A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

Kamada, Takashi; Johanis, Mary Lyn; Ng, Shean Yeaw; Phan, Chin Soon; Suleiman, Monica; Vairappan, Charles Santhanaraju

doi:10.1007/s13659-020-00232-6

Cited by 4 publications

(2 citation statements)

References 21 publications

(42 reference statements)

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“…The newly identified compound 181 showed the strongest activity, with MIC values of 12.5 and 50 μg/ml against L. thermophilum and H. sabahensis , respectively. Among the other identified diterpenoids, 182 and 183 were both moderately active with an MIC value of 100 μg/ml against L. thermophilum ( Kamada et al, 2020 ) .…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial Diterpenes: Recent Development From Natural Sources

et al. 2022

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Antimicrobial resistance has been posing an alarming threat to the treatment of infectious diseases over the years. Ineffectiveness of the currently available synthetic and semisynthetic antibiotics has led the researchers to discover new molecules with potent antimicrobial activities. To overcome the emerging antimicrobial resistance, new antimicrobial compounds from natural sources might be appropriate. Secondary metabolites from natural sources could be prospective candidates in the development of new antimicrobial agents with high efficacy and less side effects. Among the natural secondary metabolites, diterpenoids are of crucial importance because of their broad spectrum of antimicrobial activity, which has put it in the center of research interest in recent years. The present work is aimed at reviewing recent literature regarding different classes of natural diterpenes and diterpenoids with significant antibacterial, antifungal, antiviral, and antiprotozoal activities along with their reported structure–activity relationships. This review has been carried out with a focus on relevant literature published in the last 5 years following the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) guidelines. A total of 229 diterpenoids from various sources like plants, marine species, and fungi are summarized in this systematic review, including their chemical structures, classification, and significant antimicrobial activities together with their reported mechanism of action and structure–activity relationships. The outcomes herein would provide researchers with new insights to find new credible leads and to work on their synthetic and semisynthetic derivatives to develop new antimicrobial agents.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial Diterpenes: Recent Development From Natural Sources

et al. 2022

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“…13-epi-Neoverrucosan diterpene is the epimer of neoverrucosan with the isopropyl group in β configuration at C-13; this compound was first discovered in P. stephensoniana [22]. 13-epi-neoverrucosane-Type diterpenoids were also identified in the liverwort Schistochila nobilis [19], the liverwort Fossombronia alaskana [25], the liverwort Lepicolea ochroleuca [26], the marine sponge Axinyssa tethyoides [21], the liverwort P. subinflata [27], and the marine sponge Hamigera tarangaensis [28]. Few bioactivity assays showed that analogues of 13-epineoverrucosane analogues still failed to inhibit the growth of HL-60 cells at concentrations up to 50 µM [28].…”

Section: Introductionmentioning

confidence: 99%

Unprecedented Neoverrucosane and Cyathane Diterpenoids with Anti-Neuroinflammatory Activity from Cultures of the Culinary-Medicinal Mushroom Hericium erinaceus

Wei,

Li,

Feng

et al. 2023

Molecules

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The culinary medicinal mushroom Hericium erinaceus holds significant global esteem and has garnered heightened interest within increasingly ageing societies due to its pronounced neuroprotective and anti-neuroinflammatory properties. Within this study, two novel diterpenes, 16-carboxy-13-epi-neoverrucosane (1) and Erinacine L (2); three known xylosyl cyathane diterpenoids, Erinacine A (3), Erinacine C (4), and Erinacine F (5); and four lanostane-type triterpenoids, and three cyclic dipeptides (10–12), in addition to orcinol (13), were isolated from the rice-based cultivation medium of H. erinaceus. Their structures were determined by NMR, HR-ESI-MS, ECD, and calculated NMR. Compound 1 marks a pioneering discovery as the first verrucosane diterpene originating from basidiomycetes, amplifying the scope of fungal natural product chemistry, and the intricate stereochemistry of Compound 5 has been comprehensively assessed for the first time. Compounds 2–5 not only showed encouraging neurotrophic activity in rat adrenal pheochromocytoma PC-12 cells, but also significantly inhibited lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglia cell cultures with IC50 values as low as 5.82 ± 0.18 μM. To elucidate the mechanistic underpinnings of these bioactivities, molecular docking simulation was used to analyze and support the interaction of 1 and 2 with inducible NO synthase (iNOS), respectively. In particular, compound 2, a cyathane-xyloside containing an unconventional hemiacetal moiety, is a compelling candidate for the prevention of neurodegenerative diseases. In summation, this investigation contributes substantively to the panorama of fungal diterpene structural diversity, concurrently furnishing additional empirical substantiation for the role of cyathane diterpenes in the amelioration of neurodegenerative afflictions.

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