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Keywords = Tabernaemontana divaricata

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20 pages, 2320 KB  
Article
Two Novel Iboga-Type and an Oxindole Glucuronide Alkaloid from Tabernaemontana peduncularis Disclose Related Biosynthetic Pathways to Tabernaemontana divaricata
by Florian Traxler, Haoqi Zhang, Wiratchanee Mahavorasirikul, Katharina Krivanek, Xiang-Hai Cai, Wichai Aiyakool, Martin Pfeiffer, Lothar Brecker and Johann Schinnerl
Molecules 2023, 28(18), 6664; https://doi.org/10.3390/molecules28186664 - 16 Sep 2023
Cited by 3 | Viewed by 3324
Abstract
Phytochemical investigation of the two Tabernaemontana species (Apocynaceae) T. peduncularis Wall. and T. divaricata (L.) R.Br. ex Roem. & Schult. indicated closely related biosynthetic pathways leading to lipophilic and hydrophilic alkaloids. In total, 18 specialized metabolites comprising indole-derived alkaloid aglycones, three [...] Read more.
Phytochemical investigation of the two Tabernaemontana species (Apocynaceae) T. peduncularis Wall. and T. divaricata (L.) R.Br. ex Roem. & Schult. indicated closely related biosynthetic pathways leading to lipophilic and hydrophilic alkaloids. In total, 18 specialized metabolites comprising indole-derived alkaloid aglycones, three oxindole-derived alkaloid glycosides, and two iridoid glucosides could be identified in the studied species. Among the alkaloids, the two Iboga-type alkaloids 3,7-coronaridine isoindolenine, coronaridine 3,4-iminium and a javaniside derivative bearing a glucuronic acid, named javanuronic acid, could be described by spectroscopic and spectrometric methods for the first time. A docking experiment using alpha-fold was performed to generate a protein model of the enzyme 7-deoxyloganetic acid glucosyl transferase. Performed bioassays exhibited a growth reduction of neonate Spodoptera littoralis larvae and reduced cell viability of HepG2 cells of the extracts containing Iboga alkaloids, whilst the javaniside derivatives containing hydrophilic fraction did not show any effects. These findings indicate a high flexibility in the formation of bioactive indole alkaloid aglycones by Tabernaemontana species and also evidence similar accumulation trends in both species as well as indicate that biosynthetic routes leading to oxindole alkaloids like javanisides are more widespread than reported. Furthermore, the incorporation of the three novel compounds into potential biosynthetic pathways is discussed. Full article
(This article belongs to the Section Natural Products Chemistry)
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32 pages, 646 KB  
Review
Antileishmanial Activities of Medicinal Herbs and Phytochemicals In Vitro and In Vivo: An Update for the Years 2015 to 2021
by Abdalla A. Hassan, Hassan E. Khalid, Abdelwahab H. Abdalla, Maowia M. Mukhtar, Wadah J. Osman and Thomas Efferth
Molecules 2022, 27(21), 7579; https://doi.org/10.3390/molecules27217579 - 4 Nov 2022
Cited by 38 | Viewed by 7309
Abstract
Leishmaniasis is one of the most neglected tropical diseases that present areal public health problems worldwide. Chemotherapy has several limitations such as toxic side effects, high costs, frequent relapses, the development of resistance, and the requirement for long-term treatment. Effective vaccines or drugs [...] Read more.
