Pharmacognosy 生藥學

Terpenoids II (萜類)

School of Pharmacy Hsun-Shuo Chang

藥學系張訓碩

第一教學大樓7樓 藥用植物學科室 (N724)

07-3121101 ext. 2664
hschang@kmu.edu.tw
1
 Aim of study
◆ Introduction of sesquiterpenoids, diterpenoids,
triterpenoids, and tetraterpenoids
◆ Classification of sesquiterpenoids, diterpenoids,
triterpenoids, and tetraterpenoids

• Robbers JE, Speedie MK, Tyler VE. Pharmacognosy and Pharmacobiotechnology. Williams
& Wilkins, Baltimore, 1996.
• W. C. Evans. Trease and Evans Pharmacognosy. 15th edition, W. B. Saunders, London, 2002.
• W. C. Evans. Trease and Evans Pharmacognosy. 16th edition, W. B. Saunders, London, 2009.
• Concise Traditional Chinese Herbal Medicine, 2nd Edition. The Pharmaceutical Society of
Taiwan Pharmacognosy group, Taipei, 2019. 2
Sesquiterpenoids (倍半萜類)

3
 Sesquiterpenoids
◆ sesquiterpenoids are the largest class of terpenoids in nature
◆ the first sesquiterpenoids isolated from nature were β-
cadinene from oil of cade (juniper tar) and β-caryophyllene
from clove oil
◆ abscisic acid is an essential plant hormone controlling
growth and development
H
H
OH

H COOH
H O

β-cadinene (β-杜松油萜) β-caryophyllene (β-石竹烯) abscisic acid (脫落酸) 4

 Sesquiterpenoids
◆ Sesquiterpenoid lactones: O O O
O

▬ α-methylene-γ-lactone system O O
O

▬ α, β-unsaturated carbonyls a-lactone b-lactone -lactone -lactone

▬ epoxides

OCOCH3
O
O O
b a O O
a
O
O O
O O O

Costunolide Zeylaninone Linderadine

5
 Sesquiterpenoids

◆ these functional groups of sesquiterpenoid lactones

represent reactive receptor sites for biological
nucleophiles such thiol and amino groups of enzymes

◆ a wide spectrum of biological activities has been

reported for these compounds, for example,
antimicrobial and antitumor activity, and some are
highly toxic to mammals

6
 Sesquiterpenoids
◆ lactone: “suffix” used to denote a lactone is -olide, used in substance
O
class names: cardenolide: O
butenolide:
HO
CHO H
16

H OH
O
O O
H 3CO O reevesioside A
OH
O
Machicolide B O

macrolide: bufadienolide O

CH3

CH3 H O

COOH O O CH3
H H OH
H2N N O
N (CH2)6 O
H
H
NH

Erythromycin bufotoxin
7
 Sesquiterpenoids

14 14
1 9 1 9 10 9
2 10 8
2 8
1
5 7 7
3 4 6 3 6 7
5 3
11 13 13 6 13
5
11
O 12 O 4
12
15 O 12
O O 15
O

Germacranolide type Eudesmanolide type Guaianolide type

(ten-membered ring) (two fused six- (five-membered ring fused
membered rings) to a seven-membered ring)

Fig. 5 Major skeletal types of sesquiterpenoid lactones without stereochemical designations

8
 Artemisinin (Qinghaosu) 青蒿素
10,20,29

◆ leaves and flowering tops of Artemisia annua L.

(Asteraceae)
◆ traditionally been used in China for the treatment of
malaria for over a thousand years
◆ until 1972, Chinese scientists showed it to be a novel
antimalarial compound with an internal peroxide linkage
CH 3
which is essential for activity H

O O
H 3C
O
H H
Artemisinin O
CH3
(青蒿素)
O
9
 Artemisinin (Qinghaosu) 青蒿素
◆ to overcome the poor solubility of artemisinin in water:
▬ methyl ether derivative Artemether: more lipid soluble and
more potent
▬ sodium salt of the hemisuccinate ester, sodium artesunate,
which is soluble in water allowing intravenous
administration CH 3
H
CH3 CH3
H H O O
H 3C
O O O
H 3C O H 3C O
H H
O O O
H H CH3 O
H H
O 10 O
O
CH3 CH3
ONa
O OCH 3 O

