Five new <i>ent</i>-kaurane diterpenes from <i>Annona squamosa</i> L. pericarps

Chen, Ya-Yun; Ma, Chengyao; Wang, Mao‐Lin; Lü, Jiahui; Hu, Peng; Chen, Jianwei; Li, Xiang; Chen, Yong

doi:10.1080/14786419.2019.1582048

Cited by 13 publications

(9 citation statements)

References 14 publications

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“…[26b,28] The authors state that the relative stereochemistry of diastereoisomer 8 e was elucidated based on NOESY correlations alone. [27] Consequently, it is possible that natural product 3 d may have been isolated earlier, but structure 8 e may have been incorrectly assigned in that report. [27] Other terpenoids.…”

Section: Resultsmentioning

confidence: 95%

“…Although structure 3 d has not been reported previously, we noticed that NMR spectroscopic data for 3 d were consistent with equivalent data reported in the literature for ent-kaurane diastereomer 8 e (Figure 7 and Table S4, Supporting Information), which was isolated from Annona squamosa. [27] This was one of four studies reporting the isolation of ent-kauranes from Annona squamosa. [26b,28] The authors state that the relative stereochemistry of diastereoisomer 8 e was elucidated based on NOESY correlations alone.…”

Section: Resultsmentioning

confidence: 99%

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Intraspecific Variation in the Terpene Profiles of Dodonaea viscosa

et al. 2023

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Natural products isolation studies were performed on Dodonaea viscosa plant individuals sampled across seven different populations, which revealed considerable intraspecific variation in the terpene profiles across D. viscosa. In total, 14 ent‐labdane diterpenoids (seven of which are previously unreported), four ent‐kauranes (one which is previously unreported), one rare norhopene, and two previously unreported monoterpenoid wax esters were isolated. Exceedingly few terpene wax esters have been reported in Nature and the isolation of these unusual secondary metabolites is particularly notable for this reason. In each case, the proposed structures were elucidated employing various standard one‐ and two‐dimensional NMR (1H, 13C, NOESY, COSY, HSQC, HMBC) spectroscopic techniques and complemented by IR spectroscopy, mass spectrometry, and polarimetry, where appropriate. Synthetic derivatization and X‐ray crystallographic analysis were also employed to further support or secure structural assignments.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Intraspecific Variation in the Terpene Profiles of Dodonaea viscosa

et al. 2023

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“…The ent-kaurane diterpene 4α-hydroxy-17,19-dinor-ent-kaurane-16-one displayed poor anti-hepatoma potencies with IC 50 values exceeding 100 µM [32]. Moreover ent-kaurene diterpenoids hebeirubescensin K (16-OH group) was 2-3 times less potent than oridonin (15-ketone) in HCT-116 cancer cells [33].…”

Section: Discussionmentioning

confidence: 99%

New Diterpenoids from Mesona procumbens with Antiproliferative Activities Modulate Cell Cycle Arrest and Apoptosis in Human Leukemia Cancer Cells

et al. 2021

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Mesona procumbens is a popular material used in foods and herbal medicines in Asia for clearing heat and resolving toxins. However, phytochemical research on this plant is very rare. In this study, eleven new diterpenoids, mesonols A-K (1–11), comprising seven ent-kauranes, three ent-atisanes, and one sarcopetalane, were isolated from its methanolic extract. Structural elucidation of compounds 1–11 was performed by spectroscopic methods, especially 2D NMR, HRESIMS, and X-ray crystallographic analysis. All isolates were assessed for their antiproliferative activity, and compounds 1–4 showed potential antiproliferative activities against A549, Hep-3B, PC-3, HT29, and U937 cancer cells, with IC50 values ranging from 1.97 to 19.86 µM. The most active compounds, 1 and 2, were selected for further investigation of their effects on cell cycle progression, apoptosis, and ROS generation in U937 human leukemia cancer cells. Interestingly, it was found that compounds 1 and 2 induced antiproliferative effects in U937 cells through different mechanisms. Compound 1 caused cell cycle arrest at the G2/M phase and subsequent cell death in a dose- and time-dependent manner. However, 2-mediated antiproliferation of U937 cells triggered ROS-mediated mitochondrial-dependent apoptosis. These results provide insight into the molecular mechanism involved in the antiproliferative activities of compounds 1 and 2 in U937 cells. Altogether, the study showed that new diterpenoid compounds 1 and 2 from M. procumbens are potent and promising anticancer agents.

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“…Among 14 kauranes isolated from this species, 16β,17-dihydroxy-ent-kauran-19-oic acid (4) indicated significant activity against HIV-replication in H9-lymphocyte cells (Wu et al 1996). ent-11α-Hydroxy-16-kauren-15-one (5) was found to show apoptosis in human promyelocytic leukemia and their 4β,acetoxy-nor-ent-kaurene and two more kaurene derivatives showed cytotoxicity against SMMC-7721 and HepG2 cancer cell lines (Chen et al 2020).…”

Section: Annona (Annonaceae)mentioning

confidence: 99%

Dietary Diterpenoids

Asakawa

Kenmoku

2021

Handbook of Dietary Phytochemicals

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A number of foods, vegetables, fruits, and beverages (tea, coffee, and liqueur) contain many kinds of diterpenoids (mainly abietanes, cembranes, clerodanes, cyatanes, dolabellanes, fusicoccanes, kauranes, labdanes, pimaranes, taxanes, trachilobanes, totaranes) and their related compounds. This chapter summarizes the distribution of diterpenoids in dietary foods, vegetables, fruits, beverages, and processed foods, and their biological and pharmacological activity, effects, and application to our health, as well as metabolic pathways of several diterpenoids, which are widely distributed in dietary foods, by microorganisms and mammals.

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Five new ent-kaurane diterpenes from Annona squamosa L. pericarps

Cited by 13 publications

References 14 publications

Intraspecific Variation in the Terpene Profiles of Dodonaea viscosa

Intraspecific Variation in the Terpene Profiles of Dodonaea viscosa

New Diterpenoids from Mesona procumbens with Antiproliferative Activities Modulate Cell Cycle Arrest and Apoptosis in Human Leukemia Cancer Cells

Dietary Diterpenoids

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