Analysis of the Sesquiterpenoids in Processed Atractylodis Rhizoma

Wang, Kun-Teng; Chen, Lih Geeng; Yang, Lingling; Ke, Weiming; Chang, Hsing-Chang; Wan, Ching-Chiung

doi:10.1248/cpb.55.50

Cited by 33 publications

(28 citation statements)

References 21 publications

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“…Wang et al [2] analyzed atractylon contents of Atractylodis Rhizoma purchased in Taipei by using HPLC. Atractylon contents in the raw crude drugs varied in the range of 1.67-5.87 mg/g dry weight with an average content of 2.87 mg/g dry weight.…”

Section: Nmr Analysis and Purity Of Atractylonmentioning

confidence: 99%

“…This compound exhibits various pharmacological activities including anti-inflammation [1], cytotoxicity against various human cancer cell lines [2,3], acaricidal activity [4], and inhibition of Na ? ,K ?…”

Section: Introductionmentioning

confidence: 99%

“…Proton-specific quantitative NMR (qHNMR) has been shown to have an enormous potential for quantitative analysis of natural products [9]. qHNMR has various advantages over other quantitative analysis methods including HPLC: (1) it is rapid, non-invasive, and does not require laborious sample precleaning steps; (2) no standard compounds are required to prepare calibration curves; and (3) all the compounds present in the extract can be simultaneously detected. These features may make qHNMR the method of choice for quantitative determination of chemical constituents in crude drugs.…”

Section: Introductionmentioning

confidence: 99%

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Quantitative determination of atractylon in Atractylodis Rhizoma and Atractylodis Lanceae Rhizoma by 1H-NMR spectroscopy

et al. 2010

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(1)H-NMR spectroscopy was successfully applied to the quantitative determination of atractylon in Atractylodis Rhizoma (dried rhizomes of Atractylodes ovata and A. japonica) and Atractylodis Lanceae Rhizoma (dried rhizomes of Atractylodes lancea and A. chinensis). The analysis was carried out by comparing the integral of the H-12 singlet signal of atractylon, which was well separated in the range of delta 6.95-7.05 ppm in the NMR spectrum, with the integral of a hexamethyldisilane (HMD) signal at delta 0 ppm. The atractylon contents obtained by the (1)H-NMR spectroscopy were consistent with those obtained by the conventional HPLC analysis. The present method requires neither reference compounds for calibration curves nor sample pre-purification. It also allows simultaneous determination of multiple constituents in a crude extract. Thus, it is applicable to chemical evaluation of crude drugs as a powerful alternative to various chromatographic methods.

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Section: Nmr Analysis and Purity Of Atractylonmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantitative determination of atractylon in Atractylodis Rhizoma and Atractylodis Lanceae Rhizoma by 1H-NMR spectroscopy

et al. 2010

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“…In particular, isofuranodiene shows anticancer and antiangiogenic activity (15)(16)(17)(18)(19)(20)(21)(22), as well as analgesic properties when acting on brain opioid receptors (23). Atractylon exhibits antiinflammatory activity (24), cytotoxicity against various human cancer cell lines (25,26), acaricidal activity (27), and inhibition of Na + , K + -ATPase activity (28). However, previous attempts to explore the natural function of compound 1 in the Antarctic gorgonian D. acanthina have failed to recognize its feeding deterrent properties against the goldfish Carassius auratus (Linnaeus, 1758), although the compound showed toxicity to the mosquitofish Gambusia affinis (Baird & Girard, 1853) (7).…”

