PDF herunterladen
Planta Med 2022; 88(08): 685-692
DOI: 10.1055/a-1540-4978
Biological and Pharmacological Activity
Original Papers

Benzoylcyclopropane Derivatives from Hypoxis hemerocallidea Corms

Fazila Zulfiqar 
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Pankaj Pandey
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Siddharth K. Tripathi
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Zulfiqar Ali
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Amar G. Chittiboyina
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
,
Ikhlas A. Khan
1   National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
2   Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA
› InstitutsangabenGefördert durch: U.S. Department of Agriculture 58-6060-6-015
› Weitere Informationen
    Lizenzen und Reprints

Abstract

Two monobenzoylcyclopropane (hypoxhemerol A (1) and hypoxhemeroloside G (2)) and three dibenzoylcyclopropane (hypoxhemerol B (3), hypoxhemeroloside H (4), and hypoxhemeroloside I (5)) derivatives were isolated from the hydro-alcoholic extract of Hypoxis hemerocallidea corms. This is the first instance where benzoylcyclopropane analogs were isolated from any natural source. Structure elucidation was mainly based on 1D- and 2D-NMR and HRESIMS data. The absolute configuration (2R, 4R) of 1 was determined via NOESY NMR and experimental and calculated ECD data analyses. Compounds 1–5 and 11 recently reported metabolites (hypoxoside, obtuside A, interjectin, acuminoside, curcapicycloside, and hypoxhemerolosides A – F) were screened for in vitro antimicrobial activity against various bacterial and fungal strains. Curcapicycloside and acuminoside exhibited antibacterial activity against Escherichia coli with 78 and 79% inhibition at 20 µg/mL, respectively. Hypoxhemeroloside A showed mild antifungal activity against Cryptococcus neoformans with 63% inhibition at 20 µg/mL.

Key words

Hypoxis hemerocallidea - hypoxidaceae - benzoylcyclopropane - hypoxhemerol - hypoxhemeroloside - antimicrobial

Supporting Information

    The HRESIMS and NMR spectra for compounds 1–5 and antimicrobial data of extract and compounds are available as Supporting Information.

