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Article ; Online: Theonellamides J and K and 5-

Hasin, Ohad / Shoham, Shani / Kashman, Yoel / Ilan, Micha / Carmeli, Shmuel

2021 Volume 20, Issue 1

Abstract: Theonella ... ...

Abstract	Theonella swinhoei
MeSH term(s)	Animals ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Aquatic Organisms ; Cell Line, Tumor/drug effects ; Glycopeptides/chemistry ; Glycopeptides/pharmacology ; Humans ; Indian Ocean ; Pacific Ocean ; Peptides, Cyclic/chemistry ; Peptides, Cyclic/pharmacology ; Porifera ; Theonella
Chemical Substances	Antineoplastic Agents ; Glycopeptides ; Peptides, Cyclic
Language	English
Publishing date	2021-12-27
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2175190-0
ISSN	1660-3397 ; 1660-3397
ISSN (online)	1660-3397
ISSN	1660-3397
DOI	10.3390/md20010031
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Article ; Online: Theonellamides J and K and 5- cis -Apoa-theopalauamide, Bicyclic Glycopeptides of the Red Sea Sponge Theonella swinhoei

Ohad Hasin / Shani Shoham / Yoel Kashman / Micha Ilan / Shmuel Carmeli

Marine Drugs, Vol 20, Iss 31, p

2022 Volume 31

Abstract: Theonella swinhoei is a fairly common inhabitant of reefs throughout the Indian and Pacific Oceans. Metabolomic analyses of samples of T. swinhoei collected in different depths in the Gulf of Aqaba revealed two chemotypes differing in the profiles of the ...

Abstract	Theonella swinhoei is a fairly common inhabitant of reefs throughout the Indian and Pacific Oceans. Metabolomic analyses of samples of T. swinhoei collected in different depths in the Gulf of Aqaba revealed two chemotypes differing in the profiles of the theonellamides they produce, some of which seem to be unknown. Driven by this finding, we examined a sample of T. swinhoei collected more than 40 years ago in the southern part of the Gulf of Aqaba. Large-scale extract of this sample yielded four theonellamides, the known theopalauamide ( 4 ), as the major component, and three new metabolites, theonellamide J ( 1 ), 5- cis -Apoa-theopalauamide ( 2 ), and theonellamide K ( 3 ), as the minor components. The planar structure of these complex cyclic glycopeptides was elucidated by combination of 1D and 2D NMR techniques and HRESIMS. The absolute configuration of the amino acids was established by Marfey’s and advanced Marfey’s methods, and the absolute configuration of its galactose unit using “Tanaka’s method” for monosaccharides. The biological activity of the pure compounds was tested for antibacterial activity and for cytotoxicity to HTC-116 cell line. The compounds presented significant cytotoxicity against the HTC-116 cell line, illuminating the importance of the Apoa subunit for the activity.
Keywords	sponge metabolites ; Theonella swinhoei ; glycopeptide ; cytotoxicity ; structure elucidation ; NMR ; Biology (General) ; QH301-705.5
Subject code	500
Language	English
Publishing date	2022-12-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
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Article ; Online: Glutamate Toxicity to Differentiated Neuroblastoma N2a Cells Is Prevented by the Sesquiterpene Lactone Achillolide A and the Flavonoid 3,5,4'-Trihydroxy-6,7,3'-Trimethoxyflavone from Achillea fragrantissima.

Elmann, Anat / Telerman, Alona / Ofir, Rivka / Kashman, Yoel

Journal of molecular neuroscience : MN

2017 Volume 62, Issue 1, Page(s) 99–105

Abstract: Glutamate toxicity is a major contributor to the pathophysiology of numerous neurodegenerative diseases including amyotrophic lateral sclerosis and Alzheimer's disease. Therefore, protecting neuronal cells against glutamate-induced cytotoxicity might be ... ...