Artemisinin (青蒿素) Artemether (蒿甲醚) Sodium artesunate (青蒿酯鈉)10

 Artemisinin (Qinghaosu) 青蒿素
◆ potent and rapidly acting blood schizontocides in the
treatment of malaria
◆ against Plasmodium vivax
◆ against both chloroquine sensitive and chloroquine-
resistant strains of Plasmodium falciparum
◆ rapid clearance of parasites in cerebral malaria:
Artemisinin > quinine or chloroquine
◆ however, high rates of reocurrence necessitates
combination therapy with other antimalarials

11
Biosynthesis of Artemisinin 12
13
 Chamomile 洋甘菊 9,26

◆ German chamomile or matricaria: dried flower heads of

Matricaria recutita L. (Asteraceae)
◆ Roman chamomile: Chamaemelum nobile (L.) All.
▬ contains similar constituents to M. recuitita
▬ extensively cultivated in Europe
▬ carminative, spasmolytic, and anti-inflammatory activity
◆ most common form of the drug is a tea, but various extracts
and volatile-oil-containing preparations are also available
◆ chamomile is labeled the “ginseng” of Europe and has become
one of the most popular herbal teas in the United States
14
 Chamomile 洋甘菊 1

◆ owing primarily to constituents of the volatile oil, especially

the sesquiterpenoids:
OH
HO
OH
O
O
H H
H

(─)-α-Bisabolol (─)-α-Bisaboloxide A (─)-α-Bisaboloxide B

(沒藥醇) (沒藥醇氧化物A) (沒藥醇氧化物B)

OCOCH3
8 guaianolide lactone:
6
4 Matricin (prochamazulene) 母菊素
H 12
O
HO 8α-acetoxy-4α-hydroxyguaia-1(10),2-dien-12,6α-olide
O

◆ flavonoids and coumarin derivatives add to the spasmolytic

effects
15
 Chamomile 洋甘菊
◆ an infusion (tea) contains only 10 to 15 % of the volatile oil
present in the plant material, and the ingredients in the
volatile oil provide most of the anti-inflammatory activity

◆ whole plant extracts or preparations containing quantities of

the volatile oil are certainly much more effective

◆ in spite of the relatively low concentrations of lipid-soluble

active ingredients in the tea, one authority believes that,
when the tea is used over a long period of time, a cumulative
beneficial effect may result

16
 Feverfew 小白菊 4,24,27

◆ the leaves of Tanacetum parthenium (L.) Schultz-Bip.

(Asteraceae)
◆ used for centuries as an antipyretic or febrifuge
◆ effective in the prophylaxis of migraine by substantially
reducing the frequency and severity of headache
◆ Parthenolide acts as a serotonin antagonist resulting in an
inhibition of the release of serotonin from blood platelets
1 sesquiterpenoid lactone of germacranolide type:
4
5 Parthenolide 小白菊內酯
11 4α,5β-epoxygermacra-1(10),11(13)-dien-12,6α-olide

17
 Feverfew 小白菊 11,22

◆ has been used simple by chewing the fresh leaves of the

plant

◆ dried preparations either as tablets or capsules are

available, for these to be effective, it is recommended that
they contain a minimum concentration of 0.2 %
parthenolide

◆ the usual dose of dried leaves of good quality is 125 mg

daily

18
 Valerian 纈草
◆ the dried rhizome and roots of Valeriana officinalis L.
(Valerianaceae)
◆ an antianxiety agent and sleep aid for more than 1,000 years
◆ contains from 0.3 to 0.7 % of an unpleasant-smelling volatile
oil containing:
HO H3COCO
H H H

COOH COOH COOH

Bornyl acetate Valerenic acid Valerenolic acid Acetoxyvalerenolic acid

(乙酸龍腦酯) (纈草烯酸) (纈草萜烯醇酸) (乙醯氧基纈草萜烯酸)19
 Valerian 纈草 6,15,16,23

◆ also present is a mixture of lipophilic iridoid principals

known as valepotriates (sleep aid)

Valepotriates
(纈草醚酯)

◆ these bicyclic monoterpenoids are quite unstable and

occur only in the fresh plant or in material dried at
temperatures under 40 ℃
◆ the drug may be administered as a tea prepared from 2 to 3
g of the dried herb or equivalent amounts of a tincture or
extract may be employed
20
Diterpenoids (雙萜類)

