Ent-Kaurane Diterpenoids from Isodon rubescens var. rubescens

Han, Quan‐Bin; Xiao, Wei‐Lie; Shen, Yun‐Heng; Sun, Han‐Dong

doi:10.1248/cpb.52.767

Cited by 15 publications

(8 citation statements)

References 6 publications

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“…Furthermore, the offspring of the I. enanderianus sample that had a small oridonin yield did not produce oridonin. Therefore it is reasonable to conclude, as others have [29], [30], that oridonin production can occur in some populations and not others of the same species.…”

Section: Discussionmentioning

confidence: 95%

“…The phylogenetic patterns were attributed to some combination of a recent radiation, hybridization, or incomplete lineage sorting of ancestral polymorphisms in the genus Isodon [28]. Given the low phylogenetic resolution between Isodon species, published studies of the high diversity of diterpenoids in both Isodon [17] and I. rubescens [21], as well as suggestions of variability in diterpenoid production according to growing environment [29], [30], the expectation for this study was that oridonin production would be highly variable, both throughout Isodon and within I. rubescens . This variability would be indicated by multiple gains and losses of oridonin production in the evolutionary history of Isodon , and also by variation of oridonin production between individual plants, both within the same population as well as different populations of I. rubescens and also between parents and offspring.…”

Section: Introductionmentioning

confidence: 99%

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Selection for High Oridonin Yield in the Chinese Medicinal Plant Isodon (Lamiaceae) Using a Combined Phylogenetics and Population Genetics Approach

et al. 2012

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Oridonin is a diterpenoid with anti-cancer activity that occurs in the Chinese medicinal plant Isodon rubescens and some related species. While the bioactivity of oridonin has been well studied, the extent of natural variation in the production of this compound is poorly known. This study characterizes natural variation in oridonin production in order to guide selection of populations of Isodon with highest oridonin yield. Different populations of I. rubescens and related species were collected in China, and their offspring were grown in a greenhouse. Samples were examined for oridonin content, genotyped using 11 microsatellites, and representatives were sequenced for three phylogenetic markers (ITS, rps16, trnL-trnF). Oridonin production was mapped on a molecular phylogeny of the genus Isodon using samples from each population as well as previously published Genbank sequences. Oridonin has been reported in 12 out of 74 species of Isodon examined for diterpenoids, and the phylogeny indicates that oridonin production has arisen at least three times in the genus. Oridonin production was surprisingly consistent between wild-collected parents and greenhouse-grown offspring, despite evidence of gene flow between oridonin-producing and non-producing populations of Isodon. Additionally, microsatellite genetic distance between individuals was significantly correlated with chemical distance in both parents and offspring. Neither heritability nor correlation with genetic distance were significant when the comparison was restricted to only populations of I. rubescens, but this result should be corroborated using additional samples. Based on these results, future screening of Isodon populations for oridonin yield should initially prioritize a broad survey of all species known to produce oridonin, rather than focusing on multiple populations of one species, such as I. rubescens. Of the samples examined here, I. rubescens or I. japonicus from Henan province would provide the best source of oridonin.

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Section: Discussionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Selection for High Oridonin Yield in the Chinese Medicinal Plant Isodon (Lamiaceae) Using a Combined Phylogenetics and Population Genetics Approach

et al. 2012

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“…Hara yielded mainly ent-kauranoids. [4][5][6] However, five new ent-abietanoids, ent-abierubesins A-E (1-5), and two new ent-kauranoids, hubeirubesins A and B (6, 7), together with another three known diterpenoids (8-10), were isolated from this species in our present research. Although belonging to ent-abietanes, compound 5 was quite different from other ent-abietanes (1-4, 8, 9) in functional groups of A-and B-rings.…”

