Novel lipid constituents identified from the leaves of Artabotrys odoratissimus (R.Br)

Mehta, B. K.; Kori, Pramila; Mehta, Darshana; Misra, H. O.

doi:10.1016/j.arabjc.2012.11.020

Cited by 5 publications

(13 citation statements)

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“…As an endemic plant in China, A. pilosus grows only in Hainan Island of China . Previous chemical investigations and biological studies on the species of the genus Artabotrys resulted in the isolation and characterization of cyclohexenes, sesquiterpenes, alkaloids, triterpenoids, steroids, lipids, flavonoid glycosides, and long-chain hydrocarbons, which displayed various biological effects, including antimalarial, anti-inflammatory, antibacterial, antitumor, and antifertility effects. − There is only one report on the chemical constituents from A. pilosus performed by us previously . Our experimental data suggested that the 85% EtOH extract of A. pilosus stems and leaves showed anti-HIV-1 activity in vitro , having an EC 50 value of 7.18 μg/mL.…”

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confidence: 75%

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus

et al. 2021

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Two unusual phenanthrene derivatives related to aporphine alkaloids, artapilosines A (1) and B (2), as well as two biogenetically related known aporphine alkaloids, (−)-anonaine (3) and (−)-N-acetylanonaine (4), were separated and purified from Artabotrys pilosus. Artapilosine A (1) is the first compound representative of a new class of phenanthrene derivatives having an unprecedented carbon skeleton, in which the six-membered nitrogen-containing heterocyclic structure in a typical aporphine alkaloid was substituted with a unique five-membered carbocyclic ring. This is the first report of the formation of a carbon−carbon bond between C-5 and C-6a in 1 with the loss of the nitrogen atom N-6 in the classic aporphine alkaloid. Artapilosine B (2) is a novel phenanthrene derivative having a hydroxyethyl as a substituent on the phenanthrene ring. Their chemical structures as well as absolute configurations were determined based on analysis of spectroscopic data. Additionally, the potential anti-HIV activities of all isolates 1−4 were appraised. Artapilosines A (1) and B (2) showed notable anti-HIV reverse transcriptase affects, with EC 50 values of 20.93 and 125.29 nM, respectively. These results suggested that the discovery of these novel phenanthrene derivatives from A. pilosus with remarkable anti-HIV effects could be essentially important for the researching and developing of new anti-HIV agents.

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confidence: 75%

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus

et al. 2021

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“…Table 2 is designed to contain chemical groups, the alphabetic names of these isolates, and their botanical resources, whereas Figures 234567 provide fully structural images with their detailed configuration. They include alkaloids 1 – 78 , [2,4,8,10–12,18,19,24,27,28,31–45] terpenoids 79 – 142 , [11,14,21,24,25,27,35,41,46–53] sterols 143 – 154 , [11,23,24,50,51,54–57] flavonoids 155 – 176 , [4,11,20,50,57–59] polyoxygenated compound s 177 – 195 , [24,49,59–61] fatty acids 196 – 212 , [20,55,62–64] furans 213 – 217 , [11,49,65] acetogenins 218 – 221 , [24,65,66] and other types 221 – 234 [4,11,24,54,57,58,67] …”

Section: Phytochemistrymentioning

confidence: 99%

“…Sterols also appeared as the next chemical class in the isolation processes of Artabotrys extracts. Herein, twelve compounds 143 – 154 were compiled in Table 2 and Figure 4 [11,23,24,50,51,54–57] . By NMR analysis, 2 β ‐hydroxy‐stigmasta‐4‐en‐3,6‐dione‐methoxy ester ( 143 ) was elucidated as new sterol, and was arisen from A. odoratissimus leaf, while the known compound ergosterol ( 144 ) appeared in its seed [23,57] .…”

Section: Phytochemistrymentioning

confidence: 99%

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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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“…They also identified the unique derivative 24-methylenelanosta-7,9(11)-diene-3-one ( Figure 3 ) analogous to the lanostane triterpene suberosol, which has antifungal and antiviral properties [ 64 ]. β-Sitosterol and related antimicrobial lipidic compounds have been identified from the leaves of A. odoratissimus (synonym) [ 65 , 66 ].…”

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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Novel lipid constituents identified from the leaves of Artabotrys odoratissimus (R.Br)

Cited by 5 publications

References 3 publications

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus

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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