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Xia J, Chen X, Li G, Qiu P, Wang W, Shao Z. A Review of Sponge-Derived Diterpenes: 2009-2022. Mar Drugs 2024; 22:447. [PMID: 39452855 PMCID: PMC11509224 DOI: 10.3390/md22100447] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/05/2024] [Revised: 09/16/2024] [Accepted: 09/26/2024] [Indexed: 10/26/2024] Open
Abstract
Sponges are a vital source of pharmaceutically active secondary metabolites, of which the main structural types are alkaloids and terpenoids. Many of these compounds exhibit biological activities. Focusing specifically on diterpenoids, this article reviews the structures and biological activities of 228 diterpenes isolated from more than 33 genera of sponges from 2009 to 2022. The Spongia sponges produce the most diterpenoid molecules among all genera, accounting for 27%. Of the 228 molecules, 110 exhibit cytotoxic, antibacterial, antifungal, antiparasitic, anti-inflammatory, and antifouling activities, among others. The most prevalent activity is cytotoxicity, present in 54 molecules, which represent 24% of the diterpenes reported. These structurally and biologically diverse diterpenoids highlight the vast, yet largely untapped, potential of marine sponges in the discovery of new bioactive molecules for medicinal use.
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Affiliation(s)
- Jinmei Xia
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
| | - Xiangwei Chen
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
- Department of Pharmacy, NO. 971 Hospital of the People’s Liberation Army Navy, Qingdao 266000, China
| | - Guangyu Li
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
| | - Peng Qiu
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
| | - Weiyi Wang
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
| | - Zongze Shao
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China; (X.C.); (G.L.); (P.Q.)
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2
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Dembitsky VM. Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application. Biomedicines 2024; 12:1021. [PMID: 38790983 PMCID: PMC11117879 DOI: 10.3390/biomedicines12051021] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/12/2024] [Revised: 04/29/2024] [Accepted: 05/01/2024] [Indexed: 05/26/2024] Open
Abstract
The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds are sourced from marine organisms like sponges, soft corals, and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.
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Affiliation(s)
- Valery M Dembitsky
- Centre for Applied Research, Innovation and Entrepreneurship, Lethbridge College, 3000 College Drive South, Lethbridge, AB T1K 1L6, Canada
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Qiu P, Xia J, Zhang H, Lin D, Shao Z. A Review of Diterpenes from Marine-Derived Fungi: 2009-2021. Molecules 2022; 27:molecules27238303. [PMID: 36500394 PMCID: PMC9741372 DOI: 10.3390/molecules27238303] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/09/2022] [Revised: 11/20/2022] [Accepted: 11/23/2022] [Indexed: 11/30/2022] Open
Abstract
Marine-derived fungi are important sources of novel compounds and pharmacologically active metabolites. As an important class of natural products, diterpenes show various biological activities, such as antiviral, antibacterial, anti-inflammatory, antimalarial, and cytotoxic activities. Developments of equipment for the deep-sea sample collection allow discoveries of more marine-derived fungi with increasing diversity, and much progress has been made in the identification of diterpenes with novel structures and bioactivities from marine fungi in the past decade. The present review article summarized the chemical structures, producing organisms and biological activities of 237 diterpenes which were isolated from various marine-derived fungi over the period from 2009 to 2021. This review is beneficial for the exploration of marine-derived fungi as promising sources of bioactive diterpenes.
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Affiliation(s)
- Peng Qiu
- Marine Biomedical Research Institution, Guangdong Medical University, Zhanjiang 524023, China
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
- Guangdong Key Laboratory for Research and Development of Natural Drugs, Guangdong Medical University, Zhanjiang 524023, China
| | - Jinmei Xia
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
| | - Haitao Zhang
- Marine Biomedical Research Institution, Guangdong Medical University, Zhanjiang 524023, China
- Guangdong Key Laboratory for Research and Development of Natural Drugs, Guangdong Medical University, Zhanjiang 524023, China
- Correspondence: (H.Z.); (D.L.); (Z.S.)
| | - Donghai Lin
- Key Laboratory for Chemical Biology of Fujian Province, MOE Key Laboratory of Spectrochemical Analysis & Instrumentation, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
- Correspondence: (H.Z.); (D.L.); (Z.S.)
| | - Zongze Shao
- Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
- Correspondence: (H.Z.); (D.L.); (Z.S.)
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Pu DB, Guo SQ, Ni DX, Lin J, Gao JB, Li XN, Zhang RH, Li XL, Luo C, Chen SJ, Xiao WL. Spiroarborin, an ent-Clerodane Homodimer from Callicarpa arborea as an Inhibitor of the Eleven-Nineteen Leukemia (ENL) Protein by Targeting the YEATS Domain. JOURNAL OF NATURAL PRODUCTS 2022; 85:317-326. [PMID: 35029993 DOI: 10.1021/acs.jnatprod.1c00775] [Citation(s) in RCA: 9] [Impact Index Per Article: 3.0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/14/2023]
Abstract
A spiro ent-clerodane homodimer with a rare 6/6/6/6/6-fused pentacyclic scaffold, spiroarborin (1), together with four new monomeric analogues (2-5), were isolated from Callicarpa arborea. Their structures were elucidated by comprehensive spectroscopic data analysis, quantum-chemical calculations, and X-ray diffraction. A plausible biosynthetic pathway of 1 was proposed, and a biomimetic synthesis of its derivative was accomplished. Compound 1 showed a potent inhibitory effect by directly binding to the YEATS domain of the 11-19 leukemia (ENL) protein with an IC50 value of 7.3 μM. This gave a KD value of 5.0 μM, as recorded by a surface plasmon resonance binding assay.
