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Review
. 2021 Jan 18;26(2):488.
doi: 10.3390/molecules26020488.

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

Afrah E Mohammed  1 , Zainab H Abdul-Hameed  2 , Modhi O Alotaibi  1 , Nahed O Bawakid  2 , Tariq R Sobahi  2 , Ahmed Abdel-Lateff  3   4 , Walied M Alarif  5
Affiliations
Review

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

Afrah E Mohammed et al. Molecules. .

Abstract

By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (Alstonia, Rauvolfia, Kopsia, Ervatamia, and Tabernaemontana, and Rhazya) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.

Keywords: Apocynaceae; alkaloids; anti-inflammatory; antimicrobial; cytotoxicity; monoterpene.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Biogenetic numbering rule as adopted from LeMen and Tylor.
Figure 2
Figure 2
Examples of well-known biologically active terpene indole alkaloids.
Figure 3
Figure 3
The types of the structures identified monoterpenoid alkaloids from the six genera.
Figure 4
Figure 4
Common monoterpenoid indole alkaloidal skeletons of the six genera.
Figure 5
Figure 5
Compounds 1–22.
Figure 6
Figure 6
Compounds 23–30.
Figure 7
Figure 7
Compounds 31–38.
Figure 8
Figure 8
Compounds 39–51.
Figure 9
Figure 9
Compounds 52–60.
Figure 10
Figure 10
Compounds 61–70.
Figure 11
Figure 11
Compounds 71–90.
Figure 12
Figure 12
Compounds 91–97.
Figure 13
Figure 13
Compounds 98–109.
Figure 14
Figure 14
Compounds 110–114.
Figure 15
Figure 15
Compounds 115–135.
Figure 16
Figure 16
Compounds 136–145.
Figure 17
Figure 17
Compounds 146–157.
Figure 18
Figure 18
Compounds 158–170.
Figure 19
Figure 19
Compounds 171–197.
Figure 20
Figure 20
Compounds 198–227.
Figure 21
Figure 21
Compounds 228–253.
Figure 22
Figure 22
Compounds 254–268.
Figure 23
Figure 23
Compounds 269–283.
Figure 24
Figure 24
Compounds 284–303.
Figure 25
Figure 25
Compounds 304–318.
Figure 26
Figure 26
Compounds 319–332.
Figure 27
Figure 27
Compounds 333–353.
Figure 28
Figure 28
Compounds 354–369.
Figure 29
Figure 29
Compounds 370–384.
Figure 30
Figure 30
Compounds 385–394.
Figure 31
Figure 31
Compounds 395–406.
Figure 32
Figure 32
Compounds 407–417.
Figure 33
Figure 33
Compounds 418–444.
Scheme 1
Scheme 1
Biosynthesis of corynanthe, aspidosperma and iboga indoles.
Scheme 2
Scheme 2
Biosynthesis of ajmaline indole alkaloids. (SB) Sarpagan bridge enzyme; polyneuridine aldehyde reductase (PNAE), vinorine synthase (VS), vinorine hydroxylase (VH), vomilenine reductase (VR), dihydrovomilenine reductase (DHVR) 17-O-acetyl-ajmalanesterase (AAE), norajmaline-N-methyltransferase (NMT).
Figure 34
Figure 34
Number of compounds isolated from the six genera.
Figure 35
Figure 35
Percentage of reported compounds from the species.
Figure 36
Figure 36
Number of compounds identified from different organs.
Figure 37
Figure 37
Number of compounds versus biological activities.
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