Calocedrus formosana Florin (Cupressaceae) is an endemic tree species in Taiwan; its timber is recognized for natural decay resistance. To examine the antitermitic and antifungal activities of leaf essential oil and its main constituents, C. formosana leaves were extracted and the essential oils analyzed by GC-MS. Bioactivity tests against the termite Coptotermes formosanus demonstrate that the LC50 value of leaf essential oil is 27.6 mg/g. Furthermore, exposure to T-muurolol caused 100% mortality at a dosage of 5 mg/g after 14 d. Leaf oil constituents displayed activity against four fungi, Lenzites betulina, Pycnoporus coccineus, Trametes versicolor, and Laetiporus sulphureus. Two compounds, alpha-cadinol and T-muurolol, exhibited the strongest antifungal activity. The LC50 values of alpha-cadinol against L. sulphureus, L. betulina, and T. versicolor are 9.9, 28.6, and 30.4 microg/ml, respectively.
Summary
The antifungal activity of cadinane skeletal sesquiterpenoids from Taiwania (Taiwania cryptomerioides
Hayata) heartwood is demonstrated. Using spectral analyses, the absolute structures of three main cadinanes,
T-cadinol, T-muurolol, and α-cadinol, all isolated from Taiwania with HPLC, were identified.
The amount of these cadinanes was also quantified using GC. The results showed that the total amount
of cadinanes extracted from heartwood with n-C6H14 was 6.49 mg per kg of wood. This was much more
than the essential oils collected by water distillation from leaves (0.04 mg/kg), sapwood (0.36 mg/kg),
or heartwood (1.77 mg/kg). Moreover, results obtained from the antifungal assays demonstrated that αcadinol
exhibited the highest antifungal index for both Coriolus versicolor and Laetiporus sulphureus,
followed by T-cadinol and T-muurolol. As a matter of fact, α-cadinol completely inhibited the growth of
C. versicolor and L. sulphureus at the level as low as 100 ppm. Further comparison of the molecular configuration
of these cadinanes reveals that cadinane skeletal sesquiterpenoids with an equatorial hydroxyl
group at C-9 and a trans configuration at the ring junction, such as the case for α-cadinol, exhibited
the strongest antifungal activity.
This study was to isolate and identify the antifungal compounds in the ethyl acetate soluble fraction of the methanol extractives of Taiwania (Taiwania cryptomerioides Hayata) heartwood and to examine their antifungal activity. Five compounds were obtained by open column chromatography and HPLC and based upon the results from Mass, 1 H-NMR, and 13 C-NMR analyses. Their structures were identified, namely ferruginol, helioxanthin, savinin, taiwanin C, and hinokiol. According to the results of antifungal test, the order of antifungal index of these compounds for Coriolus versicolor (L. ex Fr.) Quel. was ferruginol > taiwanin C > savinin > hinokiol. For Laetiporus sulphureus (B. ex Fr.) Bond. it was taiwanin C > savinin > ferruginol > hinokiol.
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