Cucurbitane-type triterpenes from the tubers of Hemsleya penxianensis and their bioactive activity

Zhu, Nailiang; Sun, Zhonghao; Hu, Meigeng; Li, Yedan; Zhang, Dawei; Wu, Haifeng; Tian, Yu; Li, Pengfei; Yang, Jun‐Shan; Ma, Guoxu; Xu, Xudong

doi:10.1016/j.phytochem.2017.12.014

Cited by 15 publications

(10 citation statements)

References 14 publications

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“…The new saponin holothurin A5 (1) shows a remarkable structural interest because of its side chain, which has been never reported in any terpene glycosides from any organism. Some examples of a similar side chain, but not involved in a lactone ring, have been found in some triterpenoid glycosides from Cucurbitaceae [28,29] and, in the marine environment, in a single steroid glycoside from a starfish [30].…”

Section: Discussionmentioning

confidence: 99%

Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra

et al. 2019

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The saponin composition of a specimen of black sea cucumber, Holothuria atra collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of Holothuria atra turned out to be more complex than previously reported. The most abundant saponins in the extract (1–4) were isolated and characterized by 1D- and 2D-NMR experiments. Compound 1 was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin 1, unprecedented among triterpene glycosides, is characterized by an electrophilic enone function, which can undergo slow water or methanol addition under neutral conditions. The cytotoxic activity of compounds 1–4, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC50 values ranging from 1.2 to 2.5 µg/mL.

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Section: Discussionmentioning

confidence: 99%

Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra

et al. 2019

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“…The 13 C NMR and 13 C APT spectra exhibited 30 carbon resonances in total, corresponding to eight methyls, five methylenes, and seven methines, including two oxymethines at δ C 56.8 (C-16) and δ C 71.7 (C-23), and carbons at δ C 119.0 (C-6), δ C 44.4 (C-8), δ C 34.7 (C-10), δ C 56.8 (C-16), and δ C 71.7 (C-23), and 10 quaternary carbons. Taken together, these data were indicative of a cucurbitacin triterpene 4,9–11 .…”

Section: Resultsmentioning

confidence: 74%

“…Although plants can resist pest invasion through their own defense mechanisms, with the changes in the ecological environment changes, the role of plant protection agents has become increasingly important. Recent studies have reported significant antifeedant effects of cucurbitane-type compounds on insects and the inhibition of cancer cells 1–4 . In our previous studies, we isolated various cucurbitane-type compounds from Hemsleya penxianensis that exhibited significant inhibitory activity against cancer cell lines 4,5 .…”

Section: Introductionmentioning

confidence: 99%

Polyhydroxy cucurbitane triterpenes from Hemsleya penxianensis tubers

Sun

Zhu

et al. 2019

Sci Rep

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Ten new cucurbitane triterpenoids, hemsleyacins A–J ( 1 – 10 ), together with three known cucurbitane triterpenoids, dihydrocucurbitacin F ( 11 ), scandenogenin D ( 12 ), and jinfushanencin F ( 13 ), were separated from ethanolic tuber extracts of Hemsleya penxianensis . The absolute configurations of the new compounds were established based on NMR, HRESIMS, and CD spectra. Compounds 7 and 10–12 were evaluated in terms of their antifeedant activity against Plutella xylostella larvae. The result showed that compound 10 exhibited potent antifeedant activity against P . xylostella larvae after 48 h of treatment. Furthermore, the MTT test showed that compound 11 exhibited potent inhibition toward the UMUC-3 and T24 cell lines with IC 50 values of 29.12 and 35.62 μM, respectively, compared to the positive control cisplatin IC 50 values of 8.27 and 13.72 μM. Western blot analysis revealed that compound 11 treatments substantially inhibited the phosphorylation of IκBα.

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“…Furthermore, HMBC correlations of H-6 with C-5 (δ C 168.3) and C-7 (δ C 200.3), H 3 -26 with C-24 (δ C 129.0), C-25 (δ C 139.3), and C-27 (δ C 61.2) implied an α, β-unsaturated carbonyl moiety at C-5/6/7, double bond at C-24/25, and hydroxymethyl at C-27. Long-range correlations between δ H 3.25 (1H, m, H-12a) and C-11 (δ C 211.5) in the HMBC spectrum indicated that the hydroxy group at C-11 in the reported ones has been replaced by a carbonyl group in compound 1 [15,16]. C-15 was linked with C-23 through an O atom on the basis of the correlations from the proton signals at δ H 5.17 (1H, m, H-16) to C-23 (δ C 70.8) and δ H 5.10 (1H, m, H-23) to C-16 (δ C 70.9).…”

Section: Resultsmentioning

confidence: 99%

Novel Cucurbitane Triterpenes from the Tubers of Hemsleya amabilis with Their Cytotoxic Acitivity

Feng

Zhou

et al. 2019

Molecules

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Chemical research of the medicinal plant Hemsleya amabilis (Cucurbitaceae) yielded five new cucurbitane-type triterpenes hemslelis A–E (1–5) by silica gel column, ODS column, and semi-HPLC techniques. Their structures were determined by spectroscopic analysis and examined alongside existing data from prior studies. Compounds 1–5 were evaluated for their cytotoxic activities against three human tumor cell lines, Hela, HCT-8, and HepG-2, with the IC50 ranging from 5.9 to 33.9 μM compared to Cisplatin.

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Cucurbitane-type triterpenes from the tubers of Hemsleya penxianensis and their bioactive activity

Cited by 15 publications

References 14 publications

Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra

Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra

Polyhydroxy cucurbitane triterpenes from Hemsleya penxianensis tubers

Novel Cucurbitane Triterpenes from the Tubers of Hemsleya amabilis with Their Cytotoxic Acitivity

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