New Cytotoxic Isomalabaricane Triterpenes from the Sponge <i>Jaspis</i> Species

Meragelman, Karina M.; McKee, Tawnya C.; Boyd, Michael R.

doi:10.1021/np000478g

Cited by 38 publications

(46 citation statements)

References 25 publications

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“…The chemical shift of H-3 (δ 4.55, m) indicated the equatorial ( ) position of the acetoxy function. [5][6][7]11 This stereochemistry was confirmed by NOE correlations between H-3/H-5 and H-3/H 3 -28. Additional COSY couplings between H 2 -1/H 2 -2, H-5/H 2 -6, H 2 -6/H 2 -7, and H-9/H 2 -11 together with the corresponding HMBC correlations (Table 1) allowed the assemblage of the tricyclic nucleus.…”

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confidence: 59%

Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

et al. 2002

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Two new isomalabaricane triterpenes, stellettin H (1) and stellettin I (2), have been isolated from the marine sponge Rhabdastrella globostellata, collected from the Philippines. Stellettins A-D (3-6), (-)-stellettin E (7), and rhabdastrellic acid-A (8) were also isolated and characterized. Stellettin B (4) and (-)-stellettin E (7) showed selective cytotoxicity toward p21(WAF1/Cip1)-deficient human colon tumor (HCT-116) cells with IC(50) values of 0.043 and 0.039 microM, respectively.

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confidence: 59%

Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

et al. 2002

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“…There is increasing evidence that isomalabaricane is a rare class of triterpenoids with potent tumor inhibitory activities [15,16], the values of IC 50 for cancer cell lines ranging from 0.1–20 μg/mL, which has brought attention to its potential for chemotherapeutic development [17]. …”

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confidence: 99%

Geoditin A Induces Oxidative Stress and Apoptosis on Human Colon HT29 Cells

Cheung

Che

et al. 2010

Marine Drugs

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Geoditin A, an isomalabaricane triterpene isolated from the marine sponge Geodia japonica, has been demonstrated to dissipate mitochondrial membrane potential, activate caspase 3, decrease cytoplasmic proliferating cell nuclear antigen (PCNA), and induce apoptosis of leukemia cells, but the underlying mechanism remains unclear [1]. In this study, we found fragmentation of Golgi structure, suppression of transferrin receptor expression, production of oxidants, and DNA fragmentation in human colon cancer HT29 cells after treatment with geoditin A for 24 h. This apoptosis was not abrogated by chelation of intracellular iron with salicylaldehyde isonicotinoyl hydrazone (SIH), but suppressed by N-acetylcysteine (NAC), a thiol antioxidant and GSH precursor, indicating that the cytotoxic effect of geoditin A is likely mediated by a NAC-inhibitable oxidative stress. Our results provide a better understanding of the apoptotic properties and chemotherapeutical potential of this marine triterpene.

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“…This rare class of triterpenoids possesses potent tumor inhibitory activities [17,18], and thus received special attention for its potential for chemotherapeutic development [19]. …”

Section: Resultsmentioning

confidence: 99%

Anti-Melanogenic Property of Geoditin A in Murine B16 Melanoma Cells

et al. 2012

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Geoditin A, an isomalabaricane triterpene isolated from marine sponge Geodia japonica, has been demonstrated to induce apoptosis in leukemia HL60 cells and human colon HT29 cancer cells through an oxidative stress, a process also interfering with normal melanogenesis in pigment cells. Treatment of murine melanoma B16 cells with geoditin A decreased expression of melanogenic proteins and cell melanogenesis which was aggravated with adenylate cyclase inhibitor SQ22536, indicating melanogenic inhibition was mediated through a cAMP-dependent signaling pathway. Immunofluorescence microscopy and glycosylation studies revealed abnormal glycosylation patterns of melanogenic proteins (tyrosinase and tyrosinase-related protein 1), and a co-localization of tyrosinase with calnexin (CNX) and lysosome-associated membrane protein 1 (LAMP-1), implicating a post-translational modification in the ER and a degradation of tyrosinase in the lysosome. Taken together, potent anti-melanogenic property and the relatively low cytotoxicity of geoditin A have demonstrated its therapeutic potential as a skin lightening agent.

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New Cytotoxic Isomalabaricane Triterpenes from the Sponge Jaspis Species

Cited by 38 publications

References 25 publications

Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

Bioactive Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

Geoditin A Induces Oxidative Stress and Apoptosis on Human Colon HT29 Cells

Anti-Melanogenic Property of Geoditin A in Murine B16 Melanoma Cells

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