Da-Peng Qin's research works | China Pharmaceutical University and other places

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Arteannoides U–Z: Six undescribed sesquiterpenoids with anti-inflammatory activities from the aerial parts of Artemisia annua (Qinghao)

Article

July 2021

32 Reads

6 Citations

Fitoterapia

[...]

Four previously unreported sesquiterpenoid diasteromers, arteannoides U–X (1–4), together with one new norsesquiterpenoid 5 (arteannoide Y) and one undescribed rearranged cadinene sesquiterpenoid 6 (arteannoide Z) were obtained from the dried aerial parts of Artemisia annua (Qinghao). Notably, arteannoides U–X (1–4) are four stereoisomers that possess the same molecules and the same planar connectivity, but differ from each other in configuration at a certain stereocenter. Their accurate structures were unambiguously identified and distinguished by extensive spectroscopic analyses, NMR calculations with DP4+ analysis, electronic circular dichroism (ECD) calculations and X-ray diffraction analyses. Compounds 1, 3, and 4 showed inhibitory activities against the production of inflammatory cytokines (PGE2, NO, IL-6 and TNF-α) in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages.

Research on chemical constituents from Artemisia annua

Article

March 2021

59 Reads

8 Citations

China Journal of Chinese Materia Medica

[...]

Chemical constituents were isolated and purified from the water extract of Artemisia annua by column chromatography of HP-20 macroporous resin, silica gel, ODS, Sephadex LH-20, HW-40, and semi-preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. As a result, Fifteen compounds were isolated and identified as vitexnegheteroin M(1), sibricose A5(2), securoside A(3), citrusin D(4), annphenone(5), E-melilotoside(6), esculetin(7), scopoletin-7-O-β-D-glucoside(8), eleutheroside B_1(9), chrysosplenol D(10), patuletin-3-O-β-D-glucopyranoside(11), quercetin-7-O-β-D-glucoside(12), rutin(13), apigenin 6,8-di-C-β-D-glucopyranoside(14), isoschaftoside(15), among them, compounds 1-4 were identified from Artemisia for the first time. Additionally, the isolates were evaluated for their inhibitory effects on the production of PGE_2 in LPS-simulated RAW264.7 macrophages. The results showed that compounds 1, 2, 8, and 10-15 could reduce PGE_2 levels, to a certain extent.

Spiromyrrhenes A−D: Unprecedented Diterpene-Sesquiterpene Heterodimers as intermolecular [4+2] cycloaddition products from Resina Commiphora That Inhibit Tumor Stemness in Esophageal Cancer

Article

August 2020

25 Reads

8 Citations

Organic Chemistry Frontiers

[...]

The structures and stereochemistry of spiromyrrhenes A−D (1−4), isolated from Commiphora exudates, were elucidated using NMR and ECD methods. They are the first examples of hepta- and octa-cyclic heterodimers with...

Structurally diverse sesquiterpenoids from the aerial parts of Artemisia annua (Qinghao) and their striking systemically anti-inflammatory activities

Article

August 2020

30 Reads

24 Citations

Bioorganic Chemistry

[...]

Thirteen new sesquiterpenoids, arteannoides F–R (1–13), along with 13 known analogues (14–26), were isolated from the dried aerial parts of Artemisia annua L. Their structures, including absolute configurations, were unambiguously determined by a combination of physical data analyses (HRESIMS, 1D and 2D NMR, and ECD) as well as the crystal structures of 1, 5, 6, 15, 19, and 23. Among the isolated compounds, 1 features an unusual 11-oxatricyclo[6.2.1.04,9]undecan-2-ene ring system, 5 possesses an uncommon 4,11-ether bridged tricyclic framework, whereas 6 is a new eudesmane-type sesquiterpenoid formed via rearrangement of its carbon backbone. The systemically anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on PGE2, NO, TNF-α, and IL-6 production in LPS-stimulated RAW 264.7 macrophages. Moreover, the structure activity relationships of some compounds are summarized, this study will provide new structural templates for discovering potential anti-inflammatory agents.

Meroterpenoids from the Fungus Ganoderma sinensis and First Absolute Configuration Clarification of Zizhine H

December 2019

96 Reads

12 Citations

[...]

