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The ritterazine class of steroidal alkaloids comprises 26 compounds (672–697),
all of which had been discovered in the lipophilic extract of the tunicate
Ritterella tokioka collected off the Izu Peninsula by Fusetani and colleagues (Table 17).
Kobayashi et al. isolated a brand new family of abeo-9(10-19)-androstane-type steroidal alkaloids
with oxabicyclo[3.2.1]octane referred to
as cortistatins, from the Indonesian marine sponge
Corticium simplex (Fig. 17, Table 15) [314]. Up to now, this family has eleven members
(641–651), with the B and C rings linked by way of an attention-grabbing and
attribute oxo-bridge. Verdine (412) was first separated from
the bulbs of Veratrum dahuricum in 1980 [191], and its construction was
finally elucidated in 1984 by X-ray diffraction [192].
Two new steroidal alkaloids, kuroyurinidine (417) [193] and 23-isokuroyurinidine
(418) [194], bearing C-2β, C-3α, and C-6β hydroxyl groups, were discovered in the genus Fritillaria.
Entire crops of Veratrum taliense have yielded a novel steroidal alkaloid, 6,7-epoxyverdine (437),
whose structure with an epoxide functionality at C-5/C-6 was determined by
2D NMR spectroscopic analysis [195].
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Moreover, 17-HSD enzyme has been isolated and characterised from an intestinal Eubacterium sp.
[60], suggesting that colon bacteria might additionally play a role in androstenedione metabolism.
The impact of the intestine microbiota on the metabolism of androstenedione and its
completely different analogues is much less well-understood, particularly given the inter-individual variability of gut
composition, and should be examined sooner or later. Androstenedione was also found in the Fenholloway River water
column, doubtless derived from the microbial degradation of several
phytosteroids, such as stigmastanol, β-sitosterol, and campesterol.
For instance, the microbial conversion of phytosterols is being extensively applied for the production of steroidal drug intermediates similar to AD and
9-OHAD (9-hydroxy-4-androstene-3,17-dione) [30,31,32].
These phytosteroids are present in wastes created from
the conversion of pine tree into pulp [33].