21
 Diterpenoids
◆ non-volatile C20 compounds derived from geranylgeranyl
pyrophosphate
◆ some acyclic diterpenoids are known, but the vast majority
are carbocyclic compounds containing as many as five
rings
◆ are usually isolated as optically active solids that can exist
in both the normal and the antipodal stereochemical
configurations
◆ the normal series has an A/B ring fusion and those in
which the ring fusion is antipodal are known as the ent
series 22
 Diterpenoids
◆ a wide range of different biological activities:
▬ the resin acids such as abietic acid (conifers) protect the
tree from infection and insect attack
▬ the gibberellins are plant hormones that stimulate plant
growth, whereas podolactones are plant growth inhibitors
O

O
O OH
H
O OH
O O OH

HO
H H
COOH COOH
O
O
Abietic acid (松脂酸) Gibberellin A1 (赤黴素A1) Podolactone A (羅漢松內酯A23)
 Diterpenoids
◆ a wide range of different biological activities:
▬ diesters of phorbal to promote tumor formation
(pharmacological investigation)
▬ are rarely combined with sugars to form glycosides;
however, an exception is stevioside
O
O
O
12 O
13
H H

OH

O HO

OH
Stevioside (甜菊苷):
12-O-Tetradecanoylphorbol-13-acetate (TPA) about 300 times sweeter than sucrose
(佛波酯TPA) and used as a sweetening in Japan 24
 Forskolin (Colforsin) 18,32

◆ from the roots of the Indian herb Coleus forskohlii (Poin)

Briq. (Lamiaceae; Labiatae)
◆ distributed over the subtropical to temperate zones in the
mountains of Africa, Burma, Nepal, Sri Lanka, and Thailand;
cultivated in India
◆ Forskolin was discovered via a screening program in India
of plants used in Hindu and Ayurvedic (阿育吠陀)
traditional medicine
O 14
OH 11 13
labdane diterpenoid:
9
O
1
8
Forskolin (毛喉素)
OH 7β-acetoxy-8,13-epoxy-1α,6β,9α-
7
4 6
COOCH3 trihydroxylabd-14-en-11-one
H
OH 25
 Forskolin (Colforsin) 21,31

◆ Forskolin (prototype for a novel class of drugs) activates

cyclic AMP-generating systems through an ability to
stimulate adenylate cyclase in a receptor-independent
manner
◆ as important research tool in cyclic AMP related studies
◆ a therapeutic potential in diseases such as congestive
cardiomyopathy and bronchial asthma in which the repeated
use of β-adrenergic agonist drugs leads to desensitization of
the receptors and a loss of drug efficacy
◆ it also has potential for use in glaucoma and hypertension

26
 Ginkgo 銀杏
◆ a concentrated acetone-water extract of the dried leaves of
Ginkgo biloba L. (Ginkgoaceae)
◆ for the treatment of peripheral vascular disease, particularly
cerebral circulatory disturbances and other peripheral arterial
circulatory disorders
◆ a living fossil, having survived unchanged in eastern Asia
for some 200 million years
◆ the acetone-water extract of the dried leaves is dried and
adjusted to a potency of 24 % flavone glycosides and 6 %
terpenoids
27
 Ginkgo 銀杏 29

◆ The flavone glycosides (24 %) of the rutin type reduce

capillary fragility and reduce blood loss from the capillary
vessels which may prevent ischemic brain damage
◆ more important is diterpenoid lactones (6 %): Ginkgolides
A,B,C and M have been shown to inhibit platelet-activating
factor (PAF)
O O
O diterpenoid lactones (three lactones):
O
OH Ginkgolide A, R1= OH, R2= R3= H
R1 Ginkgolide B, R1=R2= OH, R3= H
O
Ginkgolide C, R1=R2=R3= OH
R3
Ginkgolide M, R1= H, R2=R3= OH
R2
O O H
28
 Ginkgo 銀杏
◆ PAF: not only induces aggregation of the blood platelets but
also causes bronchoconstriction, cutaneous vasodilation,
chemotaxis of phagocytes, hypotension, and the release of
inflammatory compounds
◆ all of above actions are blocked by the ginkgolides, resulting
in an increase in blood fluidity and circulation
◆ although the extract is sold in Europe as an approved drug, it
has not been approved in the United States
◆ ginkgo extract is sold as a dietary supplement in the United
States in the form of containing 40 mg of the extract

