Rishitin

Rishitin
Names
	IUPAC name 15-Nor-4α-eremophila-5(10),11-diene-2α,3β-diol
	Systematic IUPAC name (1S,2R,3R,7R)-1-Methyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydronaphthalene-2,3-diol
	Other names 2,3-Naphthalenediol, 1,2,3,4,5,6,7,8-octahydro-1-methyl-7-(1-methylethenyl)-, (1S,2R,3R,7R)-
Identifiers
CAS Number	18178-54-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8870;
ChemSpider	97166;
KEGG	C09715;
PubChem CID	108064;
UNII	FQY1K3HR10;
CompTox Dashboard (EPA)	DTXSID60171184 ;
	InChI InChI=1S/C14H22O2/c1-8(2)10-4-5-11-7-13(15)14(16)9(3)12(11)6-10/h9-10,13-16H,1,4-7H2,2-3H3/t9-,10+,13+,14+/m0/s1 Key: XSCYYIVXGBKTOC-GZZJDILISA-N;
	SMILES C[C@@H]1[C@H]([C@@H](CC2=C1C[C@@H](CC2)C(=C)C)O)O;
Properties
Chemical formula	C14H22O2
Molar mass	222.328 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Rishitin is a terpenoid compound, produced by some plants belonging to the Solanum family, including the potato^[1] and tomato.^[2] Rishitin belongs to a heterogeneous group of anti-microbial plant defense compounds termed phytoalexins and is produced upon pathogen attack.^[3] Same as the phytoalexin capsidiol, it belongs to the group of sesquiterpenes and is as such an FPP derivative. Rishitin was named after the potato cultivar Rishiri, where it was first discovered in 1968.^[4]

Biosynthesis

The biosynthetic pathway of rishitin has not yet been fully elucidated, and is still an active topic of research. Currently, the enzymes responsible for the synthesis of rishitin have not yet been discovered. Studies using radioisotope labeled compounds, revealed however that solavetivone, 15-hydroxysolavetivone, lubimin and 3-hydroxylubimin are precursors of rishitin. ^[5]^[6]

References

^ Katsui, N., Murai, A., Takasugi, M., Imaizumi, K., Masamune, T., & Tomiyama, K. (1968). The structure of rishitin, a new antifungal compound from diseased potato tubers. Chemical Communications, (1), 43. https://doi.org/10.1039/c19680000043
^ D’Harlingue, A., Mamdouh, A. M., Malfatti, P., Soulie, M.-C., & Bompeix, G. (1995). Evidence for rishitin biosynthesis in tomato cultures. Phytochemistry, 39(1), 69–70. https://doi.org/10.1016/0031-9422(94)00844-J
^ Kuc, J. (1972). Phytoalexins. Annual Review of Phytopathology, 10(1), 207–232. https://doi.org/10.1146/annurev.py.10.090172.001231
^ KATSUI, N., TAKAHASHI, Y., SATO, N., MURAI, A., & MASAMUNE, T. (1981). Phytoalexins Produced by Potato Variety Rishiri Inoculated with a Compatible Race of Phytophthora infestans. NIPPON KAGAKU KAISHI, 49(5), 659–664. https://doi.org/10.1246/nikkashi.1981.659
^ Sato, K., Ishiguri, Y., Doke, N., Tomiyama, K., Yagihashi, F., Murai, A., … Masamune, T. (1978). Biosynthesis of the sesquiterpenoid phytoalexin rishitin from acetate via oxylubimin in potato. Phytochemistry, 17(11), 1901–1902. https://doi.org/10.1016/S0031-9422(00)88729-4
^ Whitehead, I. M., Atkinson, A. L., & Threlfall, D. R. (1990). Studies on the biosynthesis and metabolism of the phytoalexin lubimin and related compounds in Datura stramonium L. Planta, 182(1), 81–88. https://doi.org/10.1007/BF00239988

[1] Katsui, N., Murai, A., Takasugi, M., Imaizumi, K., Masamune, T., & Tomiyama, K. (1968). The structure of rishitin, a new antifungal compound from diseased potato tubers. Chemical Communications, (1), 43. https://doi.org/10.1039/c19680000043

[2] D’Harlingue, A., Mamdouh, A. M., Malfatti, P., Soulie, M.-C., & Bompeix, G. (1995). Evidence for rishitin biosynthesis in tomato cultures. Phytochemistry, 39(1), 69–70. https://doi.org/10.1016/0031-9422(94)00844-J

[3] Kuc, J. (1972). Phytoalexins. Annual Review of Phytopathology, 10(1), 207–232. https://doi.org/10.1146/annurev.py.10.090172.001231

[4] KATSUI, N., TAKAHASHI, Y., SATO, N., MURAI, A., & MASAMUNE, T. (1981). Phytoalexins Produced by Potato Variety Rishiri Inoculated with a Compatible Race of Phytophthora infestans. NIPPON KAGAKU KAISHI, 49(5), 659–664. https://doi.org/10.1246/nikkashi.1981.659

[5] Sato, K., Ishiguri, Y., Doke, N., Tomiyama, K., Yagihashi, F., Murai, A., … Masamune, T. (1978). Biosynthesis of the sesquiterpenoid phytoalexin rishitin from acetate via oxylubimin in potato. Phytochemistry, 17(11), 1901–1902. https://doi.org/10.1016/S0031-9422(00)88729-4

[6] Whitehead, I. M., Atkinson, A. L., & Threlfall, D. R. (1990). Studies on the biosynthesis and metabolism of the phytoalexin lubimin and related compounds in Datura stramonium L. Planta, 182(1), 81–88. https://doi.org/10.1007/BF00239988

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