# Lavendamycin

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**Lavendamycin** is a naturally occurring [chemical compound](/source/Chemical_compound) discovered in [fermentation](/source/Fermentation) broth of the [soil bacterium](/source/Soil_bacterium) *[Streptomyces lavendulae](/source/Streptomyces_lavendulae)*.[1] Lavendamycin has [antibiotic](/source/Antibiotic) properties and [anti-proliferative](/source/Anti-proliferative) effects against several [cancer cell lines](/source/Cancer_cell_lines). The use of lavendamycin as a [cytotoxic](/source/Cytotoxicity) agent in [cancer therapy](/source/Cancer_therapy) failed due to poor [water solubility](/source/Water_solubility) and non-specific [cytotoxicity](/source/Cytotoxicity). The study of lavendamycin-based [analogs](/source/Analog_(chemistry)) designed to overcome these liabilities has been an area of research.[2]

## Discovery

Lavendamycin was first discovered in 1981 by Doyle et al., who isolated it from *Streptomyces lavendulae*.[2] As the compound failed to crystallize, a direct characterization of the molecular structure with [X-ray crystallography](/source/X-ray_crystallography) was not possible. Careful analysis using [NMR](/source/Nuclear_magnetic_resonance), [IR](/source/Infrared_spectroscopy), and [UV-VIS](/source/Ultraviolet%E2%80%93visible_spectroscopy) spectroscopy and [mass spectrometry](/source/Mass_spectrometry) allowed the assignment of the pentacyclic structure consisting of a [β-carboline](/source/%CE%92-carboline) unit and a quinolinequinone unit.[citation needed]

## Total syntheses

The attractive biological properties and complex structure of lavendamycin have made it the target of a large number of [total syntheses](/source/Total_syntheses).[3] Within a few years after the structural elucidation by Doyle et al., the research groups of Kende,[4] Hibino,[5] Rao,[6] and Boger[7] had already developed total syntheses for the compound independently of one another. The discovery that analogs of lavendamycin are potent inhibitors of HIV [reverse transcriptase](/source/Reverse_transcriptase) led to further attempts in the 90s to develop efficient routes to lavendamycin.[8][9][10][11] However, large numbers of steps, low overall yields (0.5–2%) or poorly available starting materials make these syntheses unattractive for further systematic development of lavendamycin and its analogs. Notably, total syntheses by Behforouz[12] and Nissen[13] offer flexible construction of the lavendamycin scaffold at high yields.

## References

1. Balitz, D. M.; Bush, J. A.; Bradner, W. T.; Doyle, T. W.; O'Herron, F. A.; Nettleton, D. E. (1982). "Isolation of lavendamycin, a new antibiotic from Streptomyces lavendulae". *The Journal of Antibiotics*. **35** (3): 259–65. [doi:10.7164/antibiotics.35.259](https://doi.org/10.7164/antibiotics.35.259). [PMID 7076573](https://pubmed.ncbi.nlm.nih.gov/7076573)

1. Hassani, M.; Cai, W.; Koelsch, K. H.; Holley, D. C.; Rose, A. S.; Olang, F.; Lineswala, J. P.; Holloway, W. G.; Gerdes, J. M.; Behforouz, M.; Beall, H. D. (2008). "Lavendamycin antitumor agents: Structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies". *Journal of Medicinal Chemistry*. **51** (11): 3104–15. [doi:10.1021/jm701066a](https://doi.org/10.1021/jm701066a). [PMID 18457384](https://pubmed.ncbi.nlm.nih.gov/18457384)

1. Bringmann, Gerhard; Reichert, Yanina; Kane, Vinayak V. (2004). ["The total synthesis of streptonigrin and related antitumor antibiotic natural products"](https://linkinghub.elsevier.com/retrieve/pii/S0040402004003333). *Tetrahedron*. **60** (16): 3539–3574. [doi:10.1016/j.tet.2004.02.060](https://doi.org/10.1016/j.tet.2004.02.060)

1. Kende, Andrew S. & Ebetino, Frank H. (1984). ["The regiospecific total synthesis of lavendamycin methyl ester"](https://linkinghub.elsevier.com/retrieve/pii/S0040403901800630). *Tetrahedron Letters*. **25** (9): 923–926. [doi:10.1016/S0040-4039(01)80063-0](https://doi.org/10.1016/S0040-4039(01)80063-0)

1. Hibino, Satoshi; Okazaki, Miko; Sato, Kohichi; Morita, Itsuko; Ichikawa, Masataka (1983). ["Synthetic Approach to the Antitumor Antibiotic Lavendamycin: a Synthesis of Demethallavendamycin Methyl Ester"](https://web.archive.org/web/20211210031822/https://www.heterocycles.jp/newlibrary/libraries/abst/10414). *Heterocycles*. **20** (10): 1957. [doi:10.3987/R-1983-10-1957](https://doi.org/10.3987/R-1983-10-1957). [ISSN 0385-5414](https://www.worldcat.org/issn/0385-5414). Archived from [the original](http://www.heterocycles.jp/library/abstract.php?doi=10414) on 2021-12-10. Retrieved 2021-12-09.