29
 Taxol (Paclitaxel)紫杉醇
◆ from the bark of Taxus brevifolia Nutt. (Taxaceae), also
known as the Pacific yew
◆ one of the most promising antineoplastic
◆ mech.: enhances the polymerization of tubulin, the protein
subunit of the spindle microtubules and induces the
formation of stable, nonfunctional microtubules
◆ disrupts the dynamic equilibrium within the microtubule
system and block cells in the late G2 phase and M phase of
the cell cycle, inhibiting cell replication

30
 Taxol (Paclitaxel)紫杉醇 5

◆ a complex diterpenoid with benzoyl ester groups, a taxane

ring system and a four-membered oxetane ring

hydroxyl group at position 2’ enhances the activity

H3COCO O
OH
9
10
OH 7
11
H 12 6
N O 8
5' 3' 1' 5
2' 15 3
13
4
O O 14 1 H O
2
OH OCOCH3
O

O
An ester side chain position 13:
Taxol
essential for the drug’s cytotoxic activity
31
 Taxol (Paclitaxel)紫杉醇
◆ Taxol is hydrophobic: for intravenous infusion is solubilized
in polyoxyethylated castor oil
◆ before injection, it must in sodium chloride or dextrose
solution or combinations thereof
◆ treatment of metastatic carcinoma of the ovary after failure
of firstline or subsequent chemotherapy
◆ treatment of breast cancer after failure of combination
chemotherapy for metastatic disease or relapse within 6
months of adjuvant chemotherapy

32
 Taxol (Paclitaxel)紫杉醇
7,12,13,17,19,25
◆ a major obstacle: limited supply of the drug
▬ complex chemistry, not economically feasible to synthesize
▬ in harvesting the bark the tree is destroyed
◆ 10-desacetylbaccatin III, isolated from the needles of Taxus
baccata, can be converted to taxol and related active agents
by a relatively simple synthetic procedure
◆ needles, in contrast to bark, can be harvested without
damage to the plant and are, therefore, a more rapidly
renewable resource of drug

33
Biosynthetic pathway of 10-desacetylbaccatin III

Geraniol Geranyl pyrophosphate Geranylgeranyl pyrophosphate Taxadiene

taxusin

10-desacetylbaccatin III
34
Semisynthesis of Taxol from 10-desacetylbaccatin III

HO O OH
H3COCO O
OSi(CH2CH 3)2
DPC, DMAP, Toluene
1. (CH3CH2)2SiCl, Pyridine
HO 2. (CH3)COCl, Pyridine
HO O
H O
H O
OH OCOCH3 O
O OH OCOCH3
O H
N OH
O
O O O
10-desacetylbaccatin III

H3COCO O H3COCO O OH
OSi(CH2CH 3)2
O OH
H H
N O N O
HCl

O O O CH3CH2OH/H2O O O H O
H
OH OH OCOCH3
OCOCH3 O
O

O O
Taxol
35
Total synthesis of Taxol from 10-desacetylbaccatin III

Chem. Soc. Rev., 2007, 36, 1207–1226

37
Triterpenoids (三萜類)

38
 Triterpenoids 8

◆ six isoprene units and share in common the C30 acyclic

precursor squalene
◆ over 4,000 triterpenoids have been isolated, and more than 40
skeletal types have been identified
◆ two main classes: tetracyclic and pentacyclic compounds
◆ small carbon fragments may be removed to produce molecules
with less than 30 carbon atoms, for example, the C27 steroids
◆ most triterpenoids are alcohols and can combine with sugars
to form glycosides, which is the case with saponins
◆ free triterpenoids are often components of resins, latex, or
cuticle of plants 39
 Triterpenoids
◆ triterpenoids that are ecologically significant include the
cucurbitacins and quassinoids which have a bitter taste that may
be a defense against herbivory
◆ the saponins are toxic to cold-blooded animals such as molluscs
◆ limonoids (tetranortriterpenoids) have insect antifeedant
properties, for example, Azadirachta indica produces the
antifeedant limonoid, azadirachtin
◆ the phytoecdysones that disrupt
metamorphosis in insects that are
feeding on plants
40
azadirachtin
Tetraterpenoids & Carotenoids
(四萜類和類胡蘿蔔素)

