Thujaplicinol

Thujaplicinol
α-Thujaplicinol	β-Thujaplicinol
Identifiers
CAS Number	α-: 16643-33-7; β-: 4356-35-8;
3D model (JSmol)	α-: Interactive image; β-: Interactive image;
ChEMBL	β-: ChEMBL550937;
ChemSpider	α-: 57499060; β-: 65481;
PubChem CID	α-: 57957991; β-: 72605;
UNII	β-: UW241P2H16;
CompTox Dashboard (EPA)	α-: DTXSID501316946; β-: DTXSID70195876;
	InChI α-: InChI=1S/C10H12O3/c1-6(2)7-4-3-5-8(11)10(13)9(7)12/h3-6H,1-2H3,(H2,11,12,13) Key: DTNGDTFARJMFLC-UHFFFAOYSA-N; β-: InChI=1S/C10H12O3/c1-6(2)7-3-4-8(11)10(13)9(12)5-7/h3-6H,1-2H3,(H2,11,12,13) Key: HVGNSPLLPQWYGC-UHFFFAOYSA-N;
	SMILES α-: CC(C)C1=CC=CC(=O)C(=C1O)O; β-: CC(C)C1=CC(=O)C(=C(C=C1)O)O;
Properties
Chemical formula	C10H12O3
Molar mass	180.203 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Thujaplicinol is either of two isomeric tropolone-related natural products. They are found in tree species primarily in bark, needles, xylem, of the family of Cupressaceae like the Cupressus, Thuja, Juniperus and Thujopsis.^[1]^[2] The thujaplicinols are structurally equivalent to the thujaplicins with an additional hydroxyl group. They belong to the class of natural terpenoids having two free hydroxyl groups at C3 and C5 position.

The thujaplicinols are highly volatile compounds. It is known that the presence of such tropolones, including alpha-tropolone and its isopropyl derivatives, result in the high natural durability of wood species, such as western red cedar, juniper and cypress.

Uses

Alpha-thujaplicinol, an isomer of thujaplicinol, is often encountered in the Asian species of Thujopsis dolabrata, and exhibits high antibacterial and antifungal activities. It has been found to be effective against Enterococcus faecalis and Legionella pneumophila, even at low inhibitory concentrations (1.56 to 50 mg/ml).^[3]

In a 2004 study, α-thujaplicinol showed to have high cytotoxic effects upon several cancer cell lines, such as human stomach cancer and murine lymphocytic leukemia.^[4]

The other isomer of the compound is called β-thujaplicinol. A recent study found out that it inhibited the development of hepatocellular carcinoma cells because it triggered the autophagic cell death and a subsequent apoptosis.^[5]

Earlier studies have shown that β-thujaplicinol can addiotionally suppress estrogen-dependent breast cancer by regulating the estrogen receptor signaling.^[6]

References

^ "alpha-Thujaplicinol". BenchChem. Retrieved 23 March 2024.
^ "Springer Handbook of Wood Science and Technology". Springer Handbooks. Cham: Springer International Publishing. 2023. pp. 254–255. doi:10.1007/978-3-030-81315-4. ISBN 978-3-030-81314-7. ISSN 2522-8692. S2CID 257902863. Chapt. 5. Wood Chemistry
^ MORITA, Yasuhiro; MATSUMURA, Eiko; TSUJIBO, Hiroshi; YASUDA, Masahide; SAKAGAMI, Yoshikazu; OKABE, Toshihiro; ISHIDA, Nakao; INAMORI, Yoshihiko (2001). "Biological Activity of α-Thujaplicin, the Minor Component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO". Biological & Pharmaceutical Bulletin. 24 (6). Pharmaceutical Society of Japan: 607–611. doi:10.1248/bpb.24.607. ISSN 0918-6158. PMID 11411545.
^ Morita, Y.; Matsumura, E.; Okabe, T.; Fukui, T.; Shibata, M.; Sugiura, M.; Ohe, T.; Tsujibo, H.; Ishida, N.; Inamori, Y. "Biological activity of alpha-thujaplicin, the isomer of hinokitiol". Biological & Pharmaceutical Bulletin. 27 6: 899–902. Retrieved 23 March 2024.
^ Zhang, Guangya; He, Jiangping; Ye, Xiaofei; Zhu, Jing; Hu, Xi; Shen, Minyan; Ma, Yuru; Mao, Ziming; Song, Huaidong; Chen, Fengling (15 March 2019). "β-Thujaplicin induces autophagic cell death, apoptosis, and cell cycle arrest through ROS-mediated Akt and p38/ERK MAPK signaling in human hepatocellular carcinoma". Cell Death & Disease. 10 (4). Springer Science and Business Media LLC: 255. doi:10.1038/s41419-019-1492-6. ISSN 2041-4889. PMC 6420571. PMID 30874538.
^ Ko, Jiwon; Bao, Cheng; Lee, Jaehoo; Park, Hyun-Chang; Lee, Hong Jin (1 October 2014). "Abstract 4226: B-thujaplicin suppressed estrogen dependent breast cancer via regulating estrogen receptor signaling". Cancer Research. 74 (19_Supplement). American Association for Cancer Research (AACR): 4226. doi:10.1158/1538-7445.am2014-4226. ISSN 0008-5472.

[1] "alpha-Thujaplicinol". BenchChem. Retrieved 23 March 2024.

[2] "Springer Handbook of Wood Science and Technology". Springer Handbooks. Cham: Springer International Publishing. 2023. pp. 254–255. doi:10.1007/978-3-030-81315-4. ISBN 978-3-030-81314-7. ISSN 2522-8692. S2CID 257902863. Chapt. 5. Wood Chemistry

[3] MORITA, Yasuhiro; MATSUMURA, Eiko; TSUJIBO, Hiroshi; YASUDA, Masahide; SAKAGAMI, Yoshikazu; OKABE, Toshihiro; ISHIDA, Nakao; INAMORI, Yoshihiko (2001). "Biological Activity of α-Thujaplicin, the Minor Component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO". Biological & Pharmaceutical Bulletin. 24 (6). Pharmaceutical Society of Japan: 607–611. doi:10.1248/bpb.24.607. ISSN 0918-6158. PMID 11411545.

[4] Morita, Y.; Matsumura, E.; Okabe, T.; Fukui, T.; Shibata, M.; Sugiura, M.; Ohe, T.; Tsujibo, H.; Ishida, N.; Inamori, Y. "Biological activity of alpha-thujaplicin, the isomer of hinokitiol". Biological & Pharmaceutical Bulletin. 27 6: 899–902. Retrieved 23 March 2024.

[5] Zhang, Guangya; He, Jiangping; Ye, Xiaofei; Zhu, Jing; Hu, Xi; Shen, Minyan; Ma, Yuru; Mao, Ziming; Song, Huaidong; Chen, Fengling (15 March 2019). "β-Thujaplicin induces autophagic cell death, apoptosis, and cell cycle arrest through ROS-mediated Akt and p38/ERK MAPK signaling in human hepatocellular carcinoma". Cell Death & Disease. 10 (4). Springer Science and Business Media LLC: 255. doi:10.1038/s41419-019-1492-6. ISSN 2041-4889. PMC 6420571. PMID 30874538.

[6] Ko, Jiwon; Bao, Cheng; Lee, Jaehoo; Park, Hyun-Chang; Lee, Hong Jin (1 October 2014). "Abstract 4226: B-thujaplicin suppressed estrogen dependent breast cancer via regulating estrogen receptor signaling". Cancer Research. 74 (19_Supplement). American Association for Cancer Research (AACR): 4226. doi:10.1158/1538-7445.am2014-4226. ISSN 0008-5472.