Abstract	Glutamate toxicity is a major contributor to the pathophysiology of numerous neurodegenerative diseases including amyotrophic lateral sclerosis and Alzheimer's disease. Therefore, protecting neuronal cells against glutamate-induced cytotoxicity might be an effective approach for the treatment of these diseases. We have previously purified from the medicinal plant Achillea fragrantissima two bioactive compounds which were not studied before: the sesquiterpene lactone achillolide A and the flavonoid 3,5,4'-trihydroxy-6,7,3'-trimethoxyflavone (TTF). We have shown that these compounds protect astrocytes from oxidative stress-induced cell death and inhibit microglial activation. The current study examined for the first time their effects on differentiated mouse neuroblastoma N2a cells and on glutamate toxicity. We have found that, although these compounds belong to different chemical families, they protect neuronal cells from glutamate toxicity. We further demonstrate that this protective effect might be, at least partially, due to inhibitory effects of these compounds on the levels of reactive oxygen species produced following treatment with glutamate.
Language	English
Publishing date	2017-05
Publishing country	United States
Document type	Journal Article
ZDB-ID	1043392-2
ISSN	1559-1166 ; 0895-8696
ISSN (online)	1559-1166
ISSN	0895-8696
DOI	10.1007/s12031-017-0916-y
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Article: Theonellamides J and K and 5-cis-Apoa-theopalauamide, Bicyclic Glycopeptides of the Red Sea Sponge Theonella swinhoei

Hasin, Ohad / Shoham, Shani / Kashman, Yoel / Ilan, Micha / Carmeli, Shmuel

Marine drugs. 2021 Dec. 27, v. 20, no. 1

2021

Abstract	Theonella swinhoei is a fairly common inhabitant of reefs throughout the Indian and Pacific Oceans. Metabolomic analyses of samples of T. swinhoei collected in different depths in the Gulf of Aqaba revealed two chemotypes differing in the profiles of the theonellamides they produce, some of which seem to be unknown. Driven by this finding, we examined a sample of T. swinhoei collected more than 40 years ago in the southern part of the Gulf of Aqaba. Large-scale extract of this sample yielded four theonellamides, the known theopalauamide (4), as the major component, and three new metabolites, theonellamide J (1), 5-cis-Apoa-theopalauamide (2), and theonellamide K (3), as the minor components. The planar structure of these complex cyclic glycopeptides was elucidated by combination of 1D and 2D NMR techniques and HRESIMS. The absolute configuration of the amino acids was established by Marfey’s and advanced Marfey’s methods, and the absolute configuration of its galactose unit using “Tanaka’s method” for monosaccharides. The biological activity of the pure compounds was tested for antibacterial activity and for cytotoxicity to HTC-116 cell line. The compounds presented significant cytotoxicity against the HTC-116 cell line, illuminating the importance of the Apoa subunit for the activity.
Keywords	antibacterial properties ; cell lines ; chemotypes ; cytotoxicity ; galactose ; glycopeptides ; metabolites ; metabolomics ; Gulf of Aqaba ; Red Sea
Language	English
Dates of publication	2021-1227
Publishing place	Multidisciplinary Digital Publishing Institute
Document type	Article
ZDB-ID	2175190-0
ISSN	1660-3397
ISSN	1660-3397
DOI	10.3390/md20010031
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Article ; Online: 3,5,4'-trihydroxy-6,7,3'-trimethoxyflavone protects against beta amyloid-induced neurotoxicity through antioxidative activity and interference with cell signaling.

Telerman, Alona / Ofir, Rivka / Kashman, Yoel / Elmann, Anat

BMC complementary and alternative medicine

2017 Volume 17, Issue 1, Page(s) 332

Abstract: Background: Alzheimer's disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major contributors ...

