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Hirseins A and B, Daphnane Diterpenoids from Thymelaea hirsuta That Inhibit Melanogenesis in B16 Melanoma Cells

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Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba 305-8572, Japan, Alliance for Research on North Africa, University of Tsukuba, Tsukuba 305-8572, Japan, and Unité de Recherche: “Physico-chimie et Moléculaire”, Institut Préparatoire aux Etudes Scientifiques et Techniques, La Marsa, Tunis, 2070 Tunisia
* To whom correspondence should be addressed. Tel & Fax: 81-29-853-4603. E-mail: [email protected]
†Graduate School of Life and Environmental Sciences, University of Tsukuba.
‡Alliance for Research on North Africa, University of Tsukuba.
§Unité de Recherche: “Physico-chimie et Moléculaire”, Institut Préparatoire aux Etudes Scientifiques et Techniques.
Cite this: J. Nat. Prod. 2009, 72, 5, 938–941
Publication Date (Web):March 13, 2009
https://doi.org/10.1021/np800808h
Copyright © 2009 The American Chemical Society and American Society of Pharmacognosy
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Abstract

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Two new daphnane diterpenoids, hirseins A (1) and B (2), were isolated from the aerial parts of Thymelaea hirsuta, and their structures were elucidated on the basis of spectroscopic data interpretation. Hirsein B (2) is an unusual daphnane in possessing a coumaroyl moiety. NOESY correlations of 2 implied that isomerization of the coumaroyl group in 2 was caused by equilibrium between the E (2e) and Z (2z) forms. Compounds 1 and 2 were found to inhibit melanogenesis in B16 murine melanoma cells.

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Cited By

This article is cited by 27 publications.

