids. Ring A substitution at position 1 is important to determine the NDA skeleton conformation. In this overview of naturally occurring highly oxygenated NDAs from traditional Aconitum and Delphinium plants, consideration is given to functional effect and to real functional evidence. Their high potential biological activity makes them useful candidate molecules for further investigation as lead compounds in the development of selective drugs.

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Four New Diterpenoid Alkaloids from the Roots of Aconitum carmichaelii

Cited by 11 publications

References 23 publications

Aconitum Diterpenoid Alkaloid Profiling to Distinguish between the Official Traditional Chinese Medicine (TCM) Fuzi and Adulterant Species Using LC-qToF-MS with Chemometrics

Aconitum Diterpenoid Alkaloid Profiling to Distinguish between the Official Traditional Chinese Medicine (TCM) Fuzi and Adulterant Species Using LC-qToF-MS with Chemometrics

Metabolite Profiling of Talatisamine in Heart Tissue After Oral Administration and Analysis of Cardiac Bioactivities

Poisonous Piperidine Plants and the Biodiversity of Norditerpenoid Alkaloids for Leads in Drug Discovery: Experimental Aspects

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