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confidence: 99%

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Giordano

Carbone

Ciavatta

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Olfaction is considered a distance sense; hence, aquatic olfaction is thought to be mediated only by molecules dissolved in water. Here, we challenge this view by showing that shrimp and fish can recognize the presence of hydrophobic olfactory cues by a "tactile" form of chemoreception. We found that odiferous furanosesquiterpenes protect both the Mediterranean octocoral Maasella edwardsi and its specialist predator, the nudibranch gastropod Tritonia striata, from potential predators. Food treated with the terpenes elicited avoidance responses in the cooccurring shrimp Palaemon elegans. Rejection was also induced in the shrimp by the memory recall of postingestive aversive effects (vomiting), evoked by repeatedly touching the food with chemosensory mouthparts. Consistent with their emetic properties once ingested, the compounds were highly toxic to brine shrimp. Further experiments on the zebrafish showed that this vertebrate aquatic model also avoids food treated with one of the terpenes, after having experienced gastrointestinal malaise. The fish refused the food after repeatedly touching it with their mouths. The compounds studied thus act simultaneously as (i) toxins, (ii) avoidance-learning inducers, and (iii) aposematic odorant cues. Although they produce a characteristic smell when exposed to air, the compounds are detected by direct contact with the emitter in aquatic environments and are perceived at high doses that are not compatible with their transport in water. The mouthparts of both the shrimp and the fish have thus been shown to act as "aquatic noses," supporting a substantial revision of the current definition of the chemical senses based upon spatial criteria. T raditionally, the sense of smell has been regarded as a distance sense (like vision), whereas the sense of taste has been treated as a contact sense (like touch). This classification of the chemical senses (olfaction and gustation) based on their spatial range persists in contemporary literature. Accordingly, biomolecules smaller than ∼300 Da, which can be transported through air, and which finally bind to odorant receptors expressed in olfactory neurons, are generally considered odorant molecules. Conversely, the molecules sensed by taste have to be in solution and in contact with the receptor (1). However, the claim that "only olfaction can provide information on the identity of the water mass encountered" by marine organisms (2) implies that water-soluble compounds, which are typically "tasted" by the tongues of terrestrial animals, act as olfactory cues in aquatic environments. Consequently, it may be asked how typical odorant molecules such as small terpenes from plants and marine sponges that combine high volatility in air with insolubility in water can produce olfactory sensations in marine organisms, thereby giving protection from predators and cues to finding food and mates.

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“…Atractylenolide-I (AO-I) is a naturally occurring sesquiterpene lactone isolated from Atractylodes macrocephala Koidz [Family: Compositae], and has been used for anti-inflammatory purposes and the treatment of cancers151617181920. Anti-inflammatory effect of AO-I displays a potent inhibitory effect on angiogenesis by a set of downregulation of NO, TNF-α, IL-1β, IL-6 and VEGF in monocytes and macrophages stimulated with LPS2122.…”

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confidence: 99%

Atractylenolide-I Sensitizes Human Ovarian Cancer Cells to Paclitaxel by Blocking Activation of TLR4/MyD88-dependent Pathway

Huang

Zhang

Shi

et al. 2014

Sci Rep

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Paclitaxel, a known TLR4 ligand, leads to activation of TLR4/MyD88-dependent pathway that mediates chemoresistance and tumor progression in epithelial ovarian carcinoma (EOC). Atractylenolide-I (AO-I), a novel TLR4-antagonizing agent, inhibits TLR4 signaling by interfering with the binding of LPS or paclitaxel to membrane TLR4 of human leukocytes. In this study, AO-I was found to attenuate paclitaxel-induced protein expression of IL-6, VEGF and survivin, and to enhance early apoptosis and growth inhibition in MyD88+ EOC cells; AO-I was shown to fit into the hydrophobic pocket of human MD-2 and to partially overlap with the binding site of paclitaxel by docking simulations, suggesting that AO-I may block the MD-2-mediated TLR4/MyD88-dependent paclitaxel signaling in MyD88+ EOC cells. Therefore, AO-I could significantly sensitize the response of MyD88+ EOC cells to paclitaxel by blocking MD-2-mediated TLR4/MyD88 signaling, and that AO-I-paclitaxel combination could be a promising strategy for the treatment of EOC with a functional TLR4/MyD88/NF-κB pathway.

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Analysis of the Sesquiterpenoids in Processed Atractylodis Rhizoma

Cited by 33 publications

References 21 publications

Quantitative determination of atractylon in Atractylodis Rhizoma and Atractylodis Lanceae Rhizoma by 1H-NMR spectroscopy

Quantitative determination of atractylon in Atractylodis Rhizoma and Atractylodis Lanceae Rhizoma by 1H-NMR spectroscopy

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Atractylenolide-I Sensitizes Human Ovarian Cancer Cells to Paclitaxel by Blocking Activation of TLR4/MyD88-dependent Pathway

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