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      A new glucosidic iridoid from Isodon rubescens

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          Abstract

          ABSTRACT One new glucosidic iridoid, 6-O-veratroylbarlerin, was isolated from the chloroform/methanol extract of Isodon rubescens (Hemsl.) H.Hara, Lamiaceae aerial parts, along with the known compounds apigenin and caffeic acid. The structure of the new compound was elucidated on the basis of 1D and 2D NMR experiments and ESI-MS technique.

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          Diterpenoids from Isodon species and their biological activities.

          Han-Dong Sun, Sheng-Xiong Huang, Quan-Bin Han (2006)
          Isodon species (Labiatae) are widely distributed plants, many of which are used in folk medicine. Over the past twenty years, they have received considerable phytochemical and biological attention. Thestructures of their many diterpenoids constituents, especially those with an ent-kaurane skeleton, have been elucidated. The significant phytochemical and pharmacological diterpenoids form the subject of this review. There are 290 references.
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            Novel nitrogen-enriched oridonin analogues with thiazole-fused A-ring: protecting group-free synthesis, enhanced anticancer profile, and improved aqueous solubility.

            Chunyong Ding, YUSONG ZHANG, Haijun Chen … (2013)
            Oridonin (1), a complex ent-kaurane diterpenoid isolated from the traditional Chinese herb Isodon rubescens , has demonstrated great potential in the treatment of various human cancers due to its unique and safe anticancer pharmacological profile. Nevertheless, the clinical development of oridonin for cancer therapy has been hampered by its relatively moderate potency, limited aqueous solubility, and poor bioavailability. Herein, we report the concise synthesis of a series of novel nitrogen-enriched oridonin derivatives with thiazole-fused A-ring through an efficient protecting group-free synthetic strategy. Most of them, including compounds 7-11, 13, and 14, exhibited potent antiproliferative effects against breast, pancreatic, and prostate cancer cells with low micromolar to submicromolar IC50 values as well as markedly enhanced aqueous solubility. These new analogues obtained by rationally modifying the natural product have been demonstrated not only to significantly induce the apoptosis and suppress growth of triple-negative MDA-MB-231 breast cancer both in vitro and in vivo but also effective against drug-resistant ER-positive MCF-7 clones.
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              α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium.

              Nunziatina De Tommasi, Alessandra Braca, Margherita Lapillo … (2016)
              Three new coumarins (1-3), a prenylated flavanone (4), and two iridoids (5 and 6), together with 17 known secondary metabolites, were isolated from the aerial parts of Arcytophyllum thymifolium. The structures of the new compounds were elucidated on the basis of their spectroscopic data. The potential hypoglycemic properties of the new and known compounds were evaluated by measuring their α-amylase and α-glucosidase inhibitory effects. The iridoid asperulosidic acid (15) and the flavonoid rhamnetin (13) showed the highest activities versus α-amylase (IC50 = 69.4 ± 3.1 and 73.9 ± 5.9 μM, respectively). In turn, the new eriodictyol derivative 4 exhibited the most potent effect as an α-glucosidase inhibitor, with an IC50 value of 28.1 ± 2.6 μM, and was more active than acarbose, used as a positive control. Modeling studies were also performed to suggest the interaction mode of compound 4 in the α-glucosidase enzyme active site.
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                Author and article information

                Contributors
                Soumia Belaabed: Role: ND
                Marinella De Leo: Role: ND
                Salvatore Velotto: Role: ND
                Nicola Malafronte: Role: ND
                Massimiliano D’Ambola: Role: ND
                Journal
                Journal ID (publisher-id): rbfar
                Title: Revista Brasileira de Farmacognosia
                Abbreviated Title: Rev. bras. farmacogn.
                Publisher: Sociedade Brasileira de Farmacognosia (Curitiba, PR, Brazil )
                ISSN (Print): 0102-695X
                ISSN (Electronic): 1981-528X
                Publication date (Print and electronic): June 2018
                Volume: 28
                Issue: 3
                Pages: 294-297
                Affiliations
                [1] Constantine orgnameUniversity Mentouri Constantine orgdiv1Development of Natural Resources, Bioactive Molecules, Physiochemical and Biological Analysis orgdiv2Research Unit Algeria
                [3] Napoli orgnameUniversità di Napoli Federico II orgdiv1Dipartimento di Medicina Veterinaria e Produzione Animale Italy
                [2] Pisa orgnameUniversità di Pisa orgdiv1Dipartimento di Farmacia Italy
                [4] Salerno orgnameUniversità di Salerno orgdiv1Dipartimento di Farmacia Italy
                Article
                Publisher ID: S0102-695X2018000300294
                DOI: 10.1016/j.bjp.2018.03.009
                SO-VID: 75220ca0-4e35-43b9-95a3-ea8e8b0a3972
                License:

                This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

                History
                Date accepted : 07 March 2018
                Date received : 26 January 2018
                Page count
                Figures: 0, Tables: 0, Equations: 0, References: 44, Pages: 4
                Product

                SciELO Brazil


                Keywords: Iridoid,NMR,Lamiaceae,Rabdosia
                Data availability:
                Keywords: Iridoid, NMR, Lamiaceae, Rabdosia

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