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Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox

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Abstract

A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (−)-chimonanthine (1, IC50 = 0.93 μM), (−)-folicanthine (2, 1.4 μM), and (−)-calycanthidine (3, 1.8 μM) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable.

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The authors have declared that there is no conflict of interest.

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Authors and Affiliations

  1. Pharmaceutical Research and Technology Institute, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan

    Toshio Morikawa, Yusuke Nakanishi, Kiyofumi Ninomiya, Takao Hayakawa & Osamu Muraoka

  2. Antiaging Centre, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan

    Toshio Morikawa, Kiyofumi Ninomiya & Osamu Muraoka

  3. Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan

    Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita & Masayuki Yoshikawa

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  1. Toshio Morikawa
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  2. Yusuke Nakanishi
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  3. Kiyofumi Ninomiya
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  4. Hisashi Matsuda
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  5. Souichi Nakashima
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  6. Hisako Miki
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  7. Yu Miyashita
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  8. Masayuki Yoshikawa
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  9. Takao Hayakawa
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  10. Osamu Muraoka
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Correspondence to Osamu Muraoka.

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Morikawa, T., Nakanishi, Y., Ninomiya, K. et al. Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox . J Nat Med 68, 539–549 (2014). https://doi.org/10.1007/s11418-014-0832-1

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  • DOI: https://doi.org/10.1007/s11418-014-0832-1

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