Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC–MS analysis and phytochemical investigation
Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the “Shock and Kill” strategy. In the present study, the first chemical study on Wikstroemia ligustrina (Thymelaeaceae) was carried out by LC–MS analysis and phy...
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| Published in | Journal of natural medicines Vol. 75; no. 4; pp. 1058 - 1066 |
|---|---|
| Main Authors | , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Singapore
Springer Singapore
01.09.2021
Springer Nature B.V |
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| Abstract | Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the “Shock and Kill” strategy. In the present study, the first chemical study on
Wikstroemia ligustrina
(Thymelaeaceae) was carried out by LC–MS analysis and phytochemical investigation. Nine daphnane diterpenoids (
1
−
9
) including seven MDOs were detected by LC–MS analysis. Further phytochemical investigation resulted in the isolation and structural elucidation of five daphnanes (
1
,
2
,
5
,
8
, and
9
) with potent anti-HIV activity. Taking the isolated MDO (
1
) as a model compound, the MS/MS fragmentation pathway was also elucidated. |
|---|---|
| AbstractList | Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the “Shock and Kill” strategy. In the present study, the first chemical study on Wikstroemia ligustrina (Thymelaeaceae) was carried out by LC–MS analysis and phytochemical investigation. Nine daphnane diterpenoids (1−9) including seven MDOs were detected by LC–MS analysis. Further phytochemical investigation resulted in the isolation and structural elucidation of five daphnanes (1, 2, 5, 8, and 9) with potent anti-HIV activity. Taking the isolated MDO (1) as a model compound, the MS/MS fragmentation pathway was also elucidated. Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the “Shock and Kill” strategy. In the present study, the first chemical study on Wikstroemia ligustrina (Thymelaeaceae) was carried out by LC–MS analysis and phytochemical investigation. Nine daphnane diterpenoids ( 1 − 9 ) including seven MDOs were detected by LC–MS analysis. Further phytochemical investigation resulted in the isolation and structural elucidation of five daphnanes ( 1 , 2 , 5 , 8 , and 9 ) with potent anti-HIV activity. Taking the isolated MDO ( 1 ) as a model compound, the MS/MS fragmentation pathway was also elucidated. Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the "Shock and Kill" strategy. In the present study, the first chemical study on Wikstroemia ligustrina (Thymelaeaceae) was carried out by LC-MS analysis and phytochemical investigation. Nine daphnane diterpenoids (1-9) including seven MDOs were detected by LC-MS analysis. Further phytochemical investigation resulted in the isolation and structural elucidation of five daphnanes (1, 2, 5, 8, and 9) with potent anti-HIV activity. Taking the isolated MDO (1) as a model compound, the MS/MS fragmentation pathway was also elucidated.Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the "Shock and Kill" strategy. In the present study, the first chemical study on Wikstroemia ligustrina (Thymelaeaceae) was carried out by LC-MS analysis and phytochemical investigation. Nine daphnane diterpenoids (1-9) including seven MDOs were detected by LC-MS analysis. Further phytochemical investigation resulted in the isolation and structural elucidation of five daphnanes (1, 2, 5, 8, and 9) with potent anti-HIV activity. Taking the isolated MDO (1) as a model compound, the MS/MS fragmentation pathway was also elucidated. |
| Author | Li, Ning Huang, Li Lee, Kuo-Hsiung Zhang, Mi Li, Wei Koike, Kazuo Otsuki, Kouharu Zhou, Di Bai, Zi-Song Tsuji, Minami Tejima, Miyuko Chen, Chin-Ho Kikuchi, Takashi |