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Affiliation(s)
- De-Bing Pu
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
| | - Si-Qi Guo
- The Center for Chemical Biology, Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
- School of Pharmacy, Nanchang University, Nanchang 330006, People's Republic of China
| | - Dong-Xuan Ni
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
| | - Jing Lin
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
| | - Jun-Bo Gao
- State Key Laboratory of CAD&CG, Zhejiang University, Hangzhou 310058, People's Republic of China
| | - Xiao-Ning Li
- School of Pharmaceutical Sciences, Yunnan University of Chinese Medicine, Kunming 650500, People's Republic of China
| | - Rui-Han Zhang
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
| | - Xiao-Li Li
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
| | - Cheng Luo
- The Center for Chemical Biology, Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
- University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China
| | - Shi-Jie Chen
- The Center for Chemical Biology, Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
- University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China
| | - Wei-Lie Xiao
- Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan Research & Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
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Kentsop RAD, Iobbi V, Donadio G, Ruffoni B, De Tommasi N, Bisio A. Abietane Diterpenoids from the Hairy Roots of Salvia corrugata. Molecules 2021; 26:5144. [PMID: 34500582 PMCID: PMC8434070 DOI: 10.3390/molecules26175144] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/07/2021] [Revised: 08/22/2021] [Accepted: 08/23/2021] [Indexed: 11/16/2022] Open
Abstract
Salvia corrugata Vahl. is an interesting source of abietane and abeo-abietane compounds that showed antibacterial, antitumor, and cytotoxic activities. The aim of the study was to obtain transformed roots of S. corrugata and to evaluate the production of terpenoids in comparison with in vivo root production. Hairy roots were initiated from leaf explants by infection with ATCC 15834 Agrobacterium rhizogenes onto hormone-free Murashige and Skoog (MS) solid medium. Transformation was confirmed by polymerase chain reaction analysis of rolC and virC1 genes. The biomass production was obtained in hormone-free liquid MS medium using Temporary Immersion System bioreactor RITA®. The chromatographic separation of the methanolic extract of the untransformed roots afforded horminone, ferruginol, 7-O-acetylhorminone and 7-O-methylhorminone. Agastol and ferruginol were isolated and quantified from the hairy roots. The amount of these metabolites indicated that the hairy roots of S. corrugata can be considered a source of these compounds.
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Affiliation(s)
- Roméo Arago Dougué Kentsop
- Dipartimento di Farmacia, Università di Genova, Viale Cembrano 4, 16148 Genova, Italy; (R.A.D.K.); (V.I.)
- Consiglio per la Ricerca e la Sperimentazione in Agricoltura—CREA Centro di Ricerca Orticoltura e Florovivaismo, Corso degli Inglesi, 508, 18038 Sanremo, Italy;
| | - Valeria Iobbi
- Dipartimento di Farmacia, Università di Genova, Viale Cembrano 4, 16148 Genova, Italy; (R.A.D.K.); (V.I.)
| | - Giuliana Donadio
- Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II 132, 84084 Salerno, Italy;
| | - Barbara Ruffoni
- Consiglio per la Ricerca e la Sperimentazione in Agricoltura—CREA Centro di Ricerca Orticoltura e Florovivaismo, Corso degli Inglesi, 508, 18038 Sanremo, Italy;
| | - Nunziatina De Tommasi
- Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II 132, 84084 Salerno, Italy;
| | - Angela Bisio
- Dipartimento di Farmacia, Università di Genova, Viale Cembrano 4, 16148 Genova, Italy; (R.A.D.K.); (V.I.)
