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16 pages, 792 KiB

Open AccessArticle

Nine New Pregnane Glycosides from the Cultivated Medicinal Plant Marsdenia tenacissima

by Qian-Qian Meng, Shun-Yao Tong, Xing-Rong Peng, Yu-Qing Zhao, Zheng-Hui Li, He-Ping Chen and Ji-Kai Liu

Molecules 2023, 28(6), 2705; https://doi.org/10.3390/molecules28062705 - 16 Mar 2023

Viewed by 1192

Abstract

The ethnobotanical plant Marsdenia tenacissima has been used for hundreds of years for Dai people in Yunnan Province, China. Previously, chemical investigations on this plant have revealed that pregnane glycosides were the main biological constituents. Nine new pregnane glycosides, marsdeosides A–I (1 [...] Read more.

The ethnobotanical plant Marsdenia tenacissima has been used for hundreds of years for Dai people in Yunnan Province, China. Previously, chemical investigations on this plant have revealed that pregnane glycosides were the main biological constituents. Nine new pregnane glycosides, marsdeosides A–I (1–9), were isolated from cultivated dried stems of the medicinal plant Marsdenia tenacissima in this study. The structures were analyzed by extensive spectroscopic analysis, including 1D, 2D NMR, HRESIMS, and IR spectroscopic analysis. The absolute configurations of the sugar moieties were identified by comparing the R_f values and specific optical rotations with those of the commercially available standard samples and the data reported in the literature. Marsdeosides A (1) featured an unusual 8,14-seco-pregnane skeleton. Compounds 1, 8, and 9 showed activity against nitric oxide production in lipopolysaccharide-activated macrophage RAW264.7, with IC₅₀ values of 37.5, 38.8, and 42.8 μM (L-NMMA was used as a positive control, IC₅₀ 39.3 μM), respectively. This study puts the knowledge of the chemical profile of the botanical plant M. tenacissima one step forward and, thereby, promotes the sustainable utilization of the resources of traditional folk medicinal plants. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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16 pages, 1691 KiB

Open AccessArticle

Effects of Compound Elicitors on the Biosynthesis of Triterpenoids and Activity of Defense Enzymes from Inonotus hispidus (Basidiomycetes)

by Jiao Zhou, Xinyue Lin, Shuangshuang Liu, Zhanbin Wang, Dongchao Liu, Yonghong Huo and Dehai Li

Molecules 2022, 27(9), 2618; https://doi.org/10.3390/molecules27092618 - 19 Apr 2022

Cited by 4 | Viewed by 1690

Abstract

Inonotus hispidus has various health-promoting activities, such as anticancer effects and immune-stimulating activity. The commercialization of valuable plant triterpenoids faces major challenges, including low abundance in natural hosts and costly downstream purification procedures. In this work, orthogonal design was used to compound methyl [...] Read more.

Inonotus hispidus has various health-promoting activities, such as anticancer effects and immune-stimulating activity. The commercialization of valuable plant triterpenoids faces major challenges, including low abundance in natural hosts and costly downstream purification procedures. In this work, orthogonal design was used to compound methyl jasmonate (MeJA), salicylic acid (SA), oleic acid, and Cu²⁺, and the effects of combinations on the total triterpenes biosynthesized were studied. The optimal combination was screened out and its effect on the activity of PAL, CAT, and SOD was studied. The optimal concentration of oleic acid was 2% when MeJA was 100 mol/L, and the total triterpenoid content and mycelia production were 3.918 g and 85.17 mg/g, respectively. MeJA treatment induced oxidative stress, and at the same time increased the activity of related defense enzymes. Oleic acid is thought to regulate cell permeability by recombining cell membranes. It promotes the material exchange process between cells and the environment without affecting cell growth. When oleic acid was used in combination with MeJA, a synergistic effect on triterpene production was observed. In conclusion, our findings provide a strategy for triterpenoid enrichment of I. hispidus. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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17 pages, 15673 KiB

Open AccessArticle

Isolation and Identification of Pennogenin Tetraglycoside from Cestrum nocturnum (Solanaceae) and Its Antifungal Activity against Fusarium kuroshium, Causal Agent of Fusarium Dieback

by Erika Valencia-Mejía, Yeli Y. León-Wilchez, Juan L. Monribot-Villanueva, Mónica Ramírez-Vázquez, Israel Bonilla-Landa and José A. Guerrero-Analco

Molecules 2022, 27(6), 1860; https://doi.org/10.3390/molecules27061860 - 13 Mar 2022

Cited by 4 | Viewed by 2649

Abstract

Antifungal assay-guided fractionation of the methanolic crude extract of Cestrum nocturnum (Solanaceae), popular known as ‘lady of the night’, led the isolation and identification of the steroidal saponin named pennogenin tetraglycoside, which was identified for the first time in this plant species by [...] Read more.

