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Ph Ch 128 3rd Exam > Mevalonate 2 > Flashcards

Mevalonate 2 Flashcards

1
Q

Contributes to the aroma of ginger

A

Gamma-bisabolene

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2
Q

Gamma-bisabolene is related to the structures of ___ & ____

A

Zingiberene and ß-sesquiphellandrene

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3
Q

Source of gamma-bisabolene

A

Zingiber officinale (Fam. Zingiberaceae)

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4
Q

Precursor cation of gamma-bisabolene

A

Bisabolyl cation

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5
Q

Formed by simple quenching of the bisabolyl cation with water

A

Alpha-bisabolol

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6
Q

Immediate precursor of bisabolol oxides by cyclization reactions on an intermediate epoxide

A

Alpha-bisabolol

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7
Q

Source of alpha-bisabolol

A

Matricaria, German chamomile, Matricaria chamomilla (Fam. Asteraceae)

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8
Q

Antimigraine agent;

Germacranolide

A

Parthenolide

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9
Q

Source of parthenolide

A

Feverfew, Tanacetum parthenium (Fam. Asteraceae)

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10
Q

Meaning of -olide

A

Lactone group

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11
Q

Cytotoxic germacranolide

A

Elephantopin

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12
Q

Source of elephantopin

A

Elephant’s foot, Elephantopus elatus (Fam. Asteraceae)

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13
Q

Causes skin allergies;

A pseudoguaianolide from a highly troublesome weed in India

A

Parthenin

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14
Q

Source of parthenin

A

Parthenium hysterophorus (Fam. Asteraceae)

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15
Q

A rearranged guaianolide

A

Pseudoguaianolide

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16
Q

Eudesmane compound with principal anthelmintic component

A

Alpha-santonin

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17
Q

Used for removal of roundworms although potential toxicity limits its application

A

Alpha-santonin

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18
Q

Source of alpha-santonin

A

Wormseed, Artemisia cinia (Fam. Asteraceae)

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19
Q

Degrade on heating, presumably by elimination of acetic acid and water, and then decarboxylation to chamazulene

A

Matricin

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20
Q

Responsible for thr blue coloration of oil distilled from matricaria flowers

A

Chamazulene

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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

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22
Q

Source of thapsigargin

A

Thapsia garganica (Fam. Apiaceae)

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23
Q

One of the many terpenoids found in juniper berries;

Used in making gin

A

Alpha-cadinene

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24
Q

Compound is derived from the 10-C ring containing cis-germacryl cation

A

Alpha-cadinene

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25
Q

Source of alpha-cadinene

A

Juniper berries, Juniperus communis (Fam. Cupressaceae)

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26
Q

Produced from amorpha-4,11-diene as its immediate precursor

A

Artemisinin

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27
Q

Artemisinin is produced through ____ and ____ via _____________ processes

A

Artemisinic acid and dihydroartemisinic acid via modest oxidation and reduction processes

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28
Q

Source of artemisinin

A

Artemisia annua (Fam. Asteraceae)

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29
Q

Found in hops

A

Humulene

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30
Q

Source of humulene

A

Hops, Humulus lupulus (Fam. Cannabaceae)

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31
Q

Found in a number of plants, such as in the oils from cloves and cinnamon

A

ß-caryophyllene

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32
Q

Sources of ß-caryophyllene

A 
Syzygium aromaticum (Fam. Myrtaceae) and
Cinnamomum zeylanicum (Fam. Lauraceae)
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33
Q

A dimeric sesquiterpene which functions as a male infertility agent and is used in China as a male contraceptive

A

Gossypol

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34
Q

Source of gossypol

A

Gossypium species (Fam. Malvaceae)

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35
Q

Group of fungi toxins found typically in infected grain foodstuffs

A

Trichothecenes

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36
Q

Where the name trichothecene came from

A

Trichothecium

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37
Q

Where trichothecenesare mostly derived from

A

Cultures of Fusarium sp.

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38
Q

A trichothecene contaminant

A

Deoxyvalenol (vomitoxin)

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39
Q

Produced from isotrichodermol by sequence of oxygenation reactions

A

Deoxyvalenol (vomitoxin)

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40
Q

Reduced form of geranylgeraniol

A

Phytol

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41
Q

Constitutes the lipophilic side-chain of chlorophylls

A

Phytol

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42
Q

Forms a part of Vit. E and K molecules

A

Phytol

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43
Q

Cyclization of acyclic diterpenes leads to formation of _____

A

Cyclic diterpenes

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44
Q

Mixture of at least 11 compounds based on the taxadiene skeleton

A

Taxine

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45
Q

Source of taxine

A

Common yew, Taxus baccata (Fam. Taxaceae)

