Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents
Abstract
In the present study, we report four new dihydro-β-agarofuran sesquiterpenes (1-4), which were isolated from the leaves of Celastrus vulcanicola, in addition to five derivatives (5-9). Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, X-ray studies, chemical correlations and biogenetic means. Compounds 1-9 and the previously reported sesquiterpenes 10-25 have been tested as potential antimycobacterial agents against sensitive and resistant Mycobacterium tuberculosis strains. 1α-Acetoxy-6β,9β-dibenzoyloxy-dihydro-β-agarofuran (20) exhibited antituberculosis activity against the MDR TB strain with a MIC value of 6.2 μg/mL, comparable to or better than isoniazid or rifampin, two of the best first-line drugs commonly used in the treatment of TB. The structure-activity relationship is discussed.
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Agarofuran compounds may act as lead compounds in designing new, less toxic, highly selective anticholinesterase agents along with other positive therapeutic effects.
“Studies conducted on the agarofuran compounds with a motive of developing some new AChE inhibitors have achieved great success in the past years and suggested that agarofuran compounds may act as lead compounds in the designing of new, less toxic, and highly selective anticholinesterase agents along with some other positive therapeutic effects [130,131].”
From Acetylcholinesterase Inhibitory Potential of Various Sesquiterpene Analogues for Alzheimer’s Disease Therapy (2021) · cites this paper as [130]
Cites
[20] Processing of X-ray diffraction data collected in oscillation mode
Otwinowski, Z., & Minor, W. (1997) · Methods in Enzymology · doi:10.1016/s0076-6879(97)76066-x · Cited by 33,475 · see citing works
WinGX suite for small-molecule single-crystal crystallography
Farrugia, L. J. (1999) · Journal of Applied Crystallography · doi:10.1107/s0021889899006020 · Cited by 18,937 · see citing works
The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement
Sharpless, K. B., Amberg, W., Bennani, Y. L., Crispino, G. A., Hartung, J., Jeong, K., Kwong, H., Morikawa, K., & Wang, Z. M. (1992) · The Journal of Organic Chemistry · doi:10.1021/jo00036a003 · Cited by 1,492 · see citing works
The Population Dynamics and Control of Tuberculosis
Dye, C., & Williams, B. G. (2010) · Science · doi:10.1126/science.1185449 · Cited by 604 · see citing works
The dihydro-β-agarofuran sesquiterpenoids
Gao, J., Wu, W., Zhang, J., & Konishi, Y. (2007) · Natural Product Reports · doi:10.1039/b601473a · Cited by 186 · see citing works
Caviedes, L., Delgado, J., & Gilman, R. H. (2002) · Journal of Clinical Microbiology · doi:10.1128/jcm.40.5.1873-1874.2002 · Cited by 119 · see citing works
Extensively drug-resistant tuberculosis
LoBue, P. A. (2009) · Current Opinion in Infectious Diseases · doi:10.1097/qco.0b013e3283229fab · Cited by 78 · see citing works
Chen, J., Yang, C.-S., Peng, C.-F., Chen, I., & Miaw, C.-L. (2008) · Journal of Natural Products · doi:10.1021/np800097t · Cited by 59 · see citing works
Rojas, R., Caviedes, L., Aponte, J. C., Vaisberg, A., Lewis, W. H., Lamas, G. L., Sarasara, C., Gilman, R. H., & Hammond, G. B. (2006) · Journal of Natural Products · doi:10.1021/np050554l · Cited by 50 · see citing works
