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Keywords = furanosesquiterpenoid

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11 pages, 467 KiB  
Article
Volatile Constituents and Antimicrobial Activity of Naio (Myoporum Sandwicense A. Gray), a Native Hawaiian Tree
by Noura S. Dosoky, Prabodh Satyal, Aaron Sorensen and William N. Setzer
Compounds 2023, 3(1), 142-152; https://doi.org/10.3390/compounds3010012 - 29 Jan 2023
Cited by 4 | Viewed by 3112
Abstract
Myoporum sandwicense A. Gray (naio) is one of the characteristic trees of Hawaiian montane–subalpine mesic forests. In this study, lab-distilled oils of M. sandwicense leaves, wood, and twigs growing on the island of Hawaii, as well as industrially produced wood oils, were characterized [...] Read more.
Myoporum sandwicense A. Gray (naio) is one of the characteristic trees of Hawaiian montane–subalpine mesic forests. In this study, lab-distilled oils of M. sandwicense leaves, wood, and twigs growing on the island of Hawaii, as well as industrially produced wood oils, were characterized by gas chromatography–mass spectrometry (GC-MS). The lab-distilled oils were screened for antimicrobial activity. M. sandwicense leaf essential oil was rich in β-caryophyllene (15.1%), α-humulene (12.8%), germacrene D (7.9%), bicyclogermacrene (12.5%), brigalow ketol (9.6%), and myoporone (16.8%), while the wood essential oils were dominated by α-bisabolol and trans-α-bisabolol oxide B. The sapwood oil was dominated by palmitic acid (35.5%), linoleic acid (19.7%), oleic acid (31.9%), and stearic acid (5.7%), whereas the oil from twigs was rich in tricosane (77.3%) and pentacosane (13.1%). M. sandwicense essential oils were screened for antimicrobial activity against a panel of potentially pathogenic bacteria and fungi. The leaf essential oil of M. sandwicense showed excellent antibacterial activity against S. pyogenes and antifungal activity against A. fumigatus. The wood essential oil showed notable activity against S. pyogenes, A. fumigatus, A. niger, and M. gypseum. The twig oil was remarkably active against mold species. This work is the first report we are aware of on the composition and antimicrobial properties of naio essential oils. Full article
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20 pages, 1759 KiB  
Article
Phytochemical Composition of Commiphora Oleogum Resins and Their Cytotoxicity against Skin Cancer Cells
by Judith Ulrich, Svenja Stiltz, Alexis St-Gelais, Menna El Gaafary, Thomas Simmet, Tatiana Syrovets and Michael Schmiech
Molecules 2022, 27(12), 3903; https://doi.org/10.3390/molecules27123903 - 17 Jun 2022
Cited by 8 | Viewed by 4715
Abstract
Oleogum resins of the genus Commiphora have been used in traditional medicines for centuries. More than 200 Commiphora species exhibit highly variable phytochemical compositions. A novel highly selective, sensitive, accurate HPLC-MS/MS method was developed and validated to quantify five characteristic phytosteroids and furanosesquiterpenoids, [...] Read more.
Oleogum resins of the genus Commiphora have been used in traditional medicines for centuries. More than 200 Commiphora species exhibit highly variable phytochemical compositions. A novel highly selective, sensitive, accurate HPLC-MS/MS method was developed and validated to quantify five characteristic phytosteroids and furanosesquiterpenoids, namely (E)-guggulsterone, (Z)-guggulsterone, curzerenone, furanoeudesma-1,3-diene, and myrrhone. The resulting contents and additionally GC analysis were used to classify and differentiate Commiphora oleogum resins of the species C. myrrha, C. erythraea, C. mukul, C. holtziana, C. confusa, and C. kua, as well as unspecified resins. Interestingly, a Commiphora sample from Ogaden, Ethiopia, comprised 446 ng/mg guggulsterones presumed to be unique to C. mukul from the Indian subcontinent. However, Commiphora from Ogaden differed considerably from C. mukul in respect to guggulsterones isomer’s ratio. Moreover, the cytotoxicity of Commiphora extracts, essential oils, botanical drugs containing Commiphora, and pure compounds against the epidermoid carcinoma A431, malignant melanoma RPMI-7951 and SK-MEL-28 cells was investigated in vitro. Thereby, especially C. mukul extract and C. myrrha essential oil exhibited high cytotoxicity against skin cancer cells with IC50 of 2.9–10.9 µg/mL, but were less toxic to normal keratinocytes. In summary, Commiphora oleogum resins and its phytochemicals warrant further investigation aiming at chemotaxonomical classification as well as application in skin cancer treatment. Full article
(This article belongs to the Special Issue Cytotoxic Activity of Plant Extracts-2nd Edition)
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14 pages, 3029 KiB  
Article
Cytotoxic Evaluation and Anti-Angiogenic Effects of Two Furano-Sesquiterpenoids from Commiphora myrrh Resin
by Ali S. Alqahtani, Fahd A. Nasr, Omar M. Noman, Muhammad Farooq, Tariq Alhawassi, Wajhul Qamar and Ali El-Gamal
Molecules 2020, 25(6), 1318; https://doi.org/10.3390/molecules25061318 - 13 Mar 2020
Cited by 40 | Viewed by 4755
Abstract
Commiphora myrrh resin (Myrrh) has been used in traditional Arabic medicine to treat various inflammatory diseases. Two furano-sesquiterpenoids, 2-methoxyfuranodiene (CM1) and 2-acetoxyfuranodiene (CM2), were isolated from the chloroform fraction of the ethanolic extract of Arabic Commiphora myrrh resin. The cytotoxicity of the compounds [...] Read more.
