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      Discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins

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          Abstract

          Ocotillol-type saponins are one kind of tetracyclic triterpenoids, sharing a tetrahydrofuran ring. Natural ocotillol-type saponins have been discovered in Panax quinquefolius L., Panax japonicus, Hana mina, and Vietnamese ginseng. In recent years, the semisynthesis of 20( S/ R)-ocotillol-type saponins has been reported. The biological activities of ocotillol-type saponins include neuroprotective effect, antimyocardial ischemia, antiinflammatory, antibacterial, and antitumor activities. Owing to their chemical structure, pharmacological actions, and the stereoselective activity on antimyocardial ischemia, ocotillol-type saponins are subjected to extensive consideration. In this review, we sum up the discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins.

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          Pseudoginsenoside-F11 (PF11) exerts anti-neuroinflammatory effects on LPS-activated microglial cells by inhibiting TLR4-mediated TAK1/IKK/NF-κB, MAPKs and Akt signaling pathways.

          Xiaoxiao Wang, Chunming Wang, Jiming Wang … (2014)
          Pseudoginsenoside-F11 (PF11), an ocotillol-type ginsenoside, has been shown to possess significant neuroprotective activity. Since microglia-mediated inflammation is critical for induction of neurodegeneration, this study was designed to investigate the effect of PF11 on activated microglia. PF11 significantly suppressed the release of ROS and proinflammatory mediators induced by LPS in a microglial cell line N9 including NO, PGE2, IL-1β, IL-6 and TNF-α. Moreover, PF11 inhibited interaction and expression of TLR4 and MyD88 in LPS-activated N9 cells, resulting in an inhibition of the TAK1/IKK/NF-κB signaling pathway. PF11 also inhibited the phosphorylation of Akt and MAPKs induced by LPS in N9 cells. Importantly, PF11 significantly alleviated the death of SH-SY5Y neuroblastoma cells and primary cortical neurons induced by the conditioned-medium from activated microglia. At last, the effect of PF11 on neuroinflammation was confirmed in vivo: PF11 mitigated the microglial activation and proinflammatory factors expression obviously in both cortex and hippocampus in mice injected intrahippocampally with LPS. These findings indicate that PF11 exerts anti-neuroinflammatory effects on LPS-activated microglial cells by inhibiting TLR4-mediated TAK1/IKK/NF-κB, MAPKs and Akt signaling pathways, suggesting its therapeutic implication for neurodegenerative disease associated with neuroinflammation.
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            Epoxide-Opening Cascades in the Synthesis of Polycyclic Polyether Natural Products

            Ivan Vilotijevic, Timothy Jamison (2009)
            The structural features of polycyclic polyether natural products can, in some cases, be traced to their biosynthetic origin. However in case that are less well understood, only biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades are proposed. We summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers (see scheme) and related natural products.The group of polycyclic polyether natural products is of special interest owing to the fascinating structure and biological effects displayed by its members. The latter includes potentially therapeutic antibiotic, antifungal, and anticancer properties, and extreme lethality. The polycyclic structural features of this class of compounds can, in some cases, be traced to their biosynthetic origin, but in others that are less well understood, only to proposed biosynthetic pathways that feature dramatic, yet speculative, epoxide-opening cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of polycyclic polyethers and related natural products.
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              Anti-amnesic effect of pseudoginsenoside-F11 in two mouse models of Alzheimer's disease.

              Chun-Ming Wang, Ming-Yan Liu, Fang Wang … (2013)
              Alzheimer's disease (AD) is a progressive neurodegenerative disease characterized by amyloid β (Aβ) deposits, elevated oxidative stress, and apoptosis of the neurons. Pseudoginsenoside-F11 (PF11), a component of Panax quinquefolium (American ginseng), has been demonstrated to antagonize the learning and memory deficits induced by scopolamine, morphine and methamphetamine in mice. In the present study, we investigated the effect of PF11 on AD-like cognitive impairment both in mice induced by intracerebroventricular injection of Aβ1-42 (410 pmol) and in Tg-APPswe/PS1dE9 (APP/PS1) mice. It was found that oral treatment with PF11 significantly mitigated learning and memory impairment in mice given Aβ1-42-treated mice for 15 days at doses of 1.6 and 8 mg/kg and APP/PS1 for 4 weeks at a dose of 8 mg/kg as measured by the Morris water maze and step-through tests. In APP/PS1 mice, PF11 8 mg/kg significantly inhibited the expressions of β-amyloid precursor protein (APP) and Aβ1-40 in the cortex and hippocampus, restored the activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) and decreased the production of malondialdehyde (MDA) in the cortex. It also noticeably improved the histopathological changes in the cortex and hippocampus and downregulated the expressions of JNK 2, p53 and cleaved caspase 3 in the hippocampus. These findings suggested that the inhibitory effect on amyloidogenesis and oxidative stress and some beneficial effects on neuronal functions might contribute to the recognition improvement effect of PF11 in APP/PS1 mice. Cumulatively, the present study indicated that PF11 may serve as a potential therapeutic agent for the treatment of AD. Copyright © 2013 Elsevier Inc. All rights reserved.
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                Author and article information

                Contributors
                Qingguo Meng
                Journal
                Journal ID (nlm-ta): J Ginseng Res
                Journal ID (iso-abbrev): J Ginseng Res
                Title: Journal of Ginseng Research
                Publisher: Elsevier
                ISSN (Print): 1226-8453
                ISSN (Electronic): 2093-4947
                Publication date PMC-release: 13 January 2017
                Publication date (Print): July 2017
                Publication date (Electronic): 13 January 2017
                Volume: 41
                Issue: 3
                Pages: 373-378
                Affiliations
                [1]School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai, China
                Author notes
                [∗ ]Corresponding author. School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, 30, Qingquan RD, Laishan District, Yantai 264005, China.School of PharmacyKey Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University)Ministry of EducationCollaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of ShandongYantai University30, Qingquan RD, Laishan DistrictYantai264005China qinggmeng@ 123456163.com
                Article
                Publisher ID: S1226-8453(16)30181-6
                DOI: 10.1016/j.jgr.2017.01.001
                PMC ID: 5489761
                PubMed ID: 28701880
                SO-VID: 074996d3-e1ee-49d7-97b0-1cb6a842a68f
                Copyright © © 2017 The Korean Society of Ginseng, Published by Elsevier Korea LLC.
                License:

                This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                Date received : 10 September 2016
                Date revision received : 31 December 2016
                Date accepted : 2 January 2017
                Categories
                Subject: Review Article

                Keywords: biological activity,discovery,metabolism,ocotillol-type saponin,semisynthesis
                Data availability:
                Keywords: biological activity, discovery, metabolism, ocotillol-type saponin, semisynthesis

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