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Planta Med 2023; 89(13): 1259-1268
DOI: 10.1055/a-2117-9233
Natural Product Chemistry and Analytical Studies
Original Papers

Vanilla pompona Leaves and Stems as New Sources of Bioactive Compounds: The Therapeutic Potential for Skin Senescence

Duanyang Wang
1   Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan
,
Yhiya Amen
2   Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt
,
Marwa Elsbaey
2   Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt
,
Maki Nagata
1   Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan
,
Masako Matsumoto
1   Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan
,
Dongmei Wang
1   Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan
,
Kuniyoshi Shimizu
1   Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan
› Author AffiliationsThis work was supported by JST SPRING, grant number JPMJSP2136.
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Abstract

A large variety of natural plants are widely produced and utilised because of their remarkable pharmacological effects. In this study, two phenolic glycosides were isolated for the first time from Vanilla pompona Schiede (Orchidaceae) from Kyushu, Japan: bis [4-(β-D – O-glucopyranosyloxy)-benzyl] (S)-2-isopropylmalate (1) and bis 4-[β-D-O-glucopyranosyloxy)-benzyl]-(2R,3S)-2-isopropyl tartrate (2). We have discovered that the crude extract of V. pompona leaves and stems and its two phenolic glycosides (compounds 1 – 2) are highly effective in reversing skin senescence. V. pompona and compounds 1 – 2 were found to promote the synthesis of collagen, hyaluronic acid, and elastin in skin fibroblasts in a normal skin cell model; in a replicative senescence model, V. pompona and compounds 1 – 2 significantly reduced the ageing phenotype in skin fibroblasts. These compounds also demonstrated a significant protective effect in a UV-induced photo-senescence model; the possible mechanisms of this effect were investigated in this study. To the best of our knowledge, this study is the first to develop V. pompona leaves and stems as new sources of bioactive compounds and to examine their therapeutic potential for skin senescence. The development potential of V. pompona leaves and stems for use in the cosmetics, cosmeceutical, and pharmaceutical industries remains to be investigated.

Key words

Vanilla pompona - Orchidaceae - Vanilloideae - bioactive compounds - cosmeceutical - senescence - skin fibroblasts

Supporting Information

    Primer sequence of target genes, NMR spectrum, HR-ESI-MS, and purity analysis information of compounds 1 – 2 and cytotoxicity of compounds 1 – 2 for NHDF-Ad and HaCaT cell are available as Supporting Information.

  • Supporting Information


Publication History

Received: 20 February 2023

Accepted after revision: 20 June 2023

Article published online:
17 July 2023

© 2023. Thieme. All rights reserved.

Georg Thieme Verlag KG
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  • References

