New Methyl Threonolactones and Pyroglutamates of Spilanthes acmella (L.) L. and Their Bone Formation Activities

Widyowati, Retno; Sulistyowaty, Melanny Ika; Uyen, Nguyen Hoang; Sugimoto, Sachiko; Yamano, Yasushi; Otsuka, Hideaki; Matsunami, Katsuyoshi

doi:10.3390/molecules25112500

Cited by 4 publications

(3 citation statements)

References 27 publications

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“…Spilanthol and other alkyl amides present in B. acmella extract also contributed significantly to its anti-inflammatory ( Sharma et al, 2011 ; Bakondi et al, 2019 ) and antioxidant ( Abeysiri et al, 2013 ; Sharma and Arumugam, 2021 ) activities. A recent study also reported that components in B. acmella extract such as 1,3-butanediol 3-pyroglutamate, 2-deoxy-d-ribono-1,4-lactone, methyl pyroglutamate, ampelopsisionoside, icariside B1, bezyl-α-1-arabinopyranosyl-(1,6)-β-d-glucopyranoside ( Widyowati et al, 2020a ), methyl threonolactones, and pyroglutamates contributed to its ALP activity and mineralization of osteoblast MC3T3-E1 cells ( Widyowati et al, 2020b ).…”

Section: Introductionmentioning

confidence: 92%

“…In addition, the use of B. acmella extracts followed by exercise activity on mice increased the bone formation rate of mouse femur trabecular ( Laswati et al, 2015 ). Methyl threonolactone glucopyranoside group, methyl threonolactonefructofuranoside, methyl pyroglutamates, and amine cell derivatives isolated from B. acmella methanol extracts were recently demonstrated to significantly increase the ALP and mineralization activities of osteoblast cells ( Widyowati et al, 2020a ; Widyowati et al, 2020b ).…”

Section: Introductionmentioning

confidence: 99%

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Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

et al. 2022

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Blainvillea acmella (L.) Philipson [Asteraceae] (B. acmella) is an important medicinal plant native to Brazil, and it is widely known as a toothache plant. A plethora of studies have demonstrated the antioxidant activities of B. acmella and few studies on the stimulatory effects on alkaline phosphatase (ALP) secretion from bone cells; however, there is no study on its antioxidant and anabolic activity on bone cells. The study aimed to evaluate the phytochemical contents of aqueous and ethanol extracts of B. acmella using gas chromatography mass spectrometry (GCMS) and liquid chromatography time of flight mass spectrometry (LCTOFMS) along with the total phenolic (TPC) and flavonoid (TFC) contents using Folin-Ciocalteu and aluminum colorimetric methods. The extracts of B. acmella leaves were used to scavenge synthetic-free radicals such as 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and ferric reducing antioxidant power (FRAP) assays. The bone anabolic effects of B. acmella extracts on MC3T3-E1 cells were measured with 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazoium bromide (MTT) at 1, 3, 5, and 7 days, Sirius-red and ALP at 7 and 14 days, and Alizarin Red S at 14 and 21 days. Comparatively, ethanol extract of B. acmella (BaE) contributed higher antioxidant activities (IC50 of 476.71 µg/ml and 56.01 ± 6.46 mg L-ascorbic acid/g against DPPH and FRAP, respectively). Anabolic activities in bone proliferation, differentiation, and mineralization were also higher in B. acmella of ethanol (BaE) than aqueous (BaA) extracts. Positive correlations were observed between phenolic content (TPC and TFC) to antioxidant (ABTS and FRAP) and anabolic activities. Conversely, negative correlations were present between phenolic content to antioxidant (DPPH) activity. These potential antioxidant and bone anabolic activities in BaE might be due to the phytochemicals confirmed through GCMS and LCTOFMS, revealed that terpenoids of α-cubebene, cryophyllene, cryophyllene oxide, phytol and flavonoids of pinostrobin and apigenin were the compounds contributing to both antioxidant and anabolic effects in BaE. Thus, B. acmella may be a valuable antioxidant and anti-osteoporosis agent. Further study is needed to isolate, characterize and elucidate the underlying mechanisms responsible for the antioxidant and bone anabolic effects.