Abstract	Background: Alzheimer's disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major contributors to Alzheimer's disease, therefore, protecting neuronal cells against Aβ-induced toxicity and oxidative stress might form an effective approach for treatment of this disease. 3,5,4'-trihydroxy-6,7,3'-trimethoxyflavone (TTF) is a flavonoid we have purified from the plant Achillea fragrantissima; and the present study examined, for the first time, the effects of this compound on Aβ-toxicity to neuronal cells. Methods: Various chromatographic techniques were used to isolate TTF from the plant Achillea fragrantissima, and an N2a neuroblastoma cell line was used to study its activities. The cellular levels of total and phosphorylated stress-activated protein kinase/c-Jun N-terminal kinase (SAPK/JNK) and of total and phosphorylated extracellular signal-regulated kinase (ERK 1/2) were determined by enzyme-linked immunosorbent assay (ELISA). Intracellular reactive oxygen species (ROS) levels were measured by using 2',7'-dichlorofluorescein diacetate (DCF-DA). Cytotoxicity and cell viability were assessed by using lactate dehydrogenase (LDH) activity in cell-conditioned media, or by crystal violet cell staining, respectively. Results: TTF prevented the Aβ-induced death of neurons and attenuated the intracellular accumulation of ROS following treatment of these cells with Aβ. TTF also inhibited the Aβ-induced phosphorylation of the signaling proteins SAPK/JNK and ERK 1/2, which belong to the mitogen-activated protein kinase (MAPK) family. Conclusion: TTF should be studied further as a potential therapeutic means for the treatment of Alzheimer's disease.
MeSH term(s)	Achillea/chemistry ; Alzheimer Disease/drug therapy ; Alzheimer Disease/metabolism ; Alzheimer Disease/physiopathology ; Amyloid beta-Peptides/metabolism ; Amyloid beta-Peptides/toxicity ; Antioxidants/chemistry ; Antioxidants/pharmacology ; Apoptosis/drug effects ; Cell Line ; Cell Survival ; Flavones/chemistry ; Flavones/pharmacology ; Humans ; JNK Mitogen-Activated Protein Kinases/metabolism ; Neurons/cytology ; Neurons/drug effects ; Neurons/metabolism ; Neuroprotective Agents/chemistry ; Neuroprotective Agents/pharmacology ; Oxidative Stress/drug effects ; Phosphorylation ; Plant Extracts/chemistry ; Plant Extracts/pharmacology ; Reactive Oxygen Species/metabolism ; Signal Transduction/drug effects
Chemical Substances	Amyloid beta-Peptides ; Antioxidants ; Flavones ; Neuroprotective Agents ; Plant Extracts ; Reactive Oxygen Species ; JNK Mitogen-Activated Protein Kinases (EC 2.7.11.24)
Language	English
Publishing date	2017-06-23
Publishing country	England
Document type	Journal Article
ZDB-ID	2050429-9
ISSN	1472-6882 ; 1472-6882
ISSN (online)	1472-6882
ISSN	1472-6882
DOI	10.1186/s12906-017-1840-y
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Article ; Online: β-amyloid cytotoxicity is prevented by natural achillolide A.

Elmann, Anat / Telerman, Alona / Ofir, Rivka / Kashman, Yoel / Lazarov, Orly

Journal of natural medicines

2018 Volume 72, Issue 3, Page(s) 626–631

Abstract: Alzheimer's disease (AD) is the most prevalent cause of dementia in adults. Current available drugs for AD transiently alleviate some of the symptoms, but do not modify the disease mechanism or cure it. Therefore, new drugs are desperately needed. Key ... ...

Abstract	Alzheimer's disease (AD) is the most prevalent cause of dementia in adults. Current available drugs for AD transiently alleviate some of the symptoms, but do not modify the disease mechanism or cure it. Therefore, new drugs are desperately needed. Key contributors to AD are amyloid beta (Aβ)- and reactive oxygen species (ROS)-induced cytotoxicities. Plant-derived substances have been shown to affect various potential targets in various diseases including AD. Therefore, phytochemicals which can protect neuronal cells against these insults might help in preventing and treating this disease. In the following research, we have isolated the sesquiterpene lactone achillolide A from the plant Achillea fragrantissima and, for the first time, characterized its effects on Aβ-treated neuroblastoma cells. Aβ is a peptide derived from the sequential cleavage of amyloid precursor protein, and is part of the pathogenesis of AD. Our current study aimed to determine whether achillolide A can interfere with Aβ-induced processes in Neuro2a cells, and protect them from its toxicity. Our results show that achillolide A decreased Aβ-induced death and enhanced the viability of Neuro2a cells. In addition, achillolide A reduced the accumulation of Aβ-induced ROS and inhibited the phosphorylation of stress-activated protein kinase/c-Jun N-terminal kinase and p44/42 mitogen-activated protein kinase in these cells. We therefore suggest that achillolide A may have therapeutic potential for the treatment of AD.
MeSH term(s)	Alzheimer Disease/genetics ; Alzheimer Disease/metabolism ; Alzheimer Disease/pathology ; Amyloid beta-Peptides/drug effects ; Humans ; Plant Extracts/chemistry ; Plant Extracts/pharmacology ; Reactive Oxygen Species/metabolism ; Sesquiterpenes/pharmacology ; Sesquiterpenes/therapeutic use
Chemical Substances	Amyloid beta-Peptides ; Plant Extracts ; Reactive Oxygen Species ; Sesquiterpenes ; achillolide A
Language	English
Publishing date	2018-03-15
Publishing country	Japan
Document type	Journal Article
ZDB-ID	2227540-X
ISSN	1861-0293 ; 1340-3443
ISSN (online)	1861-0293
ISSN	1340-3443
DOI	10.1007/s11418-018-1191-0
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Zs.A 2692: Show issues

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Jg. 1995 - 2021: Lesesall (2.OG)
ab Jg. 2022: Lesesaal (EG)

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Article ; Online: 3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone protects against beta amyloid-induced neurotoxicity through antioxidative activity and interference with cell signaling

Alona Telerman / Rivka Ofir / Yoel Kashman / Anat Elmann

BMC Complementary and Alternative Medicine, Vol 17, Iss 1, Pp 1-

2017 Volume 7

Abstract: Abstract Background Alzheimer’s disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major ... ...

