Invasion Inhibitors of Human Fibrosarcoma HT 1080 Cells from the Rhizomes of &lt;i&gt;Zingiber cassumunar&lt;/i&gt;: Structures of Phenylbutanoids, Cassumunols

Matsuda, Hisashi; Nakamura, Seikou; Iwami, Junko; Li, Xuezheng; Pongpiriyadacha, Yutana; Nakai, Megumi; Kubo, Miwa; Yoshikawa, Masayuki

doi:10.1248/cpb.59.365

Cited by 23 publications

(15 citation statements)

References 30 publications

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“…Phenylbutenoids have been isolated mainly from Z. cassumunar [2][3][4][5][6][7][8][9][10][11][12][13][14] but have been found in other Zingiberaceae plants, including Z. purpureum [14,20], Z. montanum [22], which is known as "Bangle" or "cassumunar ginger," Z. neesanum [33], and Alpinia flabellate [34]. Recently, the discovery of phenylbutenoids was reported for the plant of another family, Dryopteris fragrans (Dryopteridaceae) [35].…”

Section: Phytochemicals From Z Cassumunar 21 Phenylbutenoidsmentioning

confidence: 99%

“…In the phytochemical study of Z. cassumunar by Nakamura et al [13], six new phenylbutenoids were isolated and named phlains I-VI (25)(26)(27)(28)(29)(30). Subsequently, Matsuda et al [10] reported the isolation and identification of eight new compounds, cassumunols A-H (31)(32)(33)(34)(35)(36)(37)(38). In the high-performance liquid chromatography/electrospray tandem mass spectroscopy (MS) analyses of phenylbutenoid dimers from Z. cassumunar by [36], two new structures were tentatively identified as trans-3-(3 ,4 -dimethoxyphenyl)-4-[(E)-4 -hydroxy-3 -methoxystyryl]cyclohex-1-ene (39) and 3-(3 ,4 -dimethoxyphenyl)-4-[(Z)-2 ,4 ,5 -trimethoxystyryl]cyclohex-1-ene (40).…”

Section: Phytochemicals From Z Cassumunar 21 Phenylbutenoidsmentioning

confidence: 99%

“…Several types of compounds in Z. cassumunar have been identified such as phenylbutenoids, curcuminoids, sesquiterpenoids, benzaldehydes, quinones, and essential oils containing monoterpenoids. Phenylbutenoids are characteristic compounds of this plant and have been isolated using various isolation technics [2][3][4][5][6][7][8][9][10][11][12][13][14], including silica gel or reverse phase column chromatography [2][3][4][5][6][7][8][9][10], recrystallization [3,4], preparative thin-layer chromatography [6], countercurrent chromatography [11,12], and preparative high-performance liquid chromatography [10,13,14]. Other constituents include curcuminoids, including a high content of curcumin as a yellow pigment in the rhizome [13][14][15][16][17], two quinones [3,4,18], phenolic compounds [13,17], and sesquiterpenoids such as (−)-β-sesquiphellandrene and zerumbone [12,[19][20][21].…”

Section: Introductionmentioning

confidence: 99%

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Phytochemicals and Bioactivities of Zingiber cassumunar Roxb

et al. 2021

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Zingiber cassumunar Roxb. (Zingiberaceae), is an important medicinal plant known as “Plai (Phlai)” in Thailand, “Bangle” in Indonesia, and “Bulei” in China. Traditionally, this plant has been used to treat inflammation, pain, and respiratory problems. The rhizomes are the primary part of the plant that has been used for medicinal purposes due to their constituents with therapeutic properties, including phenylbutenoids, curcuminoids, and essential oils. Since the 1970s, many studies have been conducted on the phytochemicals and bioactivities of Z. cassumunar to establish fundamental scientific evidence that supports its use in traditional medicine. The accumulated biological studies on the extracts, solvent fractions, and constituents of Z. cassumunar have described their diverse medicinal properties, including antioxidant, anti-inflammatory, anticancer, neuroprotective/neurotrophic, cosmeceutical, and antifungal/antimicrobial bioactivities. In this review, we summarize information on the phytochemicals of Z. cassumunar and the bioactivities of its extracts and constituents.