Leishmaniasis is one of the most neglected tropical diseases that present areal public health problems worldwide. Chemotherapy has several limitations such as toxic side effects, high costs, frequent relapses, the development of resistance, and the requirement for long-term treatment. Effective vaccines or drugs to prevent or cure the disease are not available yet. Therefore, it is important to dissect antileishmanial molecules that present selective efficacy and tolerable safety. Several studies revealed the antileishmanial activity of medicinal plants. Several organic extracts/essential oils and isolated natural compounds have been tested for their antileishmanial activities. Therefore, the aim of this review is to update and summarize the investigations that have been undertaken on the antileishmanial activity of medicinal plants and natural compounds derived, rom plants from January 2015 to December 2021. In this review, 94 plant species distributed in 39 families have been identified with antileishmanial activities. The leaves were the most commonly used plant part (49.5%) followed by stem bark, root, and whole plant (21.9%, 6.6%, and 5.4%, respectively). Other plant parts contributed less (<5%). The activity was reported against amastigotes and/or promastigotes of different species (L. infantum, L. tropica, L. major, L. amazonensis, L. aethiopica, L. donovani, L. braziliensis, L. panamensis, L. guyanensis, and L. mexicana). Most studies (84.2%) were carried out in vitro, and the others (15.8%) were performed in vivo. The IC50 values of 103 plant extracts determined in vitro were in a range of 0.88 µg/mL (polar fraction of dichloromethane extract of Boswellia serrata) to 98 µg/mL (petroleum ether extract of Murraya koenigii). Among the 15 plant extracts studied in vivo, the hydroalcoholic leaf extract of Solanum havanense reduced parasites by 93.6% in cutaneous leishmaniasis. Voacamine extracted from Tabernaemontana divaricata reduced hepatic parasitism by ≈30 times and splenic parasitism by ≈15 times in visceral leishmaniasis. Regarding cytotoxicity, 32.4% of the tested plant extracts against various Leishmania species have a selectivity index higher than 10. For isolated compounds, 49 natural compounds have been reported with anti-Leishmania activities against amastigotes and/or promastigotes of different species (L. infantum, L. major, L. amazonensis, L. donovani and L. braziliensis). The IC50 values were in a range of 0.2 µg/mL (colchicoside against promastigotes of L. major) to 42.4 µg/mL (dehydrodieuginol against promastigotes of L. amazonensis). In conclusion, there are numerous medicinal plants and natural compounds with strong effects (IC50 < 100 µg/mL) against different Leishmania species under in vitro and in vivo conditions with good selectivity indices (SI > 10). These plants and compounds may be promising sources for the development of new drugs against leishmaniasis and should be investigated in randomized clinical trials. Full article
(This article belongs to the Special Issue Advances in Functional Foods)
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27 pages, 510 KB  
Review
Major Bioactive Alkaloids and Biological Activities of Tabernaemontana Species (Apocynaceae)
by Clarissa Marcelle Naidoo, Yougasphree Naidoo, Yaser Hassan Dewir, Hosakatte Niranjana Murthy, Salah El-Hendawy and Nasser Al-Suhaibani
Plants 2021, 10(2), 313; https://doi.org/10.3390/plants10020313 - 5 Feb 2021
Cited by 57 | Viewed by 11686
Abstract
Several species belonging to the genus Tabernaemontana have been well researched and utilized for their wide-ranging biological activities. A few of the most prominent species include Tabernaemontana divaricata, Tabernaemontana catharinensis, Tabernaemontana crassa, and Tabernaemontana elegans. These species and many [...] Read more.
Several species belonging to the genus Tabernaemontana have been well researched and utilized for their wide-ranging biological activities. A few of the most prominent species include Tabernaemontana divaricata, Tabernaemontana catharinensis, Tabernaemontana crassa, and Tabernaemontana elegans. These species and many others within the genus often display pharmacological importance, which is habitually related to their chemical constituents. The secondary metabolites within the genus have demonstrated huge medicinal potential for the treatment of infections, pain, injuries, and various diseases. Regardless of the indispensable reports and properties displayed by Tabernaemontana spp., there remains a wide variety of plants that are yet to be considered or examined. Thus, an additional inclusive study on species within this genus is essential. The current review aimed to extensively analyze, collate, and describe an updated report of the current literature related to the major alkaloidal components and biological activities of species within the genus Tabernaemontana. Full article
(This article belongs to the Special Issue Apocynaceae Species: Biology, Ecology and Practical Uses)
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