  • 1 Maruenda H, Vico Mdel L, Householder JE, Janovec JP, Cañari C, Naka A, Gonzalez AE. Exploration of Vanilla pompona from the Peruvian amazon as a potential source of vanilla essence: Quantification of phenolics by HPLC-DAD. Food Chem 2013; 138: 161-167
    CrossrefPubMedSearch in Google Scholar
  • 2 Toth S, Lee KJ, Havkin-Frenkel D, Belanger FC, Hartman TG. Volatile Compounds in Vanilla. Handbook of Vanilla Science and Technology. Chichester, UK: John Wiley & Sons Ltd.; 2018: 285-347
    CrossrefSearch in Google Scholar
  • 3 Ranadive AS. Quality Control of Vanilla Beans and Extracts. Handbook of Vanilla Science and Technology. Chichester, UK: John Wiley & Sons Ltd.; 2018: 237-260
    CrossrefSearch in Google Scholar
  • 4 Amiryousefi A, Hyvönen J, Poczai P. The plastid genome of Vanillon (Vanilla pompona, Orchidaceae). Mitochondrial DNA B Resour 2017; 2: 689-691
    CrossrefPubMedSearch in Google Scholar
  • 5 Inoue S, Wakai A, Konishi T, Kiyosawa S, Sawada T. Studies on Galeola septentrionalis Reichb. fil. Part 1. Isolation and structures of the constituents of Dotuusoo. Yakugaku Zasshi 1984; 104: 42-49
    CrossrefPubMedSearch in Google Scholar
  • 6 Li YM, Zhou ZL, Hong YF. New phenolic derivatives from galeola-faberi. Planta Med 1993; 59: 363-365
    Thieme ConnectPubMedSearch in Google Scholar
  • 7 Han SW, Wang XJ, Cui BS, Sun H, Chen H, Ferreira D, Li S, Hamann MT. Hepatoprotective glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates from Pleione yunnanensis. J Nat Prod 2021; 84: 738-749
    CrossrefPubMedSearch in Google Scholar
  • 8 Leyva VE, Lopez JM, Zevallos-Ventura A, Cabrera R, Cañari-Chumpitaz C, Toubiana D, Maruenda H. NMR-based leaf metabolic profiling of V. planifolia and three endemic vanilla species from the Peruvian amazon. Food Chem 2021; 358: 129365
    CrossrefPubMedSearch in Google Scholar
  • 9 Palama TL, Fock I, Choi YH, Verpoorte R, Kodja H. Biological variation of Vanilla planifolia leaf metabolome. Phytochemistry 2010; 71: 567-573
    CrossrefPubMedSearch in Google Scholar
  • 10 Tokoro K, Kawahara S, Amano A, Kanisawa T, Indo M. Glucosides in vanilla beans and changes of their contents during maturation. Flavour science and technology. New York, Brisbane, Toronto, Singapore: John Wiley & Sons Chichester; 1990: 73-76
    Search in Google Scholar
  • 11 Gray RW, Guggisberg A, Segebarth KP, Hesse M, Schmid H. Über die Konstitution von Loroglossin. Vorläufige Mitteilung. Helv Chim Acta 1976; 59: 645-649
    CrossrefPubMedSearch in Google Scholar
  • 12 Desmiaty Y, Hanafi M, Saputri FC, Elya B, Rifai EA, Syahdi RR. Two triterpenoids from Rubus fraxinifolius leaves and their tyrosinase and elastase inhibitory activities. Sci Rep 2021; 11: 20452
    CrossrefPubMedSearch in Google Scholar
  • 13 Jena K, Pandey J, Kumari R, Sinha A, Gupta V, Singh G. Tasar silk fiber waste sericin: new source for anti-elastase, anti-tyrosinase and anti-oxidant compounds. Int J Biol Macromol 2018; 114: 1102-1108
    CrossrefPubMedSearch in Google Scholar
  • 14 Wang AS, Dreesen O. Biomarkers of cellular senescence and skin aging. Front Genet 2018; 9: 247
    CrossrefPubMedSearch in Google Scholar
  • 15 Dreesen O, Chojnowski A, Ong PF, Zhao TY, Common JE, Lunny D, Lane EB, Lee SJ, Vardy LA, Stewart CL, Colman A. Lamin B1 fluctuations have differential effects on cellular proliferation and senescence. J Cell Biol 2013; 200: 605-617
    CrossrefPubMedSearch in Google Scholar
  • 16 Xiong ZM, OʼDonovan M, Sun L, Choi JY, Ren M, Cao K. Anti-aging potentials of methylene blue for human skin longevity. Sci Rep 2017; 7: 2475
    CrossrefPubMedSearch in Google Scholar
  • 17 Debacq-Chainiaux F, Leduc C, Verbeke A, Toussaint O. UV, stress and aging. Dermatoendocrinol 2012; 4: 236-240
    CrossrefPubMedSearch in Google Scholar
  • 18 Dimri GP, Lee X, Basile G, Acosta M, Scott G, Roskelley C, Medrano EE, Linskens M, Rubelj I, Pereira-Smith O, Peacocke M, Campisi J. A biomarker that identifies senescent human cells in culture and in aging skin in vivo. Proc Natl Acad Sci U S A 1995; 92: 9363-9367
    CrossrefPubMedSearch in Google Scholar
  • 19 Singh M, Piekorz RP. Senescence-associated lysosomal α-L-fucosidase (SA-α-Fuc): A sensitive and more robust biomarker for cellular senescence beyond SA-β-Gal. Cell Cycle 2013; 12: 1996
    CrossrefPubMedSearch in Google Scholar
  • 20 Sosińska P, Mikuła-Pietrasik J, Ryżek M, Naumowicz E, Książek K. Specificity of cytochemical and fluorescence methods of senescence-associated β-galactosidase detection for ageing driven by replication and time. Biogerontology 2014; 15: 407-413
