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Viridiflorol
Names
IUPAC name
6β,11-Cyclo-1β,4α,5β,10α-guaian-10-ol
Systematic IUPAC name
(1aR,4S,4aS,7R,7aS,7bS)-1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-4-ol
Other names
(+)-Viridiflorol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.186 Edit this at Wikidata
EC Number
  • 209-003-3
UNII
  • InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10+,11-,12-,13-,15+/m1/s1
    Key: AYXPYQRXGNDJFU-IMNVLQEYSA-N
  • C[C@@H]1CC[C@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CC[C@]2(C)O
Properties
C15H26O
Molar mass 222.372 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Viridiflorol is a chemical compound, classified as a sesquiterpenoid, that has been isolated from the essential oils of a variety of plants including Melaleuca quinquenervia[1] (broad-leaved paperbark), Melaleuca alternifolia[2] (tea tree), and Allophylus edulis.[3]

Viridiflorol has shown moderate antibacterial activity against Mycobacterium tuberculosis, the causative agent of tuberculosis, in an in vitro assay. [1] It is also produced by the endophytic root fungus Serendipita indica and exhibits antifungal activity against Colletotrichum truncatum [4]

References

  1. ^ a b Ireland, B.F.; Hibbert, D.B.; Goldsack, R.J.; Doran, J.C.; Brophy, J.J. (2002). "Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.). It is also produced by the endopytic fungus Serendipita indica S.T. Blake". Biochemical Systematics and Ecology. 30 (5): 457–470. doi:10.1016/s0305-1978(01)00112-0.
  2. ^ "Essential oil of Melaleuca, terpene-4-ol (tea tree oil): ISO 4730: 2017 (E)". International Organization for Standardization (ISO), Geneva, Switzerland. 2017. Retrieved 6 March 2019.
  3. ^ Trevizan, Lucas Noboru Fatori; Nascimento, Kamilla Felipe do; Santos, Joyce Alencar; Kassuya, Candida Aparecida Leite; Cardoso, Claudia Andrea Lima; Vieira, Maria do Carmo; Moreira, Flora Martinez Figueira; Croda, Julio; Formagio, Anelise Samara Nazari (2016). "Anti-inflammatory, antioxidant and anti- Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk". Journal of Ethnopharmacology. 192: 510–515. doi:10.1016/j.jep.2016.08.053. PMID 27612433.
  4. ^ Ntana, F.; Bhat, W.W.; Johnson, S.R.; Jørgensen, H.J.L.; Collinge, D.B.; Jensen, B.; Hamberger, B. (2021). "A Sesquiterpene Synthase from the Endophytic Fungus Serendipita indica Catalyzes Formation of Viridiflorol". Biomolecules. 11 (6): 898. doi:10.3390/biom11060898. PMC 8234273. PMID 34208762.