41
 Tetraterpenoids & Carotenoids
◆ carotenoids comprise an class of C40 tetraterpenoids
◆ the yellow, orange, red, and purple colors seen in living
organisms are due to the presence of carotenoids
◆ biosynthesis:
▬ in the chloroplasts of plants
▬ in the chromatophores of bacteria and fungi
◆ the precursor, geranylgeranyl pyrophosphate, undergoes a
head-to-head dimerization to give prephytoene pyrophosphate
and then phytoene, the central intermediate in the formation
of C40 carotenoids
42
 O O

O P O P O

Geranylgeranyl pyrophosphate O O

2X

O O

O P O P O

O O

prephytoene pyrophosphate

phytoene
43
 Tetraterpenoids & Carotenoids
◆ in some microbes additional isopentenyl groups may be
added onto the tetraterpenoid backbone to produce C45 and
C50 carotenoids, the homocarotenoids
◆ the C40 carotenoids may also be oxidized to carotenoids
containing less then 40 carbons, the apocarotenoids

HO
OH

Sarcinaxanthin (C50H72O2)

44
45
 Tetraterpenoids & Carotenoids 14

◆ approximately 600 carotenoids have been described that

occur naturally
C CH
◆ marine organisms including some with acetylenic groups
◆ carotenoids are either simple unsaturated hydrocarbons
based on lycopene or their oxygenated derivatives, known
as xanthophylls
(tail-to-tail)

(head-to-tail) Lycopene (head-to-tail)

HO Xanthophyll 46
 Tetraterpenoids & Carotenoids
◆ carotenoids: quench free radicals and singlet oxygen, acting
as antioxidants and preventing oxidative damage to cells
▬ in plants and microorganisms:
➢ photoprotective agents
➢ photosynthetic accessory pigments
➢ membrane stabilization components
▬ in animals:
➢ a source of vitamin A and other retinoids
➢ photoprotective and cancer prevention agents
47
 Tetraterpenoids & Carotenoids
◆ a large commercial market:
▬ colorants for foods, animals feeds, pharmaceuticals, and
cosmetics
◆ carotenoids obtained by:
▬ chemical synthesis
▬ extraction of natural products such as carrots
▬ fermentation
◆ biotechnology improving carotenoid production by:
▬ mutagenesis, carotenogenic enzymes, immobilized enzyme
systems, and bioreactors
48
 Vitamin A
◆ vitamin A is a term applied to all derivatives of β-ionone,
other than the carotenoids, that possess the biologic activity
of all-trans retinol
◆ retinol is the major natural form of the vitamin, but known
forms include the acetate and palmitate esters of the alcohol
and such oxidation products as retinol, retinoic acid, and 3-
dehydroretinol
◆ the ester forms have good stability characteristics, and the
acetate and palmitate esters of synthetically prepared all-
trans retinol are the commercial forms of vitamin A

49
 O

OH

β-Ionone Vitamin A Alcohol (retinol)

COOH
OH

Retinoic acid 3-Dehydroretinol

50
 Vitamin A
◆ Retinol is readily absorbed (80 to 90 %) from the normal
intestinal tract and is stored in body tissues, especially the
liver

◆ 1/3 vitamin A is stored under normal circumstances

◆ vitamin A from natural sources:

▬ animal organs: in heart, kidney, liver, eggs, and fish (fish

liver oils are the richest natural sources of the vitamin)

▬ from plant: in carrots and green leafy vegetables

51
 Vitamin A 2

◆ only carotenoids that possess at least one unhydroxylated β-

ionone ring can be convened to vitamin A:

a-carotene
H

b-carotene

-carotene

cryptoxanthin
HO 52
 Vitamin A
◆ β-Carotene and related carotenoids (provitamin A
substances) are cleaved by β-carotene oxygenase in mucosal
cells of the intestine to yield, retinal, most of which is
promptly reduced in the presence of NADH to retinol
◆ vitamin A is involved in vision, growth, and tissue
differentiation
◆ a deficiency of this vitamin can result in a variety of
conditions, including nyctalopia (night blindness),
xerophthalmia, hyperkeratosis of the skin, growth
retardation, decreased resistance to infection
53
 Vitamin A
◆ the function of vitamin A may relate to the synthesis of
specific glycoproteins (cell receptors or regulators); retinyl
phosphate plays an essential role in transferring sugars to
glycoprotein
◆ vitamin A: oral or IM (intramuscular injection)
◆ therapy may be discontinued when liver storage of the
vitamin is determined to be adequate
◆ vitamin A equivalent to an adult requirement for 2 years is
normally stored in the hepatic tissues of persons receiving a
balanced diet
54
 Tretinoin
◆ Tretinoin or all-trans retinoic acid:
▬ available in several formulations (cream, gel, and solution)
for topical purposes
▬ increase epidermal cell mitosis and epidermal cell turnover
▬ used to treat acne vulgaris