  • Supporting Information


Publikationsverlauf

Eingereicht: 10. Februar 2021

Angenommen nach Revision: 25. Juni 2021

Artikel online veröffentlicht:
30. Juli 2021

© 2021. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Khan F, Drewes S. The African potato (Hypoxis hemerocallidea): a chemical-historical perspective. S Afr J Sci 2004; 100: 425-430
    PubMedGoogle Scholar
  • 2 Drewes S, Elliot E, Khan F, Dhlamini J, Gcumisa M. Hypoxis hemerocallidea–not merely a cure for benign prostate hyperplasia. J Ethnopharmacol 2008; 119: 593-598
    CrossrefPubMedGoogle Scholar
  • 3 Owira PM, Ojewole JA. ‘African potato’ (Hypoxis hemerocallidea corm): a plant‐medicine for modern and 21st-century diseases of mankind? A review. Phytother Res 2009; 23: 147-152
    CrossrefPubMedGoogle Scholar
  • 4 Mofokeng MM, Araya HT, Amoo SO, Sehlola D, du Plooy CP, Bairu MW, Venter S, Mashela PW. Diversity and conservation through cultivation of Hypoxis in Africa–a case study of Hypoxis hemerocallidea . Diversity (Basel) 2020; 12: 122-145
    CrossrefPubMedGoogle Scholar
  • 5 Van Wyk BE. A broad review of commercially important southern African medicinal plants. J Ethnopharmacol 2008; 119: 342-355
    CrossrefPubMedGoogle Scholar
  • 6 Grierson D, Afolayan A. An ethnobotanical study of plants used for the treatment of wounds in the Eastern Cape, South Africa. J Ethnopharmacol 1999; 67: 327-332
    CrossrefPubMedGoogle Scholar
  • 7 Ncube B, Ndhlala AR, Okem A, Van Staden J. Hypoxis (Hypoxidaceae) in African traditional medicine. J Ethnopharmacol 2013; 150: 818-827
    CrossrefPubMedGoogle Scholar
  • 8 Kabanda MM, Mammino L, Murulana LC, Mwangi HM, Mabusela WT. Antioxidant radical scavenging properties of phenolic pent-4-en-1-yne derivatives isolated from Hypoxis rooperi. A DFT study in vacuo and in solution. Int J Food Prop 2015; 18: 149-164
    CrossrefPubMedGoogle Scholar
  • 9 Laporta O, Pérez-Fons L, Mallavia R, Caturla N, Micol V. Isolation, characterization and antioxidant capacity assessment of the bioactive compounds derived from Hypoxis rooperi corm extract (African potato). Food Chem 2007; 101: 1425-1437
    CrossrefPubMedGoogle Scholar
  • 10 Zulfiqar F, Khan SI, Ali Z, Wang YH, Ross SA, Viljoen AM, Khan IA. Norlignan glucosides from Hypoxis hemerocallidea and their potential in vitro anti-inflammatory activity via inhibition of iNOS and NF-κB. Phytochemistry 2020; 172: 112273
    CrossrefPubMedGoogle Scholar
  • 11 Boukes GJ, van de Venter M, Oosthuizen V. Quantitative and qualitative analysis of sterols/sterolins and hypoxoside contents of three Hypoxis (African potato) spp. Afr J Biotechnol 2008; 7: 1624-1629
    CrossrefPubMedGoogle Scholar
  • 12 Nair VD, Kanfer I. Sterols and sterolins in Hypoxis hemerocallidea (African potato). S Afr J Sci 2008; 104: 322-324
    PubMedGoogle Scholar
  • 13 Albrecht C, Theron E, Kruger P. Morphological characterisation of the cell-growth inhibitory activity of rooperol and pharmacokinetic aspects of hypoxoside as an oral prodrug for cancer therapy. S Afr Med J 1995; 85: 853-860
    PubMedGoogle Scholar
  • 14 Ojewole JA. Antinociceptive, anti-inflammatory and antidiabetic properties of Hypoxis hemerocallidea Fisch. & CA Mey. (Hypoxidaceae) corm [‘African Potato’] aqueous extract in mice and rats. J Ethnopharmacol 2006; 103: 126-134
    CrossrefPubMedGoogle Scholar
  • 15 Laporta O, Funes L, Garzón MT, Villalaín J, Micol V. Role of membranes on the antibacterial and anti-inflammatory activities of the bioactive compounds from Hypoxis rooperi corm extract. Arch Biochem Biophys 2007; 467: 119-131
    CrossrefPubMedGoogle Scholar
  • 16 Bae JY, Ali Z, Wang YH, Chittiboyina AG, Zaki AA, Viljoen AM, Khan IA. Anthraquinone-based specialized metabolites from rhizomes of Bulbine natalensis . J Nat Prod 2019; 82: 1893-1901
    CrossrefPubMedGoogle Scholar
  • 17 Fantoukh OI, Dale OR, Parveen A, Hawwal MF, Ali Z, Manda VK, Khan SI, Chittiboyina AG, Viljoen A, Khan IA. Safety assessment of phytochemicals derived from the globalized South African rooibos tea (Aspalathus linearis) through interaction with CYP, PXR, and P-gp. J Agric Food Chem 2019; 67: 4967-4975
    CrossrefPubMedGoogle Scholar
  • 18 Majrashi TA, Zulfiqar F, Chittiboyina AG, Ali Z, Khan IA. Isoquinoline alkaloids from Asimina triloba . Nat Prod Res 2019; 33: 2823-2829
    CrossrefPubMedGoogle Scholar
  • 19 Zulfiqar F, Khan SI, Ross SA, Ali Z, Khan IA. Prenylated flavonol glycosides from Epimedium grandiflorum: cytotoxicity and evaluation against inflammation and metabolic disorder. Phytochem Lett 2017; 20: 160-167
    CrossrefPubMedGoogle Scholar
  • 20 Fantoukh OI, Albadry MA, Parveen A, Hawwal MF, Majrashi T, Ali Z, Khan SI, Chittiboyina AG, Khan IA. Isolation, synthesis, and drug interaction potential of secondary metabolites derived from the leaves of miracle tree (Moringa oleifera) against CYP3A4 and CYP2D6 isozymes. Phytomedicine 2019; 60: 153010
