Fusicoccanes diterpenes with surprising biological functions A. H. de Boer & I. J. de Vries-van Leeuwen




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TRENDS in Plant Science


Supplementary Material

Fusicoccanes - diterpenes with surprising biological functions

A.H. de Boer & I.J. de Vries-van Leeuwen

Vrije Universiteit, Faculty Earth & Life Sciences, Dept. Structural Biology, De Boelelaan 1085, 1081 HV Amsterdam, The Netherlands



Corresponding author: de Boer, A. H. (bert.de.boer@falw.vu.nl)



Table S1. Fusicoccanes are produced by a range of different species

Name of fusicoccane compound

Structure

Producing species

Reported biological activity

Anadensin




  • Porella chilensis. Growing over rocks and trees. Collected in Lago Steffen, Rio Negro province, Argentina [S1].

  • Anastrepta orcadensis; collected at Hohne cliffs, Harz, Germany [S2].

  • Lepicolea ochroleuca, Liverwort from Chili [S3]

  • Anastrophyllum auritum [S4].

  • Chandonanthus hirtellus, Tahitian Liverwort collected at Marau mount, 1400 m altitude (Tahiti) [S5].

  • Anadensin is the only fusicoccane that was able to inhibit bacterial growth and autoinducer formation. These effects led to an inhibition of the Biofilm production. Anadensin is as potent as ciprofloxacin in Biofilm formation inhibition [S1].

  • Anadensin showed activity against HL-60 cell lines: IC50 = 17.0 g/ml [S5].

Barbifusicoccin A



  • Liverworts Barbilophozia hatcheri and Barbilophozia barbata [S6].

  • Liverwort Barbilophozia floerkei [S7].

  • ND

Barbifusicoccin B




  • Liverworts Barbilophozia hatcheri and Barbilophozia barbata [S6].

  • Liverwort Barbilophozia floerkei [S7].

  • ND

Brachialactone




  • Tropical forage grass Brachiaria humidicola (Rendle) Schweick [S8].

  • Inhibitor of biological nitrification by Nitrosomas [S8].

Brassiciccene A




  • Alternaria brassicicola, a black spot pathogen of canola [S9].




  • No significant antimicrobial activity [S9]

Cotylenin A




  • Cladosporium fungus sp. 501-7W [S10].

  • In plants: see Fusicoccin




  • In animals: induces apoptosis in tumor cells and differentiation in murine and human myeloid leukemia cells [S11,S12,S13]

Cyclooctatin




  • Streptomyces melanosporofaciens MI614-43F2, soil actinomyce, collected in Japan [S14].

  • Potent inhibitor of lysophospholipase [S15].

17-Hydroxycyclo-

octatin




  • Streptomyces strain MTE4, a soil actinomycete collected in New York State, USA [S16].

  • ND

Deoxyhypoestenone




  • Isolated from the aerial parts of Hypoestes forskalei Vahl. Roem. & Schult. [S17], a perennial bushy and leafy herb which is widely distributed throughout the southern region of Saudi Arabia and Yemen. Belongs to the Acanthaceae family.

  • ND

Dehydrohypoeste-

one




  • Isolated from the aerial parts of Hypoestes forskalei Vahl. Roem. & Schult. [S17].

  • ND

Fusicoauritone




  • Liverwort Porella chilensis. Growing over rocks and trees. Collected in Lago Steffen, Rio Negro province, Argentina [S1].

  • Chandonanthus hirtellus; Tahitian Liverwort, collected at Marau mount, Tahiti [S3].

  • Anastrophyllum auritum; Liverwort collected in Ecuador [S4].

  • ND

Fusicoccadiene




  • Plogiochila moritziana; Liverwort from Panama [S18].

  • Liverwort Plagiochila asplenioides; [S19].

  • ND

Fusicoccin A




  • Phomopsis amydali (formerly known as Fusicoccum amygdali Del. ); fungus growing on peach and almond trees [S20,S21]

  • In plants: interacts with a complex formed by 14-3-3 proteins and plasma membrane H+-ATPase. Affects stomatal opening, seed germination, cell elongation etc.

