Ten new triterpenoids, camphoratins A-J (1-10), along with 12 known compounds were isolated from the fruiting body of Taiwanofungus camphoratus. Their structures were established by spectroscopic analysis and chemical methods. Compound 10 is the first example of a naturally occurring ergosteroid with an unusual cis-C/D ring junction. Compounds 2-6 and 11 showed moderate to potent cytotoxicity with EC 50 values ranging from 0.3 to 3 μM against KB and KB-VIN human cancer cell lines. Compounds 6, 10, 11, 14-16, 18, and 21 exhibited antiinflammatory NO-production inhibition activity with IC 50 values of less than 5 μM, which was more potent than the nonspecific NOS inhibitor N ω -nitro-L-arginine methyl ester (L-NAME).Taiwanofungus camphoratus (synonym: Ganoderma camphoratum; Antrodia cinnamomea; Antrodia camphorata) (Polyporaceae, Aphyllophorales), is a rare and precious medical fungus in Taiwan and is called a "national treasure of Taiwan".1 Its Chinese name is ZhanKu or Niu-Chang-Chih. The microorganism is parasitic to the inner heart-wood wall of old hollow trunks of Cinnamomum kanehirai Hay. (Lauraceae). The growth rate of natural T. camphoratus in the wild is very slow, and it is difficult to cultivate in a greenhouse, making fruiting bodies expensive to obtain. In traditional Taiwanese folk medicine T. camphoratus has been used as an important health food for treating food, alcohol, and drug intoxication, -methylergost-8,24(28)-diene-3,11-dion-26-oate (21),10 and ergosterol peroxide (22).11 Cytotoxic activity, inhibition of nitric oxide (NO) or reactive oxygen species (ROS) production, and free radical-scavenging activity of the isolates were evaluated in our study.
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Results and DiscussionCamphoratin A (1) was obtained as a colorless powder. , suggested a 4-methylergost-8-en-11-one skeleton similar to that of antcin C (16).5 The 3α-OH functionality was deduced by the correlations from H-3 (δ 3.89, 1H, d, J = 1.6 Hz, β-orientation) to C-4 and C-1 and from H 3 -29 to C-3, C-4, and C-5 in the HMBC spectrum of 1. The hydroxy groups attached at C-7 and C-12 were further designated by the correlations from H-7 (δ 4.52, 1H, t, J = 8.4 Hz) to C-6 and C-8 and from H-12 (4.44, 1H, s) to C-13, C-14, and C-17, respectively. The C-25 carboxylic functionality was assigned due to the presence of an HMBC correlation from H-25 (δ 3.45, 1H, q, J = 6.8 Hz) to the carbon resonance at δ 176.9. A comparison of the NMR spectroscopic data of 1 with those of 165 confirmed the above elucidation and unambiguously established the structure of 1. The relative configuration of 1 was determined by the NOE correlations observed in a NOESY experiment. In the NOESY spectrum of 1, H-7 showed NOE enhancements with both H-5 and H-14, suggesting that these protons had α-orientations. Furthermore, NOE correlations between H-3 and H-4 as well as between H-12 and H 3 -18 disclosed that these protons are β-oriented.Camphoratin B (2) was obtained as a colorless syrup. The HRESIMS of 2 gave an [M + Na] + peak at m/z 495.3089 ...