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  2. Vincent Vidal, Olivier Potterat, Séverine Louvel, François Hamy, Mahdi Mojarrab, Jean-Jacques Sanglier, Thomas Klimkait, and Matthias Hamburger . Library-Based Discovery and Characterization of Daphnane Diterpenes as Potent and Selective HIV Inhibitors in Daphne gnidium. Journal of Natural Products 2012, 75 (3) , 414-419. https://doi.org/10.1021/np200855d
  3. Ling Zhang, Rong-Hua Luo, Fei Wang, Meng-Yuan Jiang, Ze-Jun Dong, Liu-Meng Yang, Yong-Tang Zheng and Ji-Kai Liu. Highly Functionalized Daphnane Diterpenoids from Trigonostemon thyrsoideum. Organic Letters 2010, 12 (1) , 152-155. https://doi.org/10.1021/ol9025638
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  5. Laurentia Opperman, Maryna De Kock, Jeremy Klaasen, Farzana Rahiman. Tyrosinase and Melanogenesis Inhibition by Indigenous African Plants: A Review. Cosmetics 2020, 7 (3) , 60. https://doi.org/10.3390/cosmetics7030060
  6. Giuseppina Sanna, Silvia Madeddu, Giuseppe Murgia, Gabriele Serreli, Michela Begala, Pierluigi Caboni, Alessandra Incani, Gianluigi Franci, Marilena Galdiero, Gabriele Giliberti. Potent and Selective Activity against Human Immunodeficiency Virus 1 (HIV-1) of Thymelaea hirsuta Extracts. Viruses 2020, 12 (6) , 664. https://doi.org/10.3390/v12060664
  7. Paola Nocera, Joanna Bajsa-Hirschel, Marco Masi, Samir A. Ross, Charles L. Cantrell, Stephen O. Duke, Giuseppe Surico, Antonio Evidente. Secondary metabolites of Thymelaea hirsuta , a plant collected from the Sicilian Island of Lampedusa. Natural Product Research 2020, 62 , 1-8. https://doi.org/10.1080/14786419.2020.1752212
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  9. Yue-Xian Jin, Lei-Ling Shi, Da-Peng Zhang, Hong-Yan Wei, Yuan Si, Guo-Xu Ma, Jing Zhang. A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies. Molecules 2019, 24 (9) , 1842. https://doi.org/10.3390/molecules24091842
  10. Myra O. Villareal, Yuki Sato, Kyoko Matsuyama, Hiroko Isoda. Daphnane diterpenes inhibit the metastatic potential of B16F10 murine melanoma cells in vitro and in vivo. BMC Cancer 2018, 18 (1) https://doi.org/10.1186/s12885-018-4693-y
  11. Maroua Yahyaoui, Jalloul Bouajila, Sylvie Cazaux, Manef Abderrabba. The impact of regional locality on chemical composition, anti-oxidant and biological activities of Thymelaea hirsuta L. extracts. Phytomedicine 2018, 41 , 13-23. https://doi.org/10.1016/j.phymed.2018.01.010
  12. Fidele Ntie-Kang, Leonel E. Njume, Yvette I. Malange, Stefan Günther, Wolfgang Sippl, Joseph N. Yong. The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae. Natural Products and Bioprospecting 2016, 6 (2) , 63-96. https://doi.org/10.1007/s13659-016-0091-9
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  14. Khawla Kerbab, Tarak Mekhelfi, Lahcene Zaiter, Samir Benayache, Fadila Benayache, Patrizia Picerno, Teresa Mencherini, Francesca Sansone, Rita P. Aquino, Luca Rastrelli. Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. et Dur.. Natural Product Research 2015, 29 (7) , 671-675. https://doi.org/10.1080/14786419.2014.979422
  15. Yukiko Sekii, Junkyu Han, Hiroko Isoda, Mohamed Bouaziz, Abdelhafidh Dhouib, Sami Sayadi, Hideyuki Shigemori. Two Isorhamnetin Glycosides from Arthrocnemum glaucum that Inhibit Adipogenesis in 3T3-L1 Adipocytes. Chemistry of Natural Compounds 2015, 51 (2) , 338-340. https://doi.org/10.1007/s10600-015-1276-x
  16. Hong-Bing Wang, Li-Ping Liu, Xiao-Yang Wang. 13 C-NMR data of daphnane diterpenoids. Magnetic Resonance in Chemistry 2013, 51 (9) , 580-592. https://doi.org/10.1002/mrc.3978
  17. Kwon Ki Bang, Cheong-Yong Yun, Chul Lee, Qinghao Jin, Jin Woo Lee, Sang-Hun Jung, Dongho Lee, Mi Kyeong Lee, Jin Tae Hong, Youngsoo Kim, Bang Yeon Hwang. Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa. Bioorganic & Medicinal Chemistry Letters 2013, 23 (11) , 3334-3337. https://doi.org/10.1016/j.bmcl.2013.03.096
  18. Mohamed Trigui, Anis Ben Hsouna, Slim Tounsi, Samir Jaoua. Chemical composition and evaluation of antioxidant and antimicrobial activities of Tunisian Thymelaea hirsuta with special reference to its mode of action. Industrial Crops and Products 2013, 41 , 150-157. https://doi.org/10.1016/j.indcrop.2012.04.011
  19. Hideyuki Shigemori, Rie Nakasone, Manami Kurisu, Manami Onodera, Yusaku Miyamae, Daisuke Matsuura, Hirotoshi Kanatani, Shingo Yano. Promoting Effects on Hepatocyte Growth Factor Production of Daphnane Diterpenoids from Daphne odora. HETEROCYCLES 2013, 87 (5) , 1087. https://doi.org/10.3987/COM-13-12687
  20. Mohamed BNOUHAM, Wafaa BENALLA, Said BELLAHCEN, Zineb HAKKOU, Abderrahim ZIYYAT, Hassane MEKHFI, Mohammed AZIZ, Abdelkhaleq LEGSSYER. Antidiabetic and antihypertensive effect of a polyphenol-rich fraction of Thymelaea hirsuta L. in a model of neonatal streptozotocin-diabetic and N G -nitro-l-arginine methyl ester-hypertensive rats. Journal of Diabetes 2012, 4 (3) , 307-313. https://doi.org/10.1111/j.1753-0407.2012.00202.x
  21. Te-Sheng Chang. Natural Melanogenesis Inhibitors Acting Through the Down-Regulation of Tyrosinase Activity. Materials 2012, 5 (9) , 1661-1685. https://doi.org/10.3390/ma5091661
  22. Myra O. Villareal, Junkyu Han, Kenjiro Ikuta, Hiroko Isoda. Mechanism of Mitf inhibition and morphological differentiation effects of hirsein A on B16 melanoma cells revealed by DNA microarray. Journal of Dermatological Science 2012, 67 (1) , 26-36. https://doi.org/10.1016/j.jdermsci.2012.04.005
  23. Paul A. Wender, Nicole Buschmann, Nathan B. Cardin, Lisa R. Jones, Cindy Kan, Jung-Min Kee, John A. Kowalski, Kate E. Longcore. Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities. Nature Chemistry 2011, 3 (8) , 615-619. https://doi.org/10.1038/nchem.1074
  24. Ahmed Akrout, Lidia Alarcon Gonzalez, Hajer El Jani, Pablo Campra Madrid. Antioxidant and antitumor activities of Artemisia campestris and Thymelaea hirsuta from southern Tunisia. Food and Chemical Toxicology 2011, 49 (2) , 342-347. https://doi.org/10.1016/j.fct.2010.11.003
  25. James R. Hanson. Diterpenoids of terrestrial origin. Natural Product Reports 2011, 28 (10) , 1755. https://doi.org/10.1039/c1np90021h
  26. Myra O Villareal, Junkyu Han, Kenjiro Ikuta, Hiroko Isoda. Daphnane diterpene hirsein B downregulates melanogenesis in B16 murine melanoma cells by cAMP pathway inhibition. BMC Proceedings 2011, 5 (Suppl 8) , P68. https://doi.org/10.1186/1753-6561-5-S8-P68
  27. Myra O. Villareal, Junkyu Han, Parida Yamada, Hideyuki Shigemori, Hiroko Isoda. Hirseins inhibit melanogenesis by regulating the gene expressions of Mitf and melanogenesis enzymes. Experimental Dermatology 2010, 19 (5) , 450-457. https://doi.org/10.1111/j.1600-0625.2009.00964.x

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