  • In animals: induces apoptosis in tumor cells, causes heterotaxia in Xenopus embryos, inhibits insulin stimulated GLUT4 vesicle fusion and trafficking, stimulates platelet aggregation through binding to glycoprotein Ib of the glycoprotein-Ib-IX-V complex

  • See main text.

Fusicogigantepoxide




  • Chandonanthus hirtellus; Tahitian Liverwort, collected at Marau mount, Tahiti [S5].

  • ND

Fusicogigantone A




  • Chandonanthus hirtellus; Tahitian Liverwort, Marau mount, Tahiti [S5].

  • Anastrophyllum auritum ;Liverwort collected in Ecuador [S4].

  • Lepicolea ochroleuca; Liverwort from Chili [S3].

  • Pleurozia gigantean;, stem-leafy Liverwort collected in East Malaysia [S22].

  • Anastrophyllum auritum ;Liverwort collected in Ecuador [S4].

  • Chandonanthus hirtellus; Tahitian Liverwort, Marau mount, Tahiti [S5].

  • ND

Fusicogigantone B




  • Chandonanthus hirtellus; Tahitian Liverwort, Marau mount, Tahiti [S5].

  • Anastrophyllum auritum ;Liverwort collected in Ecuador [S4].

  • Lepicolea ochroleuca; Liverwort from Chili [S3].

  • Pleurozia gigantean;, stem-leafy Liverwort collected in East Malaysia [S22].

  • Anastrophyllum auritum ;Liverwort collected in Ecuador [S4].

  • Chandonanthus hirtellus; Tahitian Liverwort, Marau mount, Tahiti [S5]

  • ND

Fusicoplagin A and B

A: R1=OH

B: R1=OAc



  • Liverwort Plaqiochila acanthophylla subsp. Japonica [S23]

  • ND

Fusicoplagin D




  • Liverwort Plaqiochila acanthophylla subsp. Japonica [S23].

  • ND

Fusicoserpenol A




  • Isolated from Hypoestes serpens [S24]; a herbaceous plant which grows in the central region of Madagascar.




Halloresellinic acid





  • Halorosellinia oceanica BCC 5149 marine fungus [S25].

  • Has antimalaria activity with IC50 = 13 g/ml = 3*10-5 M [S25].

Hypoestenone




  • Isolated from the aerial parts of Hypoestes forskalei [S26], a perennial bushy and leafy herb which is widely distributed Throughout the southern region of Saudi Arabia and Yemen. Belongs to the Acanthaceae family.

  • Crude extract of Hypoestes Forskalei inhibits tumor cell growth [S27].

Periconicin A and B



A: R1=-CH3

B: R1= -CH2-OH



  • Periconia sp. endophytic fungi isolated from small branches of T. cuspidate, Kangwon region of Korea [S28].

  • Periconia atropurpurea; an endophytic fungus associated with Xylopia aromatica, from Brazil [S29].

  • Periconia sp. OBW -15; endophytic fungus collected from small branches of Taxus cuspidate [S30].

  • Significant antibacterial activity against Gram-positive and Gram-negative bacteria [S28].

  • Periconicin B: potent cytotoxic agent against HeLa and CHO cells. It decreased cell viability with an IC50 of 8.0 M, showing potency similar to that of cisplatin, a well known antineoplastic agent (IC50 5.0 M) [S29].

  • Periconicin A showed potent inhibitory activity against the agents of human mycoses, including Candida albicans, Trichophyton mentagrophytes, and R. rubrum, with minimum inhibitory concentration (MIC) in the range of 3-6 g/ml. In a plant growth regulatory activity assay, periconicins inhibited hypocotyl elongation and root growth of Brassica campestris L. and Raphanus sativus L. At concentrations below 1 g/ml, however, both compounds accelerated root growth by 110- 135%. [S30].

Roseadione



  • Hypoestes Rosea; tropical shrub in the family Acanthaceae; Nigeria [S31].

  • Several members of the Acanthaceae family are used in folk medicine in West Africa .

Roseatoxide




  • Isolated from Hypoestes rosea R. Br (Acanthaceae), collected at Aponmu Forest Reserve near Akure, Nigeria. [S32].