Five new meroterpenoids, zizhines P-S and U (1−4,7), together with two known meroterpenoids (5 and 6) were isolated from Ganoderma sinensis. Their structures including absolute configurations were assigned by using spectroscopic, computational, and chemical methods. Racemics zizhines P and Q were purified by HPLC on chiral phase. Biological evaluation found that 4, 5 and 6 are cytotoxic toward human cancer cells (A549, BGC-823, Kyse30) with IC50 values in the range of 63.43–80.83 μM towards A549, 59.2 ± 2.73 μM and 64.25 ± 0.37 μM towards BGC-823, 76.28 ± 1.93 μM and 85.42 ± 2.82 μM towards Kyse30.

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Figure 1. The structures of compounds 1-13.

Figure 6. Neuroprotective activities of compounds 1−13 against H2O2-mediated oxidative stress in HT-22 cells. Cell viability was determined by CCK-8 assay. (A): Primary screening at 20 μM; (B)-(G): Dose-dependent curve of 4, 7-9, 12, and 13. Control was PBS-treated cells. "40" in bar charts means that cells were only treated by 40 μM compound. n = 3, all data in bar charts represent means ± SEM. The symbol n.s. means no significance, * p < 0.05, ** p < 0.01, *** p < 0.001, one-way ANOVA with posthoc comparison Turkey.

1 H (600 MHz) and 13 C (150 MHz) NMR data of 3 and 4 in CDCl 3 .

Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins

November 2019

95 Reads

15 Citations

[...]

Two new octanorlanostane-type triterpenes, euphraticanoids A and B (1 and 2), two new trinorsesquiterpenoids, euphraticanoids C and D (3 and 4), and eight known triterpenoids (5, 6, 8–13) along with one steroid (7) were isolated from Populus euphratica resins. The structures of these new compounds, including their absolute configurations, were characterized by spectrocsopic, chemical, and computational methods. Biological evaluation revealed that compounds 4, 7–9, 12, and 13 display neuroprotective activities in H2O2-induced HT-22 cells with 4, 8, and 9 occurring in a concentration-dependent manner and 7, 12, and 13 reaching the maximum effects at 20 μM. Meanwhile, the neuroprotective properties of all isolates were accessed using glutamate-induced SH-SY5Y cells and disclosed that compounds 3, 4, 8, and 9 could dose-dependently protect neural cell injury in a concentration range of 10–40 μM. Finally, a brief structure–activity relationship was briefly discussed.

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Commiphorines A and B, unprecedented sesquiterpenoid dimers from Resina Commiphora with striking activities on anti-inflammation and lipogenesis inhibition

Article

October 2019

99 Reads

16 Citations

Organic Chemistry Frontiers

[...]

Commiphorines A (1), an unprecedented sesquiterpenoid heterodimer featuring a 5/7(5)/4/10/5 ring system, B (2), a dimeric sesquiterpenoid possessing an unusual 1,4-dioxin motif and a 6/6/5/6/6/6 polycyclic system, and two intermediates 3 and 4, were isolated from Resina Commiphora. A plausible biosynthetic route for 1 and 2 was proposed. Compound 2 could significantly suppress LPS-induced inflammation through NF-κB and MAPK signaling pathways in mouse peritoneal macrophages. Compounds 1 and 2 could inhibit lipid synthesis in HepG2 cells.

Research progress on chemical constituents of Artemisia annua and its pharmacological activities

Article

July 2019

12 Reads

14 Citations

Chinese Traditional and Herbal Drugs

[...]

As a commonly used Chinese materia medica, Artemisia annua mainly contains sesquiterpenoids, diterpenes, phenylpropionic acids, coumarins, flavonoids, volatile oil, and other chemical compositions. Its pharmacological activities are anti-malaria, anti-tumor, anti-microbial, anti-parasitic, antipyretic, anti-inflammatory, immunoregulation and so on. The significantly anti-malarial activity has led to its earlier use in the treatment of malaria. In this paper, the chemical constituents and pharmacological activities of A. annua in recent years are reviewed in order to provide a reference for the further development and rational utilization of this plant resource. © 2019, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

Key ¹H–¹H COSY, HMBC, and ROESY correlations of 1–3

Key NOESY correlations and X-ray crystallographic analysis of 1

Lonimacranaldes A–C, three iridoids with novel skeletons from Lonicera macranthoides

July 2019

67 Reads

7 Citations

[...]

