Melanin Biosynthesis Inhibitors from Tarragon<i>Artemisia dracunculus</i>

Yamada, Masayoshi; Nakamura, Kazuhiko; Watabe, Taeko; Ohno, Osamu; Kawagoshi, Masaru; Maru, Norihito; Uotsu, Nobuo; Chiba, Tomohiro; Yamaguchi, Kohji; Uemura, Daisuke

doi:10.1271/bbb.110306

Cited by 11 publications

(11 citation statements)

References 17 publications

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“…Compounds 39 and 40 inhibition of melanin production is very significant as the excessive melanin production and deposition under the skin causes hyperpigmentation and other skin trouble like geriatric pigment spots, freckles, and melasma. Likewise, compounds 39 and 40 are also used in cosmetics as a skin whitening and depigmenting agent (Yamada et al, ).…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

“…References are numbered as follows: 1 (Su et al, ), 2 (He at el. 2012), 3 (Su et al, ), 4 (Fontaine et al, ), 5 (Sham'yanov et al, ), 6 (Wang et al, ), 7 (Ma, Sun, Zhou, Hong, & Pei, ), 8 (Shukla et al, ), 9 (Lu et al, ), 10 (Liu et al, & 2017), 11 (Zou et al, ), 12 (Choi et al, ), 13 (Mamun et al, ), 14 (Giang et al, ), 15 (Bourgou et al, ), 16 (Nguyen et al, ), 17 (Jakupovic et al, ), 18 (Lin et al, 2014), 19 (Tu et al, ), 20 (Nakamura & Hattori, ), 21 (Saadali et al, ), 22 (Yamada et al, ), 23 (Wheeler et al, ), 24 (Rashid et al, ), 25 (Umano et al, ), 26 (Bak et al, ), 27 (Kavvadias et al, ), 28 (Megdiche‐Ksouri et al, ), 29 (Kim et al, ), 30 (Choi et al, ), 31 (Geng et al, ), and 32 (Mizushina et al, ).…”

Section: Introductionmentioning

confidence: 99%

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The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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Several reviews have been published on Artemisia's derived natural products, but it is the first attempt to review the chemistry and pharmacology of more than 80 alkaloids and allied nitrogen compounds obtained from various Artemisia species (covering the literature up to June 2018). The pharmacological potential and unique skeleton types of certain Artemisia's alkaloids provoke the importance of analyzing Artemisia species for bioactive alkaloids and allied nitrogen compounds. Among the various types of bioactive Artemisia's alkaloids, the main classes were the derivatives of rupestine (pyridine–sesquiterpene), lycoctonine (diterpene), pyrrolizidine, purines, polyamine, peptides, indole, piperidine, pyrrolidine, alkamides, and flavoalkaloids. The rupestine derivatives are Artemisia's characteristic alkaloids, whereas the rest are common alkaloids found in the family Asteraceae and chemotaxonomically links the genus Artemisia with the tribes Anthemideae. The most important biological activities of Artemisia's alkaloids are including hepatoprotective, local anesthetic, β‐galactosidase, and antiparasitic activities; treatment of angina pectoris, opening blocked arteries, as a sleep‐inducing agents and inhibition of HIV viral protease, CYP450, melanin biosynthesis, human carbonic anhydrase, [3H]‐AEA metabolism, kinases, and DNA polymerase β1. Some of the important nitrogen metabolites of Artemisia include pellitorine, zeatin, tryptophan, rupestine, and aconitine analogs, which need to be optimized and commercialized further.

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Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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“…The 11,12 indicates compound 1 was (E,E)-2,4-undecadien-8,10-diynoic acid isobutylamide (anacycline, Figure 2). This is the first time that this alkamide with diene-diyne structure was isolated from A. oleracea leaves, but it has been previously isolated from Artemisia dracunculus, 11 Achillea ptarmica, and Anacyclus pyrethrum. 12,13 The molecular formula of compound 2 was determined to be C 17 H 17 NO by using HRESIMS at m/z 252.1385 [M + H] + (calcd.…”

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confidence: 99%

Plant Growth Inhibitory Activity of the Extracts of Acmella oleracea and its Growth Inhibitory Substances

Kato‐Noguchi

Suwitchayanon

Boonmee

et al. 2019

Natural Product Communications

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Aqueous methanol extracts of Acmella oleracea inhibited the growth of roots and shoots of cress (Lepidum sativum), lettuce (Lactuca sativa), Italian ryegrass (Lolium multiflorum), and barnyard grass (Echinochloa crus-galli) with the extract concentration-dependent manner. The extracts were then purified and 2 growth inhibitory substances were isolated and identified by spectral data as (E,E)-2,4-undecadien-8,10-diynoic acid isobutylamide (compound 1) and nona-(2Z)-en-6,8-diynoic acid 2-phenylethylamide (compound 2). Compound 1 inhibited the growth of cress roots and shoots at concentrations greater than 0.3 mM and that of barnyard grass root at concentrations greater than 0.03 mM. Compound 2 inhibited the growth of cress shoots and barnyard grass roots at concentrations greater than 1 mM. The inhibition on the seedling growth indicates that both compounds had growth inhibitory activity and may contribute to the inhibitory effect of A. oleracea extracts. This is the first report of having growth inhibitory activity of compounds 1 and 2 on plants.

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“…Two isolated compounds, undeca-2E,4Edien,8,10-dynoic acid isobutylamide (26) and undeca-2E,4E-dien-8,10-dynoic acid piperidylamide (27), were found to be noncytotoxic toward B16 melanoma cells (IC 50 = 34.5 and 36.5 µg/mL, respectively) and to more potently suppress cellular melanin production (EC 50 = 1.8 and 2.3 µg/mL, respectively) than arbutin (EC 50 = 24.0 µg/mL). Their safety as skin-lightening agents was also confirmed, possessing safety coefficients (EC 50 /IC 50 ) of 19.2 and 12.9, respectively [21].…”

Section: Plants For Treating Skin Hyperpigmentationmentioning

confidence: 81%

“…The traditional Asian herbal cocktail Ssanghwa-tang, which contains the medicinal herbs P. lactiflora (28 %), Angelica gigas A. dracunculs tarragon undeca-2E,4E-dien,8,10-cynoic acid isobutylamide (26), undeca-2E,4E-dien-8,10-dynoic acid piperidylamide (27) antimelanogenesis in B16 [21] Artocarpus spp. , and Zizyphus jujube Mill.…”

Section: Enzyme Inhibition Cell Culturementioning

confidence: 99%

Plants and Natural Products for the Treatment of Skin Hyperpigmentation – A Review

Kanlayavattanakul

Lourith

2018

Planta Med

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Skin hyperpigmentation is caused by several factors that upregulate melanogenesis. Plants and natural products with skin-whitening effects are gaining interest among consumers and researchers because they are perceived to be milder, safer, and healthier than synthetic alternatives. This review extensively summarizes the status of plants and natural products currently used in skin-whitening cosmetics as well as potential candidates for future use, because the scope of natural choices for efficient treatment of skin hyperpigmentation is rapidly widening. Biological activities of plants and natural extracts are therefore available for cosmetic formulators and dermatologists interested in naturally derived ingredients for skin hyperpigmentation treatment and in accordance with the consumers' preferences and expectations upon natural cosmetic products.

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Melanin Biosynthesis Inhibitors from TarragonArtemisia dracunculus

Cited by 11 publications

References 17 publications

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Plant Growth Inhibitory Activity of the Extracts of Acmella oleracea and its Growth Inhibitory Substances

Plants and Natural Products for the Treatment of Skin Hyperpigmentation – A Review

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