Amphirionin-4 with Potent Proliferation-Promoting Activity on Bone Marrow Stromal Cells from a Marine Dinoflagellate <i>Amphidinium</i> Species

Minamida, Mika; Kumagai, Kazuaki; Ulanová, Dana; Akakabe, Mai; Konishi, Yuko; Tominaga, Akira; Tanaka, Hidenori; Tsuda, Masayuki; Fukushi, Eri; Kawabata, Jun; Masuda, Atsunori; Tsuda, Masashi

doi:10.1021/ol5023504

Cited by 34 publications

(43 citation statements)

References 29 publications

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“…The 1 H and 13 C NMR of our synthetic amphirionin-4 {[α] D 23 +6.4 ( c 0.08, CHCl 3 )} are identical to the reported spectra for the natural (+)-amphirionin-4{Lit. 4 [α] D 20 +6 ( c 0.29, CHCl 3 )}, thus confirming the absolute configuration of our synthetic material.…”

supporting

confidence: 77%

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Enantioselective Total Synthesis of (+)-Amphirionin-4

Ghosh

Nyalapatla

2016

Org. Lett.

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An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically-active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective syn-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki-Hiyama-Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.

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supporting

confidence: 77%

“…Interestingly, it did not show proliferation promotion when administered to MC3T3-E1 and NIH3TC cells. 4 …”

mentioning

confidence: 99%

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Enantioselective Total Synthesis of (+)-Amphirionin-4

Ghosh

Nyalapatla

2016

Org. Lett.

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“…The escalation in proliferation rate was observed in murine osteoblastic MC3T3-E1 cells and murine bone-marrow derived stromal ST-2 cells due to a novel linear polyketide Amphirionin-4 ( Figure 1D) derived from a cultured marine dinoflagellate Amphidinium species . Amphirionin-4 ( Figure 1D) consists of a linear C 22 carbon chain with four C 1 branches (Minamida et al, 2014).…”

Section: Marine Dinoflagellatesmentioning

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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“…1) A series of macrolides, represented by amphidinolides, are well-known secondary metabolites of Amphidinium dinoflagellates 2,3) with various carbon skeletons forming 12-29-membered (including odd-numbered) macrolactone rings and biosynthetically unique partial structures such as vicinally located C 1 branches. During our investigation of bioactive Amphidinium metabolites, 4,5) we have recently reported the isolation of 22-and 23-membered Amphidinium macrolides, i.e., iriomoteolides-13a 6) and -2a, 7) respectively, from the marine benthic dinoflagellate Amphidinium species (KCA09053 and HYA024 strains, respectively). Further investigation of the cytotoxic fractions of KCA09053 strain led to the discovery of the first 21-membered Amphidinium macrolide, iriomoteolide-10a (1), together with a new 12-membered macrolide, iriomoteolide-12a (2) (Fig.…”

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confidence: 99%

Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate <i>Amphidinium</i> Species

Akakabe

Kumagai

Tsuda

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new macrolides, iriomoteolides-10a (1) and -12a (2), have been isolated from a marine dinoflagellate Amphidinium sp. (KCA09053 strain), and their structures were elucidated on the basis of a detailed two dimensional (2D)-NMR analysis. Compound 1 is a novel 21-membered Amphidinium macrolide, which contains one tetrahydrofuran ring, two ketone carbonyls, two hydroxyl groups, and six one-carbon branches. Compound 2 is a new 12-membered macrolide related to amphidinolide Q. Compound 1 exhibited cytotoxic activity against human cervix adenocarcinoma HeLa and murine hepatocellular carcinoma MH134 cells. respectively, from the marine benthic dinoflagellate Amphidinium species (KCA09053 and HYA024 strains, respectively). Further investigation of the cytotoxic fractions of KCA09053 strain led to the discovery of the first 21-membered Amphidinium macrolide, iriomoteolide-10a (1), together with a new 12-membered macrolide, iriomoteolide-12a (2) (Fig. 1). Herein, we describe the isolation and structural elucidation of 1 and 2. Key words Results and DiscussionThe dinoflagellate Amphidinium sp. (strain KCA09053) was cultivated at 25°C for 2 weeks in seawater medium under illumination. The algal cells were extracted with methanol (MeOH)-toluene (3 : 1). The toluene-soluble materials of the extract were subjected to cytotoxic assay-guided fractionation using a silica gel column with chloroform (CHCl 3 )-MeOH. One of the cytotoxic fractions was separated with an octadecylsilyl (ODS) column followed by reversed-phase HPLC to afford iriomoteolide-10a (1, 0.069% from dry weight). On the other hand, iriomoteolide-12a (2) was obtained from the less polar fraction of the first silica gel column chromatography (CC) in 0.016% yield. Known macrolides, iriomoteolides-1a, 8) -3a, 9) and -13a, 6) have been separated by the first SiO 2 gel column from a more polar fraction than those containing 1 and 2.Iriomoteolide-10a (1) was obtained as optically active and colorless amorphous solid, and the molecular formula of (Table 1) showed the 35 carbon resonances, and their chemical shifts and multiplicities assigned by heteronuclear multiple quantum coherence (HMQC) and CH 2 -selected heteronuclear single quantum coherence

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Amphirionin-4 with Potent Proliferation-Promoting Activity on Bone Marrow Stromal Cells from a Marine Dinoflagellate Amphidinium Species

Cited by 34 publications

References 29 publications

Enantioselective Total Synthesis of (+)-Amphirionin-4

Enantioselective Total Synthesis of (+)-Amphirionin-4

Marine Natural Products: New Avenue in Treatment of Osteoporosis

Iriomoteolides-10a and 12a, Cytotoxic Macrolides from Marine Dinoflagellate <i>Amphidinium</i> Species

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