Antitubercular Dihydroagarofuranoid Sesquiterpenes from the Roots of Microtropis fokienensis
Chen, J., Chou, T., Peng, C.-F., Chen, I., & Yang, S.-Z. (2007) · Journal of Natural Products · doi:10.1021/np060500r · Cited by 48 · see citing works
Rip Van Winkle Wakes Up: Development of Tuberculosis Treatment in the 21st Century
Burman, W. J. (2010) · Clinical Infectious Diseases · doi:10.1086/651487 · Cited by 46 · see citing works
Celorbicol, isocelorbicol, and their esters: new sesquiterpenoids from Celastrus orbiculatus
Smith, C. R., Miller, R. W., Weisleder, D., Rohwedder, W. K., Eickman, N. C., & Clardy, J. (1976) · The Journal of Organic Chemistry · doi:10.1021/jo00882a012 · Cited by 45 · see citing works
Cortés-Selva, F., Campillo, M., Reyes, C. P., Jiménez, I. A., Castanys, S., Bazzocchi, I. L., Pardo, L., Gamarro, F., & Ravelo, Á. G. (2003) · Journal of Medicinal Chemistry · doi:10.1021/jm0309699 · Cited by 38 · see citing works
Torres-Romero, D. F., Muñoz‐Martínez, F., Jiménez, I. A., Castanys, S., Gamarro, F., & Bazzocchi, I. L. (2009) · Organic & Biomolecular Chemistry · doi:10.1039/b915678j · Cited by 29 · see citing works
Sesquiterpenes from Celastrus vulcanicola as Photosynthetic Inhibitors
Torres-Romero, D. F., King-Dı́az, B., Jiménez, I. A., Lotina‐Hennsen, B., & Bazzocchi, I. L. (2008) · Journal of Natural Products · doi:10.1021/np070647y · Cited by 26 · see citing works
Chou, T., Chen, I., Peng, C., Sung, P., & Chen, J. (2008) · Chemistry & Biodiversity · doi:10.1002/cbdv.200890129 · Cited by 25 · see citing works
González, A. G., Muñoz, O., Ravelo, Á. G., Crespo, A., Bazzocchi, I. L., Jiménez, I. A., Soláns, X., Ruíz-Pérez, C., & Rodríguez-Romero, V. (1992) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)74179-7 · Cited by 13 · see citing works
Hohmann, J., Nagy, G., Günther, G. V., Argay, G., Kálmán, A., & Czira, G. (1994) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19940003281 · Cited by 5 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Terpene Derivatives as a Potential Agent against Antimicrobial Resistance (AMR) Pathogens
Mahizan, N. A., Yang, S.-K., Moo, C.-L., Song, A. A., Chong, C. M., Chong, C. W., Abushelaibi, A. A., Lim, S. E., & Lai, K. (2019) · Molecules · doi:10.3390/molecules24142631 · Cited by 491 · see citing works
“[71] identified one of dihydro-β agarofuran sesquiterpenes, namely 1α-acetoxy-6β, 9β-dibenzoyloxy-dihydro-β-agarofuran inhibits the growth of Bacillus spp.”
BackgroundApplication of natural antimicrobials in food preservation: Recent views
Batiha, G. E., Hussein, D. E. E., Algammal, A. M., George, T. T., Jeandet, P., Al‐Snafi, A. E., Tiwari, A., Pagnossa, J. P., Lima, C. M. G., Thorat, N. D., et al. (2021) · Food Control · doi:10.1016/j.foodcont.2021.108066 · Cited by 304 · see citing works
Plant-derived antimicrobials to fight against multi-drug-resistant human pathogens
Subramani, R., Mathivanan, N., & Feussner, K.-D. (2017) · 3 Biotech · doi:10.1007/s13205-017-0848-9 · Cited by 212 · see citing works
