Mevalonate 2 Flashcards
(173 cards)
1
Q
Contributes to the aroma of ginger
A
Gamma-bisabolene
2
Q
Gamma-bisabolene is related to the structures of ___ & ____
A
Zingiberene and ß-sesquiphellandrene
3
Q
Source of gamma-bisabolene
A
Zingiber officinale (Fam. Zingiberaceae)
4
Q
Precursor cation of gamma-bisabolene
A
Bisabolyl cation
5
Q
Formed by simple quenching of the bisabolyl cation with water
A
Alpha-bisabolol
6
Q
Immediate precursor of bisabolol oxides by cyclization reactions on an intermediate epoxide
A
Alpha-bisabolol
7
Q
Source of alpha-bisabolol
A
Matricaria, German chamomile, Matricaria chamomilla (Fam. Asteraceae)
8
Q
Antimigraine agent;
Germacranolide
A
Parthenolide
9
Q
Source of parthenolide
A
Feverfew, Tanacetum parthenium (Fam. Asteraceae)
10
Q
Meaning of -olide
A
Lactone group
11
Q
Cytotoxic germacranolide
A
Elephantopin
12
Q
Source of elephantopin
A
Elephant’s foot, Elephantopus elatus (Fam. Asteraceae)
13
Q
Causes skin allergies;
A pseudoguaianolide from a highly troublesome weed in India
A
Parthenin
14
Q
Source of parthenin
A
Parthenium hysterophorus (Fam. Asteraceae)
15
Q
A rearranged guaianolide
A
Pseudoguaianolide
16
Q
Eudesmane compound with principal anthelmintic component
A
Alpha-santonin
17
Q
Used for removal of roundworms although potential toxicity limits its application
A
Alpha-santonin
18
Q
Source of alpha-santonin
A
Wormseed, Artemisia cinia (Fam. Asteraceae)
19
Q
Degrade on heating, presumably by elimination of acetic acid and water, and then decarboxylation to chamazulene
A
Matricin
20
Q
Responsible for thr blue coloration of oil distilled from matricaria flowers
A
Chamazulene
21
Q
A guaianolide, esterified with a variety of acid groups;
With considerable pharmacological interest as a tumor promoter, and as a potent activator of cells involved in inflammatory response
A
Thapsigargin
22
Q
Source of thapsigargin
A
Thapsia garganica (Fam. Apiaceae)
23
Q
One of the many terpenoids found in juniper berries;
Used in making gin
A
Alpha-cadinene
24
Q
Compound is derived from the 10-C ring containing cis-germacryl cation
A
Alpha-cadinene
25
Source of alpha-cadinene
Juniper berries, Juniperus communis (Fam. Cupressaceae)
26
Produced from amorpha-4,11-diene as its immediate precursor
Artemisinin
27
Artemisinin is produced through ____ and ____ via _____________ processes
Artemisinic acid and dihydroartemisinic acid via modest oxidation and reduction processes
28
Source of artemisinin
Artemisia annua (Fam. Asteraceae)
29
Found in hops
Humulene
30
Source of humulene
Hops, Humulus lupulus (Fam. Cannabaceae)
31
Found in a number of plants, such as in the oils from cloves and cinnamon
ß-caryophyllene
32
Sources of ß-caryophyllene
```
Syzygium aromaticum (Fam. Myrtaceae) and
Cinnamomum zeylanicum (Fam. Lauraceae)
```
33
A dimeric sesquiterpene which functions as a male infertility agent and is used in China as a male contraceptive
Gossypol
34
Source of gossypol
Gossypium species (Fam. Malvaceae)
35
Group of fungi toxins found typically in infected grain foodstuffs
Trichothecenes
36
Where the name trichothecene came from
Trichothecium
37
Where trichothecenesare mostly derived from
Cultures of Fusarium sp.