Antifungal assay-guided fractionation of the methanolic crude extract of Cestrum nocturnum (Solanaceae), popular known as ‘lady of the night’, led the isolation and identification of the steroidal saponin named pennogenin tetraglycoside, which was identified for the first time in this plant species by spectroscopic means. The crude extract, fractions and pennogenin tetraglycoside exhibited mycelial growth inhibition of Fusarium solani and F. kuroshium. F. solani is a cosmopolitan fungal phytopathogen that affects several economically important crops. However, we highlight the antifungal activity displayed by pennogenin tetraglycoside against F. kuroshium, since it is the first plant natural product identified as active for this phytopathogen. This fungus along with its insect symbiont known as Kuroshio shot hole borer (Euwallacea kuroshio) are the causal agents of the plant disease Fusarium dieback that affects more than 300 plant species including avocado (Persea americana) among others of ecological relevance. Scanning electron microscopy showed morphological alterations of the fungal hyphae after exposure with the active fractions and 12 phenolic compounds were also identified by mass spectrometry dereplication as part of potential active molecules present in C. nocturnum leaves. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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10 pages, 1755 KiB

Open AccessArticle

Five New Terpenes with Cytotoxic Activity from Pestalotiopsis sp.

by Dan Zhao, Meigeng Hu, Guoxu Ma and Xudong Xu

Molecules 2021, 26(23), 7229; https://doi.org/10.3390/molecules26237229 - 29 Nov 2021

Cited by 2 | Viewed by 1468

Abstract

Five new compounds called Pestalotis A–E (1–5), comprising three monoterpene-lactone compounds (1–3), one tetrahydrobenzofuran derivative (4), and one sesquiterpene (5), were isolated from the EtOAc extract of Pestalotiopsis sp. The structures [...] Read more.

Five new compounds called Pestalotis A–E (1–5), comprising three monoterpene-lactone compounds (1–3), one tetrahydrobenzofuran derivative (4), and one sesquiterpene (5), were isolated from the EtOAc extract of Pestalotiopsis sp. The structures of the new compounds were elucidated by analysis of their NMR, HRMS, and ECD spectra, and the absolute configurations were established through the comparison of experimental and calculated ECD spectra. All compounds were tested for antitumor activity against SW-480, LoVo, HuH-7, and MCF-7. The results showed that compounds 2 and 4 exhibited potent antitumor activity against SW-480, LoVo, and HuH-7 cell lines. Furthermore, compound 4 was assessed against HuH-7, and the results indicated that the rate of apoptosis was dose-dependent. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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30 pages, 3516 KiB

Open AccessFeature PaperReview

Triterpene and Steroid Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities

by Natalia V. Ivanchina and Vladimir I. Kalinin

Molecules 2023, 28(6), 2503; https://doi.org/10.3390/molecules28062503 - 09 Mar 2023

Cited by 4 | Viewed by 1744

Abstract

The article is a comprehensive review concerning tetracyclic triterpene and steroid glycosides from sponges (Porifera, Demospongiae). The extensive oxidative transformations of the aglycone and the use of various monosaccharide residues, with up to six possible, are responsible for the significant structural diversity observed [...] Read more.

The article is a comprehensive review concerning tetracyclic triterpene and steroid glycosides from sponges (Porifera, Demospongiae). The extensive oxidative transformations of the aglycone and the use of various monosaccharide residues, with up to six possible, are responsible for the significant structural diversity observed in sponge saponins. The saponins are specific for different genera and species but their taxonomic distribution seems to be mosaic in different orders of Demospongiae. Many of the glycosides are membranolytics and possess cytotoxic activity that may be a cause of their anti-predatory activities. All these data reveal the independent origin and parallel evolution of the glycosides in different taxa of the sponges. The information concerning chemical structures, biological activities, biological role, and taxonomic distribution of the sponge glycosides is discussed. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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27 pages, 3109 KiB

Open AccessReview

The Complexity of Sesquiterpene Chemistry Dictates Its Pleiotropic Biologic Effects on Inflammation

by Narcy Arizmendi, Syed Benazir Alam, Khalid Azyat, Darren Makeiff, A. Dean Befus and Marianna Kulka

Molecules 2022, 27(8), 2450; https://doi.org/10.3390/molecules27082450 - 11 Apr 2022

Cited by 4 | Viewed by 3469

Abstract

Sesquiterpenes (SQs) are volatile compounds made by plants, insects, and marine organisms. SQ have a large range of biological properties and are potent inhibitors and modulators of inflammation, targeting specific components of the nuclear factor-kappaB (NF-κB) signaling pathway and nitric oxide (NO) generation. [...] Read more.

