Neo-clerodane Diterpenes from the Hallucinogenic Sage Salvia divinorum
Abstract
Seven new neo-clerodane diterpenes, salvidivins A (2), B, (3), C (4), and D (5), salvinorins H (6) and I (7), and divinorin F (8), along with eight known neo-clerodane diterpenes, salvinorins A (1)−F, divinatorins A and B, and seven other constituents, were isolated from the hallucinogenic sage Salvia divinorum. The structures of 1−7 were elucidated on the basis of 2D NMR spectroscopic studies.
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- Moonhyuk Kwon, Joseph C. Utomo, Keunwan Park, Cameron A. Pascoe, Sorina Chiorean, Iris Ngo, Kyle A. Pelot, Cheol-Ho Pan, Seon-Won Kim, Philipp Zerbe, John C. Vederas, Dae-Kyun Ro. Cytochrome P450-Catalyzed Biosynthesis of a Dihydrofuran Neoclerodane in Magic Mint (Salvia divinorum). ACS Catalysis 2022, 12
(1)
, 777-782. https://doi.org/10.1021/acscatal.1c03691
- Soumen Chakraborty, Susruta Majumdar. Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide. Biochemistry 2021, 60
(18)
, 1381-1400. https://doi.org/10.1021/acs.biochem.0c00629
- Mohammad Nur-e-Alam, Muhammad Yousaf, Sarfaraz Ahmed, Ebtesam S. Al-Sheddi, Ifat Parveen, David M. Fazakerley, Ahmed Bari, Hazem A. Ghabbour, Michael D. Threadgill, Kezia C. L. Whatley, Karl F. Hoffmann, and Adnan J. Al-Rehaily . Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense. Journal of Natural Products 2017, 80
(6)
, 1900-1908. https://doi.org/10.1021/acs.jnatprod.7b00188
- Madan Kumar Paudel, Osamu Shirota, Kaori Sasaki-Tabata, Hiroyuki Tanaka, Setsuko Sekita, and Satoshi Morimoto . Development of an Enzyme Immunoassay Using a Monoclonal Antibody against the Psychoactive Diterpenoid Salvinorin A. Journal of Natural Products 2013, 76
(9)
, 1654-1660. https://doi.org/10.1021/np400358n
- Thomas E. Prisinzano . Neoclerodanes as Atypical Opioid Receptor Ligands. Journal of Medicinal Chemistry 2013, 56
(9)
, 3435-3443. https://doi.org/10.1021/jm400388u
- Yi-Bing Wu, Zhi-Yu Ni, Qing-Wen Shi, Mei Dong, Hiromasa Kiyota, Yu-Cheng Gu, and Bin Cong . Constituents from Salvia Species and Their Biological Activities. Chemical Reviews 2012, 112
(11)
, 5967-6026. https://doi.org/10.1021/cr200058f
- Lukasz M. Kutrzeba, Daneel Ferreira and Jordan K. Zjawiony. Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System. Journal of Natural Products 2009, 72
(7)
, 1361-1363. https://doi.org/10.1021/np900181q
- Thomas E. Prisinzano. Natural Products as Tools for Neuroscience: Discovery and Development of Novel Agents to Treat Drug Abuse. Journal of Natural Products 2009, 72
(3)
, 581-587. https://doi.org/10.1021/np8005748
- Thomas E. Prisinzano and Richard B. Rothman . Salvinorin A Analogs as Probes in Opioid Pharmacology. Chemical Reviews 2008, 108
(5)
, 1732-1743. https://doi.org/10.1021/cr0782269
- Masato Nozawa,, Yuhki Suka,, Takashi Hoshi,, Toshio Suzuki, and, Hisahiro Hagiwara. Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A. Organic Letters 2008, 10
(7)
, 1365-1368. https://doi.org/10.1021/ol800101v
- Jonathan R. Scheerer,, Jonathan F. Lawrence,, Grace C. Wang, and, David A. Evans. Asymmetric Synthesis of Salvinorin A, A Potent κ Opioid Receptor Agonist. Journal of the American Chemical Society 2007, 129
(29)
, 8968-8969. https://doi.org/10.1021/ja073590a
- Denise S. Simpson,, Peter L. Katavic,, Anthony Lozama,, Wayne W. Harding,, Damon Parrish,, Jeffrey R. Deschamps,, Christina M. Dersch,, John S. Partilla,, Richard B. Rothman,, Hernan Navarro, and, Thomas E. Prisinzano. Synthetic Studies of Neoclerodane Diterpenes from Salvia divinorum: Preparation and Opioid Receptor Activity of Salvinicin Analogues. Journal of Medicinal Chemistry 2007, 50
(15)
, 3596-3603. https://doi.org/10.1021/jm070393d
