Biselyngbyaside, a Macrolide Glycoside from the Marine Cyanobacterium <i>Lyngbya</i> sp.

Teruya, Toshiaki; Sasaki, Hiroaki; Kitamura, Kazuhiro; Nakayama, Tsuneyoshi; Suenaga, Kiyotake

doi:10.1021/ol900579k

Cited by 100 publications

(57 citation statements)

References 14 publications

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“…It has been reported that Biselyngbyaside is a potent inhibitor of Ca 2+ pump with unique binding capacity (Teruya et al, 2009;Morita et al, 2015). It has an inhibitory effect on primary bone marrow macrophages as well as RANKL induced osteoclastogenesis in murine RAW 264.7 cells at low concentrations and also suppresses osteoblast-mediated osteoclast differentiation in cocultures.…”

Section: Marine Cyanobacteriamentioning

confidence: 99%

Marine Natural Products: New Avenue in Treatment of Osteoporosis

Chaugule¹,

Indap²,

Chiplunkar

2017

Front. Mar. Sci.

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Bone metabolism is a physiological process that maintains the skeletal integrity and bone functions. Skeletal integrity is always balanced by two key cell types-bone resorbing osteoclasts and bone-forming osteoblasts. Imbalance between generation and function of osteoclasts and osteoblasts often leads to pathological conditions such as osteoporosis, osteopetrosis, Paget's disease. Osteoporosis is one of the most common age-related diseases characterized by decreased bone mineral density and microarchitectural deterioration. Current therapies are indeed effective in preventing bone loss but are also followed by side effects. Since many years, marine organisms have been considered as a good source of bioactive molecules or compounds with potential pharmaceutical properties. Marine Natural Products (MNPs) derived from various marine resources such as marine cyanobacteria, dinoflagellates, algae, sponges, soft corals, molluscs, fishes, and mangroves had shown profound effect on bone metabolism through inhibiting osteoclastogenesis and up-regulating osteoblastogenesis via modulating RANK/RANKL/OPG pathway. Amongst the pre-clinically investigated MNPs for management of osteoporosis, very few are under phase I clinical trials. This review discusses the currently available pharmacological drugs and there major health concern in osteoporosis treatment. It further gives an insight into various marine resources and marine-derived bioactive products, depicting their mechanism of action, functional role, and how these can be exploited for the treatment of osteoporosis.

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Section: Marine Cyanobacteriamentioning

confidence: 99%

Marine Natural Products: New Avenue in Treatment of Osteoporosis

Chaugule¹,

Indap²,

Chiplunkar

2017

Front. Mar. Sci.

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“…8 Cryptophycin-309 and cryptophycin-249, synthetic analogs of terrestrial cyanobacterial peptide cryptophycin-1, have undergone preclinical efficacy studies, and there is sufficient interest to consider entering them into a clinical trial. 9 In our ongoing efforts to identify novel marine cyanobacterial metabolites with antitumor activity, 10 we isolated bisebromoamide (1), 11 which shows antiproliferative activity at nanomolar levels, from a cyanobacterium of the genus Lyngbya. Recently, Tao and coworkers achieved synthesis of bisebromoamide, and the stereochemistry of thiazoline moiety was revised.…”

Section: Introductionmentioning

confidence: 99%

Revised structure and structure–activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.

et al. 2011

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“…8 In common partial structures from C-3 to C-8 including C-13 and C-14, the most distinguishable feature of 1 H NMR data between the two diastereomers is a coupling constant ( J ) of H-4. While H-4 has two J values as 3.5 and 8.9 Hz which appeared to be a doublet of doublets in a syn conformation, J is 6.0 Hz as a triplet in an anti conformation which corresponds to compound 1 (Fig.…”

mentioning

confidence: 99%

“…S1). 8 Also, every possible rotamer was carefully considered by virtue of the 3 J H,H value, as well as the 1D and 2D NOE correlations (Fig. 2).…”

mentioning

confidence: 99%

A novel natural phenyl alkene with cytotoxic activity

Hwang

Kochanowska-Karamyan

et al. 2013

Tetrahedron Letters

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A novel phenyl alkene (1) was isolated from a mixture of three Florida sponges, Smenospongia aurea, Smenospongia cerebriformis, and Verongula rigida. Unlike terpenoids or amino acid derivatives, which are commonly known classes of secondary metabolites from these genera, the chemical structure of 1 showed an unprecedented linear phenyl alkene skeleton. Through comprehensive analyses of NMR and MS data, the gross structure of 1 was determined to be (E)-10-benzyl-5,7-dimethylundeca-1,5,10-trien-4-ol. The absolute configuration at C-4 was established as R by a modified Mosher’s method. Based on the relative configuration between C-4 and C-7, the absolute configuration at C-7 was assigned as S. Compound 1 showed in vitro cytotoxic activity against HL-60 human leukemia cancer cells with an IC50 value of 8.1 µM. Molecular docking study suggests that the structure of compound 1 matches the pharmacophore of eribulin required to display cytotoxic activity through the inhibition of microtubule activity.

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Biselyngbyaside, a Macrolide Glycoside from the Marine Cyanobacterium Lyngbya sp.

Cited by 100 publications

References 14 publications

Marine Natural Products: New Avenue in Treatment of Osteoporosis

Marine Natural Products: New Avenue in Treatment of Osteoporosis

Revised structure and structure–activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp.

A novel natural phenyl alkene with cytotoxic activity

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