Lonimacranaldes A and B (1 and 2), along with one biogenetically related intermediate, lonimacranalde C (3), were isolated from the flower buds of Lonicera macranthoides. Characterized by an iridoid structure and an additional C-6 unit with an aldehyde group, compounds 1 and 2 are the first examples of hybrid iridoids possessing an unexpected 6/5/6 fused tricyclic ring system, while compound 3 serves as an important precursor for their generation. The structures of lonimacranaldes A-C (1-3) were revealed by extensive spectroscopic and X-ray diffraction analyses. A plausible biogenetic pathway for them was proposed. Compound 3 showed anti-inflammatory activities by inhibiting the production of IL-6 on LPS-induced RAW 264.7 cells with an IC50 value of 6.33 μM.

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Populeuphrines A and B, two new cembrane diterpenoids from the resins of Populus euphratica

Article

July 2019

29 Reads

8 Citations

Natural Product Research

[...]

Two new cembrane diterpenoids, named populeuphrines A and B (1 and 2), together with three known analogues (3–5) were isolated from the resins of Populus euphratica. The planar structures and relative configurations of 1 and 2 were elucidated by detailed 1 D and 2 D NMR spectroscopic analyses. The absolute configurations of 1 and 2 were determined by X-ray diffraction analysis and quantum chemical computation. Biological activities of all the isolates against proliferation of human cancer cells and umbilical cord mesenchymal stem cells were evaluated.

... μmol/L [23]. In addition, chromones isolated from ethyl acetate extracts exhibited strong inhibitory activity against Staphylococcus aureus, as well as good inhibitory activity against methicillin-resistant Staphylococcus aureus [24]; Some extracts also showed inhibitory activity against Xanthomonas oryzae [25]. ...
Reference:
Exploration of the Effects of Agarwood Extract on the Inflammtory Microbiota in the Oral-Gut Axis

Research progress on chemical constituents of Artemisia annua and its pharmacological activities

Citing Article
July 2019

Chinese Traditional and Herbal Drugs

[...]

... The formation of cadinane-type sesquiterpenoids is believed to occur through the cyclic combination of myrrh type sesquiterpenoids at C-1 and C-10, with a total of 53 compounds (370-422) reported during this period. This subtype has been isolated and identified from eight species, including A. absinthium (Fraga et al. 2021), A. sieversiana (Nurbek et al. 2020;Nuermaimaiti et al. 2021), A. rupestris , A. annua (Qin et al. 2021(Qin et al. , 2020Takenaka et al. 2020;Han et al. 2022;He et al. 2023c), A. iwayomogi (Son et al. 2022), A. mongolica (Zhu et al. 2022), A. vulgaris ) and A. argyi . Among these, the greatest number of these compounds has been reported in A. annua. ...
Reference:
Unlocking the power of sesquiterpenoids: phytochemistry and bioactivities in Artemisia (2017–2023)

Arteannoides U–Z: Six undescribed sesquiterpenoids with anti-inflammatory activities from the aerial parts of Artemisia annua (Qinghao)

Citing Article
July 2021

Fitoterapia

[...]

... It is found in several plants, such as Ducrosia (aerial parts) (Morgan et al., 2014), and Ononis (aerial parts) (Mezrag et al., 2017). Other citrusins (A, B, D) are reported constituents of several plants such as Artemisia (Xiao et al., 2021), Cortex (Yang S. et al., 2019), Buxus (Saleem et al., 2019), and sweet oranges (Díaz et al., 2014). Citrusins exhibit anti-inflammatory (Yang S. et al., 2019) and antiviral activity (Tan et al., 2012). ...
Reference:
Characterization of Ikaria Heather Honey by Untargeted Ultrahigh-Performance Liquid Chromatography-High Resolution Mass Spectrometry Metabolomics and Melissopalynological Analysis

Research on chemical constituents from Artemisia annua

Citing Article
March 2021

China Journal of Chinese Materia Medica

[...]