Abstract	Abstract Background Alzheimer’s disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major contributors to Alzheimer’s disease, therefore, protecting neuronal cells against Aβ-induced toxicity and oxidative stress might form an effective approach for treatment of this disease. 3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone (TTF) is a flavonoid we have purified from the plant Achillea fragrantissima; and the present study examined, for the first time, the effects of this compound on Aβ-toxicity to neuronal cells. Methods Various chromatographic techniques were used to isolate TTF from the plant Achillea fragrantissima, and an N2a neuroblastoma cell line was used to study its activities. The cellular levels of total and phosphorylated stress-activated protein kinase/c-Jun N-terminal kinase (SAPK/JNK) and of total and phosphorylated extracellular signal-regulated kinase (ERK 1/2) were determined by enzyme-linked immunosorbent assay (ELISA). Intracellular reactive oxygen species (ROS) levels were measured by using 2′,7′-dichlorofluorescein diacetate (DCF-DA). Cytotoxicity and cell viability were assessed by using lactate dehydrogenase (LDH) activity in cell-conditioned media, or by crystal violet cell staining, respectively. Results TTF prevented the Aβ-induced death of neurons and attenuated the intracellular accumulation of ROS following treatment of these cells with Aβ. TTF also inhibited the Aβ-induced phosphorylation of the signaling proteins SAPK/JNK and ERK 1/2, which belong to the mitogen-activated protein kinase (MAPK) family. Conclusion TTF should be studied further as a potential therapeutic means for the treatment of Alzheimer’s disease.
Keywords	3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone ; Alzheimer’s disease ; Neurons ; Flavonoids ; Amyloid beta ; Achillea fragrantissima ; Other systems of medicine ; RZ201-999
Subject code	571
Language	English
Publishing date	2017-06-01T00:00:00Z
Publisher	BMC
Document type	Article ; Online
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Article ; Online: 3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone protects against beta amyloid-induced neurotoxicity through antioxidative activity and interference with cell signaling

Telerman, Alona / Ofir, Rivka / Kashman, Yoel / Elmann, Anat

BMC Complement Altern Med. 2017 Dec., v. 17, no. 1 p.332-332

2017

Abstract: BACKGROUND: Alzheimer’s disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major contributors ... ...

Abstract	BACKGROUND: Alzheimer’s disease is a neurodegenerative disease, characterized by progressive decline in memory and cognitive functions, that results from loss of neurons in the brain. Amyloid beta (Aβ) protein and oxidative stress are major contributors to Alzheimer’s disease, therefore, protecting neuronal cells against Aβ-induced toxicity and oxidative stress might form an effective approach for treatment of this disease. 3,5,4′-trihydroxy-6,7,3′-trimethoxyflavone (TTF) is a flavonoid we have purified from the plant Achillea fragrantissima; and the present study examined, for the first time, the effects of this compound on Aβ-toxicity to neuronal cells. METHODS: Various chromatographic techniques were used to isolate TTF from the plant Achillea fragrantissima, and an N2a neuroblastoma cell line was used to study its activities. The cellular levels of total and phosphorylated stress-activated protein kinase/c-Jun N-terminal kinase (SAPK/JNK) and of total and phosphorylated extracellular signal-regulated kinase (ERK 1/2) were determined by enzyme-linked immunosorbent assay (ELISA). Intracellular reactive oxygen species (ROS) levels were measured by using 2′,7′-dichlorofluorescein diacetate (DCF-DA). Cytotoxicity and cell viability were assessed by using lactate dehydrogenase (LDH) activity in cell-conditioned media, or by crystal violet cell staining, respectively. RESULTS: TTF prevented the Aβ-induced death of neurons and attenuated the intracellular accumulation of ROS following treatment of these cells with Aβ. TTF also inhibited the Aβ-induced phosphorylation of the signaling proteins SAPK/JNK and ERK 1/2, which belong to the mitogen-activated protein kinase (MAPK) family. CONCLUSION: TTF should be studied further as a potential therapeutic means for the treatment of Alzheimer’s disease.
Keywords	Achillea fragrantissima ; amyloid ; antioxidant activity ; brain ; cell lines ; cell viability ; chromatography ; cognition ; complement ; cytotoxicity ; death ; enzyme-linked immunosorbent assay ; flavonoids ; gentian violet ; lactate dehydrogenase ; memory ; mitogen-activated protein kinase ; neurodegenerative diseases ; neurons ; neurotoxicity ; oxidative stress ; phosphorylation ; reactive oxygen species ; therapeutics
Language	English
Dates of publication	2017-12
Size	p. 332.
Publishing place	BioMed Central
Document type	Article ; Online
Note	Resource is Open Access
ZDB-ID	2050429-9
ISSN	1472-6882
ISSN	1472-6882
DOI	10.1186/s12906-017-1840-y
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Modified Clerodanes from the Essential Oil of Dodonea viscosa Leaves

