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 Provisional chapter

Introductory Chapter: Terpenes and Terpenoids

Shagufta Perveen
Shagufta Perveen

Additional information is available at the end of the chapter

1. Terpenes and terpenoids

Natural products are the compounds which isolate from different natural sources such as
plants, animals, microbes, insects, plant pathogens, and endophytes and marine. These are
known as secondary metabolites since they are formed due to the enzymatic resections of
primary metabolites (amino acids, sugars, vitamins, etc.). Terpenes belong to the biggest

Figure 1. Classification of terpenes.

© 2016 The Author(s). Licensee InTech. This chapter is distributed under the terms of the Creative Commons
© 2018 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative
Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use,
Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use,
distribution, and reproduction in any medium, provided the original work is properly cited.
distribution, and reproduction in any medium, provided the original work is properly cited.
2 Terpenes and Terpenoids

class of secondary metabolites and basically consist of five carbon isoprene units which are
assembled to each other (many isoprene units) by thousands of ways. Terpenes are simple
hydrocarbons, while terpenoids are modified class of terpenes with different functional
groups and oxidized methyl group moved or removed at various positions. Terpenoids
are divided into monoterpenes, sesquiterpenes, diterpenes, sesterpenes, and triterpenes
depending on its carbon units (Figure 1). Most of the terpenoids with the variation in their
structures are biologically active and are used worldwide for the treatment of many dis-
eases. Many terpenoids inhibited different human cancer cells and are used as anticancer
drugs such as Taxol and its derivatives. Many flavorings and nice fragrances are consisting
on terpenes because of its nice aroma. Terpenes and its derivatives are used as antimalarial
drugs such as artemisinin and related compounds. Meanwhile, terpenoids play a diverse
role in the field of foods, drugs, cosmetics, hormones, vitamins, and so on. This chapter
provides introduction and information on the bioactive terpenes isolated currently from dif-
ferent natural sources.

2. Monoterpenes

Monoterpenes consist of 10 carbon atoms with two isoprene units and molecular formula
C10H16. These are naturally present in the essential and fixed oils of plants and related sources.
Monoterpenes are structurally divided into the acyclic, monocyclic, and bicyclic type of

Names Plant source Activity Ref.

9-OH-isoegomaketone Leaves of Perilla It exhibited inhibitory activity on nitric oxide (NO) [2]
[(2E)-1-(3-furanyl)-4-OH-4- frutescens var. production in lipopolysaccharide (LPS)-activated
Me-2-penten-1-one crispa RAW264.7 cells with an IC50 value of 14.4 μM. Compounds
in the SC-CO2 extracts of the radiation mutant cultivar and
the original plant were quantified by high-performance
liquid chromatography with diode array detection.

Table 1. Source and biological activities of some monoterpenes.

Figure 2. Structure of monoterpene.

 Introductory Chapter: Terpenes and Terpenoids 3

compound. The compounds belong to this class usually have strong aroma and odor and
are used in many pharmaceutical companies. Mixture of different monoterpene-based oils is
used as fragrances for making perfumes and in other cosmetics. Most of the monoterpenes
are active biologically with strong antibacterial activities. Several studies have shown in vitro
and in vivo antitumor activity of many essential oils obtained from plants. The antitumor
activity of essential oils of many species has been related to the presence of monoterpenes in
their composition [1]. Herein, we are discussing some of the recently published active mono-
terpenes (Table 1, Figure 2).

3. Sesquiterpenes

Sesquiterpenes are the class of secondary metabolites consisting of three isoprene units (C15H24)
and found in linear, cyclic, bicyclic, and tricyclic forms. Sesquiterpenes are also found in the
form of lactone ring (Table 2). Many of the latex in latex-producing plants contain sesquiter-
pene, and these are potent antimicrobial and anti-insecticidal agent. Artemisinin, a sesquiter-
pene lactone, one of the most active compounds in Artemisia annua shoots and roots (Figure 3).

Names Plant source Activity Ref.

Arvestolides H and I Artemisia vestita H and I showed inhibitory effects on nitric [3]
oxide production in BV-2 cells induced by
lipopolysaccharide with IC50 values of 43.2
and 39.9 μM, respectively.

Drimenin Canelo tree Drimys winteri Potency for drimenin at the hα4β2 AChR [4]
(0.97 μM) is several folds higher than that
for other clinically used antidepressants
using the same method. It could be used as
a molecular scaffold for the development of
more potent inhibitors with higher selectivity
for the hα4β2 AChR.

Artefreynic acid B, C, Artemisia freyniana B, C, and G exhibited inhibitory effects [5]

and G against LPS-stimulated nitric oxide (NO)
production in RAW 264.7 macrophage cells
with IC50 values of 10.8, 12.6, and 11.7 μM,
respectively.

