Abstract
A rare actinomycetal strain of the genus Actinomycetospora was found to produce a new tryptophan derivative, designated mycetoindole (1). The structure of 1 was determined to be N-3-methylcrotonoyl (Z)-dehydrotryptophan by NMR and MS analytical methods. Compound 1 reduced the root growth of lettuce Lactuca sativa seedlings at concentrations above 0.1 μM and almost completely inhibited seed germination at 10 μM.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Buy this article
- Purchase on SpringerLink
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1038%2Fs41429-021-00474-7/MediaObjects/41429_2021_474_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1038%2Fs41429-021-00474-7/MediaObjects/41429_2021_474_Fig2_HTML.png)
References
Dictionary of Natural Products 29.2 Chemical Search. https://dnp.chemnetbase.com/faces/chemical/ChemicalSearch.xhtml (accessed May 10, 2021).
Sayed AM, Abdel-Wahab NM, Hassan HM, Abdelmohsen UR. Saccharopolyspora: an underexplored source for bioactive natural products. J Appl Microbiol. 2020;128:314–29.
Blaskovich MAT, Hansford KA, Butler MS, Jia Z, Mark AE, Cooper MA. Developments in Glycopeptide Antibiotics. ACS Infect Dis. 2018;4:715–35.
Alfarisi O, Alghamdi WA, Al-Shaer MH, Dooley KE, Peloquin CA. Rifampin vs. Rifapentine: what is the preferred rifamycin for tuberculosis? Expert Rev Clin Pharmacol. 2017;10:1027–36.
Kirst HA. The spinosyn family of insecticides: realizing the potential of natural products research. J Antibiot. 2010;63:101–11.
List of prokaryotic names with standing in nomenclature. http://www.bacterio.net (accessed June 30, 2021).
Jiang Y, Wiese J, Tang SK, Xu LH, Imhoff JF, Jiang CL. Actinomycetospora chiangmaiensis gen. nov., sp. nov., a new member of the family Pseudonocardiaceae. Int J Syst Evol Microbiol. 2008;58:408–13.
Blin K, Shaw S, Steinke K, Villebro R, Ziemert N, Lee SY, et al. antiSMASH 5.0: updates to the secondary metabolite genome mining pipeline. Nucleic Acids Res. 2019;47:W81–W87.
Fu P, MacMillan JB. Thiasporines A−C, thiazine and thiazole derivatives from a marine-derived Actinomycetospora chloral. J Nat Prod. 2015;78:548–51.
Biological Resource Center, NITE (NBRC). https://www.nite.go.jp/nbrc/ (accessed Mar. 22, 2021).
Takahashi N, editor. Shokubutsu-kagaku-chosetsu-jikkenho (Experimental Protocols for Chemical Regulation of Plants). The Japanese Society for Chemical Regulation of Plants; 1989. p. 140−1 (in Japanese).
Amir-Heidari B, Thirlway J, Micklefield J. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Org Lett. 2007;9:1513–6.
Amir-Heidari B, Micklefield J. NMR confirmation that tryptophan dehydrogenation occurs with syn stereochemistry during the biosynthesis of CDA in Streptomyces coelicolor. J Org Chem. 2007;72:8950–3.
Chen D, Po KHL, Blasco P, Chen S, Li X. Convergent synthesis of calcium-dependent antibiotic CDA3a and analogues with improved antibacterial activity via late-stage serine ligation. Org Lett. 2020;22:4749−53.
Li SM. Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis. Nat Prod Rep. 2010;27:57–78.
Lai CY, Lo IW, Hewage RT, Chen YC, Chen CT, Lee CF, et al. Biosynthesis of complex indole alkaloids: elucidation of the concise pathway of okaramines. Angew Chem Int Ed. 2017;56:9478–82.
Ookubo T, Nakamura K, Nanba H, Yoshida H, Nakazawa Y. AMINO ACID DERIVATIVE. JPN. Patent WO 2010032771, 2010.
Karim MR, Harunari E, Oku N, Akasaka K, Igarashi Y. Bulbimidazoles A−C, antimicrobial and cytotoxic alkanoyl imidazoles from a marine gammaproteobacterium Microbulbifer species. J Nat Prod. 2020;83:1295–9.
Acknowledgements
We are in debt to Prof. Yasufumi Hikichi and Dr. Ayami Kanda at Kochi University for providing R. solanacearum SUPP1541. This work was supported by JSPS KAKENHI Grant Number 19K05848 to YI. P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002). C. albicans NBRC0197 was obtained from NBRC.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Saito, S., Oku, N. & Igarashi, Y. Mycetoindole, an N-acyl dehydrotryptophan with plant growth inhibitory activity from an actinomycete of the genus Actinomycetospora. J Antibiot 75, 44–47 (2022). https://doi.org/10.1038/s41429-021-00474-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1038/s41429-021-00474-7
This article is cited by
-
Species-specific secondary metabolism by actinomycetes of the genus Phytohabitans and discovery of new pyranonaphthoquinones and isatin derivatives
The Journal of Antibiotics (2023)
-
Isolation and structure determination of allopteridic acids A–C and allokutzmicin from an unexplored actinomycete of the genus Allokutzneria
The Journal of Antibiotics (2023)
-
Noaoxazole, a new heat shock metabolite produced by thermotolerant Streptomyces sp. HR41
The Journal of Antibiotics (2022)
-
Plant growth-promoting and antimicrobial chloropyrroles from a rare actinomycete of the genus Catellatospora
The Journal of Antibiotics (2022)
-
Trehangelin E, a bisacyl trehalose with plant growth promoting activity from a rare actinomycete Polymorphospora sp. RD064483
The Journal of Antibiotics (2022)