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Review
. 2021 May 26;38(5):905-980.
doi: 10.1039/d0np00066c.

Bacterial terpenome

Jeffrey D Rudolf  1 , Tyler A Alsup  1 , Baofu Xu  1 , Zining Li  1
Affiliations
Review

Bacterial terpenome

Jeffrey D Rudolf et al. Nat Prod Rep. .

Abstract

Covering: up to mid-2020 Terpenoids, also called isoprenoids, are the largest and most structurally diverse family of natural products. Found in all domains of life, there are over 80 000 known compounds. The majority of characterized terpenoids, which include some of the most well known, pharmaceutically relevant, and commercially valuable natural products, are produced by plants and fungi. Comparatively, terpenoids of bacterial origin are rare. This is counter-intuitive to the fact that recent microbial genomics revealed that almost all bacteria have the biosynthetic potential to create the C5 building blocks necessary for terpenoid biosynthesis. In this review, we catalogue terpenoids produced by bacteria. We collected 1062 natural products, consisting of both primary and secondary metabolites, and classified them into two major families and 55 distinct subfamilies. To highlight the structural and chemical space of bacterial terpenoids, we discuss their structures, biosynthesis, and biological activities. Although the bacterial terpenome is relatively small, it presents a fascinating dichotomy for future research. Similarities between bacterial and non-bacterial terpenoids and their biosynthetic pathways provides alternative model systems for detailed characterization while the abundance of novel skeletons, biosynthetic pathways, and bioactivies presents new opportunities for drug discovery, genome mining, and enzymology.

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Conflict of interest statement

Conflicts of interest

There are no conflicts of interest to declare.

Figures

Fig. 1
Fig. 1
Summary of bacterial terpenoids in the literature. (A) Number of terpenoids discovered in bacteria per year. The orange line is a moving average of five years. Count for 2020 only includes up to mid-2020. (B) Distribution of terpenoids. The parenthetical numbers represent the number of bacterial terpenoids compiled in this review.
Scheme 1
Scheme 1
The biosynthesis of terpenoids.
Scheme 2
Scheme 2
Biosynthesis of 1,8-cineole (22) and 2-MIB (23).
Scheme 3
Scheme 3
Biosynthesis of geosmin (121).
Scheme 4
Scheme 4
Biosynthesis of PNT (139) and neopentalenoketolactone (147).
Scheme 5
Scheme 5
Biosynthesis of albaflavenone (155).
Scheme 6
Scheme 6
Biosynthesis of sodorifen (178).
Scheme 7
Scheme 7
Biosynthesis of phenalinolactone A (198).
Scheme 8
Scheme 8
Biosynthesis of cyclooctatin (214).
Scheme 9
Scheme 9
Biosynthesis of cyslabdan (226).
Scheme 10
Scheme 10
Biosynthesis of GA9 (235) and GA4 (234).
Scheme 11
Scheme 11
Biosynthesis of PTM (265), PTN (266), and their thioacid analogues (278 and 279).
Scheme 12
Scheme 12
Biosynthesis of novobiocin (456).
Scheme 13
Scheme 13
Biosynthesis of virantmycin (474) and 7-hydroxylbenzastatin F (499).
Scheme 14
Scheme 14
Biosynthesis of hapalindoles 538, 539, 541, and 567 and ambiguines 578 and 591.
Scheme 15
Scheme 15
Biosynthesis of xiamycin A (613), oxiamycin (624), dixiamycin A (625), and sespenine (623).
Scheme 16
Scheme 16
Prenylation and cyclization of ComX pheromones.
Scheme 17
Scheme 17
Biosynthesis of lyngbyatoxin A (712), teleocidin B-1 (714), teleocidin B-4 (717), des-O-methylolivoretin C (721), and pendolmycin (724).
Scheme 18
Scheme 18
Biosynthesis of nocardioazine A (749).
Scheme 19
Scheme 19
Biosynthesis of lavanducyanin (799).
Scheme 20
Scheme 20
Biosynthesis of KS-505a (836).
Scheme 21
Scheme 21
Biosynthesis of furaquinocin A (855), furanonaphthoquinone I (867), napyradiomycin B1 (875), and merochlorins A–C (953–955).
Scheme 22
Scheme 22
Biosynthesis of aurachins A (985), B (986), C (987), and D (988).
Scheme 23
Scheme 23
Biosynthesis of menaquinones (1022).
Scheme 24
Scheme 24
Biosynthesis of diazepinomicin (1029).
Scheme 25
Scheme 25
Biosynthesis of moenomycin A (1034).
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References

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