Di- and Triterpenoids from the Rhizomes of <i>Isodon amethystoides</i> and Their Anti-inflammatory Activities

Ren, Wenjing; Io, Chi-Cheng; Jiang, Rong; Ng, Kei-Fong; Liu, Jia-Zheng; Bai, Liping; Zhang, Wei; Jiang, Zhi‐Hong; Liu, Yuhong; Zhu, Guo‐Yuan

doi:10.1021/acs.jnatprod.2c01136

Cited by 10 publications

(6 citation statements)

References 47 publications

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“…The absolute configuration research was conducted by the Sybyl-X 2.0 software as previously reported [ 39 , 40 ]. All calculations were conducted with an implicit solvent environment described by the conductor-like polarizable continuum model (CPCM).…”

Section: Methodsmentioning

confidence: 99%

Boswellianols A–I, Structurally Diverse Diterpenoids from the Oleo-Gum Resin of Boswellia carterii and Their TGF-β Inhibition Activity

Lin,

Bao,

Xiong

et al. 2024

Plants

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Olibanum, a golden oleo-gum resin from species in the Boswellia genus (Burseraceae family), is a famous traditional herbal medicine widely used around the world. Previous phytochemical studies mainly focused on the non-polar fractions of olibanum. In this study, nine novel diterpenoids, boswellianols A–I (1–9), and three known compounds were isolated from the polar methanolic fraction of the oleo-gum resin of Boswellia carterii. Their structures were determined through comprehensive spectroscopic analysis as well as experimental and calculated electronic circular dichroism (ECD) data comparison. Compound 1 is a novel diterpenoid possessing an undescribed prenylmaaliane-type skeleton with a 6/6/3 tricyclic system. Compounds 2–4 were unusual prenylaromadendrane-type diterpenoids, and compounds 5–9 were new highly oxidized cembrane-type diterpenoids. Compounds 1 and 5 showed significant transforming growth factor β (TGF-β) inhibitory activity via inhibiting the TGF-β-induced phosphorylation of Smad3 and the expression of fibronectin and N-cadherin (the biomarker of the epithelial–mesenchymal transition) in a dose-dependent manner in LX-2 human hepatic stellate cells, indicating that compounds 1 and 5 should be potential anti-fibrosis agents. These findings give a new insight into the chemical constituents of the polar fraction of olibanum and their inhibitory activities on the TGF-β/Smad signaling pathway.

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Section: Methodsmentioning

confidence: 99%

Boswellianols A–I, Structurally Diverse Diterpenoids from the Oleo-Gum Resin of Boswellia carterii and Their TGF-β Inhibition Activity

Lin,

Bao,

Xiong

et al. 2024

Plants

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“…From the rhizomes of Isodon amethystoides, a triterpenoid named amethystoidesic acid (114) was isolated. This acid, with an unprecedented 5/6/6/6 tetracyclic skeleton, is the first triterpenoid of its kind, derived from a contracted A ring and the 18,19-seco-E-ring of ursolic acid, and exhibited inhibitory effects on nitric oxide production [81].…”

Section: A-norsteroids and Triterpenoids Derived From Terrestrial Sou...mentioning

confidence: 99%

Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application

Dembitsky

2024

Biomedicines

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The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds are sourced from marine organisms like sponges, soft corals, and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.

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“…Concurrently, the MTT assay was employed to assess the viability of RAW264.7 cells, thereby evaluating the cytotoxic effects of the compounds under investigation. 34,35 Western Blot Analysis. In brief, RAW264.7 cells were seeded in six-well plates at a density of 5 × 10 5 cells/well and treated with various concentrations (10,20, and 40 μM) of compounds 2−4, 15, and 16 or DEX (5 μM), followed by stimulation with LPS (0.5 μg/ mL) for 24 h. Subsequently, cells were collected and lysed by using RIPA buffer.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of Carpesium abrotanoides L.

Fu,

Wang,

Tian

et al. 2024

J. Nat. Prod.

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Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (1−11), along with five known ones (12−16), were isolated from the fruits of Carpesium abrotanoides L. Compounds 1−11 are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds 2−4, 15, and 16 exhibited significant inhibitory activity against LPS-induced NO release with an IC 50 value of 5.6−9.1 μM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.

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Di- and Triterpenoids from the Rhizomes of Isodon amethystoides and Their Anti-inflammatory Activities

Cited by 10 publications

References 47 publications

Boswellianols A–I, Structurally Diverse Diterpenoids from the Oleo-Gum Resin of Boswellia carterii and Their TGF-β Inhibition Activity

Boswellianols A–I, Structurally Diverse Diterpenoids from the Oleo-Gum Resin of Boswellia carterii and Their TGF-β Inhibition Activity

Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application

NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of Carpesium abrotanoides L.

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