- Seyed Mohsen Hesamzadeh Hejazi. Evaluation of genetic diversity in different populations of six Salvia species using R-ISSR markers analysis. Genetic Resources and Crop Evolution 2023, 67 https://doi.org/10.1007/s10722-023-01795-2
- Nancy Ortiz-Mendoza, Eva Aguirre-Hernández, Itzi Fragoso-Martínez, María Eva González-Trujano, Francisco A. Basurto-Peña, Martha J. Martínez-Gordillo. A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages (Salvia Subgenus Calosphace; Lamiaceae) Emphasizing Mexican Species. Frontiers in Pharmacology 2022, 13 https://doi.org/10.3389/fphar.2022.867892
- Mohammad Nur-e-Alam, Ifat Parveen, Barrie Wilkinson, Sarfaraz Ahmed, Rahman M. Hafizur, Ahmed Bari, Timothy J. Woodman, Michael D. Threadgill, Adnan J. Al-Rehaily. A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin. Scientific Reports 2021, 11
(1)
https://doi.org/10.1038/s41598-021-87513-3
- Christopher R. McCurdy, Thomas E. Prisinzano. Opioid Receptor Ligands. 2021, 1-171. https://doi.org/10.1002/0471266949.bmc251.pub2
- Stephanie Tamdem Guetchueng, Lutfun Nahar, Kenneth James Ritchie, Fyaz Mahmood Daud Ismail, Nicola Dempster, Andrew Robert Evans, Satyajit Dey Sarker. Four new
neo
-clerodane diterpenes from the stem bark of
Croton oligandrus. Natural Product Research 2021, 35
(2)
, 298-304. https://doi.org/10.1080/14786419.2019.1628745
- Mansureh Ghavam, Maria Letizia Manca, Maria Manconi, Gianluigi Bacchetta. Chemical composition and antimicrobial activity of essential oils obtained from leaves and flowers of Salvia hydrangea DC. ex Benth.. Scientific Reports 2020, 10
(1)
https://doi.org/10.1038/s41598-020-73193-y
- Lorenzo Leonel Tlacomulco-Flores, Myrna Déciga-Campos, María Eva González-Trujano, Azucena Ibeth Carballo-Villalobos, Francisco Pellicer. Antinociceptive effects of Salvia divinorum and bioactive salvinorins in experimental pain models in mice. Journal of Ethnopharmacology 2020, 248 , 112276. https://doi.org/10.1016/j.jep.2019.112276
- Stephanie Guetchueng, Lutfun Nahar, Kenneth Ritchie, Fyaz Ismail, Andrew Evans, Satyajit Sarker. Ent-Clerodane Diterpenes from the Bark of Croton oligandrus Pierre ex Hutch. and Assessment of Their Cytotoxicity against Human Cancer Cell Lines. Molecules 2018, 23
(2)
, 410. https://doi.org/10.3390/molecules23020410
- Madan Kumar Paudel, Osamu Shirota, Seiichi Sakamoto, Satoshi Morimoto, Hiroyuki Tanaka. An immunochromatographic assay for rapid etection of salvinorin A. Journal of Immunoassay and Immunochemistry 2017, 38
(4)
, 438-448. https://doi.org/10.1080/15321819.2017.1324797
- André Cruz, Sara Domingos, Eugenia Gallardo, Ana Martinho. A unique natural selective kappa -opioid receptor agonist, salvinorin A, and its roles in human therapeutics. Phytochemistry 2017, 137 , 9-14. https://doi.org/10.1016/j.phytochem.2017.02.001
- Xiao-Ming Zhang, Yong-Qiang Tu, Fu-Min Zhang, Zhi-Hua Chen, Shao-Hua Wang. Recent applications of the 1,2-carbon atom migration strategy in complex natural product total synthesis. Chemical Society Reviews 2017, 46
(8)
, 2272-2305. https://doi.org/10.1039/C6CS00935B
- Yong-Jun Jiang, Jia Su, Xin Shi, Xing-De Wu, Xuan-Qin Chen, Juan He, Li-Dong Shao, Xiao-Nian Li, Li-Yan Peng, Rong-Tao Li, Qin-Shi Zhao. neo -Clerodanes from the aerial parts of Salvia leucantha. Tetrahedron 2016, 72
(35)
, 5507-5514. https://doi.org/10.1016/j.tet.2016.07.037
- Cláudia Margalho, Francisco Corte-Real, Manuel López-Rivadulla, Eugenia Gallardo. Salvia divinorum
: toxicological aspects and analysis in human biological specimens. Bioanalysis 2016, 8
(13)
, 1415-1425. https://doi.org/10.4155/bio-2016-0067
- Rathi Mahendran, Haikel A. Lim, Joyce Y.S. Tan, Shi Min Chua, Munidasa Winslow.