“Whole plant China Lu et al. (2011) Dihydro-b-agarofuran sesquiter penes Celastrus vulcanicola Dried leaves Spain Torres-Romero et al. (2011) n-hexane, ethanol, ethyl acetate, n-butanol, and methanol extracts Flourensia cernua Whole plant Mexico Molina-Salinas et al. (2011) 70% ethanol Allium…”
MethodArya, A., Chahal, R., Rao, R., Rahman, M. H., Kaushik, D., Akhtar, M. F., Saleem, A., Khalifa, S. M. A., El-Seedi, H. R., Kamel, M., et al. (2021) · Biomolecules · doi:10.3390/biom11030350 · Cited by 111 · see citing works
Fraga, B. M. (2012) · Natural Product Reports · doi:10.1039/c2np20074k · Cited by 105 · see citing works
Plants: A Source for New Antimycobacterial Drugs
Santhosh, R. S., & Suriyanarayanan, B. (2013) · Planta Medica · doi:10.1055/s-0033-1350978 · Cited by 82 · see citing works
Tuberculosis and nature’s pharmacy of putative anti-tuberculosis agents
Chinsembu, K. C. (2015) · Acta Tropica · doi:10.1016/j.actatropica.2015.10.004 · Cited by 80 · see citing works
Kandenols A–E, Eudesmenes from an Endophytic Streptomyces sp. of the Mangrove Tree Kandelia candel
Ding, L., Maier, A., Fiebig, H., Lin, W., Peschel, G., & Hertweck, C. (2012) · Journal of Natural Products · doi:10.1021/np300387n · Cited by 63 · see citing works
Traditional uses, secondary metabolites, and pharmacology of Celastrus species - a review:
Shen, Y. L., Chen, B., Zhang, Q., Zheng, Y., & Fu, Q. (2019) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2019.111934 · Cited by 62 · see citing works
Gupta, V. K., Kumar, M., Bisht, D., & Kaushik, A. (2017) · Pharmaceutical Biology · doi:10.1080/13880209.2017.1309440 · Cited by 52 · see citing works
Gautam, S., Qureshi, K. A., Pasha, S. B. J., Dhanasekaran, S., Aspatwar, A., Parkkila, S., Alanazi, S., Atiya, A., Khan, M. M. U., & Venugopal, D. (2023) · Antibiotics · doi:10.3390/antibiotics12030541 · Cited by 51 · see citing works
Sarmiento-Vizcaíno, A., González, V., Braña, A. F., Palacios, J. J., Otero, L., Fernández-Suárez, J., Molina, A., Kulik, A., Vázquez, F., Acuña, J. L., et al. (2016) · Microbial Ecology · doi:10.1007/s00248-016-0845-2 · Cited by 40 · see citing works
Recent Advances in the Research of Heterocyclic Compounds as Antitubercular Agents
Yan, M., & Ma, S.-T. (2012) · ChemMedChem · doi:10.1002/cmdc.201200339 · Cited by 37 · see citing works
Drug-resistant tuberculosis: emerging treatment options
Adhvaryu, M., & Vakharia (2011) · Clinical Pharmacology Advances and Applications · doi:10.2147/cpaa.s11597 · Cited by 34 · see citing works
Ardiles, A., González‐Rodríguez, Á., Nuñez, M. J., Perestelo, N. R., Pardo, V., Jiménez, I. A., Valverde, Á. M., & Bazzocchi, I. L. (2012) · Phytochemistry · doi:10.1016/j.phytochem.2012.07.025 · Cited by 33 · see citing works
“In the present work, and as a continuation of our research on Celastrus vulcanicola (Torres-Romero et al., 2008, 2009, 2010, 2011) and Maytenus jelskii (Perestelo et al., 2011), we report herein on the isolation and structural elucidation of nine new friedelane-type triterpenes (1–9), along with…”
ResultIn-Silico Analyses of Sesquiterpene-Related Compounds on Selected Leishmania Enzyme-Based Targets
Bernal, F. A., & Coy-Barrera, E. D. (2014) · Molecules · doi:10.3390/molecules19055550 · Cited by 33 · see citing works
“Agarofurans are considered as good therapies for Multidrug Resistant Drug (MDR)-agents [20,21].”