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Section: Phytochemicals From Z Cassumunar 21 Phenylbutenoidsmentioning

confidence: 99%

Section: Phytochemicals From Z Cassumunar 21 Phenylbutenoidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phytochemicals and Bioactivities of Zingiber cassumunar Roxb

et al. 2021

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“…Zingiber cassumunar Roxb has been used as anti-inflammation agents in East Asia 37 , and isolated compounds from Zingiber cassumunar Roxb have been reported as having anti-inflammatory, and anti-metastatic activity 38 , 39 . NMac1 isolated from Zingiber cassumunar Roxb.…”

Section: Discussionmentioning

confidence: 99%

Small molecule activator of Nm23/NDPK as an inhibitor of metastasis

Lee

Kim

Lee

et al. 2018

Sci Rep

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Nm23-H1/NDPK-A is a tumor metastasis suppressor having NDP kinase (NDPK) activity. Nm23-H1 is positively associated with prolonged disease-free survival and good prognosis of cancer patients. Approaches to increasing the cellular levels of Nm23-H1 therefore have significance in the therapy of metastatic cancers. We found a small molecule, (±)-trans-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene, that activates Nm23, hereafter called NMac1. NMac1 directly binds to Nm23-H1 and increases its NDPK activity. Employing various NMac1 derivatives and hydrogen/deuterium mass spectrometry (HDX-MS), we identified the pharmacophore and mode of action of NMac1. We found that NMac1 binds to the C-terminal of Nm23-H1 and induces the NDPK activation through its allosteric conformational changes. NMac1-treated MDA-MB-231 breast cancer cells showed dramatic changes in morphology and actin-cytoskeletal organization following inhibition of Rac1 activation. NMac1 also suppressed invasion and migration in vitro, and metastasis in vivo, in a breast cancer mouse model. NMac1 as an activator of NDPK has potential as an anti-metastatic agent.

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“…In addition, two main constituents of Z . cassumunar , phenylbutenoids [ 19 – 22 ] and curcuminoids [ 23 ], have been reported to exhibit anti-inflammatory [ 24 , 25 ], anti-tumor [ 21 , 22 ] and antioxidant [ 23 ] activities. The inflammatory response is believed to be closely related to melanin synthesis [ 26 , 27 ], and Albert et al have reported that inflammation of the uveal tract is associated with vitiligo [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

(E)-4-(3,4-Dimethoxyphenyl)but-3-en-1-ol Enhances Melanogenesis through Increasing Upstream Stimulating Factor-1-Mediated Tyrosinase Expression

et al. 2015

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We investigated the potential melanogenic effect of compounds from Zingiber cassumunar Roxb. Our data revealed that chloroform-soluble extract of Z. cassumunar enhanced melanin synthesis in B16F10 melanoma cells. Among the components of the chloroform extract, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol (DMPB) increased melanogenesis in both B16F10 cells and human primary melanocytes. In B16F10 cells, DMPB enhanced the activation of ERK and p38, and the level of tyrosinase. Although the level of microphthalmia-associated transcription factor was unchanged in DMPB-treated B16F10 cells, DMPB increased levels and nuclear localization of upstream stimulating factor-1 (USF1). Consistently, DMPB-mediated melanin synthesis was diminished in USF1-knockdown cells. Furthermore, DMPB induced hyperpigmentation in brown guinea pigs in vivo. Together, these data suggest that DMPB may promote melanin synthesis via USF1 dependent fashion and could be used as a clinical therapeutic agent against hypopigmentation-associated diseases.

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Invasion Inhibitors of Human Fibrosarcoma HT 1080 Cells from the Rhizomes of <i>Zingiber cassumunar</i>: Structures of Phenylbutanoids, Cassumunols

Cited by 23 publications

References 30 publications

Phytochemicals and Bioactivities of Zingiber cassumunar Roxb

Phytochemicals and Bioactivities of Zingiber cassumunar Roxb

Small molecule activator of Nm23/NDPK as an inhibitor of metastasis

(E)-4-(3,4-Dimethoxyphenyl)but-3-en-1-ol Enhances Melanogenesis through Increasing Upstream Stimulating Factor-1-Mediated Tyrosinase Expression

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