Isolation, Structural Elucidation, and Cytotoxicity of Three Newent-Kaurane Diterpenoids fromIsodon japonicavar.glaucocalyx

Liang, Hongye; Zhang, Yunxiao; Hai, Guangfan; Bai, Su-Ping; Yuan, Ye; Ye, Dandan; Zhou, Nan-Qian

doi:10.1055/s-0031-1298265

Cited by 15 publications

(2 citation statements)

References 12 publications

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“…Except for the sugar moiety, there were five oxygenated methines at δH 3.17 (dd, 1H, 9.5, 4.0), 3.52 (s, 1H), 3.56 (m, 1H), 4.64 (s, 1H) and 4.86 (m, 1H), respectively. Considering the structures of diterpenoids previously isolated from the plant [4][5][6][7][8] and structure characteristics of the ent-kaurane diterpenoid, compound 1 was assigned an ent-kaurane diterpenoid glycoside and the ent-kaurane diterpenoid has five hydroxy groups and one of them with a glucose generated the glycoside. The key work was to comfirm the positions of the five hydroxy groups.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from n-Butanol Extract of Rabdosia japonica var. glaucocalyx

Xiang¹,

Liu²,

Heng³

et al. 2014

Asian J. Chem.

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The genus Rabdosia japonica (Burm. f.) Hara var. glaucocalyx (Maxim.) Hara is a member of the family Labiatae, subfamily Ocimoideae, tribe Plectrantheae and is mainly distributed in northeast Asia, such as China, Russian, Korea and Japan 1 . It possesses some pharmacological functions, such as antitumor, antioxidation, antiinflammatory and antibacteria 2 . Results of toxicological tests indicated that the Rabdosia japonica var. glaucocalyx is safe to human within the scope of the experimental dose 3 . As for the chemical constituents of the plant, diterpenoids 4-8 , flavonoids 9-11 and triterpenoids 12,13 are the major constituents in the whole plant. In the course of further studies, six compounds were obtained and their structures were identified as glaucocalyxin G (1), arjunglucoside (2) 14 , kaempferol-3-O-rutinoside (3) 15 , quercetin-3-O -α-Lrhamnoside (4) 16 , rutin (5) 16 and acacetin-7-O-β-D -glucoside (6) 11 on the basis of their NMR spectral data and by comparison of their physical properties with those reported in the literatures. Compound 1 was a new ent-kaurane diterpenoid glycoside from R. japonica var. glaucocalyx, though the diterpenoids have been regarded as the marking composition of tribe Plectrantheae, there was few report about diterpenoids glycoside of the tribe. compounds 2 and 3 have not been reported before from the plant source. EXPERIMENTALESI-MS and HRESI-MS were performed with a Mat-212 and a Micro mass Auto Spec Q-TOF spectrometers, respectively. 1 H and 13 C NMR spectra were recorded on a Bruker DRX-500 spectrometer with tetramethylsilane as an internal Chemical Constituents from n-Butanol Extract of Rabdosia japonica var. glaucocalyx

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Section: Resultsmentioning

confidence: 99%

Chemical Constituents from n-Butanol Extract of Rabdosia japonica var. glaucocalyx

Xiang¹,

Liu²,

Heng³

et al. 2014

Asian J. Chem.

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“…The apoptosis was detected by Beckman A00-1-1102 flow cytometry. GLA was obtained according to the method reported in our previous work [25][26] .…”

Section: Materials and Reagentsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Novel Thiazole-Fused Glaucocalyxin A Derivatives

Zhang¹,

Li²,

Nanqian³

et al. 2021

Chinese Journal of Organic Chemistry

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Glaucocalyxin A (GLA) is an active natural tetracyclic diterpenoid isolated from the traditional Chinese herb Isodon glaucocalyx (maxin) Hara. In this work, a series of thiazole type derivatives based on GLA were designed and prepared. Their antiproliferative activities against six tumor cell lines (HepG2, NCI-H460, JEG-3, K562, HL-60 and Hela) were evaluated in-vitro. The results revealed that the introduction of aminothiazole substructures into A-ring of the GLA could improve their antiproliferative effects significantly. Among them, N-alkyl thiazole derivatives showed remarkably activities to the six tumor cell lines. Especially, compounds 6 and 8 presented significant antitumor activities against HL-60 and Hela cell lines with IC50 as low as 0.51 µmol•L -1 , which were better than the positive drug adriamycin. The apoptosis morphology and flow cytometry studies indicated that the thiazole-fused GLA derivatives could induce apoptosis of tumor cells.

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Glycosylation of Glaucocalyxin a and Evaluation of Its Cytotoxic Activity

et al. 2020

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Isolation, Structural Elucidation, and Cytotoxicity of Three Newent-Kaurane Diterpenoids fromIsodon japonicavar.glaucocalyx

Cited by 15 publications

References 12 publications

Chemical Constituents from n-Butanol Extract of Rabdosia japonica var. glaucocalyx

Chemical Constituents from n-Butanol Extract of Rabdosia japonica var. glaucocalyx

Design, Synthesis and Biological Evaluation of Novel Thiazole-Fused Glaucocalyxin A Derivatives

Glycosylation of Glaucocalyxin a and Evaluation of Its Cytotoxic Activity

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