Sesquiterpenoids from the rhizomes of Atractylodes macrocephala and their protection against lipopolysaccharide-induced neuroinflammation in microglia BV-2 cells

Si, Jin-Guang; Zhang, Haixin; Meng, Yijun; Li, Lingyu; Zhang, Hongwu; Jia, Hongmei; Ma, Ling; Qin, Lingling; Zhang, Tao; Zou, Zhong‐Mei

doi:10.1016/j.jff.2021.104541

Cited by 9 publications

(25 citation statements)

References 9 publications

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“…Eudesmane lactone structure consist of eudesmane with lactone ring. Atractylon ( 46 ), [29,33,38,42,43] atractylenolide I (8,9‐dehydroasterolide, 49 ), [26–30,33–35,38,43–53] iso‐atractylenolide I ( 50 , [44] 8β‐methoxy‐atractylenolide I ( 51 ), [30,54,55] 3β‐acetoxy‐atractylenolide I ( 52 ), [44,55] atractylenolide II (asterolide, 53 ), [26–30,32–35,38,43–45,48,53,54,56,57] asterolid (8‐epiasterolid, 54 ), [26,33,57] 13‐hydroxy‐atractylenolide II ( 55 ), [26] 8β,9α‐dihydroxy‐atractylenolide II ( 56 ), [33,43] 3β‐acetoxy‐8‐epiasterolid ( 57 ), [55] 8α‐methoxy‐epiasterolid ( 58 ), [55] 8β‐methoxy‐atractylenolide ( 51 ), [26] 4R,15‐epoxy‐atractylenolide II ( 59 ), [43] 4R,15‐epoxy‐8β‐hydroxy‐atractylenolide II ( 60 ), [33,43] 8S,9S‐epoxyatractylenolide II ( 61 ), [33] 4‐oxo‐8S,9S‐epoxyatractylenolide II ( 62 ), [33] 4R,5R,8S,9S‐diepoxyatractylenolide II ( 63 ), [33] atractylenolide III (8β‐hydroxyasterolide, 64 ), [26,28,30,32–35,38,42–44,47–49,51–54,58,59] 8β‐ethoxyasterolide (8β‐ethoxyatractylenolide III, 65 ), [35] 4‐oxo‐atractylenolide III (4‐ketone‐atractylenolide III, 66 ), [26] 4,15‐epoxy‐8β‐hydroxyasterolide ( 67 ), [52] atractylenolide IV (3β‐acetyl‐atractylenolide III, 68 ), [33,53,55] ...…”

Section: Resultsmentioning

confidence: 99%

“…A. macrocephala [29,33,38,42,43] A. japonica [18,20] A. lancea [10,64] A. chinensis [9,67] A. ovata [8,68–70] …”

Section: Resultsmentioning

confidence: 99%

“…A. macrocephala [26–30,33–35,38,43–53] A. japonica [18,20–22,60,61] A. ovata [68,70,71] A. chinensis [67] A. lancea [64] …”

Section: Resultsmentioning

confidence: 99%

“…A. macrocephala [26–30,32–35,38,43–45,48,53,54,56,57] A. japonica [18] A. lancea [11,64,66] A. ovata [68,70] A. chinensis [67] …”

Section: Resultsmentioning

confidence: 99%

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Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Kim

2022

Chemistry & Biodiversity

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Atractylodes plants have been used in traditional herbal medicine to treat gastrointestinal diseases and contain various chemical compounds. Sesquiterpenoids are the most important therapeutic compounds in Atractylodes rhizomes. Based on studies reported from 2000 to 2022, we classified sesquiterpenoids by their chemical skeletons and original resources. Moreover, we discussed their biosynthesis and physicochemical and pharmacological features. We reported sesquiterpenoids with skeletal moieties, such as monocyclic sesquiterpenes (bisabolene-and elemene-type), bicyclic sesquiterpenes (eudesmane-, isopterocarpolone-, hydroxycarissone-, eremophilane-, bisesquiterpenoid-, guaiane-and spirovetivane-type and eudesmane lactones) and tricyclic sesquiterpenes (cyperene-and patchoulene-type), with their biosynthetic pathways, chemical modifications and in vivo metabolites. The pharmacological activities of sesquiterpenoids as anti-inflammatory, anti-tumor, anti-diabetic and anti-microbial and for treating gastrointestinal disorders have been reported for this genus.

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Section: Resultsmentioning

confidence: 99%

“…A. macrocephala [29,33,38,42,43] A. japonica [18,20] A. lancea [10,64] A. chinensis [9,67] A. ovata [8,68–70] …”

Section: Resultsmentioning

confidence: 99%

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Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Kim

2022

Chemistry & Biodiversity

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“…Sesquiterpenes are the main components of terpenoids in AM rhizome, which are proven to have good antioxidant activity ( 10 ). In our subsequent study on active sesquiterpenoids, we isolated a variety of eudesmane sesquiterpenoids ( 11 – 13 ).…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpene Lactams and Lactones With Antioxidant Potentials From Atractylodes macrocephala Discovered by Molecular Networking Strategy

Wang

Zhao

et al. 2022

Front. Nutr.

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Atractylodes macrocephala rhizome (called Bái-zhú in China) has a long history as a functional food and herbal medicine in East Asia, especially China. Sesquiterpenoids are one of the main active compounds of Atractylodes macrocephala rhizome. This study aimed to explore the unknown sesquiterpenoids of A. macrocephala rhizome using a molecular networking strategy. Two new nitrogen-containing sesquiterpenoids, atractylenolactam A (1) and atractylenolactam B (2), and 2 new sesquiterpene lactones, 8-methoxy-atractylenolide V (6) and 15-acetoxyl atractylenolide III (7), along with 12 known analogs (3-5 and 8-16) were discovered and isolated. All the structures were assigned based on detailed spectroscopic analyses. The absolute configurations of 1, 2, 6, and 7 were established by time-dependent density functional theory ECD (TDDFT-ECD) calculations. All these compounds had different degrees of concentration-dependent activating effects on nuclear-factor-E2-related factor-2 (Nrf2).

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Atramacrolodes A−D (1–4), Four Undescribed Eudesmane‐Type Sesquiterpenes from the Rhizome of Atractylodes macrocephala

Li,

Tian,

Guo

et al. 2024

Chemistry & Biodiversity

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Four undescribed sesquiterpenes, atramacrolodes A‐D (1‐4), along with six known compounds 5‐10 were isolated from the rhizome of Atractylodes macrocephala. Compound 3 possessed a new skeleton based on an unprecedented carton‐carton connection. Their structures were determined by UV, IR, HRESIMS, NMR spectra, 13C NMR calculation with DP4+ analysis, and the comparison of experimental and calculated ECD spectra. Compounds 5 and 8 showed protective effects against paracetamol‐induced liver cell injury.

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Sesquiterpenoids from the rhizomes of Atractylodes macrocephala and their protection against lipopolysaccharide-induced neuroinflammation in microglia BV-2 cells

Cited by 9 publications

References 9 publications

Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Sesquiterpenoids Isolated from the Rhizomes of Genus Atractylodes

Sesquiterpene Lactams and Lactones With Antioxidant Potentials From Atractylodes macrocephala Discovered by Molecular Networking Strategy

Atramacrolodes A−D (1–4), Four Undescribed Eudesmane‐Type Sesquiterpenes from the Rhizome of Atractylodes macrocephala

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