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183
Apoptoticmolecules
(ATF3, Apaf -1,AIF,
Thrombone, PTEN,
Integrin apha-5 andbeta-6,
Rab27a,FADD, E-cadherin)
MechanismofActionof
C.speciosusasanticancer
in in-vitro stud ies
Up regulatory
mechanismofaction
by followingmolecules
Down regulatory
mechanismofaction
by followingmolecules
P21, P27,P53
Caspase
Bax
ROS
P13- Kinase/Akt
Cell Cycleregulatory
components:Cdk-1,2,4
Cdc(25 B,42)
Cyclin (A,B,D)
Cell CyclePhase Arrest:
G0/G1, G1,G1/S, G2/M
Bcl-2, Bcl-xL,STAT, JAK,
MMPs,Angiogenesis,
CXCR-4,CXCL-12, P100,
P52,P38
Fig. 8.5 Action mechanism of C. speciosus as anticancer potential in in-vitro studies [55]
AntiapoptoticMolecules:
Actin, Beta-Catenin,
ERKK,C-FLIP,
EGFR,SMO,TNF-alpa,
hTERT, HGF,MAPKs
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S. Aslam etal.
8.7.1 Medicinal Uses ofDiosgenin
Diosgenin has a number of health advantages, including the inhibition of colon cancer, climacteric syndrome, and heart disease [57]. Diosgenin was exhibited the potential to reduce postmenopausal symptoms [58]. Diosgenin is an antispasmodic that
can be used to treat contractions, coughing, and muscle twinges [59]. Diosgenin is a
potent phytochemical and is utilized for the purpose of inducing apoptosis in cancer
cells and lower the blood pressure [60]. Diosgenin has been utilized in traditional
medicine as an antihypertriacylglycerolimia, antihyperglycemic, antidiabetic, antihypercholesterolemia, and antileukemia drug [61], according to recent investigations. Diosgenin has been used to maintain the healthy blood cholesterol levels as
well as generation of dehydroepiandrosterone. The continual release of diosgenin has
been reported to inhibit bone loss in the same way as estrogen does [62]. Consumption
of diosgenin also exhibited anti-stress and anti-inammatory properties (Fig.8.6) [59].
8.7.2 Role ofDisogenin inSkin Aging
Skin ageing is the result of both natural ageing and ageing caused by environmental
factors like UV light exposure. It is related with impaired epidermal cell degenerative and turnover alterations in dermal elastic bres, resulting in dry skin, epidermal
Fig. 8.6 Medicinal properties of Diosgenin
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thinning, wrinkles or lentigines, [63]. A research aiming to evaluate the efcacy of
diosgenin against skin ageing, it was discovered that diosgenin may increase DNA
synthesis as well as keratinocyte proliferation by activating cAMP signals without
involving oestrogen receptors. Diosgenin raised bromodeoxyuridine absorption and
intracellular cAMP level in adult human keratinocytes invitro and increased DNA
synthesis in a human 3D skin comparable model. An adenylate cyclase inhibitor
blocked the increase in bromodeoxyuridine accumulation by diosgenin but not antisense oligonucleotides against an orphan G-protein-coupled receptors GPR30, or
oestrogen receptor, indicating the involvement of cAMP but not oestrogen receptor,
or GPR30. In vivo, diosgenin treatment enhanced epidermal thickness in ovariectomized mice, a climacteric model, without affecting fat formation. To test the safety
of diosgenin, breast cancer-ridden mice were given diosgenin and 17-estradiol. In a
climacteric mouse model, diosgenin (0.01%, 0.02%, and 0.04% mixed in baseline
diet) enhances epidermal thickness [64]. Furthermore, diosgenin (1–50mol/L) suppresses melanogenesis in B16 melanoma cells via the PI3K pathway activation,
suggesting that diosgenin may be an effective hyperpigmentation inhibitor in the
therapeutical treatment of skin illnesses such as acquired hyperpigmentation situations [65]. The ndings demonstrated that, whereas 17-estradiol increased tumour
development, diosgenin did not. Moreover, discovery of keratinocyte proliferation
restoration in aged skin shows that diosgenin may have promise as a safe healthy
food for climacterics [64].