BackgroundGao, L., Zhang, R., Lan, J., Ning, R., Wu, D., Chen, D., & Zhao, W. (2016) · Journal of Natural Products · doi:10.1021/acs.jnatprod.6b00648 · Cited by 31 · see citing works
Traditional Medicinal Plants as a Source of Antituberculosis Drugs: A System Review
Xu, Y., Liang, B., Kong, C., & Sun, Z. (2021) · BioMed Research International · doi:10.1155/2021/9910365 · Cited by 30 · see citing works
Tang, J., Zhang, F., Wang, D., Tian, J., Dong, S., & Gao, J. (2013) · International Journal of Molecular Sciences · doi:10.3390/ijms141019484 · Cited by 24 · see citing works
“Compound 2, obtained through acylation [19] of 1 in the presence of triethylamine (Et3N) and catalytic dimethylaminopyridine (DMAP) in dry dichloromethane (DCM), showed an accurate [M + Na] + ion at m/z 615.”
BackgroundThe potential of plant systems to break the HIV‐TB link
Habibi, P., Daniell, H., Soccol, C. R., & Grossi‐de‐Sá, M. F. (2019) · Plant Biotechnology Journal · doi:10.1111/pbi.13110 · Cited by 22 · see citing works
Callies, O., Sánchez‐Cañete, M. P., Gamarro, F., Jiménez, I. A., Castanys, S., & Bazzocchi, I. L. (2015) · Journal of Natural Products · doi:10.1021/np500903a · Cited by 21 · see citing works
Opportunities and Challenges for Natural Products as Novel Antituberculosis Agents
Farah, S. I., Abdelrahman, A. A., North, E. J., & Chauhan, H. (2015) · Assay and Drug Development Technologies · doi:10.1089/adt.2015.673 · Cited by 21 · see citing works
“2 mg/mL.(44) Extracts from Artemisia ludoviciana, Chamaedora tepejilote, Lantana hispida, Juniperus communis, and Malva parviflora have shown potent activity against MDR-TB strains.”
Kumaran, R. S., & Mehta, G. (2015) · Tetrahedron · doi:10.1016/j.tet.2015.01.039 · Cited by 19 · see citing works
Perestelo, N. R., Jiménez, I. A., Tokuda, H., Vázquez, J. T., Ichiishi, E., & Bazzocchi, I. L. (2016) · Journal of Natural Products · doi:10.1021/acs.jnatprod.6b00469 · Cited by 18 · see citing works
Natural Remedies against Multi-Drug Resistant Mycobacterium tuberculosis
Pandit, R., Singh, P. K., & Kumar, V. (2015) · Journal of Tuberculosis Research · doi:10.4236/jtr.2015.34024 · Cited by 17 · see citing works
Wibowo, M., Wang, Q., Holst, J., White, J. M., Hofmann, A., & Davis, R. A. (2016) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.201600462 · Cited by 15 · see citing works
Five new agarofuran sesquiterpene polyesters from Osyris lanceolata
Yeboah, E. M. O., & Majinda, R. R. T. (2013) · Phytochemistry Letters · doi:10.1016/j.phytol.2013.07.005 · Cited by 14 · see citing works
Purino, M. A., Ardiles, A., Callies, O., Jiménez, I. A., & Bazzocchi, I. L. (2016) · Chemistry - A European Journal · doi:10.1002/chem.201600294 · Cited by 14 · see citing works
Jiang, Y., Li, B.-B., Li, N., Meng, X., Lin, X., Wang, D., Xiong, D.-X., Sun, Y., Chen, L., & Cui, L. (2020) · Phytochemistry Letters · doi:10.1016/j.phytol.2020.01.004 · Cited by 10 · see citing works
Salaterpene E, a eudesmane-type sesquiterpene from Salacia longipes var. camerunensis
Mba’ning, B. M., Ndjakou, B. L., Talontsi, F. M., Lannang, A. M., Dittrich, B., Ngouela, S. A., Tsamo, E., Sewald, N., & Laatsch, H. (2016) · Zeitschrift für Naturforschung B · doi:10.1515/znb-2015-0106 · Cited by 9 · see citing works
Triterpenoids from Cassine xylocarpa and Celastrus vulcanicola (Celastraceae)