| Author_xml | – sequence: 1 givenname: Kouharu surname: Otsuki fullname: Otsuki, Kouharu organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 2 givenname: Mi surname: Zhang fullname: Zhang, Mi organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 3 givenname: Takashi surname: Kikuchi fullname: Kikuchi, Takashi organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 4 givenname: Minami surname: Tsuji fullname: Tsuji, Minami organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 5 givenname: Miyuko surname: Tejima fullname: Tejima, Miyuko organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 6 givenname: Zi-Song surname: Bai fullname: Bai, Zi-Song organization: School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University – sequence: 7 givenname: Di surname: Zhou fullname: Zhou, Di organization: School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University – sequence: 8 givenname: Li surname: Huang fullname: Huang, Li organization: Surgical Science, Department of Surgery, Duke University Medical Center – sequence: 9 givenname: Chin-Ho surname: Chen fullname: Chen, Chin-Ho organization: Surgical Science, Department of Surgery, Duke University Medical Center – sequence: 10 givenname: Kuo-Hsiung surname: Lee fullname: Lee, Kuo-Hsiung organization: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chinese Medicine Research and Development Center, China Medical University and Hospital – sequence: 11 givenname: Ning surname: Li fullname: Li, Ning email: liningsypharm@163.com organization: School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University – sequence: 12 givenname: Kazuo surname: Koike fullname: Koike, Kazuo organization: Faculty of Pharmaceutical Sciences, Toho University – sequence: 13 givenname: Wei orcidid: 0000-0003-4143-8597 surname: Li fullname: Li, Wei email: liwei@phar.toho-u.ac.jp organization: Faculty of Pharmaceutical Sciences, Toho University |
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| Cites_doi | 10.1021/acs.orglett.9b03539 10.1371/journal.pone.0026677 10.1016/j.fitote.2015.09.017 10.1021/acsmedchemlett.8b00012 10.1021/acsmedchemlett.5b00339 10.1021/acs.jmedchem.9b00339 10.1016/S0031-9422(97)00529-3 10.1021/np50037a018 10.1021/acs.jnatprod.5b00660 10.1002/pca.2776 10.1016/j.bmcl.2013.03.025 10.1016/j.phytochem.2018.01.021 10.1021/acs.jmedchem.5b01233 10.1039/c5np00073d 10.1021/cr0782832 10.1021/acs.jnatprod.9b00993 10.1111/j.1751-0813.1975.tb06976.x 10.1021/ol200889s 10.1021/np1005746 10.1016/S0040-4039(01)83271-8 |
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| Keywords | Anti-HIV Thymelaeaceae Macrocyclic daphnane orthoester LC–MS |
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| References | Wu, Raven, Db (CR9) 2007 Powell, Weisleder, Smith (CR15) 1985; 48 Yan, Lu, Chen, Zhao, Lee, Chen (CR4) 2015; 78 Liu, Cheng, Li, Huang, Asada, Hsieh, Morris-Natschke, Chen, Koike, Lee (CR12) 2019; 62 Asada, Sukemori, Watanabe, Malla, Yoshikawa, Li, Koike, Chen, Akiyama, Qian, Nakagawa-Goto, Morris-Natschke, Lee (CR3) 2011; 13 Li, Jiao, Zhang, Chao, Jia, Shi, Zhang (CR8) 2018; 151 Demarque, Crotti, Vessecchi, Lopes, Lopes (CR18) 2016; 33 Roberts, McClure, Ritchie, Taylor, Freeman (CR14) 1975; 51 Li, Sun, Hong, Li, Wu, Xia, Ikejima, Peng, Song (CR17) 2013; 23 Huang, Lai, Zhu, Li, Wei, Lee, Xie, Chen (CR11) 2018; 9 Dang, Zhu, Lai, Bogerd, Lee, Huang, Chen (CR21) 2016; 7 Abe, Iwase, Yamauchi, Kinjo, Yaga, Ishii, Iwahana (CR6) 1998; 47 Hayes, Chow, Somerville, Fletcher, De Voss (CR16) 2010; 73 Trinel, Jullian, Le Lamer, Mhamdi, Mejia, Castillo, Cabanillas, Fabre (CR19) 2018; 29 Huang, Ho, Yu, Zhu, Lee, Chen (CR10) 2011; 6 Zhao, Lu, Yan, Chen, Morris-Natschke, Lee, Chen (CR20) 2020; 83 Zayed, Adolf, Hafez, Hecker (CR13) 1977; 18 Lai, Huang, Zhu, Ferrari, Chan, Li, Lee, Chen (CR2) 2015; 58 Otsuki, Li, Asada, Chen, Lee, Koike (CR5) 2020; 22 Liao, Chen, Yue (CR1) 2009; 109 Guo, Tian, Yao, Zhu, Xue, Luo, Zhang, Zhang, Zhang (CR7) 2015; 106 Z Dang (1551_CR21) 2016; 7 HB Roberts (1551_CR14) 1975; 51 F Li (1551_CR17) 2013; 23 M Trinel (1551_CR19) 2018; 29 HD Zhao (1551_CR20) 2020; 83 Q Liu (1551_CR12) 2019; 62 F Abe (1551_CR6) 1998; 47 J Guo (1551_CR7) 2015; 106 PY Hayes (1551_CR16) 2010; 73 M Yan (1551_CR4) 2015; 78 S Zayed (1551_CR13) 1977; 18 Y Asada (1551_CR3) 2011; 13 SF Li (1551_CR8) 2018; 151 K Otsuki (1551_CR5) 2020; 22 DP Demarque (1551_CR18) 2016; 33 L Huang (1551_CR10) 2011; 6 L Huang (1551_CR11) 2018; 9 SG Liao (1551_CR1) 2009; 109 RG Powell (1551_CR15) 1985; 48 W Lai (1551_CR2) 2015; 58 Z Wu (1551_CR9) 2007 |
