Diterpenoids from Leonurus japonicus

Wu, Hongyi; Wang, Sensheng; Liu, Haijuan; E, Yan; Wang, Jinjin; Wang, Xiangbei; Wei, Wuran; Xu, Zhigang; Sun, Shanshan; Li, Yan; Liu, Ruijin; Li, Gang; Shi, Yunfeng

doi:10.5012/jkcs.2015.59.2.179

Cited by 4 publications

(3 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition to the above 18 new compounds, 20 known labdane diterpenoids including leojapone B ( 3 ), leojapone A ( 4 ), leojaponin ( 5 ), heteronone B ( 6 ), 6β-hydroxy-15,16-epoxylabda-8,13(16),14-trienone ( 7 ), heteronone A ( 8 ), 15,16-epoxy-6β,9α-dihydroxylabda-13(16),14-diene-3,7-dione ( 9 ), leoheterin ( 10 ), leojapone D ( 13 ), leojaponin C ( 14 ), 6β-15,16-epoxy-15-ethoxy-6,13-dihydroxylabd-8-en-7-one ( 15 ), sibiricinone C ( 22 ), leoheteronin B ( 23 ), leojaponin D ( 25 ), leojaponin B ( 26 ), labda-7,13 E -dien-15-ol ( 27 ), 8(17),13 E -labdien-15-ol ( 28 ), illenol ( 29 ), 1-{(1 S ,3 R ,3a S )-3-[2-(furan-3-yl)ethyl]-3-methoxy-3a,7,7-trimethyloctahydroisobenzofuran-1-yl}propan-1-one ( 35 ), and seco -labdane ( 36 ) were also isolated and identified from this plant. Their structures (Figure ) were elucidated by comparison of their NMR and MS data with reported literature.…”

Section: Resultsmentioning

confidence: 99%

Structurally Diverse Labdane Diterpenoids from Leonurus japonicus and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells

et al. 2020

View full text Add to dashboard Cite

A phytochemical study on the aerial parts of Leonurus japonicus led to the isolation and identification of 38 labdane diterpenoids, including 18 new (1, 2, 11, 12, 16–21, 24, 30–34, 37, 38) and 20 known (3–10, 13–15, 22, 23, 25–29, 35, 36) analogues. Their structures were elucidated based on physical data analysis, including 1D and 2D NMR, HRMS, UV, IR, and X-ray diffraction. The structure of the known compound 4 was confirmed by single-crystal X-ray diffraction data. These compounds can be divided into furanolabdane (1–10), tetrahydrofuranolabdane (11–15), lactonelabdane (16–23), labdane (24–29), and seco-labdane (30–38) type diterpenoids. All compounds were screened by lipopolysaccharide (LPS)-induced nitric acid (NO) production in RAW264.7 cells to evaluate anti-inflammatory effects. Compounds 1, 5, 10–13, 16–19, 31–33, and 38 inhibited NO production with IC50 values lower than 50 μM, with compound 30 being the most active, with an IC50 value of 3.9 ± 1.7 μM. Further studies show that compound 30 inhibits pro-inflammatory cytokine production and IKK α/β phosphorylation and restores the IκB expression levels in the NF-κB signaling pathway.

show abstract

Section: Resultsmentioning

confidence: 99%

Structurally Diverse Labdane Diterpenoids from Leonurus japonicus and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Niemeyer and co‐workers reported the isolation of 5,5‐spiroketal containing 8,9‐ seco ‐labdanes 95 – 96 from H. parvifolius in 1991 (Figure 6). [87] Persianone ( 97 ) was isolated from Ballota aucheri in 1995, Leonurus sibiricus in 2014 and Leonurus japonicus in 2015 and 2020 [88–91] . Persianone ( 97 ) contains a similar ketal motif to 95 – 96 , and was shown to inhibit human liver cytosol estrogen sulfotransferase (E‐ST), an enzyme that is involved in the maintenance of cellular estrogen levels [88–90] …”

Section: Isolation and Bioactivitymentioning

confidence: 99%

“…In 2015, multiple other seco ‐labdanes were isolated from Leonurus species. These include 107 , 108 and 109 from L. japonicus as well as 110 from L. sibiricus [89, 90] . In 2020, Xiao and co‐workers reported the isolation of a further 38 labdanes from L. japonicus , including seven previously unreported seco ‐labdanes, 111 – 117 , and two known seco ‐labdanes, persianone ( 97 ) and 108 [91] .…”

Section: Isolation and Bioactivitymentioning

confidence: 99%

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

Grant

Brimble

2021

Chemistry A European J

View full text Add to dashboard Cite

The cleavage of a C−C bond is a complexity generating process, which complements oxidation and cyclisation events in the biosynthesis of terpenoids. This process leads to increased structural diversity in a cluster of related secondary metabolites by modification of the parent carbocyclic core. In this review, we highlight the diversifying effect of C−C bond cleavage by examining the literature related to seco‐labdanes—a class of diterpenoids arising from such C−C bond cleavage events.

show abstract

Leonurus japonicus (Chinese motherwort), an excellent traditional medicine for obstetrical and gynecological diseases: A comprehensive overview

Miao

Zhou

Peng

et al. 2019

Biomedicine & Pharmacotherapy

View full text Add to dashboard Cite

Diterpenoids from Leonurus japonicus

Cited by 4 publications

References 17 publications

Structurally Diverse Labdane Diterpenoids from Leonurus japonicus and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells

Structurally Diverse Labdane Diterpenoids from Leonurus japonicus and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

Leonurus japonicus (Chinese motherwort), an excellent traditional medicine for obstetrical and gynecological diseases: A comprehensive overview

Contact Info

Product

Resources

About