  • ND

Serpendione




  • Isolated from Hypoestes serpens (Vahl) R. Br. (Acanthaceae) a herbaceous plant growing in the central and south highland of Madagascar [S33].



  • According to ethnobotanical field work, Hypoestes serpens is used in traditional medicine to lower blood pressure and maintain it at a normal value for several months after only two weeks of treatment [S33].

  • Serpendione at a concentration of 0.05 mg/mL, strongly depressed the maximal responses to the noradrenaline-induced contraction of rat aorta with a percentage inhibition of 92% [S33].

Transversianal




  • Cercospora traversiana; Fungus growing on fenugreek (Trigonella foenumgraecum L.) [S34]

  • Highly toxic to brine shrimp and snails, and to lyse human red blood cells at low concentrations (5*10-7 M). [S34].

Nd = not determined.



aFusicoccanes are produced by a range of different species. Liverworts are a rich source of fusicoccanes, several of which have biological activities (in light green). Two Streptomyces strains, soil actinomycetes, produce (17-hydroxy)cycloocatin, an inhibitor of lysophospolipases (blanc). In addition to fusicoccin-like molecules, other fusicoccanes with biological activity are produced by fungi as well (in pink). Both monocot (grass Brachiaria humidicola) and dicot (Hypoestes species) plants produce fucicoccanes that have very interesting biological activities (in dark green).
Supplementary references

S1 Gilabert M. et al. (2011) Bioactive Sesqui- and Diterpenoids from the Argentine Liverwort Porella chilensis. J. Natural Products 74, 574-579

S2 Huneck, S. (1983) Anadensin, a new fusicoccane diterpenoid from the liverwort Anastrepta orcadensis. Crystal structure analysis. Tetrahedron Letters, 124, 3787-3788

S3 Liu H.-J. et al. (2000) Sesquiterpenoids and diterpenoids from the Chilean liverwort Lepicolea ochroleuca. Phytochem. 53, 845-849

S4 Zapp J. et al. (1994) Sphenolobane and fusicoccane diterpenoids from the liverwort anastrophyllum-auritum. Phytochem. 37, 787-793

S5 Komala I. et al. (2010) Zierane sesquiterpene lactone, cembrane and fusicoccane diterpenoids, from the Tahitian liverwort Chandonanthus hirtellus. Phytochem. 71, 1387-1394

S6 Nagashima F. et al. (1999) Sesqui- and diterpenoids from Ptilidium ciliare and Barbilophozia species (liverworts). Phytochem. 51, 563-566

S7 Tori M. et al. (1993) Terpenoids from 6 Lophoziaceae Liverworts. Phytochem. 34, 181-190

S8 Subbarao G.V. et al. (2009) Evidence for biological nitrification inhibition in Brachiaria pastures. Proc. Natl. Acad. Sci. USA 106, 17302-17307

S9 MacKinnon S.L. et al. (1999) Components from the phytotoxic extract of Alternaria brassicicola, a black spot pathogen of canola. Phytochem. 51, 215-221

S10 Sassa T. et al. (1998) Structural confirmation of cotylenin A, a novel fusicoccane-diterpene glycoside with potent plant growth-regulating activity from Cladosporium fungus sp. 501-7W. Biosc. Biotechn. Biochem. 62, 1815-1818

S11 Asahi K. et al. (1997) Cotylenin A, a plant-growth regulator, induces the differentiation in murine and human myeloid leukemia cells. Biochem. Biophys. Res. Comm. 238, 758-763

S12 Honma Y. (2002) Cotylenin A - A plant growth regulator as a differentiation-inducing agent against myeloid leukemia. Leukemia & Lymphoma 43, 1169-1178

S13 Honma Y. et al. (2005) Antitumor effect of cotylenin A plus interferon-alpha: Possible therapeutic agents against ovary carcinoma. Gynec. Onc. 99, 680-688

S14 Kim S.Y. et al. (2009) Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two P450 hyroxylases. Chem. Biol. 16, 736-743