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Ren AQ, Wang HJ, Zhu HY, Ye G, Li K, Chen DF, Zeng T, Li H. Glycoproteins From Rabdosia japonica var. glaucocalyx Regulate Macrophage Polarization and Alleviate Lipopolysaccharide-Induced Acute Lung Injury in Mice via TLR4/NF-κB Pathway. Front Pharmacol 2021; 12:693298. [PMID: 34366849 PMCID: PMC8333617 DOI: 10.3389/fphar.2021.693298] [Citation(s) in RCA: 8] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/10/2021] [Accepted: 06/24/2021] [Indexed: 01/04/2023] Open
Abstract
Background and Aims:Rabdosia japonica var. glaucocalyx is a traditional Chinese medicine (TCM) for various inflammatory diseases. This present work aimed to investigate the protective effects of R. japonica var. glaucocalyx glycoproteins on lipopolysaccharide (LPS)-induced acute lung injury (ALI) and the potential mechanism. Methods: Glycoproteins (XPS) were isolated from R. japonica var. glaucocalyx, and homogeneous glycoprotein (XPS5-1) was purified from XPS. ANA-1 cells were used to observe the effect of glycoproteins on the secretion of inflammatory mediators by enzyme-linked immunosorbent assay (ELISA). Flow cytometry assay, immunofluorescence assay, and Western blot analysis were performed to detect macrophage polarization in vitro. The ALI model was induced by LPS via intratracheal instillation, and XPS (20, 40, and 80 mg/kg) was administered intragastrically 2 h later. The mechanisms of XPS against ALI were investigated by Western blot, ELISA, and immunohistochemistry. Results:In vitro, XPS and XPS5-1 downregulated LPS-induced proinflammatory mediators production including tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, and nitric oxide (NO) and upregulated LPS-induced IL-10 secretion. The LPS-stimulated macrophage polarization was also modulated from M1 to M2. In vivo, XPS maintained pulmonary histology with significantly reducing protein concentration and numbers of mononuclear cells in bronchoalveolar lavage fluid (BALF). The level of IL-10 in BALF was upregulated by XPS treatment. The level of cytokines including TNF-α, IL-1β, and IL-6 was downregulated. XPS also decreased infiltration of macrophages and polymorphonuclear leukocytes (PMNs) in lung. XPS suppressed the expression of key proteins in the TLR4/NF-κB signal pathway. Conclusion: XPS was demonstrated to be a potential agent for treating ALI. Our findings might provide evidence supporting the traditional application of R. japonica var. glaucocalyx in inflammation-linked diseases.
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Affiliation(s)
- An-Qi Ren
- Department of Pharmacology, School of Pharmacy, Fudan University, Shanghai, China
| | - Hui-Jun Wang
- The MOE Key Laboratory for Standardization of Chinese Medicines and the SATCM Key Laboratory for New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai, China
| | - Hai-Yan Zhu
- Department of Biological Medicines and Shanghai Engineering Research Center of Immuno Therapeutics, School of Pharmacy, Fudan University, Shanghai, China
| | - Guan Ye
- Central Research Institute, Shanghai Pharmaceuticals Holding Co., Ltd., Shanghai, China
| | - Kun Li
- Central Research Institute, Shanghai Pharmaceuticals Holding Co., Ltd., Shanghai, China
| | - Dao-Feng Chen
- Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, China
| | - Tao Zeng
- Clinical Trial Institution, Obstetrics and Gynecology Hospital of Fudan University, Shanghai, China
| | - Hong Li
- Department of Pharmacology, School of Pharmacy, Fudan University, Shanghai, China
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Isolation of secondary metabolites of two endemic species: Salvia rosifolia Sm. and Salvia cerino-pruinosa Rech. f. var. elazigensis (Lamiaceae). JOURNAL OF FOOD MEASUREMENT AND CHARACTERIZATION 2021. [DOI: 10.1007/s11694-021-01065-8] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/21/2022]
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8
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Wiemann J, Al-Harrasi A, Csuk R. Cytotoxic Dehydroabietylamine Derived Compounds. Anticancer Agents Med Chem 2021; 20:1756-1767. [PMID: 32183684 DOI: 10.2174/1871520620666200317110010] [Citation(s) in RCA: 10] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/19/2019] [Revised: 10/19/2019] [Accepted: 11/12/2019] [Indexed: 12/28/2022]
Abstract
BACKGROUND AND METHODS Chemotherapy remains one of the most important methods for the treatment of cancer. More recently in this context, some products derived from natural products have raised scientific interest which especially include many terpenes. Thereby, diterpenoids represent a special class, and within this class of important secondary natural products, especially compounds derived from Dehydroabietylamine (DA), are of particular interest. RESULTS This review not only gives a summary of the most important findings on the cytotoxic behavior of DAderived compounds but also shows some drawbacks of these compounds, such low bioavailability and/or poor solubility of several derivatives of DA. It focusses on the chemical aspects and summarizes the DA related biological effects without deep discussion of underlying biochemical pathways. CONCLUSION Dehydroabietylamine-derived cytotoxic compounds hold a high potential to be developed into efficient antitumor active drugs.
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Affiliation(s)
- Jana Wiemann
- Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
| | - Ahmed Al-Harrasi
- University of Nizwa, Chair of Oman's Medicinal Plants and Marine Natural Products, P.O. Box 33, PC 616, Birkat Al-Mauz, Nizwa, Oman
| | - René Csuk
- Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
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9
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Hu Z, Ye Y, Zhang Y. Large-scale culture as a complementary and practical method for discovering natural products with novel skeletons. Nat Prod Rep 2021; 38:1775-1793. [PMID: 33650608 DOI: 10.1039/d0np00069h] [Citation(s) in RCA: 36] [Impact Index Per Article: 9.0] [Reference Citation Analysis] [Abstract] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/21/2022]
Abstract
Covering: up to July 2020Fungal metabolites with diverse and novel scaffolds can be assembled from well-known biosynthetic precursors through various mechanisms. Recent examples of novel alkaloids (e.g., cytochalasans and diketopiperazine derivatives), terpenes (e.g., sesterterpenes and diterpenes) and polyketides produced by fungi are presented through case studies. We show that large-scale culture is a complementary and practical method for genome mining and OSMAC approaches to discover natural products of unprecedented skeletal classes from fungi. We also summarize the discovery strategies and challenges for characterizing these compounds.