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46
Q

Possess a 4-membered oxetane ring and a complex ester side-chain in their structures, both of which are essential for antitumor activity

A

Taxol (Paclitaxel)

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47
Q

Sidechains of taxol contains aromatic rings derived from shikimate via ____

A

Phenylalanine

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48
Q

Source of taxol

A

Bark of Pacific yew, Taxus brevifolia (Fam. Taxaceae)

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49
Q

Fungus isolated from inner bark of Taxus brevifolia

A

Taxomyces adreanae

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50
Q

Recently isolated fugus from inner bark of Himalayan yew, Taxus wallachiana

A

Pestalotiopsis microspora

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51
Q

5 taxane derivatives

A 
Baccatin III
10-deacetylbaccatin III
10-deacetyltaxol
Cephalomannine
10-deacetylcephalomannine
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52
Q

A side-chain analogue of taxol, which has also been produced by semi synthesis from 10-deacetylbaccatin III

A

Docetaxel (Taxotere)

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53
Q

With improved water-solubility compared with taxol, and is being used clinically against ovarian and breast cancers

A

Docetaxel (Taxotere)

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54
Q

Diterpene esters which is toxic; can cause poisoning in humans and animals, skin dematitis, cell proliferation, and tumour promotion

A

Phorbol

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55
Q

Source of phorbol

A

Euphorbia sp. (Fam. Euphorbiaceae)

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56
Q

Ester of phorbol

A

12-O-myristoylphorbol 13-acetate

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57
Q

Diterpenoid from castor oil plants

A

Casbene

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58
Q

Source of casbene

A

Ricinus communis (Fam. Euphorbiaceae)

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59
Q

Cyclization mechanism

A

Protonation of GGPP —> cyclization sequence —> loss of proton from a methyl
Alternative folding controlled by enzyme surface affects stereochemistry

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60
Q

Produced from a sequence of cyclizations and rearrangement, all catalyzed by a single enzyme from copalyl PP

A

Ent-kaurene

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61
Q

Precursor of stevioside

A

Ent-kaurene

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62
Q

From simple hydroxylation, oxidation, glucosylation reactions of ent-kaurene

A

Stevioside

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63
Q

100-300 times as sweet as sucrose, and is being used commercially as sweetening agents

A

Stevioside

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64
Q

Amount of stevioside present in the plant leaf

A

3-10%

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65
Q

Source of stevioside

A

Stevia rebaudiana (Fam. Asteraceae)

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66
Q

Help confer the intensely sweet taste of stevioside

A

Glucosyl ester and glucoside linkages

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67
Q

The major component of the rosin fraction of turpentine from pines and other conifers

A

Abietic acid

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68
Q

Produced from different rxns such as loss of protons, methyl migration, and sequential oxidations of labdadienyl Pp

A

Abietic acid

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69
Q

Wound site of pine trees may be fractionated by distillation to give ____ & _____

A

Turpentine oil and rosin

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70
Q

With antifungal and insecticidal properties

A

Abietic acid

71
Q

Highly oxidized diterpene trilactones producedfrom extensive modification of the labdadienyl diterpene skeleton

A

Ginkgolides

72
Q

Source of ginkgolides

A

Ginkgo biloba (Fam. Ginkgoaceae)

73
Q

Standardized extracts of the leaves are marketed against cerebral vascular disease and senile dementia; improve peripheral and cerebrovascular circulation

A

Ginkgolides

74
Q

Improves blood circulation and assists with other symptoms of vertigo, tinnitus, hearing loss

A

Ginkgolides

75
Q

Contains a related C-15 skeleton and is most likely a partialy degraded ginkgolide

A

Bilobalide

76
Q

Amount of terpene lactones in dried leaves of Ginkgo biloba

A

0.1-0.25%

77
Q

Amount of bilobalide in Gingko biloba leaves

A

30-40% of the mixture

78
Q

5 ginkgolides

A 
A
B
C
J
M
79
Q

Predominant ginkgolide ~30%

A

Ginkgolide A

80
Q

Potent and selective antagonistic activity towards platelet-activating factor

A

Ginkgolides

81
Q

With hypotensive and antispasmodic activity

A

Forskolin

82
Q

Potent stimulator of adenylate cyclase activity, and is being investigated for its cardiovascular and bronchospasmolytic effects

A

Forskolin

83
Q

Source of forskolin

A

Coleus forskohlii (Fam. Lamiaceae)

84
Q

Types of diterpenoids

A

Abietane
Amphilectan
Beyerane
Briarane

85
Q

Major diterpene in Taxus brevifolia

A

Paclitaxol?