Chrysanthemulide A Chrysanthemum indicum Mechanistic study revealed that the potential [6]
anti-inflammatory activity of A appears to be
mediated via suppression of an LPS-induced
NF-κB pathway and downregulation of
MAPK activation.

14-O-Acetylinsulicolide Marine-derived Aspergillus These compounds were evaluated for their [7]
A, 6β,9α-dihydroxy-14-p- ochraceus fungus cytotoxicities against three renal carcinoma
nitrobenzoylcinnamolide, cell lines, ACHN, OS-RC-2, and 786-O cells,
insulicolide A and it displayed activities with IC50 values of
0.89–8.2 μM. Further studies indicated that
it arrested the cell cycle at the G0/G1 phase
at a concentration of 1 μM and induced late
apoptosis at a concentration of 2 μM after a
72 h treatment of 786-O cells.
4 Terpenes and Terpenoids

Names Plant source Activity Ref.

Santhemoidin A Tarchonanthus camphoratus A was the most active compound found [8]
and Schkuhria pinnata in this study, with IC50 values of 0.10 μM
against Trypanosoma brucei rhodesiense
trypomastigotes and selectivity indices of
20.5, respectively.

Table 2. Source and biological activities of some sesquiterpenes.

Figure 3. Structures of sesquiterpenes.

 Introductory Chapter: Terpenes and Terpenoids 5

4. Diterpenes

Diterpenoids belong to a versatile class of chemical constituents found in different natural

sources having C20H32 molecular formula and four isoprene units (Figure 4). This class of com-
pounds showed significant biological activities including anti-inflammatory, antimicrobial,

Figure 4. Structure of diterpenes.

6 Terpenes and Terpenoids

Names Plant source Activity Ref.

Genkwanine P and Buds of Wikstroemia Compounds exhibited potential antihepatitis [9]
laurifolioside A chamaedaphne B virus activities with IC50 46.5 and 88.3 mg/mL
against HBsAg.

Cephinoids H Cephalotaxus fortunei var. H demonstrated an inhibition of 49.0% by [10]

alpina and C. lanceolata administration to zebra fish at a dose of 60.0 ng/mL,
compared to cisplatin (DDP, 22.4%) at 15.0 μg/mL. It
might affect the NF-κB signaling pathway rather than
binding to microtubules. Additionally, it showed
almost equal anti-inflammatory activities compared
to the positive control, MG132.

Nudiflopene F and I Leaves of Callicarpa F and I have strong interactions with the iNOS [11]
nudiflora protein by targeting residues of the active cavities of
iNOS n BV-2 cells (IC50 28.1 and 23.3).

Drechmerin B Endophytic fungus B displayed antimicrobial activity against C. albicans [12]

Drechmeria sp. with an MIC value of 12.5 μg/mL.

Nicaeenin F Latex of Euphorbia F showed significant potential to inhibit [13]

nicaeensis P-glycoprotein (P-gp) activity in two MDR cancer
cells (NCI-H460/R and DLD1-TxR).

Nicaeenin G Latex of E. nicaeensis G showed significant potential to inhibit [13]

P-glycoprotein (P-gp) activity in two MDR
cancer cells (NCI-H460/R and DLD1-TxR). G also
significantly stronger chemosensitized NCI-H460/R
cells to DOX compared to Dexverapamil due to
prolonged effect of P-gp inhibition that persisted for
72 h.

Eupheliotriol F and L Euphorbia helioscopia F and L exhibited significant cytotoxicity against [14]
MCF-7 and PANC-1 cell lines.

Table 3. Source and biological activities of some diterpenes.

anticancer, and antifungal activities. Some of the diterpenes also have cardiovascular activity,
such as grayanotoxin, forskolin, eleganolone, marrubenol, and 14-deoxyandrographolide.
Kaurane and pimarane-type diterpenes are also biologically active metabolites isolated from
the roots and leaves of different plants (Table 3).

5. Sesterpenes

Sesterpenes consist of 25 carbon atoms with 5 isoprene units and molecular formula
C25H40 (Figure 5). These are naturally present in the fungus, marine organism, insects,
sponges, lichens, and protective waxes of insects. These types of compounds are biologi-
cally active having anti-inflammatory, anticancer, antimicrobial, and antifungal activities
(Table 4).
 Introductory Chapter: Terpenes and Terpenoids 7

Figure 5. Structures of sesterpenes.

Names Plant source Activity Ref.

Cybastacines A Nostoc sp. Cyanobacterium A and B showed moderate in vitro antibiotic [15]
and B activities. Sesterterpenes are rare among microbial
secondary metabolites, with only one report
of a previous alkaloid—sesterterpene found in
cyanobacteria. This discovery represents a significant
addition to the novel chemical structures active
against resistant bacterial strains.