S
alvia divinorum
: An overview of the usage, misuse, and addiction processes. Asia-Pacific Psychiatry 2016, 8
(1)
, 23-31. https://doi.org/10.1111/appy.12225
- Kevin C. Potter, Jiachen Zi, Young J. Hong, Samuel Schulte, Brandi Malchow, Dean J. Tantillo, Reuben J. Peters. Blocking Deprotonation with Retention of Aromaticity in a Plant
ent
‐Copalyl Diphosphate Synthase Leads to Product Rearrangement. Angewandte Chemie 2016, 128
(2)
, 644-648. https://doi.org/10.1002/ange.201509060
- Kevin C. Potter, Jiachen Zi, Young J. Hong, Samuel Schulte, Brandi Malchow, Dean J. Tantillo, Reuben J. Peters. Blocking Deprotonation with Retention of Aromaticity in a Plant
ent
‐Copalyl Diphosphate Synthase Leads to Product Rearrangement. Angewandte Chemie International Edition 2016, 55
(2)
, 634-638. https://doi.org/10.1002/anie.201509060
- Hiroyuki Tanaka, Madan Kumar Paudel, Osamu Shirota, Kaori Sasaki-Tabata, Setsuko Sekita, Satoshi Morimoto. Enzyme Immunoassay for Salvinorin A (a Main Component in Salvia divinorum). 2016, 749-756. https://doi.org/10.1016/B978-0-12-800212-4.00070-4
- Rongtao Li, Susan L. Morris-Natschke, Kuo-Hsiung Lee. Clerodane diterpenes: sources, structures, and biological activities. Natural Product Reports 2016, 33
(10)
, 1166-1226. https://doi.org/10.1039/C5NP00137D
- Dongman Chao, Ying Xia. The Role of δ-Opioid Receptors in Brain Ionic Homeostasis Under Physiological Condition. 2015, 117-246. https://doi.org/10.1007/978-3-319-25495-1_5
- Eirini Kouloura, Job Tchoumtchoua, Maria Halabalaki, Alexios‐Leandros Skaltsounis. Plant Sesquiterpenes and other Terpenoids. 2014, 1-53. https://doi.org/10.1002/9780470027318.a9928
- Rui-Juan Li, Yi Sun, Bin Sun, Xiao-Ning Wang, Shan-Shan Liu, Jin-Chuan Zhou, Jian-Ping Ye, Yu Zhao, Lei Liu, Kuo-Hsiung Lee, Hong-Xiang Lou. Phytotoxic cis-clerodane diterpenoids from the Chinese liverwort Scapania stephanii. Phytochemistry 2014, 105 , 85-91. https://doi.org/10.1016/j.phytochem.2014.05.019
- Hongjian Du, Congying Li, Yaya Wen, Yanbei Tu, Yujiao Zhong, Zhipeng Yuan, Yanfang Li, Bing Liang. Secondary metabolites from pericarp of Juglans regia. Biochemical Systematics and Ecology 2014, 54 , 88-91. https://doi.org/10.1016/j.bse.2013.12.023
- Ivan Casselman, Catherine J. Nock, Hans Wohlmuth, Robert P. Weatherby, Michael Heinrich. From local to global—Fifty years of research on Salvia divinorum. Journal of Ethnopharmacology 2014, 151
(2)
, 768-783. https://doi.org/10.1016/j.jep.2013.11.032
- Fúlvio R. Mendes Giuseppina Negri, Joaquim M. Duarte‐Almeida, Ricardo Tabach, Elisaldo A. Carlini. The Action of Plants and their Constituents on the Central Nervous System. 2012, 161-204. https://doi.org/10.1002/9781118260005.ch5
- . Salvia divinorum
Epling & Jativa and Salvinorin A. 2012, 961-967. https://doi.org/10.1002/9781118105955.ch65
- HR Sumnall, F Measham, SD Brandt, JC Cole. Salvia divinorum
use and phenomenology: results from an online survey. Journal of Psychopharmacology 2011, 25
(11)
, 1496-1507. https://doi.org/10.1177/0269881110385596