86
Q

Major diterpene in Gibberella fujikuroi

A

Gibberellins

87
Q

25-C terpenes; 5 isoprene units

A

Sesterterpenoids

88
Q

Parent compound of a series of marine sponge metabolites belonging to this class

A

Manoalide

89
Q

Manoalide has activity as an antibiotic against ____ & ______

A

Streptomyces pyogenes and

Staphylococcus aureus

90
Q

Potent inhibitor of phospholipase A2

A

Manoalide

91
Q

Source of manoalide

A

Luffariella variabilis (Fam. Thorectidae)

92
Q

Arise from geranylfarnesyl PP

A

Ophiobolene and ophiobolin A

93
Q

Source of ophiobolene and ophiobolin A

A

Helminthosporium maydis (Fam. Pleomassariaceae)

94
Q

Shows a broad spectrum of biological activity against bacteria, fungi, and nematodes

A

Ophiobolin A

95
Q

Exemplifies most common type of marine sesterterpenoid

A

Scalarolide and scalarin

96
Q

Source of scalarolide

A

Cacospongia sponges

97
Q

Source of scalarin

A

Ircinia sponges

98
Q

Structure of scalarolide and scalarin can be visualized as the result of a _____ ______ _______

A

Concerted cyclization sequence

99
Q

A novel sesterterpenoid with a new carbon skeleton

A

Asperterpenoid

100
Q

Structure of asperterpenoid was characterized by extensive _______ methods

A

Spectroscopic

101
Q

The absolute config of asperterpenoid was determined by _____

A

Single crystal x-ray diffraction analysis

102
Q

Exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB)

A

Asperterpenoid

103
Q

Compounds with 6 isoprene units

A

Triterpenoids

104
Q

Where triterpenoids are derived from, biosynthetically

A

Squalene

105
Q

Colorless, crystalline, has high MP, optically active substances

A

Triterpenoids

106
Q

Addition of 3 gtt acetic anhydride to sample,
Mixing, and
A drop of conc. sulfuric acid

A

Liebermann-Burchard reaction

107
Q

Positive result of Liebermann-Burchard rxn

A

Blue green color with most triterpenoid and sterols

108
Q

3 occurences of triterpenoids

A

Free state
Esters
Glycosides

109
Q

Structural classification of triterpenoids

A

Acyclic
Tetracyclic
Pentacyclic

110
Q

Acyclic triterpenes

A

Squalene

Ambrein

111
Q

Tetracyclic triterpenes

A

Lanosterol
Agnosterol
Cycloaudinol

112
Q

Pentacyclic triterpenes

A

Alpha-amyrin group
ß-amyrin group
Lupeol group

113
Q

Alpha-amyrin group

A

Alpha-amyrin
Ursolic acid
Asiatic acid

114
Q

ß-amyrin group

A

ß-amyrin
Oleanolic acid
Glycyrrhetic acid

115
Q

Lupeol group

A

Lupeol
Betulin
Taraxasterol

116
Q

Formed by joining 2 molecules of farnesyl PP tail-to-tail to yield squalene

A

Triterpenoids (biosynthesis)

117
Q

Biosynthesis of triterpenoids are catalyzed by _____

A

Squalene synthase or farnesyl transferase (NADPH dependent enzyme)

118
Q

6 Steps in formation of squalene

A 
Electrophilic addition
Formation of cyclopropane ring
Formation of primary cation
Wagner-Meerwein rearrangement
Formation of allylic cation
Stabilization of allylic cation forming squalene
119
Q

Cyclization of squalene via ______

A

Squalene 2,3-oxide

120
Q

Precursor cation of lanosterol and cycloartenol

A

Protosteryl cation

121
Q

Precursor cation of cucurbitacin E

A

Protosteryl cation

122
Q

Geoup of extremely cytotoxic triterpenes encountered in the family Cucurbitaceae;
Bitter tasting and purgative

A

Cucurbitacins

123
Q

Precursor cation of euphol

A

Dammarenyl cation

124
Q

Precursor cation of dammarenediols

A

Dammarenyl cation

125
Q

Precursor cation of baccharenyl cation

A

Dammarenyl cation

126
Q

Precursor cation of lupenyl cation

A

Baccharenyl cation

127
Q

Precursor cation of lupeol

A

Lupenyl cation

128
Q

Precursor cation of ß-amyrin

A

Oleanyl cation

129
Q

Precursor cation of oleanyl cation

A

Lupenyl cation

130
Q

Precursor cation of taraxasterol and alpha-amyrin

A

Taraxasteryl cation

131
Q

Precursor cation of taraxasteryl cation

A

Oleanyl cation

132
Q

Glycosides which even at low concentrations, produce a frothing in aqueous solution because they have surfactant and soap-like properties

A

Saponins

133
Q

Can cause hemolysis, lysing RBCs by increasing the permeability of the plasma membrane