... In the form of teas or tinctures, it is used to stimulate the appetite and improve digestion, which is a consequence of its bitter taste, which stimulates the secretion of digestive juices. Artemisia annua has been used in traditional Chinese medicine to remove toxins from the blood, treat arthritis and fever, prevent the recurrence of malaria and treat jaundice (Qin et al., 2020). Due to the presence of different active substances in the plants, the chemical composition of A. absinthium and A. annua differs. ...
Reference:
Influence of the Ratio of Water and Organic Solvents on the Antioxidative Activity and Content of Bioactive Components in Artemisia annua L. and Artemisia absinthium L. Extracts

Structurally diverse sesquiterpenoids from the aerial parts of Artemisia annua (Qinghao) and their striking systemically anti-inflammatory activities

Citing Article
August 2020

Bioorganic Chemistry

[...]

... As previously reported, tumour heterogeneity plays a critical role in therapeutic resistance due to the presence of cancer cells with distinct features, such as CSCs. Previous studies have reported the ability of marine natural products to impact the development of these type of malignant cells, such as polysaccharides [71], carotenoids [72], and terpenes [38,[73][74][75]. Those compounds decreased viability, number, and area of CSCs-enriched tumourspheres derived from distinct tissues, and modulated the expression levels of several genes/ proteins linked with stemness properties such as SOX2, Oct4 and Nanog. ...
Reference:
Disclosing the antitumour potential of the marine bromoditerpene sphaerococcenol A on distinct cancer cellular models

Spiromyrrhenes A−D: Unprecedented Diterpene-Sesquiterpene Heterodimers as intermolecular [4+2] cycloaddition products from Resina Commiphora That Inhibit Tumor Stemness in Esophageal Cancer

Citing Article
August 2020

Organic Chemistry Frontiers

[...]

... A recent comprehensive review by us summarized the chemistry and biological activity of recent substances, highlighting our contribution to this field [7]. The tears of Populus euphratica were collected for systematic research by us, accompanied by discovering a series of structurally intriguing and biologically significant compounds, including various terpenoids [8]. As a continuous study on this topic, five prenylaromadendrane-type diterpenes euphraticanoids N-R (1-5) and two aromadendrane-type sesquiterpenes euphraticanoids S and T (6 and 7) were identified ( Figure 1). ...
Reference:
Euphraticanoids N–T: Aromadendrane-Type Diterpenes and Sesquiterpenes with Fungicidal Activities from Populus euphratica Resins

Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins

Citing Article
Full-text available
November 2019

[...]

... Alternatively, the dimeric sesquiterpenes may interact with either monomeric or dimeric proteins (Alexander et al., 2009;Ni et al., 2011). According to reports, several sesquiterpenes exhibit significant biological properties such as anti-inflammatory, anti-tumor, and anti-AIDS virus (Chi et al., 2019;Dong et al., 2019;Liu et al., 2019, Xue et al., 2019. However, there is limited research on the potential application of sesquiterpenes in treating Vitiligo. ...
Reference:
Guaianolide sesquiterpenes and their activity from Artemisia mongolica

Commiphorines A and B, unprecedented sesquiterpenoid dimers from Resina Commiphora with striking activities on anti-inflammation and lipogenesis inhibition

Citing Article
October 2019

Organic Chemistry Frontiers

[...]

... Populus euphratica, a deciduous plant belonging to the Salicaceae family, is a tree species commonly found in wasteland [1]. In China, this species is primarily found in the western region, specifically in non-living environments such as deserts or saline and alkaline lands [2,3]. Populus euphratica resin is used in both traditional Chinese and Uyghur medicine. ...
Reference:
Structurally Diverse Terpenoids from the Resins of Populus euphratica

Populeuphrines A and B, two new cembrane diterpenoids from the resins of Populus euphratica

Citing Article
July 2019

Natural Product Research

[...]