- Maria Carmela Bonito, Carla Cicala, Maria Carla Marcotullio, Francesco Maione, Nicola Mascolo. Biological Activity of Bicyclic and Tricyclic Diterpenoids from
Salvia Species
of Immediate Pharmacological and Pharmaceutical Interest. Natural Product Communications 2011, 6
(8)
, 1934578X1100600. https://doi.org/10.1177/1934578X1100600839
- Christopher W. Cunningham, Richard B. Rothman, Thomas E. Prisinzano, . Neuropharmacology of the Naturally Occurring κ-Opioid Hallucinogen Salvinorin A. Pharmacological Reviews 2011, 63
(2)
, 316-347. https://doi.org/10.1124/pr.110.003244
- Hisahiro Hagiwara, Takashi Nojima, Yuhki Suka, Takashi Hoshi, Toshio Suzuki. First Total Synthesis of the Neo-Clerodane Diterpenoid Salvinorin F. Natural Product Communications 2011, 6
(3)
, 1934578X1100600. https://doi.org/10.1177/1934578X1100600306
- Christopher R. McCurdy, Thomas E. Prisinzano. Opioid Receptor Ligands. 2010, 569-736. https://doi.org/10.1002/0471266949.bmc251
- James R. Hanson. Natural Products from the Hallucinogenic Sage. Science Progress 2010, 93
(2)
, 171-180. https://doi.org/10.3184/003685010X12626983776947
- Jeffrey Comparin. Drugs. 2010, 153-279. https://doi.org/10.1201/EBK1439826584-c6
- Gordon M. Cragg, David J. Newman, David G.I. Kingston. Terrestrial Plants as a Source of Novel Pharmaceutical Agents. 2010, 5-39. https://doi.org/10.1016/B978-008045382-8.00033-2
- Hisahiro Hagiwara, Yuhki Suka, Takashi Nojima, Takashi Hoshi, Toshio Suzuki. Second-generation synthesis of salvinorin A. Tetrahedron 2009, 65
(25)
, 4820-4825. https://doi.org/10.1016/j.tet.2009.04.053
- Kimberly M Lovell, Denise S Simpson, Christopher W Cunningham, Thomas E Prisinzano. Utilizing nature as a source of new probes for opioid pharmacology. Future Medicinal Chemistry 2009, 1
(2)
, 285-301. https://doi.org/10.4155/fmc.09.22
- Denise S. Simpson, Kimberly M. Lovell, Anthony Lozama, Nina Han, Victor W. Day, Christina M. Dersch, Richard B. Rothman, Thomas E. Prisinzano. Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors. Organic & Biomolecular Chemistry 2009, 7
(18)
, 3748. https://doi.org/10.1039/b905148a
- Kenji Tsujikawa, Kenji Kuwayama, Hajime Miyaguchi, Tatsuyuki Kanamori, Yuko T. Iwata, Takemi Yoshida, Hiroyuki Inoue. Determination of salvinorin A and salvinorin B in Salvia divinorum-related products circulated in Japan. Forensic Science International 2008, 180
(2-3)
, 105-109. https://doi.org/10.1016/j.forsciint.2008.07.008
- Zhongze Ma, David Y.W. Lee. Synthesis of deacetyl-1,10-didehydrosalvinorin G. Tetrahedron Letters 2008, 49
(11)
, 1782-1785. https://doi.org/10.1016/j.tetlet.2008.01.065
- Xue-Long Hou, Zhen Yang, Kap-Sun Yeung, Henry N.C. Wong. Chapter 5.3 Five-membered ring systems: furans and benzofurans. 2008, 176-207. https://doi.org/10.1016/S0959-6380(08)80009-8
- Xiao-Ning Wang, Sheng Yin, Cheng-Qi Fan, Li-Ping Lin, Jian Ding, Jian-Min Yue. Eight new limonoids from Turraea pubescens. Tetrahedron 2007, 63
(34)
, 8234-8241. https://doi.org/10.1016/j.tet.2007.05.107
- James R. Hanson. Diterpenoids. Natural Product Reports 2007, 24
(6)
, 1332. https://doi.org/10.1039/b705951p