A

Triterpenoid saponins

134
Q

Plant which contains exceptionally high amounts of saponins, ~10%

A

Quillaia bark

135
Q

Sapogenin or aglycone portion of quillaia saponins

A

Quillaic acid

136
Q

Used as emulsifying agent in pharmaceutical preparations in the form of tincture

A

Quillaia saponins

137
Q

50-100x as sweet as sucrose

A

Glycyrrhizin

138
Q

Used to mask the taste of bitter drugs;
Demulcent, mild expectorant;
Exploited in treament of rheumatoid arthritis, Addison’s disease, and various inflammatory condition

A

Glycyrrhizin

139
Q

Sapogenin of glycyrrhizin

A

Glycyrrhetic acid

140
Q

Source of glycyrrhizin

A

Glycyrrhiza glabra (Fam. Fabaceae)

141
Q

Inhibit enzymes that catalyze the conversion of prostaglandins and glucocorticoids into inactive metabolites resulting into increased levels of prostaglandins

A

Glycyrrhetic acid

142
Q

Semi-synthetic deriv. of glycyrrhetic widely prescribed for treatment of gastric and duodenal ulcers

A

Carbenoxolone sodium

143
Q

Used in herbal preparations as an inflammatory and anti-bruising remedy

A

Aescin

144
Q

Sapogenins of aescin

A

Protoaescigenin and barringtogenol

145
Q

Source of aescin

A

Horse chestnut, Aesculus hippocastrum (Fam. Hippocastanaceae)

146
Q

Modified triterpenoids

A

Limonoids
Quassinoids
Steroids

147
Q

Modification of tetranotriterpenoids

A

4 terminal carbons from side chain are removed

148
Q

Plant family sources of tetranotriterpenoids

A

Rutaceae, Meliaceae, and Simaroubaceae

149
Q

One of the most complex limonoid structure to be encountered;
Has potent insect antifeedant properties;
Used as agricultural pesticide

A

Azadirachtin

150
Q

Source of azadirachtin

A

Neem tree, Azadirachta indica (Fam. Meliaceae)

151
Q

Modification of quassinoids

A

Lost 10 Cs: 9 from side chain and 1 from C4 methyls

152
Q

Plant family source of quassinoids

A

Simaroubaceae

153
Q

Have cytotoxic, antimalarial, and amoebicidal properties

A

Quassin

154
Q

Source of quassin

A

Quassia wood, Quassia amara (Fam. Simaroubaceae)

155
Q

Triterpenoid compounds that appear to take the place of the sterols that are typically found in the membranes of higher organisms

A

Hopanoids

156
Q

Arise from squalene by a similar carbocation cyclization mechanism without initial epoxidation to oxidosqualene

A

Hopanoids

157
Q

Source of hopene

A

Alicyclobacillus acidocaldarius

158
Q

Source of tetrahymanol

A

Tetrahymena pyriformis

159
Q

An agent that helps the body to adapt to stress, improving stamina and concentration, and providing a normalizing and restorative effect

A

Adaptogen

160
Q

Possess antioxidant activity, can affects both CNS and neuroendocrine functions, can alter carbohydrate and lipid metabolism, and modulate immune function

A

Ginseng

161
Q

Aglycones of ginsenosides or panaxosides

A

Protopanaxadiol and protopanaxatriol

162
Q

Usually the major component representqtive of the triol series

A

Ginsenoside Rg1

163
Q

Produced by hydrolysis of the total saponins of P. ginseng, and is present in some saponin structures (chikusetsusaponins)

A

Pentacyclictriterpenoid sapogenin oleanolic acid

164
Q

Saponin content of Sanchi-ginseng

A

~12%

165
Q

Botanical origin of Sanchi-ginseng

A

Panax notoginseng (Fam. Araliaceae)

166
Q

Saponin content of American ginseng

A

~6%

167
Q

Botanical origin of American ginseng

A

Panax quinquefolium (Fam. Araliaceae)

168
Q

Saponin content of Panax ginseng

A

1.5-2%

169
Q

Inexpensive substitute for ginseng;

Have adaptogenic properties similar to P. ginseng;

A

Russian or Siberian ginseng

170
Q

Botanical origin of Russian/Siberian ginseng

A

Eleutherococcus senticosus (Fam. Araliaceae)

171
Q

Main active anti-stress constituents of eleutherosides

A

Lignan glycosides

Phenylpropane glycosides

172
Q

Fundamental sesquiterpene precursor;
Product of geranyl PP and C5 IPP unit;
Can give rise to linear and cyclic sesquiterpenes

A

Farnesyl PP or Nerolidyl PP

173
Q

Eleutherosides in Eleutherococcus senticosus

A 
Syringin (eleutheroside B)
Syringaresinol diglucoside (eleutheroside E)

Ph Ch 128 3rd Exam (4 decks)

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