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Affiliation(s)
- Zhengxi Hu
- Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
| | - Ying Ye
- Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
| | - Yonghui Zhang
- Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
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10
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Liu KX, Qin DP, Zhu YX, Wang SX, Jiao YB, Ge PL, Cheng YX. Populeuphrines A and B, two new cembrane diterpenoids from the resins of Populus euphratica. Nat Prod Res 2019; 34:3108-3116. [PMID: 31264446 DOI: 10.1080/14786419.2019.1610753] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/25/2023]
Abstract
Two new cembrane diterpenoids, named populeuphrines A and B (1 and 2), together with three known analogues (3-5) were isolated from the resins of Populus euphratica. The planar structures and relative configurations of 1 and 2 were elucidated by detailed 1 D and 2 D NMR spectroscopic analyses. The absolute configurations of 1 and 2 were determined by X-ray diffraction analysis and quantum chemical computation. Biological activities of all the isolates against proliferation of human cancer cells and umbilical cord mesenchymal stem cells were evaluated.
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Affiliation(s)
- Kai-Xin Liu
- Department of Pharmacology, School of Basic Medical Sciences, Heilongjiang University of Chinese Medicine, Harbin, China
| | - Da-Peng Qin
- School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen, China
| | - Yan-Xia Zhu
- School of Basic Medicine, Shenzhen University Health Science Center, Shenzhen, China
| | - Shao-Xiang Wang
- School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen, China
| | - Ya-Bin Jiao
- School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen, China
| | - Peng-Ling Ge
- Department of Pharmacology, School of Basic Medical Sciences, Heilongjiang University of Chinese Medicine, Harbin, China
| | - Yong-Xian Cheng
- School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen, China
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11
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Wang MS, Wang Z, Chen W, Yang X, Zhang H. Synthesis of Oxa-Bridged Medium-Sized Carbocyclic Rings via Prins Cyclization. Org Lett 2019; 21:1881-1884. [PMID: 30816720 DOI: 10.1021/acs.orglett.9b00491] [Citation(s) in RCA: 14] [Impact Index Per Article: 2.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/24/2022]
Abstract
Herein, we report a new method for the synthesis of oxa-bridged carbocyclic units based on intramolecular Prins reaction of dioxinones. Our new synthetic approach is flexible and practical and has been successfully applied to the preparation of highly functionalized seven-, eight-, and nine-membered carbocycles. The potential utility of this approach has also been demonstrated in a model study toward construction of the 7,8-fused ring system presented in neoabyssomicin D.
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Affiliation(s)
- Min-Shou Wang
- Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P. R. China
| | - Zheng Wang
- Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P. R. China
| | - Wen Chen
- Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P. R. China
| | - Xiaodong Yang
- Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P. R. China
| | - Hongbin Zhang
- Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , P. R. China
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12
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Salazar FJ, Quintero A, de Domínguez NG, Concepción JL, Acosta ME, Tropper E, Villamizar JE. Synthesis, Antimalarial and Antileishmanial Activity of Novel 13-Benzyl-15,16-Bisnorlabdane Derivatives. JOURNAL OF CHEMICAL RESEARCH 2019. [DOI: 10.3184/174751913x13794472538261] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/17/2022]
Affiliation(s)
- Franklin J. Salazar
- Centro de Química, Instituto Venezolano de Investigaciones Científicas (IVIC), Caracas 1020-A, Venezuela
| | - Alberto Quintero
- Departamento de Química Medicinal, Instituto Venezolano de Investigaciones Científicas (IVIC), Caracas 1020-A, Venezuela
| | - Neira Gamboa de Domínguez
- Unidad de Bioquimica, Facultad de Farmacia, Universidad Central de Venezuela (UCV), Caracas 1051, Venezuela
| | - Juan L. Concepción
- Laboratorio de Enzimología de Parásitos, Facultad de Ciencias, Universidad de Los Andes (ULA), Mérida 5101, Venezuela
| | - María E. Acosta
- Unidad de Bioquimica, Facultad de Farmacia, Universidad Central de Venezuela (UCV), Caracas 1051, Venezuela
| | - Eleonora Tropper
- Centro de Química, Instituto Venezolano de Investigaciones Científicas (IVIC), Caracas 1020-A, Venezuela
| | - José E. Villamizar
- Centro de Química, Instituto Venezolano de Investigaciones Científicas (IVIC), Caracas 1020-A, Venezuela
- Departamento de Química Medicinal, Instituto Venezolano de Investigaciones Científicas (IVIC), Caracas 1020-A, Venezuela
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13
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Reveglia P, Cimmino A, Masi M, Nocera P, Berova N, Ellestad G, Evidente A. Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity. Chirality 2018; 30:1115-1134. [DOI: 10.1002/chir.23009] [Citation(s) in RCA: 24] [Impact Index Per Article: 3.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/05/2018] [Revised: 07/16/2018] [Accepted: 07/25/2018] [Indexed: 01/18/2023]
Affiliation(s)
- Pierluigi Reveglia
