Semisynthesis of salviandulin E analogues and their antitrypanosomal activity

Aoyagi, Yutaka; Fujiwara, Koji; Yamazaki, Akira; Sugawara, Naoto; Yano, Reiko; Fukaya, Haruhiko; Hitotsuyanagi, Yukio; Takeya, Koichi; Ishiyama, Aki; Iwatsuki, Masato; Otoguro, Kazuhiko; Yamada, Hideaki; Ōmura, Satoshi

doi:10.1016/j.bmcl.2013.12.052

Cited by 10 publications

(4 citation statements)

References 12 publications

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“…The linearolactone from S. polystachia had amoebicidal and giardicidal activities at IC 50 = 22.9 µM and IC 50 = 28.2 µM ( Calzada et al, 2015 ) ( Supplementary Table S2 ). Finally, the salviandulin E from S. leucantha had activity against Trypanosoma brucei at IC 50 0.72 μg/ml ( Aoyagi et al, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages (Salvia Subgenus Calosphace; Lamiaceae) Emphasizing Mexican Species

et al. 2022

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Salvia is the most diverse genus within the mint family (Lamiaceae), many of its species are well-known due to their medicinal and culinary uses. Most of the ethnopharmacological and phytochemical studies on Salvia are centred on species from the European and Asian clades. However, studies about the most diverse clade, the Neotropical sages (Salvia subgenus Calosphace; 587 spp.), are relatively scarce. This review aims to compile the information on the traditional medicinal uses, pharmacological and phytochemistry properties of the Neotropical sages. To do so, we carried out a comprehensive review of the articles available in different online databases published from the past to 2022 (i.e., PubMed, Scopus, and Web of Science, among others) and summarized the information in tables. To uncover phylogenetic patterns in the distribution of four different groups of metabolites (mono-, sesqui-, di-, and triterpenes), we generated presence-absence matrices and plotted the tip states over a dated phylogeny of Salvia. We found several studies involving Mexican species of Salvia, but only a few about taxa from other diversity centres. The main traditional uses of the Mexican species of Calosphace are medicinal and ceremonial. In traditional medicine 56 species are used to treat diseases from 17 categories according to the WHO, plus cultural-bound syndromes. Pharmacological studies reveal a wide range of biological properties (e.g., antinociceptive, anti-inflammatory, anxiolytic, cytotoxic, and antidiabetic, etc.) found in extracts and isolated compounds of 38 Neotropical sages. From extracts of these species, at least 109 compounds have been isolated, identified and evaluated pharmacologically; 73 of these compounds are clerodanes, 21 abietanes, six flavonoids, five sesquiterpenoids, and four triterpenoids. The most characteristic metabolites found in the Neotropical sages are the diterpenes, particularly clerodanes (e.g., Amarisolide A, Tilifodiolide), that are found almost exclusively in this group. The Neotropical sages are a promising resource in the production of herbal medication, but studies that corroborate the properties that have been attributed to them in traditional medicine are scarce. Research of these metabolites guided by the phylogenies is recommended, since closely related species tend to share the presence of similar compounds and thus similar medicinal properties.

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Section: Resultsmentioning

confidence: 99%

A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages (Salvia Subgenus Calosphace; Lamiaceae) Emphasizing Mexican Species

et al. 2022

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“…[26] Most of the compounds can be considered as non-cytotoxic on WI38 cells (IC 50 > 70 μm). In this sense, Aoyagi et al reported an improvement of 14-fold in the activity of dihydrosalviandulin E against T. brucei brucei by esterification with butanoic acid.…”

Section: Discussionmentioning

confidence: 99%

Secochiliolide ester derivatives: Preparation and evaluation of their antitrypanosomal and antimalarial efficacy

et al. 2018

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In the present study, a series of new esters of secochiliolide acid (SA), a diterpene isolated from Nardophyllum bryoides, were synthesized in good yield. All compounds were evaluated for their in vitro antiparasitic properties (on Plasmodium falciparum and Trypanosoma brucei brucei) and cytotoxicity (on WI38, normal mammalian cells). They displayed moderate antitrypanosomal activity with IC values between 2.55 and 18.14 μm, with selectivity indices >10, and low antiplasmodial effects with IC > 29 μm. The only exception was the n-hexyl ester of SA, which showed a strong and selective antiplasmodial activity (IC = 1.99 μm and selectivity index = 117.0). The in vivo antimalarial efficacy of this compound was then assessed according to the 4-day suppressive test of Peters in mice. An intraperitoneal treatment at 50 mg kg day induced a slight parasitaemia reduction by 56% which was statistically significant on day 4 post-infection and an increase in the survival time.

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“…Compound 1 itself showed potent biological activity (IC 50 = 2.04 µM). A similar diterpene isolated from the same plant, 6,7-dehydrodugesin A ( 2 ), did not show antitrypanosomal activity (IC 50 > 37.19 µM) [ 22 ]. The synthetic derivative butanoyl 3,4-dihydro salviandulin showed the best IC 50 = 0.14 µM and SI = 1236 [ 22 ].…”

Section: Biological Activitymentioning

confidence: 99%

“…A similar diterpene isolated from the same plant, 6,7-dehydrodugesin A ( 2 ), did not show antitrypanosomal activity (IC 50 > 37.19 µM) [ 22 ]. The synthetic derivative butanoyl 3,4-dihydro salviandulin showed the best IC 50 = 0.14 µM and SI = 1236 [ 22 ]. Although is known that Tbb and Tbr are genetically almost identical [ 7 ], some compounds showed different bioactivity against the two parasites [ 7 ].…”

Section: Biological Activitymentioning

confidence: 99%

Salvia Species as Sources of Natural Products with Antiprotozoal Activity

Llurba-Montesino

Schmidt

2018

IJMS

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Natural products from plants have been used since ancestral times to treat a wide variety of diseases worldwide. Plants of the genus Salvia (Sage) have been reported to be used for the prevention and treatment of various diseases and ailments. In particular, some Salvia species have been used in traditional medicine to treat diseases caused by protozoan parasites of the genera Trypanosoma, Leishmania and Plasmodium and scientific studies have demonstrated the activity of various isolated constituents from these plants against these pathogens. The current review attempts to give a critical overview of published information about the antiprotozoal activity of species of the genus Salvia and their chemical constituents. It is meant to give a unified overview of these results in order to avoid repetitions caused, e.g., by limited access to some primary reports, and to stimulate further research to possibly facilitate the development of new molecular leads against protozoal neglected tropical diseases (NTDs) based on Salvia constituents.

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Semisynthesis of salviandulin E analogues and their antitrypanosomal activity

Cited by 10 publications

References 12 publications

A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages (Salvia Subgenus Calosphace; Lamiaceae) Emphasizing Mexican Species

A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages (Salvia Subgenus Calosphace; Lamiaceae) Emphasizing Mexican Species

Secochiliolide ester derivatives: Preparation and evaluation of their antitrypanosomal and antimalarial efficacy

Salvia Species as Sources of Natural Products with Antiprotozoal Activity

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