... Germacrane [56] eudesm-4(15)-ene-1β,6α-diol C. myrrha, C. opobalsamum Eudesmane [56,77] eudesmane-1β,5α,11-triol C. opobalsamum Eudesmane [85] β-selinene C. holtziana Eudesmane [86] 11-hydroxy-4α-methoxy-selinane C. opobalsamum Eudesmane [56] 1β,4β-epoxy-eudesmane-11-ol C. opobalsamum Eudesmane [56] 9-nor-9,10-seco-isolindestrenolide C. myrrha Eudesmane [87] 9,10-seco-isohydroxylindestrenolide C. myrrha Eudesmane [87] lindestrenolide C. myrrha Eudesmane [87] atractylenolide C. myrrha Eudesmane [87] 4β-hydroxy-8,12-epoxyeudesma-7,11-diene-1,6-dione C. 2-methoxyfuranoguaia-9-ene-8-one C. molmol Guaiane [80] (1R,2R,4S)-1,2-epoxyfuranogermacr-10(15)-en-6-one Resina Commiphora Guaiane [78] alismol C. myrrha, C. opobalsamum Guaiane [83] 6α,7α-epoxy-1β-guai-10(14)-en-4α-ol C. opobalsamum Guaiane [57] 5β-10α-hydroxy-2α-methoxy-6-oxoguaia-7(11),8-dien-8,12-olide C. opobalsamum Guaiane [57] (1R,4S,5R)-guaia-6,10(14)-diene C. opobalsamum Guaiane [57] myrrhterpenoid O Resina Commiphora Guaiane [78] myrrhterpenoid G C. myrrha Guaiane [84] myrrhterpenoid H C. myrrha Guaiane [84] myrrhterpenoid I C. myrrha Guaiane [84] myrrhterpenoid K C. myrrha Guaiane [89] myrrhterpenoid L C. myrrha Guaiane [89] guaia-4β,7β,10α-trihydroxy-5-ene C. opobalsamum Guaiane [56] myrrhanoperoxide C. myrrha Guaiane [87] rel-(+)-(1S,4R,7S)-11-acetyl-guai-10(14)-en-4,11-ol C. myrrha Guaiane [87] rel-(+)-(4R,5R,7S)-11-acetyl-guai-1(10)-en-4,11-ol C. myrrha Guaiane [87] commiphorane J Resina Commiphora Guaiane [88] guai-1(10),5,7 (11) δ-elemene C. holtziana Elemane [86] γ-elemene C. myrrha, C. holtziana Elemane [86] isogermafurenolide C. myrrha Elemane [87] hydroxyisogermafurenolide C. myrrha Elemane [87] methoxyisogermafurenolide C. myrrha Elemane [87] α-bisabolene C. guidotti Others [70] β-bisabolene C. guidotti Others [70,74] α-santalene C. guidotti Others [70] α-cubebene C. myrrha Others [86] β-bourhonene C. holtziana Others [86] commipholactam A Resina Commiphora Others [88] commiphorane C Resina Commiphora Others [64] commiphorane D Resina Commiphora Others [64] 2-methyl-5- nepetaefolinF Resina Commiphora Abietane [98] 3β-hydroxy-dehydroabietic acid Resina Commiphora Abietane [88] (1E,5E,9E)-1,5,9-trimethyl-12-(1methylethenyl)cyclotetradeca-1,5,9-triene C. mukul Cembrane [62] (2E,6E,10E)-3,7,11-trimethyl-14-(1methylethenyl)cyclotetradeca-2,6,10-trien-1-ol C. mukul Cembrane [62] (1E,3E,6E,10E)-3,7,11-trimethyl-14-(1methylethyl)cyclotetradeca-1,3,6,10-tetraene C. mukul Cembrane [62] (2E,6E,10E)-3,7,11-trimethyl-14-(1methylethyl)cyclotetradeca-2,6,10-trien-1-ol C. ...
Reference:
The Genus Commiphora: An Overview of Its Traditional Uses, Phytochemistry, Pharmacology, and Quality Control

Anti-Mycobacterium tuberculosis Terpenoids from Resina Commiphora

Citing Article
Full-text available
April 2019

[...]