Arnaud Marvilliers / Bertrand Illien / Emmanuelle Gros / Jonathan Sorres / Yoel Kashman / Hermann Thomas / Jacqueline Smadja / Anne Gauvin-Bialecki

Molecules, Vol 25, Iss 4, p

2020 Volume 850

Abstract: Dodonea viscosa (L.) Jacq from Reunion Island (Indian Ocean) was investigated for its leaf essential oil composition. The plant was extracted by hydrodistillation and its essential oil analysed by gas chromatography coupled to mass spectrometry. This ... ...

Abstract	Dodonea viscosa (L.) Jacq from Reunion Island (Indian Ocean) was investigated for its leaf essential oil composition. The plant was extracted by hydrodistillation and its essential oil analysed by gas chromatography coupled to mass spectrometry. This study revealed that oxygenated nor-diterpenes and diterpenes were one of the major chemical classes (> 50%) mainly consisting of three modified cyclopropylclerodanes containing a bicyclo[5.4.0]undecane ring system: one new furanoid norditerpene, dodovisate C, and two furanoid diterpenes, the known methyl dodovisate A and the new methyl iso-dodovisate A. These three compounds were isolated by liquid chromatography and their structures established on the basis of spectroscopic studies. The absolute configuration of dodovisate C was elucidated through a joint experimental and theoretical (B3LYP/6-311+G(d,p)) electronic circular dichroism study. The relative configurations of methyl dodovisate A and methyl iso-dodovisate A were determined using linear regressions of theoretical chemical shifts versus experimental values with the (B3LYP/6-311+G(d,p)) method.
Keywords	dodonea viscosa ; essential oil ; furanoid (nor)diterpenes ; bicyclo[5.4.0]undecane skeleton ; electronic circular dichroism ; density functional theory ; Organic chemistry ; QD241-441
Subject code	540
Language	English
Publishing date	2020-02-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Bisdioxycalamenene: A Bis-Sesquiterpene from the Soft Coral Rhytisma fulvum fulvum.

Trifman, Yuval J / Aknin, Maurice / Gauvin-Bialecki, Anne / Benayahu, Yehuda / Carmeli, Shmuel / Kashman, Yoel

Marine drugs

2016 Volume 14, Issue 2

Abstract: A dichloromethane extract of the soft coral Rhytisma fulvum fulvum collected in Madagascar afforded a novel compound possessing an unprecedented pentacyclic skeleton, bisdioxycalamenene (1), as well as seven known sesquiterpenes. The structures of the ... ...

Abstract	A dichloromethane extract of the soft coral Rhytisma fulvum fulvum collected in Madagascar afforded a novel compound possessing an unprecedented pentacyclic skeleton, bisdioxycalamenene (1), as well as seven known sesquiterpenes. The structures of the compounds were elucidated using 1D and 2D NMR techniques, as well as high-resolution mass spectrometry. The absolute configuration of 1 was determined using X-ray diffraction analysis and anomalous dispersion effects. The structure elucidation and a possible biogenesis of the compound are discussed.
MeSH term(s)	Animals ; Anthozoa/chemistry ; Madagascar ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Sesquiterpenes/chemistry ; Sesquiterpenes/isolation & purification ; Terpenes/chemistry ; Terpenes/isolation & purification ; X-Ray Diffraction
Chemical Substances	Sesquiterpenes ; Terpenes
Language	English
Publishing date	2016-02-19
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2175190-0
ISSN	1660-3397 ; 1660-3397
ISSN (online)	1660-3397
ISSN	1660-3397
DOI	10.3390/md14020041
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