    CrossrefPubMedSearch in Google Scholar
  • 21 Doura T, Kamiya M, Obata F, Yamaguchi Y, Hiyama TY, Matsuda T, Fukamizu A, Noda M, Miura M, Urano Y. Detection of LacZ-positive cells in living tissue with single-cell resolution. Angew Chem Int Ed Engl 2016; 128: 9772-9776
    CrossrefPubMedSearch in Google Scholar
  • 22 Wang AS, Ong PF, Chojnowski A, Clavel C, Dreesen O. Loss of lamin B1 is a biomarker to quantify cellular senescence in photoaged skin. Sci Rep 2017; 7: 1-8
    CrossrefPubMedSearch in Google Scholar
  • 23 Nakamura Y, Mochida A, Nagaya T, Okuyama S, Ogata F, Choyke PL, Kobayashi H. A topically-sprayable, activatable fluorescent and retaining probe, SPiDER-βGal for detecting cancer: advantages of anchoring to cellular proteins after activation. Oncotarget 2017; 8: 39512
    CrossrefPubMedSearch in Google Scholar
  • 24 Asanuma D, Sakabe M, Kamiya M, Yamamoto K, Hiratake J, Ogawa M, Kosaka N, Choyke PL, Nagano T, Kobayashi H, Urano Y. Sensitive β-galactosidase-targeting fluorescence probe for visualizing small peritoneal metastatic tumours in vivo. Nat Commun 2015; 6: 1-7
    CrossrefPubMedSearch in Google Scholar
  • 25 Poljšak B, Dahmane R. Free radicals and extrinsic skin aging. Dermatol Res Pract 2012; 2012: 135206
    CrossrefPubMedSearch in Google Scholar
  • 26 Poljsak B. Decreasing Oxidative Stress and Retarding the Aging Process. New York: Nova Biomedical Books; 2010
    Search in Google Scholar
  • 27 McDaniel D, Farris P, Valacchi G. Atmospheric skin aging–Contributors and inhibitors. J Cosmet Dermatol 2018; 17: 124-137
    CrossrefPubMedSearch in Google Scholar
  • 28 Fisher GJ, Voorhees JJ. editors. Molecular mechanisms of photoaging and its prevention by retinoic acid: ultraviolet irradiation induces MAP kinase signal transduction cascades that induce Ap-1-regulated matrix metalloproteinases that degrade human skin in vivo. J Investig Dermatol Symp Proc 1998; 3: 61-68
    PubMedSearch in Google Scholar
  • 29 Umar SA, Tasduq SA. Integrating DNA damage response and autophagy signalling axis in ultraviolet-B induced skin photo-damage: a positive association in protecting cells against genotoxic stress. RSC Adv 2020; 10: 36317-36336
    CrossrefPubMedSearch in Google Scholar
  • 30 Mohamed MAA, Jung M, Lee SM, Lee TH, Kim J. Protective effect of Disporum sessile D. Don extract against UVB-induced photoaging via suppressing MMP-1 expression and collagen degradation in human skin cells. J Photochem Photobiol B 2014; 133: 73-79
    CrossrefPubMedSearch in Google Scholar
  • 31 Jean K. The role of UVA rays in skin aging. Eur J Dermatol 2001; 11: 170-171
    PubMedSearch in Google Scholar
  • 32 Bernerd F, Asselineau D. UVA exposure of human skin reconstructed in vitro induces apoptosis of dermal fibroblasts: Subsequent connective tissue repair and implications in photoaging. Cell Death & Differ 1998; 5: 792-802
    CrossrefPubMedSearch in Google Scholar
  • 33 Rittié L, Fisher GJ. UV-light-induced signal cascades and skin aging. Ageing Res Rev 2002; 1: 705-720
    CrossrefPubMedSearch in Google Scholar
  • 34 Massague J. TGF-β signal transduction. Annu Rev Biochem 1998; 67: 753-791
    CrossrefPubMedSearch in Google Scholar
  • 35 Itoh S, Itoh F, Goumans MJ, Ten Dijke P. Signaling of transforming growth factor-β family members through Smad proteins. Eur J Biochem 2000; 267: 6954-6967
    CrossrefPubMedSearch in Google Scholar
  • 36 Dennler S, Goumans MJ, Ten Dijke P. Transforming growth factor β signal transduction. J Leukoc Biol 2002; 71: 731-740
    CrossrefPubMedSearch in Google Scholar
  • 37 Salem MA, Manaa EG, Osama N, Aborehab NM, Ragab MF, Haggag YA, Ibrahim MT, Hamdan DI. Coriander (Coriandrum sativum L.) essential oil and oil-loaded nano-formulations as an anti-aging potentiality via TGFβ/SMAD pathway. Sci Rep 2022; 12: 6578
    CrossrefPubMedSearch in Google Scholar
  • 38 Poomanee W, Yaowiwat N, Pattarachaidaecharuch T, Leelapornpisid P. Optimized multiherbal combination and in vivo anti-skin aging potential: A randomized double blind placebo controlled study. Sci Rep 2023; 13: 5633
    CrossrefPubMedSearch in Google Scholar
  • 39 Zhong J, Hu N, Xiong X, Lei Q, Li L. A novel promising therapy for skin aging: dermal multipotent stem cells against photoaged skin by activation of TGF-β/Smad and p 38 MAPK signaling pathway. Med Hypotheses 2011; 76: 343-346
    CrossrefPubMedSearch in Google Scholar
  • 40 Han KH, Choi HR, Won CH, Chung JH, Cho KH, Eun HC, Kim KH. Alteration of the TGF-β/SMAD pathway in intrinsically and UV-induced skin aging. Mech Ageing Dev 2005; 126: 560-567
    CrossrefPubMedSearch in Google Scholar