... Germacrane [56] eudesm-4(15)-ene-1β,6α-diol C. myrrha, C. opobalsamum Eudesmane [56,77] eudesmane-1β,5α,11-triol C. opobalsamum Eudesmane [85] β-selinene C. holtziana Eudesmane [86] 11-hydroxy-4α-methoxy-selinane C. opobalsamum Eudesmane [56] 1β,4β-epoxy-eudesmane-11-ol C. opobalsamum Eudesmane [56] 9-nor-9,10-seco-isolindestrenolide C. myrrha Eudesmane [87] 9,10-seco-isohydroxylindestrenolide C. myrrha Eudesmane [87] lindestrenolide C. myrrha Eudesmane [87] atractylenolide C. myrrha Eudesmane [87] 4β-hydroxy-8,12-epoxyeudesma-7,11-diene-1,6-dione C. 2-methoxyfuranoguaia-9-ene-8-one C. molmol Guaiane [80] (1R,2R,4S)-1,2-epoxyfuranogermacr-10(15)-en-6-one Resina Commiphora Guaiane [78] alismol C. myrrha, C. opobalsamum Guaiane [83] 6α,7α-epoxy-1β-guai-10(14)-en-4α-ol C. opobalsamum Guaiane [57] 5β-10α-hydroxy-2α-methoxy-6-oxoguaia-7(11),8-dien-8,12-olide C. opobalsamum Guaiane [57] (1R,4S,5R)-guaia-6,10(14)-diene C. opobalsamum Guaiane [57] myrrhterpenoid O Resina Commiphora Guaiane [78] myrrhterpenoid G C. myrrha Guaiane [84] myrrhterpenoid H C. myrrha Guaiane [84] myrrhterpenoid I C. myrrha Guaiane [84] myrrhterpenoid K C. myrrha Guaiane [89] myrrhterpenoid L C. myrrha Guaiane [89] guaia-4β,7β,10α-trihydroxy-5-ene C. opobalsamum Guaiane [56] myrrhanoperoxide C. myrrha Guaiane [87] rel-(+)-(1S,4R,7S)-11-acetyl-guai-10(14)-en-4,11-ol C. myrrha Guaiane [87] rel-(+)-(4R,5R,7S)-11-acetyl-guai-1(10)-en-4,11-ol C. myrrha Guaiane [87] commiphorane J Resina Commiphora Guaiane [88] guai-1(10),5,7 (11) δ-elemene C. holtziana Elemane [86] γ-elemene C. myrrha, C. holtziana Elemane [86] isogermafurenolide C. myrrha Elemane [87] hydroxyisogermafurenolide C. myrrha Elemane [87] methoxyisogermafurenolide C. myrrha Elemane [87] α-bisabolene C. guidotti Others [70] β-bisabolene C. guidotti Others [70,74] α-santalene C. guidotti Others [70] α-cubebene C. myrrha Others [86] β-bourhonene C. holtziana Others [86] commipholactam A Resina Commiphora Others [88] commiphorane C Resina Commiphora Others [64] commiphorane D Resina Commiphora Others [64] 2-methyl-5- nepetaefolinF Resina Commiphora Abietane [98] 3β-hydroxy-dehydroabietic acid Resina Commiphora Abietane [88] (1E,5E,9E)-1,5,9-trimethyl-12-(1methylethenyl)cyclotetradeca-1,5,9-triene C. mukul Cembrane [62] (2E,6E,10E)-3,7,11-trimethyl-14-(1methylethenyl)cyclotetradeca-2,6,10-trien-1-ol C. mukul Cembrane [62] (1E,3E,6E,10E)-3,7,11-trimethyl-14-(1methylethyl)cyclotetradeca-1,3,6,10-tetraene C. mukul Cembrane [62] (2E,6E,10E)-3,7,11-trimethyl-14-(1methylethyl)cyclotetradeca-2,6,10-trien-1-ol C. ...
Reference:
The Genus Commiphora: An Overview of Its Traditional Uses, Phytochemistry, Pharmacology, and Quality Control

Commipholactam A, a cytotoxic sesquiterpenoidal lactam from Resina Commiphora

Citing Article
March 2019

Fitoterapia

[...]

Da-Peng Qin’s research while affiliated with China Pharmaceutical University and other places

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