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Studies in Natural
Products Chemistry
Volume 49
Edited by
Atta-ur-Rahman, FRS
International Center for Chemical and Biological Sciences
H.E.J. Research Institute of Chemistry
University of Karachi
Karachi, Pakistan
AMSTERDAM • BOSTON • HEIDELBERG • LONDON

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Contributors
Dmitry L. Aminin (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,

Vladivostok, Russia
Nilton S. Arakawa (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Sergey A. Avilov (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
Vladivostok, Russia
Jaume Bastida (107), Universitat de Barcelona, Barcelona, Spain
Rubia Casagrande (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Zhi Chao (265), Southern Medical University, Guangzhou, China
Rosaria Costa (279), University of Messina, Messina, Italy
Armando C. Duarte (1), CESAM, University of Aveiro, Aveiro, Portugal
Ana C. Freitas (1), CESAM, University of Aveiro, Aveiro, Portugal; ISEIT/Viseu,
Viseu, Portugal
Ana R. Gomes (1), University of Aveiro, Aveiro, Portugal
Carla F.S. Guazelli (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Wilfried Hess (207), University of Oxford, Oxford, United Kingdom
Miriam S.N. Hohmann (243), Universidade Estadual de Londrina, Londrina,
PR, Brazil
Tomohito Kakegawa (157), Josai International University, Togane, Chiba, Japan
Vladimir I. Kalinin (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
Vladivostok, Russia
Holger B. Kramer (207), University of Oxford, Oxford, United Kingdom
Masahiko Kurokawa (157), Kyushu University of Health and Welfare, Nobeoka,
Miyazaki, Japan
Daniela T. Longhi-Balbinot (243), Universidade Estadual de Londrina, Londrina,
PR, Brazil
Mukram M. Mackeen (207), Universiti Kebangsaan Malaysia, Bangi, Malaysia
Vijay Laxminarayan Maheshwari (189), North Maharashtra University, Jalgaon,
Maharashtra, India
Ekaterina S. Menchinskaya (55), G.B. Elyakov Pacific Institute of Bioorganic
Chemistry, Vladivostok, Russia
Snigdha Mishra (307), Banaras Hindu University, Varanasi, Uttar Pradesh, India
xi
xii Contributors
Kunj B. Mishra (307), Banaras Hindu University, Varanasi, Uttar Pradesh, India
Danijela Mišić (363), Institute for Biological Research “Siniša Stanković”, University
of Belgrade, Serbia
Motofumi Miura (157), Nihon University, Funabashi, Chiba, Japan
Shigeyasu Motohashi (157), Nihon University, Funabashi, Chiba, Japan
Jerald J. Nair (107), University of KwaZulu-Natal Pietermaritzburg, Scottsville,
South Africa
Suelen A. Navarro (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Ravindra H. Patil (189), R. C. Patel Arts, Commerce and Science College, Shirpur,
Maharashtra, India
Mohini P. Patil (189), R. C. Patel Arts, Commerce and Science College, Shirpur,
Maharashtra, India
Evgeny A. Pislyagin (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
Vladivostok, Russia
Teresa A.P. Rocha-Santos (1), CESAM, University of Aveiro, Aveiro, Portugal
Yukihiro Shoyama (265), Nagasaki International University, Sasebo, Nagasaki, Japan
Akhilesh K. Shukla (307), CSIR-Central Drug Research Institute, Lucknow,
Uttar Pradesh, India
Alexandra S. Silchenko (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,
Vladivostok, Russia
Branislav Šiler (363), Institute for Biological Research “Siniša Stanković”, University
of Belgrade, Serbia
Yi Sun (157), China Academy of Chinese Medical Sciences, Beijing, China,
Nihon University, Funabashi, Chiba, Japan
Hiroyuki Tanaka (265), Kyushu University, Higashi-ku, Fukuoka, Japan
Vinod K. Tiwari (307), Banaras Hindu University, Varanasi, Uttar Pradesh, India
Rama P. Tripathi (307), CSIR-Central Drug Research Institute, Lucknow, Uttar
Pradesh, India
Nguen Huu Tung (265), Nagasaki International University, Sasebo, Nagasaki, Japan
K. Upadhaya (307), CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh,
India
Johannes Van Staden (107), University of KwaZulu-Natal Pietermaritzburg,
Scottsville, South Africa
Waldiceu A. Verri Jr. (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Ken Yasukawa (157), Nihon University, Funabashi, Chiba, Japan
Ana C. Zarpelon (243), Universidade Estadual de Londrina, Londrina, PR, Brazil
Preface
The 49th volume of this long-standing series contains many interesting articles
highlighting the huge biodiversity of natural products and their potential appli-
cations in medicine.
A large number of exciting natural products have been discovered from
marine sources, with interesting biological activities, including antimicrobial,
anticancer, and anti-inflammatory activities, many of which have potential
therapeutic applications. The terpene glycosides found in starfishes and sea
cucumbers possess many important bioactivities. The article by Gomes et al.
comprehensively reviews the compounds obtained from echinoderms during
2009–2014 in Chapter 1. The structure, occurrence, biosynthetic origin, bio-
logical activities, and, where available, their mode of action, are discussed.
In Chapter 2, the anticancer triterpene glycosides in the sea cucumber are
discussed by Aminin et al. Recent studies on the cytotoxic, cancer-preventive,
and antitumor activities of holothurian triterpene glycosides are presented.
The isoquinoline alkaloids found in plants of the Amaryllidaceae family,
such as galanthamine, have attracted a wide interest because of their useful
biological activities. In Chapter 3, Bastida et al. present an overview of recent
developments in the study with a particular focus on the cytotoxic effects of
these alkaloids in various cancer cell lines. Yasukawa et al. present the antitu-
mor-promoting, antiinflammatory, cytotoxic, antimicrobial, anti-influenza, and
antiherpes simplex-1 virus activities of diarylheptanoids isolated from the rhi-
zome of Alpinia officinarum in Chapter 4.
Endophytic fungi have been known as important sources of bioactive sec-
ondary metabolites with diverse biological activities. Novel antibiotics, anti-
mycotics, immunosuppressants, anticancer compounds, and compounds with
other biological activities have been reported from these microorganisms. The
important anticancer drug, paclitaxel (Taxol), was obtained from Taxomyces
andreanae, an endophytic fungus isolated from the yew plant, Taxus brevifolia.
In Chapter 5, Maheshwari et al. have reviewed the recent developments in the
field of bioactive secondary metabolites found in endophytic fungi, including
advances in isolation techniques, mode of cultivation, culture conditions, and
biological activities of the metabolites derived from endophytic microorganisms.
The ubiquitin-proteasome system plays a fundamentally important role
toward protein turnover in eukaryotic cells. This involves the ubiquitin conju-
gation system comprising an enzyme cascade of E1, E2, and E3 enzymes; the
xiii
xiv Preface
deubiquitinases; and the proteasome. A number of natural product inhibitors of