Nuñez, M. J., Ardiles, A., Martínez, M. L., Torres-Romero, D. F., Jiménez, I. A., & Bazzocchi, I. L. (2012) · Phytochemistry Letters · doi:10.1016/j.phytol.2012.12.003 · Cited by 9 · see citing works
Antitubercular Natural Terpenoids: Recent Developments and Syntheses
Sansinenea, E., & Ortíz, A. (2014) · Current Organic Synthesis · doi:10.2174/1570179411666140321180629 · Cited by 9 · see citing works
Babiaka, S. B., Ntie‐Kang, F., Lifongo, L. L., Ndingkokhar, B., Mbah, J. A., & Yong, J. N. (2015) · RSC Advances · doi:10.1039/c5ra01912e · Cited by 8 · see citing works
Recent updates in natural terpenoids as potential anti-mycobacterial agents
Jagatap, V., Ahmad, I., & Patel, H. (2021) · Indian Journal of Tuberculosis · doi:10.1016/j.ijtb.2021.07.006 · Cited by 8 · see citing works
Nuñez, M. J., Ardiles, A., Martínez, M. L., Torres-Romero, D. F., Jiménez, I. A., & Bazzocchi, I. L. (2012) · Phytochemistry Letters · doi:10.1016/j.phytol.2012.01.004 · Cited by 8 · see citing works
Two new p-coumaroylated sesquiterpenoids from Pilea cavaleriei
Ren, H.-C., Zhang, J., & Liang, H. (2017) · Journal of Asian Natural Products Research · doi:10.1080/10286020.2017.1320990 · Cited by 8 · see citing works
A dihydro-β-agarofuran sesquiterpene from Maytenus boaria
Paz, C., von Dossow, D., Tiznado, V., Suárez, S., Cukiernik, F. D., & Baggio, R. (2017) · Acta Crystallographica Section C Structural Chemistry · doi:10.1107/s2053229617006817 · Cited by 8 · see citing works
“JAGREO (Hori et al., 1987), with only one OH group in its structure, but a very high melting point and a comparable PI (566 K, 68.5%), or OSOVUO (Torres-Romero et al., 2011), which in spite of presenting four OH groups, generates just a one-dimensional hydrogen-bonded structure, with a rather low…”
BackgroundInfluentialKumaran, R. S., & Mehta, G. (2015) · Tetrahedron · doi:10.1016/j.tet.2015.01.033 · Cited by 7 · see citing works
Gao, Z., Zhou, B., Zhao, J.-Y., Cao, F., Zhou, L., & Geng, H. (2015) · International Journal of Molecular Sciences · doi:10.3390/ijms16059119 · Cited by 6 · see citing works
“characteristics of natural dihydro-β-agarofuran sesquiterpenes [4,5].”
Medicinal Plants in Targeting Tuberculosis II
Koirala, N., Modi, B., Subba, R. K., Panthi, M., & Xiao, J. (2021) · Springer eBooks · doi:10.1007/978-981-33-6850-7_8 · Cited by 5 · see citing works
Ponnusamy, N., & Arumugam, M. (2021) · Infectious Disorders - Drug Targets · doi:10.2174/1871526521666210913110834 · Cited by 5 · see citing works
Sesquiterpenoids from Pilea cavaleriei
Zhou, Y. L., Li, L., Xu, Y., Zhang, Q., Liang, H., & Tu, P. (2019) · Natural Product Research · doi:10.1080/14786419.2019.1660330 · Cited by 4 · see citing works
(2023) · Studies in natural products chemistry · doi:10.1016/b978-0-323-91296-9.00006-x · Cited by 4 · see citing works
Isrul, M., Alam, G., Sartini, S., & Massi, N. (2017) · International Journal of PharmTech Research · doi:10.20902/ijptr.2017.1018 · Cited by 3 · see citing works
Natural products encompassing antituberculosis activities
Monga, A., & Sharma, A. (2020) · Studies in natural products chemistry · doi:10.1016/b978-0-12-817903-1.00009-7 · Cited by 3 · see citing works
Goel, R., Tomar, A., & Bawari, S. (2024) · Microbial Pathogenesis · doi:10.1016/j.micpath.2024.107116 · Cited by 2 · see citing works