38
A trichothecene contaminant
Deoxyvalenol (vomitoxin)
39
Produced from isotrichodermol by sequence of oxygenation reactions
Deoxyvalenol (vomitoxin)
40
Reduced form of geranylgeraniol
Phytol
41
Constitutes the lipophilic side-chain of chlorophylls
Phytol
42
Forms a part of Vit. E and K molecules
Phytol
43
Cyclization of acyclic diterpenes leads to formation of _____
Cyclic diterpenes
44
Mixture of at least 11 compounds based on the taxadiene skeleton
Taxine
45
Source of taxine
Common yew, Taxus baccata (Fam. Taxaceae)
46
Possess a 4-membered oxetane ring and a complex ester side-chain in their structures, both of which are essential for antitumor activity
Taxol (Paclitaxel)
47
Sidechains of taxol contains aromatic rings derived from shikimate via ____
Phenylalanine
48
Source of taxol
Bark of Pacific yew, Taxus brevifolia (Fam. Taxaceae)
49
Fungus isolated from inner bark of Taxus brevifolia
Taxomyces adreanae
50
Recently isolated fugus from inner bark of Himalayan yew, Taxus wallachiana
Pestalotiopsis microspora
51
5 taxane derivatives
```
Baccatin III
10-deacetylbaccatin III
10-deacetyltaxol
Cephalomannine
10-deacetylcephalomannine
```
52
A side-chain analogue of taxol, which has also been produced by semi synthesis from 10-deacetylbaccatin III
Docetaxel (Taxotere)
53
With improved water-solubility compared with taxol, and is being used clinically against ovarian and breast cancers
Docetaxel (Taxotere)
54
Diterpene esters which is toxic; can cause poisoning in humans and animals, skin dematitis, cell proliferation, and tumour promotion
Phorbol
55
Source of phorbol
Euphorbia sp. (Fam. Euphorbiaceae)
56
Ester of phorbol
12-O-myristoylphorbol 13-acetate
57
Diterpenoid from castor oil plants
Casbene
58
Source of casbene
Ricinus communis (Fam. Euphorbiaceae)
59
Cyclization mechanism
Protonation of GGPP ---> cyclization sequence ---> loss of proton from a methyl
Alternative folding controlled by enzyme surface affects stereochemistry
60
Produced from a sequence of cyclizations and rearrangement, all catalyzed by a single enzyme from copalyl PP
Ent-kaurene
61
Precursor of stevioside
Ent-kaurene
62
From simple hydroxylation, oxidation, glucosylation reactions of ent-kaurene
Stevioside
63
100-300 times as sweet as sucrose, and is being used commercially as sweetening agents
Stevioside
64
Amount of stevioside present in the plant leaf
3-10%
65
Source of stevioside
Stevia rebaudiana (Fam. Asteraceae)
66
Help confer the intensely sweet taste of stevioside
Glucosyl ester and glucoside linkages
67
The major component of the rosin fraction of turpentine from pines and other conifers
Abietic acid
68
Produced from different rxns such as loss of protons, methyl migration, and sequential oxidations of labdadienyl Pp
Abietic acid
69
Wound site of pine trees may be fractionated by distillation to give ____ & _____
Turpentine oil and rosin
70
With antifungal and insecticidal properties
Abietic acid
71
Highly oxidized diterpene trilactones producedfrom extensive modification of the labdadienyl diterpene skeleton
Ginkgolides
72
Source of ginkgolides
Ginkgo biloba (Fam. Ginkgoaceae)
73
Standardized extracts of the leaves are marketed against cerebral vascular disease and senile dementia; improve peripheral and cerebrovascular circulation
Ginkgolides
74
Improves blood circulation and assists with other symptoms of vertigo, tinnitus, hearing loss
Ginkgolides
75
Contains a related C-15 skeleton and is most likely a partialy degraded ginkgolide
Bilobalide
76
Amount of terpene lactones in dried leaves of Ginkgo biloba
0.1-0.25%
77
Amount of bilobalide in Gingko biloba leaves
30-40% of the mixture
78
5 ginkgolides
```
A
B
C
J
M
```
79
Predominant ginkgolide ~30%
Ginkgolide A
80
Potent and selective antagonistic activity towards platelet-activating factor
Ginkgolides
81
With hypotensive and antispasmodic activity
Forskolin
82
Potent stimulator of adenylate cyclase activity, and is being investigated for its cardiovascular and bronchospasmolytic effects
Forskolin
83
Source of forskolin
Coleus forskohlii (Fam. Lamiaceae)
84
Types of diterpenoids
Abietane
Amphilectan
Beyerane
Briarane
85
Major diterpene in Taxus brevifolia
Paclitaxol?