| References_xml | – volume: 22 start-page: 11 issue: 1 year: 2020 end-page: 15 ident: CR5 article-title: Daphneodorins A-C, Anti-HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from publication-title: Org Lett doi: 10.1021/acs.orglett.9b03539 – volume: 6 start-page: e26677 issue: 10 year: 2011 ident: CR10 article-title: Picomolar dichotomous activity of gnidimacrin against HIV-1 publication-title: PLoS One doi: 10.1371/journal.pone.0026677 – volume: 106 start-page: 242 year: 2015 end-page: 246 ident: CR7 article-title: Three new 1α-alkyldaphnane-type diterpenoids from the flower buds of publication-title: Fitoterapia doi: 10.1016/j.fitote.2015.09.017 – volume: 9 start-page: 268 issue: 3 year: 2018 end-page: 273 ident: CR11 article-title: Elimination of HIV-1 latently infected cells by gnidimacrin and a selective HDAC inhibitor publication-title: ACS Med Chem Lett doi: 10.1021/acsmedchemlett.8b00012 – volume: 7 start-page: 240 issue: 3 year: 2016 end-page: 244 ident: CR21 article-title: Aloperine and its derivatives as a new class of HIV-1 entry inhibitors publication-title: ACS Med Chem Lett doi: 10.1021/acsmedchemlett.5b00339 – volume: 62 start-page: 6958 issue: 15 year: 2019 end-page: 6971 ident: CR12 article-title: Synthesis and structure-activity relationship correlations of gnidimacrin derivatives as potent HIV-1 inhibitors and HIV latency reversing agents publication-title: J Med Chem doi: 10.1021/acs.jmedchem.9b00339 – volume: 47 start-page: 833 issue: 5 year: 1998 end-page: 837 ident: CR6 article-title: Minor daphnane-type diterpenoids from publication-title: Phytochemistry doi: 10.1016/S0031-9422(97)00529-3 – volume: 48 start-page: 102 issue: 1 year: 1985 end-page: 107 ident: CR15 article-title: Daphnane diterpenes from : vesiculosin and isovesiculosin publication-title: J Nat Prod doi: 10.1021/np50037a018 – volume: 78 start-page: 2712 issue: 11 year: 2015 end-page: 2718 ident: CR4 article-title: Stelleralides D-J and anti-HIV daphnane diterpenes from publication-title: J Nat Prod doi: 10.1021/acs.jnatprod.5b00660 – volume: 29 start-page: 627 issue: 6 year: 2018 end-page: 638 ident: CR19 article-title: Profiling of Hura crepitans L. latex by ultra-high-performance liquid chromatography/atmospheric pressure chemical ionisation linear ion trap Orbitrap mass spectrometry publication-title: Phytochem Anal doi: 10.1002/pca.2776 – volume: 23 start-page: 2500 issue: 9 year: 2013 end-page: 2504 ident: CR17 article-title: Daphnane-type diterpenes with inhibitory activities against human cancer cell lines from publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2013.03.025 – volume: 151 start-page: 17 year: 2018 end-page: 25 ident: CR8 article-title: Diterpenes from buds of showing anti-hepatitis B virus activities publication-title: Phytochemistry doi: 10.1016/j.phytochem.2018.01.021 – volume: 58 start-page: 8638 issue: 21 year: 2015 end-page: 8646 ident: CR2 article-title: Gnidimacrin, a potent anti-HIV diterpene, can eliminate latent HIV-1 ex vivo by activation of protein kinase C β publication-title: J Med Chem doi: 10.1021/acs.jmedchem.5b01233 – volume: 33 start-page: 432 issue: 3 year: 2016 end-page: 455 ident: CR18 article-title: Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products publication-title: Nat Prod Rep doi: 10.1039/c5np00073d – volume: 109 start-page: 1092 issue: 3 year: 2009 end-page: 1140 ident: CR1 article-title: Plant orthoesters publication-title: Chem Rev doi: 10.1021/cr0782832 – volume: 83 start-page: 134 issue: 1 year: 2020 end-page: 141 ident: CR20 article-title: Rapid recognition and targeted isolation of anti-HIV Daphnane Diterpenes from guided by UPLC-MS publication-title: J Nat Prod doi: 10.1021/acs.jnatprod.9b00993 – volume: 51 start-page: 325 issue: 6 year: 1975 end-page: 326 ident: CR14 article-title: Letter: The isolation and structure of the toxin of responsible for St. George disease of cattle publication-title: Aust Vet J doi: 10.1111/j.1751-0813.1975.tb06976.x – volume: 13 start-page: 2904 issue: 11 year: 2011 end-page: 2907 ident: CR3 article-title: Stelleralides