- Dipartimento di Scienze Chimiche Università di Napoli Federico II; Complesso Universitario Monte S. Angelo; Naples Italy
| | - Alessio Cimmino
- Dipartimento di Scienze Chimiche Università di Napoli Federico II; Complesso Universitario Monte S. Angelo; Naples Italy
| | - Marco Masi
- Dipartimento di Scienze Chimiche Università di Napoli Federico II; Complesso Universitario Monte S. Angelo; Naples Italy
| | - Paola Nocera
- Dipartimento di Scienze Chimiche Università di Napoli Federico II; Complesso Universitario Monte S. Angelo; Naples Italy
| | - Nina Berova
- Department of Chemistry; Columbia University; New York NY USA
| | - George Ellestad
- Department of Chemistry; Columbia University; New York NY USA
| | - Antonio Evidente
- Dipartimento di Scienze Chimiche Università di Napoli Federico II; Complesso Universitario Monte S. Angelo; Naples Italy
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14
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Kacprzak K, Skiera I, Piasecka M, Paryzek Z. Alkaloids and Isoprenoids Modification by Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition (Click Chemistry): Toward New Functions and Molecular Architectures. Chem Rev 2016; 116:5689-743. [DOI: 10.1021/acs.chemrev.5b00302] [Citation(s) in RCA: 176] [Impact Index Per Article: 19.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/14/2022]
Affiliation(s)
- Karol Kacprzak
- Bioorganic Chemistry Department, Faculty of Chemistry, Adam Mickiewicz University, Ul. Umultowska 89b, 61-614 Poznań, Poland
| | - Iwona Skiera
- Bioorganic Chemistry Department, Faculty of Chemistry, Adam Mickiewicz University, Ul. Umultowska 89b, 61-614 Poznań, Poland
| | - Monika Piasecka
- Bioorganic Chemistry Department, Faculty of Chemistry, Adam Mickiewicz University, Ul. Umultowska 89b, 61-614 Poznań, Poland
| | - Zdzisław Paryzek
- Bioorganic Chemistry Department, Faculty of Chemistry, Adam Mickiewicz University, Ul. Umultowska 89b, 61-614 Poznań, Poland
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15
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Lei H. Diterpenoids of Gorgonian Corals: Chemistry and Bioactivity. Chem Biodivers 2016; 13:345-65. [DOI: 10.1002/cbdv.201500030] [Citation(s) in RCA: 19] [Impact Index Per Article: 2.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/30/2015] [Accepted: 04/27/2015] [Indexed: 12/17/2022]
Affiliation(s)
- Hui Lei
- Industrial Innovation Center for Nutrition and Health of Huzhou; Shanghai Institutes for Biological Sciences of Chinese Academy of Sciences; Huzhou 313000 P. R. China
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16
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Khan MF, Azad CS, Kumar A, Saini M, Narula AK, Jain S. Novel Imbricatolic acid derivatives as protein tyrosine phosphatase-1B inhibitors: Design, synthesis, biological evaluation and molecular docking. Bioorg Med Chem Lett 2016; 26:1988-92. [DOI: 10.1016/j.bmcl.2016.03.003] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/23/2015] [Revised: 02/17/2016] [Accepted: 03/01/2016] [Indexed: 12/13/2022]
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17
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Zerbe P, Rodriguez SM, Mafu S, Chiang A, Sandhu HK, O'Neil-Johnson M, Starks CM, Bohlmann J. Exploring diterpene metabolism in non-model species: transcriptome-enabled discovery and functional characterization of labda-7,13E-dienyl diphosphate synthase from Grindelia robusta. THE PLANT JOURNAL : FOR CELL AND MOLECULAR BIOLOGY 2015; 83:783-93. [PMID: 26119826 DOI: 10.1111/tpj.12925] [Citation(s) in RCA: 20] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 05/05/2015] [Revised: 06/16/2015] [Accepted: 06/19/2015] [Indexed: 06/04/2023]
Abstract
Grindelia robusta or gumweed, is a medicinal herb of the sunflower family that forms a diverse suite of diterpenoid natural products. Its major constituents, grindelic acid and related grindelane diterpenoids accumulate in a resinous exudate covering the plants' surfaces, most prominently the unopened composite flower. Recent studies demonstrated potential pharmaceutical applications for grindelic acid and its synthetic derivatives. Mining of the previously published transcriptome of G. robusta flower tissue identified two additional diterpene synthases (diTPSs). We report the in vitro and in vivo functional characterization of an ent-kaurene synthase of general metabolism (GrTPS4) and a class II diTPS (GrTPS2) of specialized metabolism that converts geranylgeranyl diphosphate (GGPP) into labda-7,13E-dienyl diphosphate as verified by nuclear magnetic resonance (NMR) analysis. Tissue-specific transcript abundance of GrTPS2 in leaves and flowers accompanied by the presence of an endocyclic 7,13 double bond in labda-7,13E-dienyl diphosphate suggest that GrTPS2 catalyzes the first committed reaction in the biosynthesis of grindelic acid and related grindelane metabolites. With the formation of labda-7,13E-dienyl diphosphate, GrTPS2 adds an additional function to the portfolio of monofunctional class II diTPSs, which catalytically most closely resembles the bifunctional labda-7,13E-dien-15-ol synthase of the lycopod Selaginella moellendorffii. Together with a recently identified functional diTPS pair of G. robusta producing manoyl oxide, GrTPS2 lays the biosynthetic foundation of the diverse array of labdane-related diterpenoids in the genus Grindelia. Knowledge of these natural diterpenoid metabolic pathways paves the way for developing biotechnology approaches toward producing grindelic acid and related bioproducts.