86
Major diterpene in Gibberella fujikuroi
Gibberellins
87
25-C terpenes; 5 isoprene units
Sesterterpenoids
88
Parent compound of a series of marine sponge metabolites belonging to this class
Manoalide
89
Manoalide has activity as an antibiotic against ____ & ______
Streptomyces pyogenes and
| Staphylococcus aureus
90
Potent inhibitor of phospholipase A2
Manoalide
91
Source of manoalide
Luffariella variabilis (Fam. Thorectidae)
92
Arise from geranylfarnesyl PP
Ophiobolene and ophiobolin A
93
Source of ophiobolene and ophiobolin A
Helminthosporium maydis (Fam. Pleomassariaceae)
94
Shows a broad spectrum of biological activity against bacteria, fungi, and nematodes
Ophiobolin A
95
Exemplifies most common type of marine sesterterpenoid
Scalarolide and scalarin
96
Source of scalarolide
Cacospongia sponges
97
Source of scalarin
Ircinia sponges
98
Structure of scalarolide and scalarin can be visualized as the result of a _____ ______ _______
Concerted cyclization sequence
99
A novel sesterterpenoid with a new carbon skeleton
Asperterpenoid
100
Structure of asperterpenoid was characterized by extensive _______ methods
Spectroscopic
101
The absolute config of asperterpenoid was determined by _____
Single crystal x-ray diffraction analysis
102
Exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB)
Asperterpenoid
103
Compounds with 6 isoprene units
Triterpenoids
104
Where triterpenoids are derived from, biosynthetically
Squalene
105
Colorless, crystalline, has high MP, optically active substances
Triterpenoids
106
Addition of 3 gtt acetic anhydride to sample,
Mixing, and
A drop of conc. sulfuric acid
Liebermann-Burchard reaction
107
Positive result of Liebermann-Burchard rxn
Blue green color with most triterpenoid and sterols
108
3 occurences of triterpenoids
Free state
Esters
Glycosides
109
Structural classification of triterpenoids
Acyclic
Tetracyclic
Pentacyclic
110
Acyclic triterpenes
Squalene
| Ambrein
111
Tetracyclic triterpenes
Lanosterol
Agnosterol
Cycloaudinol
112
Pentacyclic triterpenes
Alpha-amyrin group
ß-amyrin group
Lupeol group
113
Alpha-amyrin group
Alpha-amyrin
Ursolic acid
Asiatic acid
114
ß-amyrin group
ß-amyrin
Oleanolic acid
Glycyrrhetic acid
115
Lupeol group
Lupeol
Betulin
Taraxasterol
116
Formed by joining 2 molecules of farnesyl PP tail-to-tail to yield squalene
Triterpenoids (biosynthesis)
117
Biosynthesis of triterpenoids are catalyzed by _____
Squalene synthase or farnesyl transferase (NADPH dependent enzyme)
118
6 Steps in formation of squalene
```
Electrophilic addition
Formation of cyclopropane ring
Formation of primary cation
Wagner-Meerwein rearrangement
Formation of allylic cation
Stabilization of allylic cation forming squalene
```
119
Cyclization of squalene via ______
Squalene 2,3-oxide
120
Precursor cation of lanosterol and cycloartenol
Protosteryl cation
121
Precursor cation of cucurbitacin E
Protosteryl cation
122
Geoup of extremely cytotoxic triterpenes encountered in the family Cucurbitaceae;
Bitter tasting and purgative
Cucurbitacins
123
Precursor cation of euphol
Dammarenyl cation
124
Precursor cation of dammarenediols
Dammarenyl cation
125
Precursor cation of baccharenyl cation
Dammarenyl cation
126
Precursor cation of lupenyl cation
Baccharenyl cation
127
Precursor cation of lupeol
Lupenyl cation
128
Precursor cation of ß-amyrin
Oleanyl cation
129
Precursor cation of oleanyl cation
Lupenyl cation
130
Precursor cation of taraxasterol and alpha-amyrin
Taraxasteryl cation
131
Precursor cation of taraxasteryl cation
Oleanyl cation
132
Glycosides which even at low concentrations, produce a frothing in aqueous solution because they have surfactant and soap-like properties
Saponins
133
Can cause hemolysis, lysing RBCs by increasing the permeability of the plasma membrane
Triterpenoid saponins