Commiphora myrrh resin (Myrrh) has been used in traditional Arabic medicine to treat various inflammatory diseases. Two furano-sesquiterpenoids, 2-methoxyfuranodiene (CM1) and 2-acetoxyfuranodiene (CM2), were isolated from the chloroform fraction of the ethanolic extract of Arabic Commiphora myrrh resin. The cytotoxicity of the compounds was evaluated using human liver carcinoma, breast cancer cells (HepG2 and MCF-7, respectively) and normal human umbilical vein endothelial cells (HUVECs) cell lines. The development toxicity and anti-angiogenic activity of both compounds were also evaluated using zebrafish embryos. Cell survival assays demonstrated that both compounds were highly cytotoxic in HepG2 and MCF7 cells, with IC50 values of 3.6 and 4.4 µM, respectively. Both compounds induced apoptosis and caused cell cycle arrest in treated HepG2 cells, which was observed using flow cytometric analysis. The development toxicity in zebrafish embryos showed the chronic toxicity of both compounds. The toxicity was only seen when the embryos remained exposed to the compounds for more than three days. The compound CM2 showed a significant level of anti-angiogenic activity in transgenic zebrafish embryos at sublethal doses. Thus, we demonstrated the cytotoxic properties of both compounds, suggesting that the molecular mechanism of these compounds should be further assessed. Full article
(This article belongs to the Special Issue Zebrafish-Based Drug Screening)
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13 pages, 293 KiB  
Article
Protective Effects of Commiphora erythraea Resin Constituents Against Cellular Oxidative Damage
by Maria Carla Marcotullio, Federica Messina, Massimo Curini, Antonio Macchiarulo, Marco Cellanetti, Donata Ricci, Laura Giamperi, Anahi Bucchini, Alba Minelli, Anna Lisa Mierla and Ilaria Bellezza
Molecules 2011, 16(12), 10357-10369; https://doi.org/10.3390/molecules161210357 - 14 Dec 2011
Cited by 14 | Viewed by 5830
Abstract
By bioguided fractionation of the hexane extract of Commiphora erythraea resin we isolated four furanosesquiterpenoids that were tested for their protective activity against oxidative stress. Furanodienone and 1,10(15)-furanogermacra-dien-6-ones showed to be potent inhibitors of lipid peroxidation (IC50 of ~0.087 μM), being more [...] Read more.
By bioguided fractionation of the hexane extract of Commiphora erythraea resin we isolated four furanosesquiterpenoids that were tested for their protective activity against oxidative stress. Furanodienone and 1,10(15)-furanogermacra-dien-6-ones showed to be potent inhibitors of lipid peroxidation (IC50 of ~0.087 μM), being more active than the methoxylated analogues. Furthermore, using BV2 microglial cells, we found that furanodienone from C. erythraea is able to counteract LPS-induced cell death and decrease LPS-induced NO generation thus protecting microglial cells from LPS-induced cytotoxicity. Finally, docking studies were undertaken to gain insight into the possible binding mode of the isolated compounds at 5-LOX binding site. Full article
(This article belongs to the Section Natural Products Chemistry)
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