Sesquiterpenes (SQs) are volatile compounds made by plants, insects, and marine organisms. SQ have a large range of biological properties and are potent inhibitors and modulators of inflammation, targeting specific components of the nuclear factor-kappaB (NF-κB) signaling pathway and nitric oxide (NO) generation. Because SQs can be isolated from over 1600 genera and 2500 species grown worldwide, they are an attractive source of phytochemical therapeutics. The chemical structure and biosynthesis of SQs is complex, and the SQ scaffold represents extraordinary structural variety consisting of both acyclic and cyclic (mono, bi, tri, and tetracyclic) compounds. These structures can be decorated with a diverse range of functional groups and substituents, generating many stereospecific configurations. In this review, the effect of SQs on inflammation will be discussed in the context of their complex chemistry. Because inflammation is a multifactorial process, we focus on specific aspects of inflammation: the inhibition of NF-kB signaling, disruption of NO production and modulation of dendritic cells, mast cells, and monocytes. Although the molecular targets of SQs are varied, we discuss how these pathways may mediate the effects of SQs on inflammation. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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53 pages, 7118 KiB

Open AccessReview

Structure and Biological Activity of Ergostane-Type Steroids from Fungi

by Vladimir N. Zhabinskii, Pavel Drasar and Vladimir A. Khripach

Molecules 2022, 27(7), 2103; https://doi.org/10.3390/molecules27072103 - 24 Mar 2022

Cited by 19 | Viewed by 3036

Abstract

Mushrooms are known not only for their taste but also for beneficial effects on health attributed to plethora of constituents. All mushrooms belong to the kingdom of fungi, which also includes yeasts and molds. Each year, hundreds of new metabolites of the main [...] Read more.

Mushrooms are known not only for their taste but also for beneficial effects on health attributed to plethora of constituents. All mushrooms belong to the kingdom of fungi, which also includes yeasts and molds. Each year, hundreds of new metabolites of the main fungal sterol, ergosterol, are isolated from fungal sources. As a rule, further testing is carried out for their biological effects, and many of the isolated compounds exhibit one or another activity. This study aims to review recent literature (mainly over the past 10 years, selected older works are discussed for consistency purposes) on the structures and bioactivities of fungal metabolites of ergosterol. The review is not exhaustive in its coverage of structures found in fungi. Rather, it focuses solely on discussing compounds that have shown some biological activity with potential pharmacological utility. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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29 pages, 3993 KiB

Open AccessReview

Phytochemistry and Pharmacological Activities of the Diterpenoids from the Genus Daphne

by Yi-Wen Nie, Yuan Li, Lan Luo, Chun-Yan Zhang, Wei Fan, Wei-Ying Gu, Kou-Rong Shi, Xiao-Xiang Zhai and Jian-Yong Zhu

Molecules 2021, 26(21), 6598; https://doi.org/10.3390/molecules26216598 - 31 Oct 2021

Cited by 14 | Viewed by 2699

Abstract

There are abundant natural diterpenoids in the plants of the genus Daphne from the Thymelaeaceae family, featuring a 5/7/6-tricyclic ring system and usually with an orthoester group. So far, a total of 135 diterpenoids has been isolated from the species of the genus [...] Read more.

There are abundant natural diterpenoids in the plants of the genus Daphne from the Thymelaeaceae family, featuring a 5/7/6-tricyclic ring system and usually with an orthoester group. So far, a total of 135 diterpenoids has been isolated from the species of the genus Daphne, which could be further classified into three main types according to the substitution pattern of ring A and oxygen-containing functions at ring B. A variety of studies have demonstrated that these compounds exert a wide range of bioactivities both in vitro and in vivo including anticancer, anti-inflammatory, anti-HIV, antifertility, neurotrophic, and cholesterol-lowering effects, which is reviewed herein. Meanwhile, the fascinating structure–activity relationship is also concluded in this review in the hope of providing an easy access to available information for the synthesis and optimization of efficient drugs. Full article

(This article belongs to the Special Issue Terpenes, Steroids and Their Derivatives)

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