134
Plant which contains exceptionally high amounts of saponins, ~10%
Quillaia bark
135
Sapogenin or aglycone portion of quillaia saponins
Quillaic acid
136
Used as emulsifying agent in pharmaceutical preparations in the form of tincture
Quillaia saponins
137
50-100x as sweet as sucrose
Glycyrrhizin
138
Used to mask the taste of bitter drugs;
Demulcent, mild expectorant;
Exploited in treament of rheumatoid arthritis, Addison's disease, and various inflammatory condition
Glycyrrhizin
139
Sapogenin of glycyrrhizin
Glycyrrhetic acid
140
Source of glycyrrhizin
Glycyrrhiza glabra (Fam. Fabaceae)
141
Inhibit enzymes that catalyze the conversion of prostaglandins and glucocorticoids into inactive metabolites resulting into increased levels of prostaglandins
Glycyrrhetic acid
142
Semi-synthetic deriv. of glycyrrhetic widely prescribed for treatment of gastric and duodenal ulcers
Carbenoxolone sodium
143
Used in herbal preparations as an inflammatory and anti-bruising remedy
Aescin
144
Sapogenins of aescin
Protoaescigenin and barringtogenol
145
Source of aescin
Horse chestnut, Aesculus hippocastrum (Fam. Hippocastanaceae)
146
Modified triterpenoids
Limonoids
Quassinoids
Steroids
147
Modification of tetranotriterpenoids
4 terminal carbons from side chain are removed
148
Plant family sources of tetranotriterpenoids
Rutaceae, Meliaceae, and Simaroubaceae
149
One of the most complex limonoid structure to be encountered;
Has potent insect antifeedant properties;
Used as agricultural pesticide
Azadirachtin
150
Source of azadirachtin
Neem tree, Azadirachta indica (Fam. Meliaceae)
151
Modification of quassinoids
Lost 10 Cs: 9 from side chain and 1 from C4 methyls
152
Plant family source of quassinoids
Simaroubaceae
153
Have cytotoxic, antimalarial, and amoebicidal properties
Quassin
154
Source of quassin
Quassia wood, Quassia amara (Fam. Simaroubaceae)
155
Triterpenoid compounds that appear to take the place of the sterols that are typically found in the membranes of higher organisms
Hopanoids
156
Arise from squalene by a similar carbocation cyclization mechanism without initial epoxidation to oxidosqualene
Hopanoids
157
Source of hopene
Alicyclobacillus acidocaldarius
158
Source of tetrahymanol
Tetrahymena pyriformis
159
An agent that helps the body to adapt to stress, improving stamina and concentration, and providing a normalizing and restorative effect
Adaptogen
160
Possess antioxidant activity, can affects both CNS and neuroendocrine functions, can alter carbohydrate and lipid metabolism, and modulate immune function
Ginseng
161
Aglycones of ginsenosides or panaxosides
Protopanaxadiol and protopanaxatriol
162
Usually the major component representqtive of the triol series
Ginsenoside Rg1
163
Produced by hydrolysis of the total saponins of P. ginseng, and is present in some saponin structures (chikusetsusaponins)
Pentacyclictriterpenoid sapogenin oleanolic acid
164
Saponin content of Sanchi-ginseng
~12%
165
Botanical origin of Sanchi-ginseng
Panax notoginseng (Fam. Araliaceae)
166
Saponin content of American ginseng
~6%
167
Botanical origin of American ginseng
Panax quinquefolium (Fam. Araliaceae)
168
Saponin content of Panax ginseng
1.5-2%
169
Inexpensive substitute for ginseng;
| Have adaptogenic properties similar to P. ginseng;
Russian or Siberian ginseng
170
Botanical origin of Russian/Siberian ginseng
Eleutherococcus senticosus (Fam. Araliaceae)
171
Main active anti-stress constituents of eleutherosides
Lignan glycosides
| Phenylpropane glycosides
172
Fundamental sesquiterpene precursor;
Product of geranyl PP and C5 IPP unit;
Can give rise to linear and cyclic sesquiterpenes
Farnesyl PP or Nerolidyl PP
173
Eleutherosides in Eleutherococcus senticosus
```
Syringin (eleutheroside B)
Syringaresinol diglucoside (eleutheroside E)
```