Scalarane Mushroom species, Pleurotus This compound exhibited moderate micromolar [16]
sesterterpenes ostreatus and Scleroderma activity against P. falciparum 3D7 and T. cruzi
areolatum Tulahuen C4 parasites. It showed <50% inhibition at
25 μM, when incubated with the tumoral liver cell
line, HepG2 (HB-8065) for 72 h.

Table 4. Source and biological activities of some sesterpenes.

8 Terpenes and Terpenoids

6. Triterpenes

A major class of secondary metabolites are known as triterpenes and it usually contains
30 carbon atoms consisting of 6 isoprene units (Figure 6). It is derived from the squalene
biosynthetic pathway. Triterpenes have many methyl groups and it can be oxidized into
alcohols, aldehydes, and carboxylic acids, which make it complex and differentiate it bio-
logically. Triterpenes have many active sites for the glycosylation which converts it into
another big class of compounds, namely, saponins (triterpene glycoside). Herein, we are
discussing some recently published bioactive triterpenes (Table 5).

Figure 6. Structure of triterpenes.

 Introductory Chapter: Terpenes and Terpenoids 9

Names Plant source Activity Ref.

Polyporenic acid B Fruiting bodies of It showed strong cytotoxicity against the HCT116, A549, [17]
Fomitopsis palustris and HepG2 cell lines with IC50 values of 8.4, 12.1, and
12.2 μM, respectively.
Pardinol B Tricholoma pardinum Compound showed strong cytotoxicity against HL-60 [18]
SMMC-7721 A-549 MCF-7 SW480, 8.3, 15.0, 14.4, 12.7,
15.0 μM, respectively.
Pardinol E T. pardinum E exhibited strong cytotoxicity against HL-60 SMMC- [18]
7721 A-549 MCF-7 SW480, 9.8, 11.7, 9.8 11.9, 15.6, μM,
respectively
Pardinol F T. pardinum F showed strong cytotoxicity against HL-60 SMMC-7721 [18]
A-549 MCF-7 SW480, 11.2, 15.6, 12.6, 10.5, 14.1 μM,
respectively.
Xuedanencins G Tubers of Hemsleya G and H were evaluated for cytotoxic activity against [19]
and H penxianensis the Hela human cancer cell line and compounds showed
significant cytotoxicity with IC50 value at 1.82 and
2.45 μM, respectively.
Cyclocariols A, B, Leaves of Cyclocarya A, B, and H were tested against human colon tumor [20]
and H paliurus (HCT-116) cell lines, exhibited good activities with IC50
values of 6.53, 4.94, and 6.48 μM, respectively.

Table 5. Source and biological activities of some triterpenes.

7. Meroterpenes

Meroterpenes are the secondary metabolites with partial terpenoid skeleton. Meroterpenoids
were partially derived from mevalonic acid pathways and widely derived from animals, plants,

Figure 7. Structures of meroterpenes.

10 Terpenes and Terpenoids

Names Plant source Activity Ref.

Amestolkolide B Mangrove endophytic B showed strong anti-inflammatory activity [22]
fungus Talaromyces in vitro by inhibiting nitric oxide (NO)
amestolkiae YX1 production in lipopolysaccharide activated in
RAW264.7 cells with IC50 value of 1.6 ± 0.1 mM.

6-OH-3-Me-8- Liverwort Radula This compound showed activity against the [23]
phenylethylbenzo[b] sumatrana human cancer cell lines MCF-7, PC-3, and
oxepin-5-one SMMC-7721, with IC50 values of 3.86, 6.60, and
3.58 μM, respectively, and induced MCF-7
cell death through a mitochondria-mediated
apoptosis pathway.

Spiroapplanatumines G Ganoderma applanatum Biological evaluation of compound 7 inhibited [24]

JAK3 kinase with IC50 values of 7.0 μM

Table 6. Source and biological activities of some meroterpenes.

bacteria, and fungi [21] (Figure 7). Meroterpene biosynthesis expands the diversity available
to isoprenoid pathways alone and allows for the assembly of natural products with highly
unique structural attributes. Organisms belonging to the fungal kingdom have become profi-
cient at exploiting this broad chemical synthesis platform for complex metabolite production.
Herein, we are discussing some of the recently published bioactive meroterpenes (Table 6).

Acknowledgements

This research project was supported by a grant from the “Research Center of the Female
Scientific and Medical Colleges,” Deanship of Scientific Research, King Saud University.

Author details

Shagufta Perveen

Address all correspondence to: [email protected]

Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh,

Saudi Arabia

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