185
8.7.3 Role ofDisogenin inDiabetes
Diabetes mellitus is a severe as well as widespread metabolic disorder that poses a
major threat to human health. Diabetes’ hyperglycemia and long-term metabolic
abnormalities will harm the tissues and organs of entire body, culminating in catastrophic consequences. Diabetes is classied into two types: type I (T1DM) and
type II (T2DM) (T2DM). T1DM is an insulin-dependent illness caused by inadequate insulin secretion [66]. T2DM is caused by insulin release abnormalities or is
the result of insulin usage disorders [67, 68]. According to the International
Federation of Diabetes, the global diabetes population has reached 425 million,
with T1DM accounting for 5–10% of the diabetic population and T2DM accounting
for 90–95% [69–71]. Diabetes affects a large number of individuals worldwide, and
diabetes treatment remains a challenging issue. Because the medications on the
market for treating diabetes have severe adverse effects, new therapies are urgently
needed. Natural therapy using phytochemicals is a potential way towards the safe
and effective treatment of diabetes. Diosgenin is a potent bioactive natural steroidal
sapogenin [72]. Diosgenin has been shown in studies to help treat diabetes by reducing oxidative stress and malfunctioning lipid metabolism [73]. Based on the pharmacological actions of Diosgenin including hypoglycemic activity, hypolipidemic,
anti-proliferative, anti-inammatory, and as a potent anti-oxidant, it has a positive
impact on diabetes and its consequences via many targets and pathways. In recent
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years, an increasing number of anti-diabetic studies have revealed that diosgenin
exhibited excellent anti-diabetic potential both in in vitro and in vivo, consequently
it is becoming increasingly popular as a natural treatment. However, no comprehensive investigation has been conducted to assess the preventive and possible mechanisms of diosgenin for diabetes and its consequences [74–76].
S. Aslam etal.
8.7.4 Medicinal Uses ofDioscin
Dioscin is a biologically active molecule with antioxidative, antiobesity [77], hepatoprotective [78], and antitumor [79] capabilities, anti-inammatory, among other
ethnopharmacological and physiological properties. This phytochemical protects
against cancer, gastrointestinal illnesses, cardiovascular and cerebrovascular diseases, organ toxicity by adjusting various cellular targets and inuencing different
signaling pathways in the human body. Dioscin’s advantages have been widely recognised in traditional Chinese medicine for decades [78].
Millions of individuals throughout the world are suffering from diabetes mellitus. By altering illness-associated signalling pathways, dioscin controls disease
development in diabetics. The effects of dioscin on glycolipid metabolism in
insulin- induced HepG2 cells, and spontaneous T2DM KK-Ay mice were reported.
Dioscin effectively decreased the lipid accumulation, hyperglycemia, and hyperlipidaemia, as well as enhanced insulin resistance, and improved the concentration of
hepatic glycogen. It also caused miR-125a-5p to have an inhibitory impact on
STAT3 (signal transducer and activator of transcription 3) signalling, which is generally stimulated throughout the sickness [79].The pharmacological activities of
dioscin are widely recognized [80, 81].
Obesity is regarded as a severe health issue, since it is linked to hypertension,
heart disease, and an increased risk of death. To combat the side effects of the high
cost of bariatric surgery and antiobesity medicines, phytochemicals like dioscin are
becoming a new target of study for reducing disease severity [82].
8.8 Synthesis ofPotent Phytochemicals
In this section synthesis of different potent phytochemicals of Costus plant are
briey discussed.
8.8.1 Biosynthesis ofDiosgenin
Many steroidal medications, including anti-inammatory, antioxidants, steroids,
cortisone, sex hormones, fertility control chemicals, contraceptives, as well as anabolic agents, are made from diosgenin [83–85]. C-16,22-Dihydroxylase and C-26
HO
4
Diosgenin
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OH
OH
187
HO
SpontaneousDzinCYP90G6
O
HO
Cholestrol
HO
Scheme 8.1 Biosynthetic pathway of Diosgenin
Dihydroxycholestrol
O
O
Spontaneous
HO
DzinCYP94D14
OH
HO
O
HO
hydroxylase [86] are two P450 enzymes that are used to catalyze the production of
diosgenin from the starting material such as cholesterol in Dioscorea [87]
(Scheme 8.1).
