Two novel antiviral terpenoids from the cultured Perovskia atriplicifolia

Jiang, Zhi‐Yong; Zhou, Jun; Huang, Chao‐Guan; Hu, Qiu‐Fen; Huang, Xiang‐Zhong; Wang, Wei; Zhang, Lizhu; Li, Gan‐Peng; Xia, Futing

doi:10.1016/j.tet.2015.04.017

Cited by 21 publications

(9 citation statements)

References 15 publications

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“…Villagers in the Isfahan province of Iran apply a poultice, made of crushed roots of the plant, water, sesame oil, and wax, on lesions caused by cutaneous leishmaniasis [2]. Previous phytochemical investigations on the genus Perovskia afforded structurally unique diterpenoids possessing abietane and rearranged icetexane scafolds [3][4][5]. From the aerial parts of P. abrotanoides, a series of isoprenoids with complex scaffolds have been reported.…”

Section: Antiprotozoal Diterpenes From Perovskia Abrotanoides* Introdmentioning

confidence: 99%

“…The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5R,10S)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2), 12hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6), and 12-methoxybarbatusol (9) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one-and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism).…”

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confidence: 99%

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Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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As part of a screening for new antiparasitic natural products from Iranian plants, -hexane and ethyl acetate extracts from the aerial parts of were found to exhibit strong inhibitory activity against and. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1: -17: ), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5,10)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2: ), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6: ), and 12-methoxybarbatusol (9: ) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against , and. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7-ethoxyrosmanol (4: ) with an IC of 0.8 µM against (SI 14.9) and an IC of 1.8 µM (SI 6.9) against , ferruginol (8: ) with an IC of 2.9 µM (SI 19.2) against , and miltiodiol (10: ) with an IC of 0.5 µM (SI 10.5) against . None of the compounds exhibited selective toxicity against (SI ≤ 1.6).

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Section: Antiprotozoal Diterpenes From Perovskia Abrotanoides* Introdmentioning

confidence: 99%

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confidence: 99%

Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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“…Our previous investigation suggested that the petroleum ether extract of P . atriplicifolia showed anti‐HBV (Hepatitis B virus) activity and some bioactive chemicals had been isolated from the petroleum ether extract . But the BuOH extract showed no anti‐HBV activity during the preceding investigation.…”

Section: Introductionmentioning

confidence: 99%

Four New Diterpene Glucosides from Perovskia atriplicifolia

Zhou

Zhu

Zhang

et al. 2017

Chemistry & Biodiversity

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Four new diterpene glucosides, namely perovskiaditerpenosides A - D (1 - 4), were isolated from the BuOH extract of Perovskia atriplicifolia. Their structures were well elucidated by chemical methods and comprehensive spectroscopic analyses including MS, IR, and NMR (1D and 2D). The newly isolated compounds were screened for their cytotoxic activity against HepG2, NB4, HeLa, K562, MCF7, PC3, and HL60. The obtained results indicated that the new compounds possessed considerable cytotoxic activity.

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“…This structural motif is present in a number of biologically active and medicinally important natural products. For example, norperovskatone 2, recently isolated from Perovskia atriplicifolia, possesses remarkable anti-HBV (Hepatitis B Virus) activity [4] and (+)-okilactomycin 3 [5] exhibits in vitro cytotoxicity against a number of human cancer cell lines, including lymphoid leukemia L1210 or leukemia P388. This compound also shows in vivo activity against Ehrlich ascites carcinoma.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,2,6-Trisubstituted 5-Methylidene-tetrahydropyran-4-ones with Anticancer Activity

et al. 2020

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In our continuous search for new, relatively simple 2-alkylidene-1-oxoheterocycles as promising anticancer drug candidates, herein we report an efficient synthesis of 2,2,6-trisubstituted 5-methylidenetetrahydropyran-4-ones. These compounds were obtained in a four step reaction sequence, in which starting diethyl 2-oxopropylphosphonate was transformed into 2,2-disubstituted 5-diethoxyphosphoryldihydropyran-4-ones, followed by Michael addition of various Grignard reagents and Horner-Wadsworth-Emmons reaction of the obtained adducts with formaldehyde. Stereochemistry of the intermediate Michael adducts is also discussed. Final 5-methylidenetetrahydropyran-4-ones were tested for their possible antiproliferative effect against three cancer cell lines and 6-isopropyl-2,2-dimethyl-5-methylidenetetrahydropyran-4-one (11c), which showed very high cytotoxic activity against HL-60 human leukemia cells and was three times more active than known anticancer drug carboplatin, was selected for further biological evaluation, in order to disclose its mechanism of action. The obtained results indicated that 11c induced apoptosis in HL-60 cells and caused the arrest of the cell cycle in the G2/M phase, which may suggest its cytotoxic and cytostatic activity.

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Two novel antiviral terpenoids from the cultured Perovskia atriplicifolia

Cited by 21 publications

References 15 publications

Antiprotozoal Diterpenes from Perovskia abrotanoides

Antiprotozoal Diterpenes from Perovskia abrotanoides

Four New Diterpene Glucosides from Perovskia atriplicifolia

Synthesis of 2,2,6-Trisubstituted 5-Methylidene-tetrahydropyran-4-ones with Anticancer Activity

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