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Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

et al. 2022

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“…Twenty-two known compounds were identified as quercetin-3- O - β -D-rhamnopyranoside ( 4 ) [ 17 ], 6-methoxy-naringenin ( 5 ) [ 18 ], 6-methoxy-kaempferol ( 6 ) [ 19 ], kaempferol ( 7 ) [ 20 ], apigenin ( 8 ) [ 21 ], abscisic acid ( 9 ) [ 22 ], (+)-dehydrovomifoliol ( 10 ) [ 23 ], grasshopper ketone ( 11 ) [ 24 ], roseoside ( 12 ) [ 25 ], citroside A ( 13 ) [ 23 ], 4′-(6-amino-9 H -purin-9-yl)pentan-2′-one ( 14 ) [ 26 ], seco-( S -Pro- R -Val) (1 5 ) [ 27 ], cyclo-( L -Pro- L -Ala) ( 16 ) [ 28 ], 3-methoxyl-1 H -pyrrole ( 17 ) [ 29 ], cyclo-(Ala-Val) ( 18 ) [ 30 ], indole-3-carboxyl- β -D-glucopyranoside ( 19 ) [ 31 ], uridine ( 20 ) [ 32 ], thymidine ( 21 ) [ 33 ], adenosine ( 22 ) [ 34 ], hypoxanthine ( 23 ) [ 35 ], aurantiamide acetate ( 24 ) [ 36 ], and L -pyroglutamic acid methyl ester ( 25 ) [ 37 ].…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Flowers of Carthamus tinctorius L. and Their Lung Protective Activity

et al. 2022

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A new flavonoid, saffloflavanside (1), a new sesquiterpene, safflomegastigside (2), and a new amide, saffloamide (3), together with twenty-two known compounds (4–25), were isolated from the flowers of Carthamus tinctorius L. Their structures were determined based on interpretation of their spectroscopic data and comparison with those reported in the literature. The protective effects against lipopolysaccharide (LPS)-stimulated damage on human normal lung epithelial (BEAS-2B) cells of the compounds were evaluated using MTT assay and cellular immunofluorescence assay. The results showed that compounds 2–3, 8–11, and 15–19 exhibited protective effects against LPS-induced damage to BEAS-2B cells. Moreover, compounds 2–3, 8–11, and 15–19 can significantly downregulate the level of nuclear translocation of NF-κB p-p65. In summary, this study revealed chemical constituents with lung protective activity from C. tinctorius, which may be developed as a drug for the treatment of lung injury.

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Potential Antioxidant and Anti-Inflammatory Effects of Spilanthes acmella and Its Health Beneficial Effects: A Review

Rahim

Jayusman

Muhammad

et al. 2021

IJERPH

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Oxidative stress and inflammation are two common risk factors of various life-threatening disease pathogenesis. In recent years, medicinal plants that possess antioxidant and anti-inflammatory activities were extensively studied for their potential role in treating and preventing diseases. Spilanthes acmella (S. acmella), which has been traditionally used to treat toothache in Malaysia, contains various active metabolites responsible for its anti-inflammatory, antiseptic, and anesthetic bioactivities. These bioactivities were attributed to bioactive compounds, such as phenolic, flavonoids, and alkamides. The review focused on the summarization of in vitro and in vivo experimental reports on the antioxidant and anti-inflammatory actions of S. acmella, as well as how they contributed to potential health benefits in lowering the risk of diseases that were related to oxidative stress. The molecular mechanism of S. acmella in reducing oxidative stress and inflammatory targets, such as inducible nitric oxide synthase (iNOS), transcription factors of the nuclear factor-κB family (NF-κB), cyclooxygenase-2 (COX-2), and mitogen-activated protein kinase (MAPK) signaling pathways were discussed. Besides, the antioxidant potential of S. acmella was measured by total phenolic content (TPC), total flavonid content (TFC), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and superoxide anion radical scavenging (SOD) and thiobarbituric acid reactive substance (TBARS) assays. This review revealed that S. acmella might have a potential role as a reservoir of bioactive agents contributing to the observed antioxidant, anti-inflammatory, and health beneficial effects.

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New Methyl Threonolactones and Pyroglutamates of Spilanthes acmella (L.) L. and Their Bone Formation Activities

Cited by 4 publications

References 27 publications

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

Phytochemical Analysis, Antioxidant and Bone Anabolic Effects of Blainvillea acmella (L.) Philipson

Chemical Constituents from the Flowers of Carthamus tinctorius L. and Their Lung Protective Activity

Potential Antioxidant and Anti-Inflammatory Effects of Spilanthes acmella and Its Health Beneficial Effects: A Review

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