COOH

Tretinoin

55
 Isotretinoin
◆ Isotretinoin or 13-cis retinoic acid:
▬ oral use in special situations
▬ use for recalcitrant cystic acne
▬ use for keratinization disorders of the skin (preneoplastic)
▬ should not be used by women who are pregnant, and
contraception should be continued for at least one month
after termination of therapy

COOH
Isotretinoin 56
 b-Carotene 28

◆ b-carotene:
▬ being a provitamin A substance
▬ reducing photosensitivity with erythropoietic protoporphyria
(紅血球生成性原紫質病)
▬ not act as a sunscreen in normal individuals
▬ provide to the treatment of a specific type of photosensitivity
◆ ingested over a period of several weeks, the drug produces
carotenemia, a yellowing of the skin often first observed in
the palms of the hand or on the soles of the feet
◆ during the course of therapy, elevated blood carotene levels
are observed, but vitamin A levels do not rise above normal
57
 Summary

◆ Classification of sesquiterpenoids, diterpenoids,

triterpenoids, and tetraterpenoids

◆ Sesquiterpenoids: Artemisinin, Chamomile, Feverfew,

Valerian

◆ Diterpenoids: Forskolin, Ginkgo, Taxol

◆ Tetraterpenoids: Vitamin A, Tretinoin, Isotretinoin, b-

Carotene

58
 國考題
1. 下列何者之主要成分為(-)-α-bisabolol及 (-)-α-bisaboloxides A, B 等? (101/7)
(A) Rosemary (B) Chamomile (C) Violet (D) Jasmine

2. β-Carotene 由幾個isoprene unit構成? (102/2) (A) 3 (B) 5 (C) 6 (D) 8

3. 下列何者非sesquiterpene類化合物 ? (102/2)
(A) Abscisic acid (B) Anethole (C) Cadinene (D) Caryophyllene

4. 下列何者為生藥feverfew之基原? (102/2)
(A) Tanacetum parthenium (B) Matricaria recutita
(C) Valeriana officinalis (D) Coleus forskohlii

5. Taxol結構中，含benzamide之側鏈係接在taxane環骨架之第幾位碳上? (102/7)
(A) 10 (B) 11 (C) 12 (D) 13

6. 下列何種植物具抗焦慮及幫助睡眠之作用? (102/7)
(A) Tanacetum parthenium (B) Matricaria recutita
(C) Valeriana officinalis (D) Coleus forskohlii
59
 國考題
7. 下列有關taxol之敘述，何者錯誤? (102/7)
(A)為卵巢癌、乳癌之化療藥物 (B)具taxane和4-membered oxetane ring骨架
(C)為水溶性，靜脈點滴使用 (D)環上第13位之側鏈為細胞毒活性所必備

8. 三萜類生合成之途徑中，下列何者為其環化前之共同中間體? (103/2)
(A) Squalene (B) Phytol (C) Limonene (D) Trertinoin

9. 下列何種生藥適用於解痙攣及抗發炎？ (103/2)
(A) Valerian (B) Feverfew (C) Chamomile (D) Forskolin

10. 具有抗瘧疾活性之青蒿素(artemisinin)為下列何類成分? (103/7)

(A) Mnoterpene (B) Sesquiterpene (C) Diterpene (D) Triterpene

11. 下列有關parthenolide的敘述，何者正確? (103/7)

(A) 其為Valeriana officinalis L. 的主要成分
(B) 可刺激血小板釋放serotonin
(C) 屬於germacranolide型之倍半萜類
(D) 富含在feverfew的花中，每日咀嚼其花可抗癌 60
 國考題
12. 下列有關臨床使用的抗癌藥Taxol之敘述，何者錯誤? (104/2)
(A)主要源自Taxus brevifolia植物的樹皮
(B)其化學構造屬triterpenoids
(C) Taxane環之C-13位上所接酯類側鏈為活性必須基團
(D)可由葉部所含10-deacetylbaccatin III當前驅物，經半合成製得