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confidence: 52%

New ent-Abietane and ent-Kaurane Diterpenoids from Isodon rubescens

Liu

Zhan

Wang

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Five new ent-abietane diterpenoids, ent-abierubesins A-E (1-5), and two new ent-kauranoids, hubeirubesins A and B (6, 7), together with three known diterpenoids (8-10), were isolated from the aerial parts of Isodon rubescens. Their structures were identified by means of extensive spectroscopic analysis, and the absolute stereochemistry of 1 was determined by single-crystal X-ray diffraction experiment. Isodon rubescens; ent-abietane; ent-abierubesin; ent-kaurane; hubeirubesin As an important class of diterpenoids, ent-abietanoids are not so widely spread and structurally diverse as their enantiomers, abietanoids. Among ent-abietanes, 12,17-olide-type ones are in a majority and isolated from plants of Euphorbiaceae and Acanthaceae families. Key words1) However, another type of ent-abietanes without 12,17-olide moieties have been obtained from the genus Isodon of Lamiaceae family.2,3) Our previous investigations on chemical constituents of Isodon rubescens (Hemsl.) Hara yielded mainly ent-kauranoids. [4][5][6] However, five new ent-abietanoids, ent-abierubesins A-E (1-5), and two new ent-kauranoids, hubeirubesins A and B (6, 7), together with another three known diterpenoids (8-10), were isolated from this species in our present research. Although belonging to ent-abietanes, compound 5 was quite different from other ent-abietanes (1-4, 8, 9) in functional groups of A-and B-rings. In contrast, 5 exhibited the same structural characteristics (even including the configuration of C-16) as the known ent-kauranoid (10) so that 5 might be assumed as an 8,15-seco product of 10. Current paper describes the isolation, structure elucidation, and cytotoxic evaluation of selected compounds. Results and DiscussionThe aerial parts of I. rubescens (10 kg) were extracted with 90% aqueous EtOH at room temperature and then the extract was partitioned between EtOAc and H 2 O. Repeated chromatography of the EtOAc soluble portion (550 g) yielded five new (1-5) and two known (8, 9) ent-abietane diterpenoids, together with two new (6, 7) and one known (10) ent-kaurane diterpenoids (Fig. 1). By comparing the spectroscopic data with literature values, three known compounds (8-10) were identified as hebeiabinin B (8), 7) ent-abienervonin C (9), 8) and rubescensin G (10), 9) respectively. ent-Abierubesin A (1) was obtained as colorless pieces in MeOH. The molecular formula was determined by positive high resolution-electrospray ionization mass spectrometry C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1, signals of a ketone carbonyl, a trisubstituted olefine, nine methylenes (including three oxygenated ones), three methines, one oxygenated and two nonoxygenated quaternary carbons, and two methyl groups were present (Tables 1, 3). Compound 1 retained three degrees of unsaturation except above-mentioned olefinic and carbonyl groups, and lacked one nonoxygenated quaternary carbon relative to the classical entkaurane skeleton, suggesting 1 to be a tricyclic diterpenoid.Comparison of NMR spectra of 1 and the ...

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“…Recent laboratory and clinical data suggested that ORI was a very effective anti-tumor agent with profound effects on a number of malignant diseases such as prostate cancer, breast cancer, and non-small cell lung cancer [8][9][10]. It has been considered to be chemoprevention agents for potential new cancer [11].…”

Section: Introductionmentioning

confidence: 99%

The anti-tumor effect of folate-targeted liposome microbubbles loaded with oridonin as ultrasound-triggered tumor-targeted therapeutic carrier system

Wang

2016

Journal of Drug Targeting

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In this study, folate receptor (FR) targeted liposome microbubbles loaded with oridonin (ORI) (F-LMB-ORI), liposome loaded with ORI (L-ORI) and liposome microbubbles loaded with ORI (LMB-ORI) were prepared. In vitro release properties, cellular uptake and cytotoxicity in HepG-2 cells as well as in vivo antitumor effects in HepG-2 cells tumor-bearing mice of F-LMB-ORI, L-ORI and LMB-ORI were evaluated upon ultrasound exposure. Results showed cytotoxicity assay on F-LMB-ORI gave IC of 0.508 ± 0.018 µmol/mL on HepG-2 cells and LMB-ORI; L-ORI gave IC of 2.424 ± 0.116 µmol/mL, 3.031 ± 0.122 µmol/mL in vitro, respectively. These drug delivery carriers were able to control the release of ORI. F-LMB-ORI exhibited higher binding to HepG-2 cells in comparison to LMB-ORI and L-ORI. F-LMB-ORI improved antitumor activity of ORI obviously in comparison to L-ORI, LMB-ORI under in vivo ultrasound. After the treatment for 14 d, the tumor inhibition ratio for F-LMB-ORI (the dose of ORI: 1.5 × 10g·kg, once a day) was 87.6%, obviously higher than that of LMB-ORI group, L-ORI group and free ORI (the dose of ORI: 1.5 × 10g·kg, once a day) which were 71.5%, 64.3% and 43.4%, respectively.

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Ent-Kaurane Diterpenoids from Isodon rubescens var. rubescens

Cited by 15 publications

References 6 publications

Selection for High Oridonin Yield in the Chinese Medicinal Plant Isodon (Lamiaceae) Using a Combined Phylogenetics and Population Genetics Approach

Selection for High Oridonin Yield in the Chinese Medicinal Plant Isodon (Lamiaceae) Using a Combined Phylogenetics and Population Genetics Approach

New <i>ent</i>-Abietane and <i>ent</i>-Kaurane Diterpenoids from <i>Isodon rubescens</i>

The anti-tumor effect of folate-targeted liposome microbubbles loaded with oridonin as ultrasound-triggered tumor-targeted therapeutic carrier system

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