Three new p -coumaroylated sesquiterpenoids from Pilea cavaleriei
Zhou, Y., Ren, H.-C., Zhang, Q., Liang, H., & Tu, P. (2020) · Natural Product Research · doi:10.1080/14786419.2020.1826481 · Cited by 2 · see citing works
Phytochemicals: An Alternate Approach Towards Various Disease Management
Nema, V., Dhas, Y., Banerjee, J., & Mishra, N. (2018) · Springer eBooks · doi:10.1007/978-981-13-1123-9_27 · Cited by 2 · see citing works
Chemotherapeutic Strategies and Targets Against Resistant TB
Shakya, N., Agrawal, B., & Kumar, R. K. (2012) · InTech eBooks · doi:10.5772/30882 · Cited by 1 · see citing works
Plant-derived Molecules for the Treatment of Tuberculosis: A Review
Yadav, M. K., & Sharma, P. (2022) · Iraqi Journal of Pharmaceutical Sciences · doi:10.31351/vol31iss2pp1-13 · Cited by 1 · see citing works
Therapeutic Applications of Herbal Medicines for the Prevention and Management of Cancer
Pathak, M., Pandey, R. K., Singh, L., Kumar, A., Mishra, G. P., Pandey, R. K., Gidwani, B., & Shukla, S. S. (2023) · Reference series in phytochemistry · doi:10.1007/978-3-031-21973-3_23-1 · Cited by 1 · see citing works
Najem, A. M. (2021) · Journal of Al-Nahrain University-Science · doi:10.22401/anjs.24.4.09 · Cited by 1 · see citing works
“[26] acyclic sesquiterpene (farnesol) revealed moderate anti biofilm activity against Streptococcus sobrinus and Streptococcus mutans, [27].”
BackgroundTherapeutic Applications of Herbal Medicines for the Prevention and Management of Cancer
Pathak, M., Pandey, R. K., Singh, L., Kumar, A., Mishra, G. P., Pandey, R. K., Gidwani, B., & Shukla, S. S. (2024) · Reference series in phytochemistry · doi:10.1007/978-3-031-43199-9_23
Medicinal Plants in the Treatment of Tuberculosis: A Systematic Review
Agrawal, R., Murti, Y., Mangla, M., Sandhuja, M., Sharma, A. K., Kumari, V., & Kulshreshtha, M. (2024) · Central Nervous System Agents in Medicinal Chemistry · doi:10.2174/0118715249285282240902091640
- Authors
- Torres-Romero, D., Jiménez, I. A., Rojas, R., Gilman, R. H., López, M., & Bazzocchi, I. L.
- Affiliations
- Universidad de La Laguna (ES)
- Universidad Peruana Cayetano Heredia (PE)
- Corresponding author
- Bazzocchi, Isabel L.
- Venue
- Bioorganic & Medicinal Chemistry
- Publisher
- Elsevier BV
- Published
- 2011-04
- Volume
- 19
- Issue
- 7
- Pages
- 2182-2189
- ISSN
- 0968-0896 (ISSN-L)
- OpenAlex
- W2076888660
- Cited by
- 54
- References
- 18
- Citations by year
- 2024: 3 · 2023: 3 · 2022: 1 · 2021: 7 · 2020: 3 · 2019: 4 · 2018: 1 · 2017: 5 · 2016: 6 · 2015: 8 · 2014: 2 · 2013: 3 · 2012: 7
- FWCI
- 1.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Bioorganic & Medicinal Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive Natural Diterpenoids Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical compounds biological activities
- Keywords
- Mycobacterium tuberculosis, multidrug-resistant tuberculosis, antimycobacterial activity, natural product isolation, structure elucidation, structure-activity relationship, sesquiterpene derivatives, leaves
- MeSH terms
- Antitubercular Agents, Furans, Models, Molecular, Mycobacterium tuberculosis, Sesquiterpenes, Structure-Activity Relationship, Molecular Structure, Crystallography, X-Ray, Drug Resistance, Multiple, Bacterial, Celastrus
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