13. 下列有關臨床使用的抗癌藥Taxol之敘述，何者錯誤? (104/2)

(A)為一脂溶性diterpenoid化合物
(B)可讓cell cycle停在S phase
(C)目前多由10-deacetylbaccatin III經反應而得
(D) C-13位上之酯取代基為其細胞毒活性之必要取代基

14. Lycopene及其氧化衍生物所形成的carotenoids，又稱為： (104/2)

(A) Xanthophylls (B) Chlorophylls (C) Erythrophylls (D) Vitamin A series

15. 下列有關Valeriana officinalis之敘述，何者錯誤? (105/2)

(A) valerenic acid為雙萜類 (B) valerenolic acid為其成分之一
(C)藥用部位為根莖與根 (D) valepotriates可幫助睡眠
61
 國考題
16. 下列何者為纈草根之主要用途? (105/7)
(A) antihypertension (B) antiulcer (C) antianxiety (D) antidiabetics

17. 下列有關taxol之敘述，何者錯誤? (105/7)

(A) 10-desacetylbaccatin III為其半合成原料 (B)屬雙萜類結構
(C)第13號碳上的酯類支鏈為抗癌活性之必要基團 (D)可抑制微管蛋白(tubulin)的聚合

18. 下列生藥與成分之配對，何者錯誤? (106/2)

(A) Cinnamomum camphora－camphor (B) Chamaemelum nobile－(─)-α-bisabolol
(C) Mentha piperita－forskolin (D) Tanacetum parthenium－parthenolide

19. Taxol可由下列何者製備而得? (106/2)

(A) baccatin III (B) procaine (C) salicin (D) stigmasterol

20. 下列何種成分具有peroxide鍵結? (106/7)

(A) parthenolide (B) loganin (C) artemisinin (D) terpin hydrate

21. 下列何種成分可能用於青光眼與高血壓之治療？ (106/7)

(A) bilobalide (B) ginkgolides (C) ginkgotoxin (D) forskolin
62
 國考題
22. 下列有關feverfew敘述，何者錯誤? (107/2)
(A)用於解熱 (B)使用部位為葉部 (C)屬菊科植物 (D)含guaianolide type sesquiterpene

23. 下列何者不屬於倍半萜結構? (107/7)

(A) matricin (B) valepotriates (C) valerenic acid (D) eudesmol

24. 下列有關萜類生藥之敘述，何者錯誤? (108/2)

(A) 洋甘菊Matricaria recutita之使用部位為花 (B) Tanacetum parthenium之使用部位為葉子
(C) feverfew具解熱作用 (D) parthenolide為雙萜類化合物

25. 下列關於taxol之敘述，何者正確? (108/7)

(A)屬於sesquiterpene (B)水溶性佳
(C)主要由Taxus brevifolia枝葉取得 (D) 10-desacetylbaccatin III為其半合成原料

26. 有關artemisinin之敘述，下列何者正確? (108/7)

(A)是labdane型雙萜 (B) Artemisia與Chamaemelum均屬菊科
(C)其生合成前驅物是geranyl pyrophosphate (D)主含於其基原植物之根部
63
 國考題
27. Parthenolide屬於下列何種倍半萜內酯類之骨架類型? (109/2)
(A) germacranolide (B) guaianolide (C) eudesmanolide (D) xanthanolide

28. β-Carotene 為生合成vitamin A 之重要中間物，如過度使用易造成何種副作用? (109/7)

(A)貧血 (B)高血壓 (C)皮膚色素沉積 (D)高血脂

29. 青蒿素可治療瘧疾，是從那一屬植物中提煉出來? (110/2)

(A)Artemisia (B)Pyrethrum (C)Valeriana (D)Magnolia

30. 下列有關ginkgolide A之敘述，何者錯誤? (110/2)

(A) 具內酯（lactone）結構 (B) 分離自銀杏葉
(C) 具有anti-PAF作用 (D) 化學性質不穩定

31. 下列關於生藥成分forskolin之敘述，何者錯誤? (110/7)

(A)屬於sesquiterpenoid類成分 (B)基原植物為Coleus forskohlii
(C)得自基原植物之根部 (D)具治療青光眼及高血壓之潛力

64
 國考題
32. Coleus forskohlii含forskolin，其植物科別為何? (111/7)
(A) Apiaceae (B) Lamiaceae (C) Asteraceae (D) Valerianaceae

65