A-C, novel potent anti-HIV daphnane-type diterpenoids from L publication-title: Org Lett doi: 10.1021/ol200889s – year: 2007 ident: CR9 publication-title: Flora of China – volume: 73 start-page: 1907 issue: 11 year: 2010 end-page: 1913 ident: CR16 article-title: Daphnane- and tigliane-type diterpenoid esters and orthoesters from publication-title: J Nat Prod doi: 10.1021/np1005746 – volume: 18 start-page: 3481 issue: 39 year: 1977 end-page: 3482 ident: CR13 article-title: New highly irritant 1-alkyldaphnane derivatives from several species of thymelaeaceae publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(01)83271-8 – volume: 13 start-page: 2904 issue: 11 year: 2011 ident: 1551_CR3 publication-title: Org Lett doi: 10.1021/ol200889s – volume: 151 start-page: 17 year: 2018 ident: 1551_CR8 publication-title: Phytochemistry doi: 10.1016/j.phytochem.2018.01.021 – volume: 22 start-page: 11 issue: 1 year: 2020 ident: 1551_CR5 publication-title: Org Lett doi: 10.1021/acs.orglett.9b03539 – volume: 47 start-page: 833 issue: 5 year: 1998 ident: 1551_CR6 publication-title: Phytochemistry doi: 10.1016/S0031-9422(97)00529-3 – volume: 109 start-page: 1092 issue: 3 year: 2009 ident: 1551_CR1 publication-title: Chem Rev doi: 10.1021/cr0782832 – volume: 62 start-page: 6958 issue: 15 year: 2019 ident: 1551_CR12 publication-title: J Med Chem doi: 10.1021/acs.jmedchem.9b00339 – volume: 7 start-page: 240 issue: 3 year: 2016 ident: 1551_CR21 publication-title: ACS Med Chem Lett doi: 10.1021/acsmedchemlett.5b00339 – volume: 58 start-page: 8638 issue: 21 year: 2015 ident: 1551_CR2 publication-title: J Med Chem doi: 10.1021/acs.jmedchem.5b01233 – volume: 29 start-page: 627 issue: 6 year: 2018 ident: 1551_CR19 publication-title: Phytochem Anal doi: 10.1002/pca.2776 – volume: 73 start-page: 1907 issue: 11 year: 2010 ident: 1551_CR16 publication-title: J Nat Prod doi: 10.1021/np1005746 – volume: 6 start-page: e26677 issue: 10 year: 2011 ident: 1551_CR10 publication-title: PLoS One doi: 10.1371/journal.pone.0026677 – volume: 18 start-page: 3481 issue: 39 year: 1977 ident: 1551_CR13 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(01)83271-8 – volume: 78 start-page: 2712 issue: 11 year: 2015 ident: 1551_CR4 publication-title: J Nat Prod doi: 10.1021/acs.jnatprod.5b00660 – volume: 9 start-page: 268 issue: 3 year: 2018 ident: 1551_CR11 publication-title: ACS Med Chem Lett doi: 10.1021/acsmedchemlett.8b00012 – volume-title: Flora of China year: 2007 ident: 1551_CR9 – volume: 33 start-page: 432 issue: 3 year: 2016 ident: 1551_CR18 publication-title: Nat Prod Rep doi: 10.1039/c5np00073d – volume: 51 start-page: 325 issue: 6 year: 1975 ident: 1551_CR14 publication-title: Aust Vet J doi: 10.1111/j.1751-0813.1975.tb06976.x – volume: 23 start-page: 2500 issue: 9 year: 2013 ident: 1551_CR17 publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2013.03.025 – volume: 83 start-page: 134 issue: 1 year: 2020 ident: 1551_CR20 publication-title: J Nat Prod doi: 10.1021/acs.jnatprod.9b00993 – volume: 106 start-page: 242 year: 2015 ident: 1551_CR7 publication-title: Fitoterapia doi: 10.1016/j.fitote.2015.09.017 – volume: 48 start-page: 102 issue: 1 year: 1985 ident: 1551_CR15 publication-title: J Nat Prod doi: 10.1021/np50037a018 |
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| Snippet | Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the “Shock and Kill”... Macrocyclic daphnane orthoesters (MDOs) have attracted significant research interest for the drug discovery to cure HIV infection based on the "Shock and Kill"... |
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| SubjectTerms | antiretroviral agents antiretroviral properties Antiviral activity Biological products Biomedical and Life Sciences Biomedicine Complementary & Alternative Medicine Diterpenes diterpenoids HIV HIV infections Human immunodeficiency virus Medicinal Chemistry ortho esters Orthoesters Pharmacology/Toxicology Pharmacy Phytochemicals Plant Sciences Wikstroemia |
| Title | Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC–MS analysis and phytochemical investigation |
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