Phorbasins G-I: Three New Diterpenoids from the Sponge Phorbas gukulensis

Lee, Hyi‐Seung; Park, Su Young; Sim, Chung Ja; Rho, Jung‐Rae

doi:10.1248/cpb.56.1198

Cited by 25 publications

(10 citation statements)

References 13 publications

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“…There are some examples of other sesquiterpenoids, 7-9 as well as diterpenes, 10,11 with cyclohexane carboxylic acid fragments. The structure of ganodermycin is also related to juvabione, a juvenile hormone from balsam fir.…”

Section: Structure Elucidationmentioning

confidence: 99%

Ganodermycin, a novel inhibitor of CXCL10 expression from Ganoderma applanatum

et al. 2011

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CXCL10 (inducible protein-10) is a highly inducible chemoattractant, which contributes to the recruitment of inflammatory cells, such as macrophages and T-lymphocytes, and thereby has important roles in chronic inflammatory conditions. In a search for new inhibitors of CXCL10 expression in MonoMac6 cells, a novel compound, designated as Ganodermycin, was isolated from fermentations of the basidiomycete Ganoderma applanatum. The structure was determined by a combination of spectroscopic techniques. Ganodermycin inhibited the lipopolysaccharide (LPS)/interferon (IFN)-c-induced CXCL10 promoter activity in transiently transfected MonoMac6 cells in a dose-dependent manner with IC 50 values of 15-20 lg ml À1 (53-71 lM). Ganodermycin also reduced LPS/IFN-c-induced CXCL10 protein synthesis and excretion.

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Section: Structure Elucidationmentioning

confidence: 99%

Ganodermycin, a novel inhibitor of CXCL10 expression from Ganoderma applanatum

et al. 2011

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“…Ansellones B (66) and C (67), epimers at C-13, feature an unprecedented heterocyclic skeleton that contains an oxocane ring [53]. Ansellone A (65) and E (69) are epimers whose difference lies in the configuration at C-11; ansellone D (68) has an O-methyl instead of hydroxyl in the same orientation as ansellone A (65). Ansellone F (70) displays two epoxide functions and ansellone G (71) has an α,β-unsaturated carbonyl function [54].…”

Section: Ansellonesmentioning

confidence: 99%

“…The difference between these dimers is the presence of an acetate substituent linked to the phorbasin F (92), which is absent in E (91) [61,62,64]. 2008), isolated and identified three new diterpenes that were also named phorbasins G-I (93-95) [65] from Phorbas gukhulensis, collected in South Korea (Figure 26). These molecules, identified by FAB-MS and NMR experiments, feature a cyclohexane ring differently from their congeners previously discussed, which exhibit a cyclohexene moiety.…”

Section: Phorbasinsmentioning

confidence: 99%

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Caso¹,

Silva²,

Esposito³

et al. 2021

Preprint

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Porifera, commonly referred to as marine sponges, have stood out as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention along years. They are widespread in all continents, and several structurally unique compounds have been identified from species of this genus. Terpenes, mainly sesterterpenoids, represent the great majority of secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have shown a variety of biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial and anti-inflammatory activities, have been isolated and structurally characterized. This work brings an overview of Phorbas secondary metabolites reported since the first study published in 1993 until 2020, and their biological activities.

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“…72–76 Members of this class have been reported to possess a range of antibiotic and cytotoxic properties, with phorbasin C attracting the attention of the Micalizio laboratory (Figure 23A). While the structure of the target was not clear from the reported isolation, the Micalizio laboratory began a synthesis campaign that targeted the development of a regio- and stereoselective allylic alcohol–alkyne coupling process for establishment of the C6–C7 bond.…”

Section: Alkene–alkyne Cross-couplingmentioning

confidence: 99%