1. Rao, A.V.Rama; Chavan, Subhash P.; Sivadasan, Latha (1986). ["Synthesis of lavendamycin"](https://linkinghub.elsevier.com/retrieve/pii/S0040402001880583). *Tetrahedron*. **42** (18): 5065–5071. [doi:10.1016/S0040-4020(01)88058-3](https://doi.org/10.1016/S0040-4020(01)88058-3)

1. Boger, Dale L.; Duff, Steven R.; Panek, James S.; Yasuda, Masami (1985). ["Total synthesis of lavendamycin methyl ester"](https://pubs.acs.org/doi/abs/10.1021/jo00350a070). *The Journal of Organic Chemistry*. **50** (26): 5790–5795. [doi:10.1021/jo00350a070](https://doi.org/10.1021/jo00350a070). [ISSN 0022-3263](https://www.worldcat.org/issn/0022-3263)

1. Ciufolini, Marco A. & Bishop, Michael J. (1993). ["Studies towards streptonigrinoids: formal synthesis of lavendamycin methyl ester"](http://xlink.rsc.org/?DOI=c39930001463). *Journal of the Chemical Society, Chemical Communications*. '***(18): 1463–1464. [doi:10.1039/c39930001463](https://doi.org/10.1039/c39930001463). [ISSN 0022-4936](https://www.worldcat.org/issn/0022-4936)***

1. Molina, Pedro; Fresneda, Pilar M.; Cánovas, Mercedes (1992). ["Iminophosphorane-mediated synthesis of 1-substituted-β-carbolines: investigative studies on the preparation of alkaloids lavendamycin and eudistomins framework."](https://linkinghub.elsevier.com/retrieve/pii/S0040403900788885). *Tetrahedron Letters*. **33** (20): 2891–2894. [doi:10.1016/S0040-4039(00)78888-5](https://doi.org/10.1016/S0040-4039(00)78888-5)

1. Molina, Pedro; Murcia, Fernando; Fresneda, Pilar M. (1994). ["A straightforward and practical formal synthesis of lavendamycin ethyl ester"](https://linkinghub.elsevier.com/retrieve/pii/S0040403900762447). *Tetrahedron Letters*. **35** (9): 1453–1456. [doi:10.1016/S0040-4039(00)76244-7](https://doi.org/10.1016/S0040-4039(00)76244-7)

1. Rocca, Patrick; Marsais, Francis; Godard, Alain; Quéguiner, Guy (1993). ["A new approach to the synthesis of lavendamycin analogues."](https://linkinghub.elsevier.com/retrieve/pii/S0040403900604860). *Tetrahedron Letters*. **34** (18): 2937–2940. [doi:10.1016/S0040-4039(00)60486-0](https://doi.org/10.1016/S0040-4039(00)60486-0)

1. Behforouz, Mohammad; Gu, Zhengxiang; Cai, Wen; Horn, Mark A.; Ahmadian, Mohammad (1993). ["A highly concise synthesis of lavendamycin methyl ester"](https://pubs.acs.org/doi/abs/10.1021/jo00077a032). *The Journal of Organic Chemistry*. **58** (25): 7089–7091. [doi:10.1021/jo00077a032](https://doi.org/10.1021/jo00077a032). [ISSN 0022-3263](https://www.worldcat.org/issn/0022-3263)

1. Nissen, Felix & Detert, Heiner (2011). ["Total Synthesis of Lavendamycin by a \[2+2+2\] Cycloaddition"](https://onlinelibrary.wiley.com/doi/10.1002/ejoc.201100131). *European Journal of Organic Chemistry*. **2011** (15): 2845–2853. [doi:10.1002/ejoc.201100131](https://doi.org/10.1002/ejoc.201100131)

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Adapted from the Wikipedia article [Lavendamycin](https://en.wikipedia.org/wiki/Lavendamycin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Lavendamycin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.