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Affiliation(s)
- Philipp Zerbe
- Department of Plant Biology, University of California-Davis, 1 Shields Avenue, Davis, CA, 95616, USA
- Michael Smith Laboratories, University of British Columbia, 2185 East Mall, Vancouver, BC, V6T 1Z4, Canada
| | - Selina M Rodriguez
- Department of Plant Biology, University of California-Davis, 1 Shields Avenue, Davis, CA, 95616, USA
| | - Sibongile Mafu
- Department of Plant Biology, University of California-Davis, 1 Shields Avenue, Davis, CA, 95616, USA
| | - Angela Chiang
- Michael Smith Laboratories, University of British Columbia, 2185 East Mall, Vancouver, BC, V6T 1Z4, Canada
| | - Harpreet K Sandhu
- Michael Smith Laboratories, University of British Columbia, 2185 East Mall, Vancouver, BC, V6T 1Z4, Canada
| | - Mark O'Neil-Johnson
- Sequoia Sciences, 1912 Innerbelt Business Center Drive, Saint Louis, MO, 63114, USA
| | - Courtney M Starks
- Sequoia Sciences, 1912 Innerbelt Business Center Drive, Saint Louis, MO, 63114, USA
| | - Jörg Bohlmann
- Michael Smith Laboratories, University of British Columbia, 2185 East Mall, Vancouver, BC, V6T 1Z4, Canada
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18
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Abstract
The first total synthesis of an anti-leukemic diterpene natural product EBC-329 (1) has been accomplished starting from readily available 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione (7). An efficient and general approach has been reported for the synthesis of EBC-329 in 13 steps with an overall yield of 10%.
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Affiliation(s)
- Raju S Thombal
- Division of Organic Chemistry, National Chemical Laboratory (CSIR-NCL), Pune-411008, India.
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19
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20
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Durán-Peña MJ, Botubol Ares JM, Hanson JR, Collado IG, Hernández-Galán R. Biological activity of natural sesquiterpenoids containing a gem-dimethylcyclopropane unit. Nat Prod Rep 2015; 32:1236-48. [DOI: 10.1039/c5np00024f] [Citation(s) in RCA: 49] [Impact Index Per Article: 4.9] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/18/2022]
Abstract
The biological activity of sesquiterpenes containing the gem-dimethylcyclopropane unit is described.
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Affiliation(s)
| | | | | | - Isidro G. Collado
- Department of Organic Chemistry
- Faculty of Science
- University of Cádiz
- Puerto Real
- Spain
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21
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Usui K, Kanbe M, Nakada AM. Total Synthesis of (−)-Bucidarasin A Starting from an Original Chiral Building Block. Org Lett 2014; 16:4734-7. [DOI: 10.1021/ol502129u] [Citation(s) in RCA: 17] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Kenji Usui
- Department of Chemistry and
Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
| | - Misaki Kanbe
- Department of Chemistry and
Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
| | - and Masahisa Nakada
- Department of Chemistry and
Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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22
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Maslovskaya LA, Savchenko AI, Krenske EH, Pierce CJ, Gordon VA, Reddell PW, Parsons PG, Williams CM. EBC-219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond. Angew Chem Int Ed Engl 2014. [DOI: 10.1002/ange.201310923] [Citation(s) in RCA: 13] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/10/2022]
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23
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Maslovskaya LA, Savchenko AI, Krenske EH, Pierce CJ, Gordon VA, Reddell PW, Parsons PG, Williams CM. EBC-219: A New Diterpene Skeleton, Crotinsulidane, from the Australian Rainforest Containing a Bridgehead Double Bond. Angew Chem Int Ed Engl 2014; 53:7006-9. [DOI: 10.1002/anie.201310923] [Citation(s) in RCA: 31] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/17/2013] [Indexed: 12/12/2022]
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24
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Yang Q, Draghici C, Njardarson JT, Li F, Smith BR, Das P. Evolution of an oxidative dearomatization enabled total synthesis of vinigrol. Org Biomol Chem 2014; 12:330-44. [PMID: 24258093 PMCID: PMC3901359 DOI: 10.1039/c3ob42191k] [Citation(s) in RCA: 33] [Impact Index Per Article: 3.0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/10/2023]
Abstract
The evolution of the synthetic strategy resulting in a total synthesis of vinigrol is presented. Oxidative dearomatization/intramolecular Diels-Alder cycloaddition has served as the successful cornerstone for all of the approaches. Extensive radical cyclization efforts to form the tetracyclic core resulted in interesting and surprising reaction outcomes, none of which could be advanced to vinigrol. These cyclization obstacles were successfully overcome by using Heck instead of radical cyclizations. The total synthesis features a trifluoroethyl ether protecting group being used for the first time in organic synthesis. The logic of its selection and the group's importance beyond protecting the C8a hydroxyl group is presented along with a discussion of strategies for its removal. Because of the compact tetracyclic cage the route is built around many unusual reaction observations and solutions have emerged. For example, a first of its kind Grob fragmentation reaction featuring a trifluoroethyl leaving group has been uncovered, interesting interrupted selenium dioxide allylic oxidations have been observed as well as intriguing catalyst and counterion dependent directed hydrogenations.
