Spirostane saponins with a rearranged A/B ring system isolated from the rhizomes of Ophiopogon japonicus

Liu, Bo; Li, Bingxin; Chen, Gang; Pan, Yingni; Zhou, Di; Li, Ning

doi:10.1016/j.phytochem.2021.112975

Cited by 8 publications

(8 citation statements)

References 39 publications

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“…Lastly, three nortriterpenes from the roots of Ziziphus mauritiana, zizimauritic acids A (120), B (121), and C (122), with a unique A-nor-E-seco spiro-lactone ceanothane-type triterpene skeleton, were identified. These compounds displayed cytotoxicity, with IC 50 values ranging from 5.05 to 11.94 µg/mL, and compounds 120 and 122 inhibited the growth of Staphylococcus aureus, with IC 50 values of 2.17 and 12.79 µg/mL, respectively [86].…”

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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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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“…Other examples of compounds containing the tetrahydropyran unit include natural product III , which was isolated from the Chinese liverwort Jamesoniella autumnalis , and protein-coupled receptor modulator IV . In addition, both tetrahydrofuran and tetrahydropyran scaffolds are also found in compounds V and IV , which were isolated from the bile of the toad Bufo bufo gargarizans and the rhizomes of Ophiopogon japonicus , respectively. Due to their biological activities, many strategies for the construction of these heterocycles have been developed in the past several decades .…”

Section: Introductionmentioning

confidence: 99%

Access to Saturated Oxygen Heterocycles and Lactones via Electrochemical Sulfonylative Oxycyclization of Alkenes with Sulfonyl Hydrazides

et al. 2023

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A facile electrochemical sulfonylative cycloetherification of linear unsaturated alcohols with sulfonyl hydrazides under mild conditions has been accomplished. This catalyst-and oxidant-free protocol proceeds via electro-oxidation, followed by radical addition, as well as an intramolecular oxygen nucleophilic process. This methodology is compatible with a broad substrate scope and good functional group compatibility, which provides a valuable and convenient synthetic tool for the synthesis of saturated five-, six-, seven-, and eight-membered ring oxygen heterocycles. Furthermore, sulfonylative cycloesterification of linear unsaturated acids toward the lactone products has also been established under this electrochemical system. In addition, control experiments indicated that the N−H bonds of the sulfonyl hydrazide molecule are non-essential.

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“…Previous studies have shown that steroidal saponins and homoisoflavones are the major components of this formulation, including ophiopogonin D, ophiopogonin D , dioscin, methylprotodioscin, officinalisnin-II, aspacochinosides N, aspacochinosides O, aspacochinosides P, ophiopogonanone D and Methylophiopogonone B, etc. [2][3][4][5][6][7][8][9][10][11], which displays significant anti-inflammatory, antibacterial, antioxidant and immunomodulatory activities [12][13][14][15][16][17][18]. EDG modulates inflammatory responses and has been employed to prevent and treat pulmonary diseases; such as acute lung injury (ALI) by reducing pulmonary edema, and the secretion of TNF-α and IL-6, and increasing the expression of aquaporin-1 (AQP-1) and aquaporin-5 (AQP-5) proteins in the lung tissue [19]; it also markedly reduces the expression of TNF-α, interleukin-10 (IL-10), and transforming growth factor-β1 (TGF-β1) and promotes the apoptosis of gastric cancer cells to delay the occurrence and development of lung tumors in Molecules 2023, 28, 295 2 of 16 rats [20].…”

Section: Introductionmentioning

confidence: 99%

Screening and Identification of Anti-Inflammatory Compounds from Erdong Gao via Multiple-Target-Cell Extraction Coupled with HPLC-Q-TOF-MS/MS and Their Structure–Activity Relationship

Luo

Huang

et al. 2022

Molecules

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Erdong Gao (EDG), consisting equally of roots of Asparagi Radix and Ophiopogonis Radix, is a well-known traditional Chinese formulation that has been used to treat cough and throat pain for centuries. However, the bioactive components in EDG remain to be elucidated. In this study, a rapid and effective method involving live cell bio-specific extraction and HPLC-Q-TOF-MS/MS was established to rapidly screen and identify the anti-inflammatory compounds of an EDG extract. One hundred and twenty-four components were identified in EDG extract using HPLC-Q-TOF-MS/MS analysis. After co-incubation with 16HBE, HPAEpiCs and HUVECs, which have been validated as the key target cells for pulmonary diseases, sixteen components were demonstrated to exhibit an affinity for binding to them. Furthermore, fifteen components were subsequently verified to exert anti-inflammatory effects on lipopolysaccharide (LPS)-induced 16HBE, HPAEpiCs and HUVECs via inhibiting the release of TNF-α and IL-6, indicating that nine steroidal saponins may possess potential for the treatment of lung-related diseases. Taken together, our study provides evidence that live cell biospecific extraction combined with the HPLC-Q-TOF-MS/MS technique was an efficient method for rapid screening potential bioactive components in traditional Chinese medicines and the structure activity relationship of steroidal saponins in EDG was summarized for the first time.

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Spirostane saponins with a rearranged A/B ring system isolated from the rhizomes of Ophiopogon japonicus

Cited by 8 publications

References 39 publications

Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application

Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application

Access to Saturated Oxygen Heterocycles and Lactones via Electrochemical Sulfonylative Oxycyclization of Alkenes with Sulfonyl Hydrazides

Screening and Identification of Anti-Inflammatory Compounds from Erdong Gao via Multiple-Target-Cell Extraction Coupled with HPLC-Q-TOF-MS/MS and Their Structure–Activity Relationship

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