Bioactive benzylisoquinoline alkaloids from Artabotrys hexapetalus

Zhou, Qi; Fu, Yan-Hui; Li, Xiaobao; Chen, Guang‐Ying; Wu, Shou-Yuan; Song, Xiao‐Ping; Liu, Yan-Ping; Han, Chang‐Ri

doi:10.1016/j.phytol.2015.01.017

Cited by 29 publications

(20 citation statements)

References 27 publications

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“…These small differences in the chemical shifts of these isomers are clearly observed due to the stereochemistry of the nitrogen affected by the α and β position of oxygen. Comparisons of the 1 H- and 13 C-NMR data obtained for compounds 6 and 7 with data of molecules with close structures such as hexapetaline A and hexapetaline B [ 30 ] support the data described in Table 1 without ambiguity.…”

Section: Resultssupporting

confidence: 59%

“…In addition, the 1 H-NMR spectrum of 5 also showed signals for two methoxy groups resonating at δ H 3.93 (3H, s) and δ H 3.95 (3H, s), and signals for two methylene groups resonating at δ H 2.79 (2H, t, J = 7.8 Hz) and δ H 3.89 (2H, t, J = 7.8 Hz), attributed to H-4 and H-3, respectively ( Table 1 ). These data indicated that alkaloid 5 has a benzyltetrahydroisoquinoline skeleton [ 28 , 29 , 30 ].…”

Section: Resultsmentioning

confidence: 99%

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Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

et al. 2021

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Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL−1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL−1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL−1 (33.70 µmol·L−1) and 18.99 µg·mL−1 (40.56 µmol·L−1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL−1, and HCT116, with an IC50 value of 17.31 µg·mL−1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.

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Section: Resultssupporting

confidence: 59%

Section: Resultsmentioning

confidence: 99%

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

et al. 2021

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“…This species is a crucial medicinal species that is widely renowned by various local names such as ‘Ylang Ylang’, ‘Manorangini’, ‘Hari Champa’, ‘Hara Champaka’, or ‘Katchampa’, [9,17] Its flower is useful for cholera, antibacterial infection, and is also used as a tea‐like beverage [17,18] . It turns out that the root and fruit of this plant should be suitable for malaria and scrofula treatments, respectively [19] . Ylang‐Ylang oil can alleviate depression, lower blood pressure, and heart rate reduction [6]…”

Section: Traditional Usesmentioning

confidence: 99%

Botanical Description, Traditional Uses, Phytochemistry, and Pharmacology of the Genus Artabotrys: A Review

Hợp

Son

2022

Chemistry & Biodiversity

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Artabotrys is a genus of small trees in the family Annonaceae. This genus contained over 100 perennial medicinal plants available in the old world tropics. Artabotrys plants have a lengthy history of use in medicine for malaria, diarrhea, backache, and scrofula treatments, as well as some of which were used as tea-like beverages. About 90 reports were reviewed from inception to now, in which the decoctions of about 9 species were used in traditional folk medicines. With 234 isolated compounds, Artabotrys metabolites can be classified as alkaloids, terpenoids, sterols, flavonoids, polyoxygenated cyclohexenes, fatty acids, acetogenins, etc. Significantly, alkaloidal aporphines were separated and identified as the main isolates. Artabotrys plants are also rich in the essential oils. Especially, A. hexapetalus exerted a great role in perfumery industry. Artabotrys constituents possessed various pharmacological values, such as antioxidative, antidiabetic, hepatoprotective, and mosquito repellency, but cytotoxic and antimicrobial activities are the most striking features. In conclusion, Artabotrys plant extracts and their metabolites are of great socio-economic importance, thereby more and more phytochemical and pharmacological investigations are expected.

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“…Hex-A proved to be more cytotoxic toward cancer cells than Hex-B. Its antiproliferative action was comparable to that of the reference anticancer drug cisplatin [ 52 ].…”

Section: Phytochemical Content Of Yingzhaomentioning

confidence: 99%

Advocacy for the Medicinal Plant Artabotrys hexapetalus (Yingzhao) and Antimalarial Yingzhaosu Endoperoxides

Bailly

Hénichart

2022

Molecules

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The medicinal plant Artabotrys hexapetalus (synonyms: A. uncinatus and A. odoratissimus) is known as yingzhao in Chinese. Extracts of the plant have long been used in Asian folk medicine to treat various symptoms and diseases, including fevers, microbial infections, ulcers, hepatic disorders and other health problems. In particular, extracts from the roots and fruits of the plant are used for treating malaria. Numerous bioactive natural products have been isolated from the plant, mainly aporphine (artabonatines, artacinatine) and benzylisoquinoline (hexapetalines) alkaloids, terpenoids (artaboterpenoids), flavonoids (artabotrysides), butanolides (uncinine, artapetalins) and a small series of endoperoxides known as yingzhaosu A-to-D. These natural products confer antioxidant, anti-inflammatory and antiproliferative properties to the plant extracts. The lead compound yingzhaosu A displays marked activities against the malaria parasites Plasmodium falciparum and P. berghei. Total syntheses have been developed to access yingzhaosu compounds and analogues, such as the potent compound C14-epi-yingzhaosu A and simpler molecules with a dioxane unit. The mechanism of action of yingzhaosu A points to an iron(II)-induced degradation leading to the formation of two alkylating species, an unsaturated ketone and a cyclohexyl radical, which can then react with vital parasitic proteins. A bioreductive activation of yingzhaosu A endoperoxide can also occur with the heme iron complex. The mechanism of action of yingzhaosu endoperoxides is discussed, to promote further chemical and pharmacological studies of these neglected, but highly interesting bioactive compounds. Yingzhaosu A/C represent useful templates for designing novel antimalarial drugs.

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Bioactive benzylisoquinoline alkaloids from Artabotrys hexapetalus

Cited by 29 publications

References 27 publications

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Botanical Description, Traditional Uses, Phytochemistry, and Pharmacology of the Genus Artabotrys: A Review

Advocacy for the Medicinal Plant Artabotrys hexapetalus (Yingzhao) and Antimalarial Yingzhaosu Endoperoxides

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