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Affiliation(s)
- Qingliang Yang
- Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853, USA
| | - Cristian Draghici
- Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853, USA
| | - Jon T. Njardarson
- Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA. Fax: (+1) 520-621-8407; Tel: (+1) 520 621-0754
| | | | - Brandon R. Smith
- Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA. Fax: (+1) 520-621-8407; Tel: (+1) 520 621-0754
| | - Pradipta Das
- Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA. Fax: (+1) 520-621-8407; Tel: (+1) 520 621-0754
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25
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Wang B, Wang L, Li Y, Liu Y. Heterocyclic terpenes: linear furano- and pyrroloterpenoids. RSC Adv 2014. [DOI: 10.1039/c3ra48040b] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022] Open
Abstract
This review of furano- and pyrroloterpenoids covers the literature, 180 articles in all, published from January 2006 to December 2013.
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Affiliation(s)
- Bin Wang
- CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology
- South China Sea Institute of Oceanology
- Chinese Academy of Sciences
- Guangzhou, China
- Shenzhen Shajing Affiliated Hospital of Guangzhou Medical University
| | - Lishu Wang
- CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology
- South China Sea Institute of Oceanology
- Chinese Academy of Sciences
- Guangzhou, China
- Jilin Provincial Academy of Chinese Medicine Sciences
| | - Yinglei Li
- CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology
- South China Sea Institute of Oceanology
- Chinese Academy of Sciences
- Guangzhou, China
- Jilin Provincial Academy of Chinese Medicine Sciences
| | - Yonghong Liu
- CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology
- South China Sea Institute of Oceanology
- Chinese Academy of Sciences
- Guangzhou, China
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26
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Li D, Xu S, Cai H, Pei L, Zhang H, Wang L, Yao H, Wu X, Jiang J, Sun Y, Xu J. Enmein-type diterpenoid analogs from natural kaurene-type oridonin: Synthesis and their antitumor biological evaluation. Eur J Med Chem 2013; 64:215-21. [DOI: 10.1016/j.ejmech.2013.04.012] [Citation(s) in RCA: 29] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/24/2013] [Revised: 04/03/2013] [Accepted: 04/03/2013] [Indexed: 10/27/2022]
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27
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Liu W, Fan BL, Guo HY, Yuan YL, Liang HJ, Bai SP. Isolation and identification of a new ent-kaurane diterpenoid from the leaves of Isodon japonica. Nat Prod Res 2012; 27:1388-92. [PMID: 23227889 DOI: 10.1080/14786419.2012.746339] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/27/2022]
Affiliation(s)
- Wei Liu
- a School of Pharmacy, Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
- b Department of Pharmacy , The Third Hospital of Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
| | - Bing-Lin Fan
- c School of Basic Medical Sciences, Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
| | - Hong-Yun Guo
- b Department of Pharmacy , The Third Hospital of Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
| | - Yong-Liang Yuan
- a School of Pharmacy, Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
| | - Hui-Juan Liang
- b Department of Pharmacy , The Third Hospital of Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
| | - Su-Ping Bai
- a School of Pharmacy, Xinxiang Medical University , Xinxiang , Henan , 453003 , P. R. China
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28
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29
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Echinohalimane A, a bioactive halimane-type diterpenoid from a Formosan gorgonian Echinomuricea sp. (Plexauridae). Mar Drugs 2012; 10:2246-2253. [PMID: 23170081 PMCID: PMC3497020 DOI: 10.3390/md10102246] [Citation(s) in RCA: 14] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/05/2012] [Revised: 09/24/2012] [Accepted: 10/08/2012] [Indexed: 11/17/2022] Open
Abstract
A new halimane-type diterpenoid, echinohalimane A (1), was isolated from a gorgonian, identified as Echinomuricea sp. The structure of 1 was determined by spectroscopic methods and this compound was found to exhibit cytotoxicity toward various tumor cells and display an inhibitory effect on the release of elastase by human neutrophils. Echinohalimane A (1) is the first halimane analogue from the marine organisms belonging to phylum Cnidaria.