    CrossrefPubMedGoogle Scholar
  • 21 Gunasekera SP, Cranick S, Pomponi SA. New sterol ester from a deep water marine sponge, Xestospongia sp. J Nat Prod 1991; 54: 1119-1122
    CrossrefPubMedGoogle Scholar
  • 22 Rao MR, Faulkner DJ. Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa . J Nat Prod 2002; 65: 386-388
    CrossrefPubMedGoogle Scholar
  • 23 Steenkamp V, Gouws M, Gulumian M, Elgorashi E, Van Staden J. Studies on antibacterial, anti-inflammatory and antioxidant activity of herbal remedies used in the treatment of benign prostatic hyperplasia and prostatitis. J Ethnopharmacol 2006; 103: 71-75
    CrossrefPubMedGoogle Scholar
  • 24 Katerere D, Eloff J. Anti-bacterial and anti-oxidant activity of Hypoxis hemerocallidea (Hypoxidaceae): can leaves be substituted for corms as a conservation strategy?. S Afr J Bot 2008; 74: 613-616
    CrossrefPubMedGoogle Scholar
  • 25 Hutton HM, Schaefer T. Proton coupling constants in substituted cyclopropanes. Can J Chem 1963; 41: 684-689
    CrossrefPubMedGoogle Scholar
  • 26 Schaefer TP, Hruska F, Kotowycz G. Correlations of proton coupling constants in the cyclopropane ring with electronegativity. Proton resonance spectrum of cyclopropyllithium. Can J Chem 1965; 43: 75-80
    CrossrefPubMedGoogle Scholar
  • 27 Hutton H, Schaefer T. The proton magnetic resonance spectra of chrysanthemum ethyl ester and the related cis-and trans-chrysanthemumic acids. Can J Chem 1962; 40: 875-881
    CrossrefPubMedGoogle Scholar
  • 28 CLSI. Reference Method for Broth Dilution antifungal Susceptibility Testing of filamentous Fungi; Approved Standard M38-A2. 2nd edition. Wayne, PA: Clinical and Laboratory Standards Institute; 2008
    Google Scholar
  • 29 CLSI. Reference Method for Broth Dilution antifungal Susceptibility Testing of Yeasts; Approved Standard M27-A3. Wayne, PA: Clinical and Laboratory Standards Institute; 2008
    Google Scholar
  • 30 CLSI. Methods for Dilution antimicrobial Susceptibility Tests for Bacteria that grow aerobically; Approved Standard M7-A9, 9th edition. Wayne, PA: Clinical and Laboratory Standards Institute; 2012
    Google Scholar
  • 31 Wang YH, Avula B, Fu X, Wang M, Khan IA. Simultaneous determination of the absolute configuration of twelve monosaccharide enantiomers from natural products in a single injection by a UPLC-UV/MS method. Planta Med 2012; 78: 834-837
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 32 Franzblau SG, Witzig RS, McLaughlin JC, Torres P, Madico G, Hernandez A, Degnan MT, Cook MB, Quenzer VK, Ferguson RM. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 1998; 36: 362-366
    CrossrefPubMedGoogle Scholar
  • 33 Wang X, Liu J, Pandey P, Chen J, Fronczek FR, Parnham S, Qi X, Doerksen RJ, Ferreira D, Sun H. Assignment of the absolute configuration of hepatoprotective highly oxygenated triterpenoids using X-ray, ECD, NMR J-based configurational analysis and HSQC overlay experiments. Biochim Biophys Acta Gen Subj 2017; 1861: 3089-3095
    CrossrefPubMedGoogle Scholar
  • 34 Li F, Pandey P, Janussen D, Chittiboyina AG, Ferreira D, Tasdemir D. Tridiscorhabdin and didiscorhabdin, the first discorhabdin oligomers linked with a direct C–N bridge from the sponge Latrunculia biformis collected from the deep sea in Antarctica. J Nat Prod 2020; 83: 706-713
    CrossrefPubMedGoogle Scholar
  • 35 Schrödinger Release 2020–4: Maestro version 12.6.144. Schrödinger LLC, New York, NY, 2020. Accessed April 12, 2021 at: https://www.schrodinger.com/downloads/releases?release=561125
    PubMedGoogle Scholar
  • 36 Schrödinger Release 2020–4: LigPrep. Schrödinger LLC, New York, NY, 2020. Accessed April 12, 2021 at: https://www.schrodinger.com/downloads/releases?release=561125
    PubMedGoogle Scholar
  • 37 Schrödinger Release 2020–4: MacroModel. Schrödinger LLC, New York, NY, 2020. Accessed April 12, 2021 at: https://www.schrodinger.com/downloads/releases?release=561125
    PubMedGoogle Scholar
  • 38 Mennucci B, Tomasi J. Continuum solvation models: a new approach to the problem of soluteʼs charge distribution and cavity boundaries. J Chem Phys 1997; 106: 5151-5158
    CrossrefPubMedGoogle Scholar
  • 39 Li XC, Ferreira D, Ding Y. Determination of absolute configuration of natural products: theoretical calculation of electronic circular dichroism as a tool. Curr Org Chem 2010; 14: 1678-1697
    CrossrefPubMedGoogle Scholar
  • 40 Autschbach J. Time‐dependent density functional theory for calculating origin‐independent optical rotation and rotatory strength tensors. Chemphyschem 2011; 12: 3224-3235
    CrossrefPubMedGoogle Scholar
  • 41 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery jr. JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16, Revision B.01. Gaussian, Inc., Wallingford CT, 2016. Accessed April 12, 2021 at: https://gaussian.com/
    PubMedGoogle Scholar