## 2 The Phytochemistry of _Artemisia annua_ L. (Qinghao)
### Sesquiterpenenoids
#### 2.6.3.2. Cadinanes, Muurolanes and Amorphanes
\begin{tabular}{|l|l|l|l|} \hline _epj_-Deoxyarteanuin B (**478**) & Deoxyisourtemisinin B & [84237-06-9] & [68, 96, 97, 129, 158, 160, 163, 164, 197] \\ \hline Dihydroorientennuin B (**479**) & 3H-Oxierno[7,8]naphth[8a,1-b]furan-3-one, & [64390-16-5] & [166] \\  & decahydro-4,7,9a-trimethyl- [1 aR- & & \\  & (1 aa,1 bk,4a,4 aB,7b,7 aI,9 aa9a)]- & & \\ \hline
11\(R\)-(-)Dihydroortnismic acid (**480**) & 4,11(13)-Amorphaden-12-oic acid (11\(R\),13-dihydro) & [85031-59-0] & [20, 32, 43, 135, 166, 167, 216] \\ \hline Dihydroortnismic acid hydroperoxide (**481**) & 4-Hydroxperoyders-5-amorphen-12-oic acid, 4a, 11\(R\) & [85031-60-3] & [167, 170, 185] \\ \hline Dihydroortnismic alcohol (**482**) & 1-Naphthalene[1,1,2,3,4a,5,6,8a-octahydro- & [855425-50-2] & [135] \\  & _a.4_,7-trimethyl-, (1\(R\),4\(R\),4\(S\),4\(S\),4\(S\))- & & \\ \hline Dihydroortnismic aldehyde (**483**) & 1-Naphthalene[nacetaldehyde, 1,3,4,4a,5,6,8a- & [855425-51-3] & [135] \\  & octahydro-a,4,7-trimethyl-, (1\(R\),4\(R\),4\(S\),4\(S\))- & & \\ \hline Dihydro-deoxyartenunin B (**484**) & 2H-Naphtho, 18-furan-2-one, 3a,4,5,6,8a,7,8a- & [89956-69-4] & [129] \\  & octahydro-3,6,9-trimethyl- [3\(R\)-(3a,3\(R\),6\(R\),6\(R\),6\(R\),9\(R\))]- & & \\ \hline Dihydro-_epi_-deoxyartenunin B (**485**) & 4-Cadinen-12,6-olide (66,10 BH,12 cH) & [104196-16-9] & [60, 68, 129, 166, 68, 127] \\ \hline Dihydrooxyethanolo (**486**) & & & [217] \\ \hline _a_-Epoxy-arteranuninic acid (**487**) & & & [129, 160, 194] \\ \hline _a_-Epoxy-difluorxperoydersaninic (**488**) & & & [9] \\ \hline _a_-Epoxy-difluorxperoydersanine (**488**) & & & [9] \\ \hline _a_-Epoxy-6a-hydroxy anorphan-12-oic acid (**489**) & & & [9] \\ \hline Isoannulide (**490**) & Naphtho[1,8-bc]pyran-2(3\(H\))-one, 3a,4,5,6,6a,7,9a,9b- & [103739-94-2] & [97, 128, 129, 182, 197] \\  & octahydro-6,9-dimethyl-3-methylene-, [3a\(R\)- & & [97] \\  & (3 aa,6a,6a,9 aI,9 ba)]- & & \\ \hline
2-Naphthalene, decahydro-1-methyl-6- & & & [159662-33-6] & [66] \\  & methylene-4-(1-methylenvelop)- (**491**) & & \\ \hline Verboccidentene (**492**) & Amorpha-4,7(11)-diene & [79982-58-4] & [134] \\ \hline \end{tabular}   
\begin{tabular}{|l|l|l|} \hline _epj_-Deoxyarteanuin B (**478**) & Deoxyisourtemisinin B & [84237-06-9] & [68, 96, 97, 129, 158, 160, 163, 164, 197] \\ \hline Dihydroartenninin B (**479**) & 3H-Oxierno[7,8]naphth[8a,1-b]furan-3-one, & [64390-16-5] & [166] \\  & decahydro-4,7,9a-trimethyl- [1 aR- & & \\  & (1 aa,1 bk,4a,4 aB,7b,7 aI,9 aa9a)]- & & \\ \hline
11\(R\)-(-)Dihydroortnismic acid (**480**) & 4,11(13)-Amorphaden-12-oic acid (11\(R\),13-dihydro) & [85031-59-0] & [20, 32, 43, 135, 166, 167, 216] \\ \hline Dihydroortnismic acid hydroperoxide (**481**) & 4-Hydroxperoyders-5-amorphen-12-oic acid, 4a, 11\(R\) & [85031-60-3] & [167, 170, 185] \\ \hline Dihydroortnismic alcohol (**482**) & 1-Naphthalene[1,1,2,3,4a,5,6,8a-octahydro- & [855425-50-2] & [135] \\  & _a.4_,7-trimethyl-, (1\(R\),4\(R\),4\(S\),4\(S\),4\(S\))- & & \\ \hline Dihydroortnismic aldehyde (**483**) & 1-Naphthalene[1,2,3,4,4a  
It is interesting to note that nine of the structures reported in Tables 36 and 38 occur in both their 11,13-dihydro and 11,13-dehydro forms. These nine pairs are listed in Table 37.  
Feeding labelled dihydroartemisinin acid (**480**) to _A. annua_ resulted in sixteen labelled amorphane and cadinane sesquiterpenes [185], which included all nine of the 11,13-dihydro forms in the \"pairs\" in Table 37 (*The complete list of metabolites of (**480**) is: artemisinin (**495**), dihydroarteannuin B (**479**), dihydro-_epi_-deoxyarteannuin B (**485**), arteannuin M (**470**), the _seco_-cadinane (**493**), the tertiary hydroperoxide of dihydroartemisinin acid (**481**), dihydro-deoxyarteannuin B (**484**), deoxyartemisinin (**499**), arteannuin K (**468**), arteannuin L (**469**), arteannuin H (**465**), arteannuin I (**466**), arteannuin J (**467**) and \(\alpha\)-epoxy-dihydroartemisinin acid (**488**).