30
H. Zhu et al.
ring. The pyrichalasin group in total contains 46 members (Tables 8, 9 and 10 and
Figs. 8, 9 and 10), including several compounds obtained by bioconversion or gene
manipulation procedures.
2.2.1 Carbocyclic Pyrichalasins
This type of pyrichalasin contains a tricyclic [5.6.11] core structure (Table 8 and
Fig. 8), and is similar to the [5.6.11]-cytochalasins—and therefore the most common
type of pyrichalasins. Pyrichalasin H (164) [89], the first example of a pyrichalasin,
was isolated from Pyricularia grisea IFO7287 by Nukina in 1987, when the name
“pyrichalasin” was first introduced for this type of compound.
As mentioned previously, bioconversion of L-696,474 (26) using Actinoplanes sp.
ATCC 53771, provided a series of new pyrichalasins, including 22,29-dihydroxy-L696,474 (165), 22,28-dihydroxy-L-696,474 (166), 22,28,29-trihydroxy-L-696,474
(167), and 16β,22,28-trihydroxy-L-696,474 (168) as well as two new cytochalasins
[14]. Thus, this bioconversion process introduced hydroxy groups at C-16 and C-21
and also on the benzene ring of L-696,474 (26).
During the investigation of the biosynthesis pathway of pyrichalasin H (164),
Skellam and coworkers obtained a series of new pyrichalasins (175–189) from
Magnaporthe grisea NI980, using a gene knockout strategy [8], and this study
also revealed that the non-proteinogenic amino acid O-methyltyrosine is the true
precursor of pyrichalasin H (164). Interestingly, both compounds 181 and 184 exhibit
Table 8 [5.6.11]- and [5.6.13]-Pyrichalasins
Compound
Origin
References
Pyrichalasin H (164)
Pyricularia sp. IFO 7287
[89]
22,29-Dihydroxy-L-696,474 (165)
Actinoplanes sp. ATCC 53771
[14]
22,28-Dihydroxy-L-696,474 (166)
Actinoplanes sp. ATCC 53771
[14]
22,28,29-Trihydroxy-L-696,474 (167)
Actinoplanes sp. ATCC 53771
[14]
16β,22,28-Trihydroxy-L-696,474 (168)
Actinoplanes sp. ATCC 53771
[14]
4 -Hydroxy-deacetyl-18-deoxycytochalasin H
(169)
Trichoderma harzianum
[95]
Phomopsichalasin F (170)
Phomopsis spp. xy21 and xy22 [53]
Phomopsichalasin G (171)
Phomopsis spp. xy21 and xy22 [53]
Compound 19 (172)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
Compound 20 (173)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
Compound 21 (174)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
(continued)
H. Zhu et al.
ring. The pyrichalasin group in total contains 46 members (Tables 8, 9 and 10 and
Figs. 8, 9 and 10), including several compounds obtained by bioconversion or gene
manipulation procedures.
2.2.1 Carbocyclic Pyrichalasins
This type of pyrichalasin contains a tricyclic [5.6.11] core structure (Table 8 and
Fig. 8), and is similar to the [5.6.11]-cytochalasins—and therefore the most common
type of pyrichalasins. Pyrichalasin H (164) [89], the first example of a pyrichalasin,
was isolated from Pyricularia grisea IFO7287 by Nukina in 1987, when the name
“pyrichalasin” was first introduced for this type of compound.
As mentioned previously, bioconversion of L-696,474 (26) using Actinoplanes sp.
ATCC 53771, provided a series of new pyrichalasins, including 22,29-dihydroxy-L696,474 (165), 22,28-dihydroxy-L-696,474 (166), 22,28,29-trihydroxy-L-696,474
(167), and 16β,22,28-trihydroxy-L-696,474 (168) as well as two new cytochalasins
[14]. Thus, this bioconversion process introduced hydroxy groups at C-16 and C-21
and also on the benzene ring of L-696,474 (26).
During the investigation of the biosynthesis pathway of pyrichalasin H (164),
Skellam and coworkers obtained a series of new pyrichalasins (175–189) from
Magnaporthe grisea NI980, using a gene knockout strategy [8], and this study
also revealed that the non-proteinogenic amino acid O-methyltyrosine is the true
precursor of pyrichalasin H (164). Interestingly, both compounds 181 and 184 exhibit
Table 8 [5.6.11]- and [5.6.13]-Pyrichalasins
Compound
Origin
References
Pyrichalasin H (164)
Pyricularia sp. IFO 7287
[89]
22,29-Dihydroxy-L-696,474 (165)
Actinoplanes sp. ATCC 53771
[14]
22,28-Dihydroxy-L-696,474 (166)
Actinoplanes sp. ATCC 53771
[14]
22,28,29-Trihydroxy-L-696,474 (167)
Actinoplanes sp. ATCC 53771
[14]
16β,22,28-Trihydroxy-L-696,474 (168)
Actinoplanes sp. ATCC 53771
[14]
4 -Hydroxy-deacetyl-18-deoxycytochalasin H
(169)
Trichoderma harzianum
[95]
Phomopsichalasin F (170)
Phomopsis spp. xy21 and xy22 [53]
Phomopsichalasin G (171)
Phomopsis spp. xy21 and xy22 [53]
Compound 19 (172)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
Compound 20 (173)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
Compound 21 (174)
Org Lett (2019) 21:8756
Hypoxylon fragiforme MUCL
51264
[55]
(continued)