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30
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Echinoclerodane A: a new bioactive clerodane-type diterpenoid from a gorgonian coral Echinomuricea sp. Molecules 2012; 17:9443-50. [PMID: 22871646 PMCID: PMC6268545 DOI: 10.3390/molecules17089443] [Citation(s) in RCA: 12] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/09/2012] [Revised: 08/01/2012] [Accepted: 08/02/2012] [Indexed: 11/23/2022] Open
Abstract
A new clerodane-type diterpenoid, echinoclerodane A (1), was isolated from a Formosan gorgonian coral Echinomuricea sp. The structure of 1 was elucidated by spectroscopic methods. Echinoclerodane A (1) is the first clerodane-type compound obtained from the marine organisms belonging to the phylum Cnidaria. Echinoclerodane A (1) exhibited moderate cytotoxicity toward MOLT-4, HL-60, DLD-1 and LoVo tumor cells and inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.
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31
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Bioactive compounds from a gorgonian coral Echinomuricea sp. (Plexauridae). Mar Drugs 2012; 10:1169-1179. [PMID: 22822364 PMCID: PMC3397453 DOI: 10.3390/md10051169] [Citation(s) in RCA: 14] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/11/2012] [Revised: 05/09/2012] [Accepted: 05/21/2012] [Indexed: 11/25/2022] Open
Abstract
A new labdane-type diterpenoid, echinolabdane A (1), and a new sterol, 6-epi-yonarasterol B (2), were isolated from a gorgonian coral identified as Echinomuricea sp. The structures of metabolites 1 and 2 were elucidated by spectroscopic methods. Echinolabdane A (1) possesses a novel tetracyclic skeleton with an oxepane ring jointed to an α,β-unsaturated-γ-lactone ring by a hemiketal moiety, and this compound is the first labdane-type diterpenoid to be obtained from marine organisms belonging to the phylum Cnidaria. 6-epi-Yonarasterol B (2) is the first steroid derivative to be isolated from gorgonian coral belonging to the genus Echinomuricea, and this compound displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.
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32
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Barrero AF, Herrador MM, Arteaga P, Arteaga JF, Arteaga AF. Communic acids: occurrence, properties and use as chirons for the synthesis of bioactive compounds. Molecules 2012; 17:1448-67. [PMID: 22310167 PMCID: PMC6268269 DOI: 10.3390/molecules17021448] [Citation(s) in RCA: 27] [Impact Index Per Article: 2.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/25/2011] [Revised: 01/31/2012] [Accepted: 01/31/2012] [Indexed: 11/16/2022] Open
Abstract
Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). This paper also includes a detailed explanation of their use as chiral building blocks for the synthesis of bioactive natural products. Among other uses, communic acids have proven useful as chirons for the synthesis of quassinoids (formal), abietane antioxidants, ambrox and other perfume fixatives, podolactone herbicides, etc., featuring shorter and more efficient processes.
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Affiliation(s)
- Alejandro F. Barrero
- Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Campus de Fuente Nueva, s/n. 18071 Granada, Spain;
- Authors to whom correspondence should be addressed; (A.F.B.); (M.M.H.); Tel.: +34-958-243-318; Fax: +34-958-243-318
| | - M. Mar Herrador
- Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Campus de Fuente Nueva, s/n. 18071 Granada, Spain;
- Authors to whom correspondence should be addressed; (A.F.B.); (M.M.H.); Tel.: +34-958-243-318; Fax: +34-958-243-318
| | - Pilar Arteaga
- Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, Campus de Fuente Nueva, s/n. 18071 Granada, Spain;
| | - Jesús F. Arteaga
- Departamento de Ingeniería Química, Química Fisíca y Químíca Orgánica, Facultad de Ciencias Experimentales, Universidad de Huelva, Campus el Carmen, s/n, 21071, Huelva, Spain;
| | - Alejandro F. Arteaga
- Departamento de Ingeniería Química, Facultad de Ciencias, Universidad de Granada, Campus de Fuente Nueva, s/n. 18071 Granada, Spain;
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34
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Abstract
The so-called Deslongchamps annulation of deprotonated γ,δ-unsaturated β-ketoesters 15 to 2-(alkoxycarbonyl)cyclohex-2-en-1-ones or similarly activated cyclohex-2-en-1-ones offers a versatile access to various kinds of decalindiones. The scope of Deslongchamps annulations was extended by establishing acceptor-substituted benzoquinone monoketals such as 13 as viable substrates. They gave octalindiones such as 35 with diastereoselectivities ≥ 95:5.
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Affiliation(s)
- Denis Petrović
- Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstr. 21, 79104 Freiburg im Breisgau, Germany
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