S15 Aoyagi T. et al. (1992) Cyclooctatin, a new inhibitor of lysophospholipase, produced by streptomyces-melanosporofaciens mi614-43f2 - taxonomy, production, isolation, physicochemical properties and biological-activities. J. Antibiotics 45, 1587-1591

S16 Kawamura A. et al. (2011) 17-Hydroxycyclooctatin, a Fused 5-8-5 Ring Diterpene, from Streptomyces sp. MTE4a. J. Nat. Prod .74, 492-495

S17 Muhammad I. et al. (1998) Additional diterpene ketones from Hypoestes forskalei. Phytochemistry 47: 1331-1336

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S19 Adio A.M. (2005) Isolation and structure elucidation of sesquiterpenoids from the essential oils of some liverworts (hepaticae). PhD Thesis, Univ of Hamburg.

S20 Ballio A, Mauri M, Chain EB, Deleo P, Tonolo A, et al. (1964) Fusicoccin - new wilting toxin produced by Fusicoccum amygdali del. Nature 203, 297

S21 Barrow K.D. et al. (1968) Constitution of Fusicoccin. Chem. Comm. 1198-1200

S22 Asakawa Y. et al. (1990) Chemosystematics of Bryophytes .38. Fusicoccane-Type, Dolabellane-Type and Rearranged Labdane-Type Diterpenoids from the Liverwort Pleurozia-Gigantea. Phytochem. 29, 2597-2603

S23 Hashimoto T. et al. (1985) New highly oxidized fusicoccane diterpenoids from the liverwort plagiochila-acanthophylla subsp japonica. Tetrahedron Letters 26, 6473-6476

S24 Rasoamiaranjanahary L. et al. (2003) Antifungal diterpenes from Hypoestes serpens (Acanthaceae). Phytochem. 62, 333-337

S25 Chinworrungsee M. et al. (2001) Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica. Bioorganic & Medicinal Chem. Letters 11, 1965-1969

S26 Muhammad I, Mossa JS, AlYahya MA, ElFeraly FS, McPhail AT (1997) Hypoestenone: A fusicoccane diterpene ketone from Hypoestes forskalei. Phytochem. 44, 125-129

S27 Mothana RAA, Kriegisch S, Harms M, Wende K, Lindequist U (2011) Assessment of selected Yemeni medicinal plants for their in vitro antimicrobial, anticancer, and antioxidant activities. Pharm. Biol. 49, 200-210

S28 Kim S, Shin DS, Lee T, Oh KB (2004) Periconicins, two new fusicoccane diterpenes produced by an endophytic fungus Periconia sp with antibacterial activity. J. Natural Products 67, 448-450

S29 Teles HL, Sordi R, Silva GH, Castro-Gamboa I, Bolzani VD, et al. (2006) Aromatic compounds produced by Periconia atropurpurea, an endophytic fungus associated with Xylopia aromatica. Phytochem. 67, 2686-2690

S30 Shin DS, Oh MN, Yang HC, Oh KB (2005) Biological characterization of periconicins, bioactive secondary metabolites, produced by Periconia sp OBW-15. J.Microbiol. and Biotechn. 15, 216-220

S31 Adesomoju AA, Okogun JI, Cava MP, Carroll PJ (1983) Roseadione, a Diterpene Ketone from Hypoestes-Rosea. Phytochem. 22: 2535-2536

S32 Adesomoju AA, Okogun JI (1984) Roseatoxide and dihypoestoxide - additional new diterpenoids from Hypoestes rosea. J. Natural Products 47, 308-311

S33 Andriamihaja B, Martin MT, Rasoanaivo P, Frappier F (2001) A new diterpene from Hypoestes serpens. J. Natural Products 64, 217-218



S34 Stoessl A, Cole RJ, Abramowski Z, Lester HH, Towers GHN (1989) Some Biological Properties of Traversianal, a Strongly Molluscicidal Diterpenoid Aldehyde from Cercospora-Traversiana. Mycopathologia 106: 41-46




Figure S1. Naturally occurring fusicoccanes that have the same unsaturation pattern (C1=C2 and C10=C14) of their 5-8-5 ring structure as Fusicoccin-A. (a) Fusicoccins (b) Cotylenins (c) Brassicicenes.





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