Parviflorenes B–F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

Toume, Kazufumi; Takahashi, Masae; Yamaguchi, Kentaro; Koyano, Takashi; Kowithayakorn, Thaworn; Hayashi, Masahiko; Komiyama, Kanki; Ishibashi, Masami

doi:10.1016/j.tet.2004.09.043

Cited by 31 publications

(14 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the structure of Backbone I, further unambiguous evidence was provided from the X-ray crystal analysis of parviflorene B (4). 62 Parviflorene B (4) had an a-hydroxyketone group at B-ring, and the carbon framework was the same as that of parviflorene A (1). Parviflorene B (4) was crystallized from methanol solution to give yellow prisms, and the structure of 4 was unequivocally established by X-ray crystallographic analysis.…”

Section: A Chemistry Of Cytotoxic Dimeric Sesquiterpenes From Curcummentioning

confidence: 99%

“…Treatment of the TRAIL-resistant KOB cells with FCB and TRAIL resulted in apparent apoptosis, which was not induced by either agent alone. 82 During our studies on search for bioactive natural products, [56][57][58][59][60][61][62][63] we have recently examined myxomycetes as unexplored natural resources. 55,83,84 The myxomycetes (true slime molds) are an unusual group of primitive organisms that may be assigned to one of the lowest classes of eukaryotes.…”

Section: F U L I G O C a N D I N B H A V I N G S Y N E R G I S T mentioning

confidence: 99%

See 1 more Smart Citation

Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis

Ishibashi

Ohtsuki

2008

Medicinal Research Reviews

Self Cite

View full text Add to dashboard Cite

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) induces apoptosis in many transformed cells but not in normal cells and, hence, has been expected as a new anticancer strategy. During our studies on search for bioactive natural products from various natural resources such as plants and microorganisms, we recently identified several natural products which exhibited activities related to TRAIL signaling. Dimeric sesquiterpenoids isolated from Zingiberaceous plant, Curcuma parviflora, showed enhancement activity of gene expression of TRAIL-receptor and TRAIL-receptor protein level. Several new isoflavone natural products, named brandisianins, were isolated from Leguminosaeous plant, Millettia brandisiana, by our screening study targeting TRAIL-receptor expression enhancement activity. A dihydroflavonol (BB1) that was extracted from Compositaeous plant, Blumea balsamifera, and fuligocandin B, a new anthranilylproline-indole alkaloid isolated from myxomycete were found to exhibit reversal effect of TRAIL resistance activity.

show abstract

Section: A Chemistry Of Cytotoxic Dimeric Sesquiterpenes From Curcummentioning

confidence: 99%

Section: F U L I G O C a N D I N B H A V I N G S Y N E R G I S T mentioning

confidence: 99%

Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis

Ishibashi

Ohtsuki

2008

Medicinal Research Reviews

Self Cite

View full text Add to dashboard Cite

show abstract

“…[11][12][13][14][15] Structures were elucidated by extensive spectral studies as well as X-ray crystal analysis and chemical derivatization experiments.…”

Section: Dimeric Sesquiterpenoids From Curcuma Parvifloramentioning

confidence: 99%

“…By western blotting analysis in PANC1, 52 and 53 clearly decreased the expression of PTCH and apoptosis-inhibiting protein BCL2. From Adenium obesum, 17 cardenolides including 3 new compounds (12)(13)(14)(15) were isolated as potent inhibitors. 53 These compounds showed strong inhibitory activities (IC 50 : 0.1-0.5 mM).…”

Section: Screening Study For Inhibition Of Gli1-mediatedmentioning

confidence: 99%

Search for Bioactive Natural Products Targeting Cancer-Related Signaling Pathways

Ishibashi

Arai

2009

J. Synth. Org. Chem. Jpn.

Self Cite

View full text Add to dashboard Cite

During our studies related to the search for bioactive natural products, we recently examined extracts of various natural resources including unexplored myxomycetes, marine organisms, as well as several medicinal plants collected in the north-eastern part of Thailand and Bangladesh. Here we describe our recent results from our screening programs targeting signaling molecules in cancer-related biological pathways such as TRAIL, Wnt, and Hedgehog signalings.

show abstract

“…Thiobinupharidine (63) Several novel cytotoxic unsymmetrical sesquiterpenedimers with three backbone skeletons have been isolated from Curcuma parviflora (Zingiveraceae) [51]. The structures of the sesquiterpene-dimers were elucidated by means of NMR studies and the structure of 68 was further established by Xray crystallographic analysis [51]. Further investigation led to the isolation of several other dimers from the underground part of the plant; parviflorene B-F (68)(69)(70)(71)(72).…”

mentioning

confidence: 99%

Natural and Synthetic Biologically Active Dimeric Molecules: Anticancer Agents, Anti-HIV Agents, Steroid Derivatives and Opioid Antagonists

Bérubé¹

2006

CMC

View full text Add to dashboard Cite

Symmetry plays a crucial role in a variety of biological processes. For instance, many protein receptors, upon activation, dimerize to its active form and subsequently produce its biological action. Hence, there is a renewal of curiosity for the synthesis of dimeric molecules (or bivalent ligands) capable, not only to interact with specific biologic receptors, but also to induce greater biological responses than the corresponding monomeric counterpart. This is a vast and diverse theme of research. Hence, this review will discuss recent developments into this flourishing research field and will focus mainly into four specific topics namely dimeric 1) anticancer agents, 2) anti-HIV, 3) steroid derivatives and 4) opioid antagonists.

show abstract

Parviflorenes B–F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

Cited by 31 publications

References 8 publications

Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis

Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis

Search for Bioactive Natural Products Targeting Cancer-Related Signaling Pathways

Natural and Synthetic Biologically Active Dimeric Molecules: Anticancer Agents, Anti-HIV Agents, Steroid Derivatives and Opioid Antagonists

Contact Info

Product

Resources

About