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ß-Barbatene (= gymnomitrene) (4), a ubiquitous sesquiterpene hydrocarbon, from liverwort like Plagiochila sciophila and many others. Jungermanniales liverworts was treated in the same manner using Aspergillus niger for 1 day gave a triol, 4ß,9ß,10ß-trihydoxy-ß -barbatene (27, 8%) (Hashimoto et al., 2003c).

Pinguisane sesquiterpenoids have been isolated from the Jungermanniales, Metzgeriales, and Marchantiales. In particular, the Lejeuneaceae and Porellaceae are rich sources of this unique type of sesquiterpenoids. One of the major furanosesquitepene (373) was biodegradated by Aspergillus niger to afford primary alcohol (375), which might be formed from 374 as shown in Figure 15.106 (Lahlou et al., 2000) (Figure 15.107).

In order to obtain more pharmacologically active compounds, the secondary metabolites from crude drugs and animals, for example, nardosinone (376) isolated from the crude drug, Nardostachys chinensis, which has been used for headache, stomachache, and diuresis possesses antimalarial activity. Hinesol (384), possessing spasmolytic activity, obtained from Atractylodis lanceae rhi-zoma, animal perfume (-)-ambrox (391) from ambergris were biotransformed by Aspergillus niger, Aspergillus cellulosae, Botryosphaeria dothidea, and so on.

Nardosinone (376) was incubated in the same medium including Aspergillus niger as described above for 1 day to give six metabolites (377, 45%; 378, 3%; 379, 2%; 380, 5%; 381, 6%; and 382, 3%). Compounds 380-382 are unique trinorsesquiterpenoids although their yields are very poor. Compound 380 might be formed by the similar manner to that of phenol from cumene (383) (Figure 15.108) (Hashimoto et al., 2003b) (Figure 15.109).

A. cellulosae

FIGURE 15.102 Biotransformation of maalioxide (349) by Aspergillus niger, Aspergillus cellulosae, and Mucor plumbeus.

A. cellulosae

FIGURE 15.102 Biotransformation of maalioxide (349) by Aspergillus niger, Aspergillus cellulosae, and Mucor plumbeus.

From hinesol (384), two allylic alcohols (386, 387) and their oxygenated derivative (385), and three unique metabolites (388-390) having oxirane ring were obtained. The metabolic pathway is very similar to that of oral administration of hinesol since the same metabolites (395-387) were obtained from the urine of rabbits (Hashimoto et al., 1998, 1999b, 2001) (Figure 15.110).

To obtain a large amount of ambrox (391), a deterrence, labda-12,14-dien-7a ,8-diol obtained from the liverwort, Porella pettottetiana as a major component, was chemically converted into

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