8.8.2 Chemical Synthesis ofDioscin
The most frequent steroid saponins in plants are spirostan-type saponins. They have
a hexacyclic aglycone, like tigogenin or diosgenin or with an oligosaccharide chain
attached to the 3-OH group. Dioscin is among the most extensively distributed steroid saponins in plants, has been discovered in a variety of traditional Chinese
herbal remedies and possesses anti-inammatory, antifungal, anticancer, immunestimulatory, and antiviral properties. To synthesize dioscin, a number of methods
were explored, the most easy and efcient of which was produced in ve stages
from diosgenin. The TMSOTf-catalyzed glycosylation reaction between diosgenin
and perbenzoylated glucopyranosyl N-phenyl triuoroacetimidate donor 1 was the
rst step in the synthesis. In 92% of cases, this reaction yielded the equivalent
3-O-glycoside intermediate 2. The 2′,4′-diol acceptor was then obtained in 60%
yield after successive elimination of benzoyl groups and selective 3′,6′-OPiv protection. In a 66 percent yield, intermediate 2 was combined with peracetylated
l- rhamnopyranosyl N-phenyl triuoroacetimidate to generate the desired monodes-
mosidic trisaccharide derivative, which was then deprotected globally to obtain
dioscin [88] (Schemes 8.2 and 8.3).
188
HO
Dioscin(SteroidSaponin)
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S. Aslam etal.
Scheme 8.2 Synthesis of
Dioscin. Reaction
conditions: (a) TMSOtf,
CH
, rt; NaOMe,
2Cl2
MeOH, rt, 92%; PivCl,
pyr., 0°C, 60%; (b)
TMSOtf, CH
NaOH, MEOH, H
2Cl2
, rt, 66%,
O, THF,
2
rt, 90%
BzO
BzO
HO
HO
OBz
O
O
OBz
NPh
(1)
OBz
BzO
BzO
OH
O
O
HO
O
CF
O
OBz
O
+
3
HO
Diosgenin
O
(2)
O
O
O
O
O
O
O
8.9 Future Prospective ofCostus Plant
C. speciosus is a rich source of bioactive metabolites of economic value, such as
diosgenin and dioscin, as well as with strong therapeutic potential. In addition, different investigations are underway to uncover the long-term medicinal and healing
qualities of this plant for designing the novel drugs. The mode of action of the bioactive phytochemicals found in C. speciosus, as well as the in vivo toxicity of various extracts, should be further investigated. This might lead to the identication of
new biological active lead compounds and treatment approaches. To maintain the
conservation and long-term use of this vital medicinal plant across the world,
researchers must look at molecular diversity, in vitro growth approaches, and other
biotechnological factors such as metabolic pathway engineering to produce optimal
HO
HO
OH
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OBz
BzO
BzO
BzO
BzO
O
O
OBz
NPh
TMSOTf,4AMS, ,CH
OBz
O
O
OBz
CF
3
+Diosgenin
t
r
2Cl2
O
O
1-NaOMe, MeOH,rt
2-PivCl,pyr,0
o
C
AcO
AcO
OAc
HO
PivO
HO
HO
O
OAc
189
O
OH
O
O
O
O
HO
HO
O
HO
HO
OH
NPh
CF
3
TMSOTf,
4A MS,
CH
2Cl2
O
OPiv
O
O
OH
O
Dioscin
NaOMe, MeOH,THF
O
,rt
O
2Cl2
O
o
-
6
C
1
O
HO
AcO
HO
H
BzO
H
H
BzO
H
AcO
O
H
H H
OH
HO
3
AgOTf, 4AMS,,CH
,OEt2,4AMS
BF
3
O
Br
OBz
HN
CCl
O
O
OH
OAc
OH
O
O
HO
HO
O
O
PolyphyllinD
OH
Scheme 8.3 Chemical synthesis of Dioscin and Polyphyllin D
levels of bioactive metabolites. Finally, the next drive area of study for economic
viability would be elite chemotype discovery and manufacturing of therapeutically
relevant lead compounds from C. speciosus.
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