the proteasome have been studied in recent years. Such natural product inhibi-
tors of ubiquitin conjugation and deconjugation are discussed by Kramer et al.
in Chapter 6.
Sesquiterpene lactones are an important class of natural products many of
which exhibit pronounced anti-inflammatory properties. These may be due to
several mechanisms including inhibition of the production of cytokines, lipid
mediators, and other related molecules; modulation of pro- and antioxidant con-
tents; and regulation of intracellular signaling pathways. Hohmann et al. discuss
these developments in Chapter 7. Ginsenosides are active compounds found in
many Panax species. Shoyama et al. in Chapter 8 have presented an overview of
the application of monoclonal antibodies against ginsenosides including a gen-
erally applicable procedure for their detection and isolation. Many mushrooms
have found wide use in traditional systems of medicine and the extracts from
them are widely used as health supplements. In Chapter 9 by Costa the analyti-
cal determination of bioactive substances isolated from mushrooms, including
modern chromatographic and spectroscopic methods, are discussed.
In Chapter 10 by Tiwari et al., the major developments in the synthesis and
analysis of biologically significant carbohydrate-based molecules with poten-
tial for development as drugs are reviewed. In the final Chapter 11, Šiler and
Mišić present an overview on the secondary metabolites found in the Genus
Centaurium s.l. (Gentianaceae) including the biotechnological enhancement of
their accumulation and the progress in respect of application of various herbal
extracts and isolated compounds in medicinal studies.
The present volume is representative of the vast panorama of structures and
bioactivities found in natural products. It is hoped that it will be received with
the same enthusiasm and interest as the previous volumes of this important
series.
I would like to express my sincere thanks to Mr. Mahmood Alam for his sup-
port in the preparation of this volume. I would also like to thank Miss Taqdees
Malik and Ms. Humaira Hashmi for technical assistance.
Atta-ur-Rahman, FRS
International Center for Chemical and Biological Sciences
H.E.J. Research Institute of Chemistry
University of Karachi
Karachi, Pakistan
Chapter 1
Echinoderms: A Review
of Bioactive Compounds
With Potential Health Effects
Ana R. Gomes*,1, Ana C. Freitas§,¶, Armando C. Duarte§,
Teresa A.P. Rocha-Santos§
*University of Aveiro, Aveiro, Portugal; §CESAM, University of Aveiro, Aveiro, Portugal;
¶ISEIT/Viseu, Viseu, Portugal
1Corresponding author: E-mail: aaritagomes@gmail.com
Chapter Outline
Introduction1 Saponins20
Biological Activities With Potential Peptides42
Benefit for Health 3 Sphingolipids and Fatty Acids 43
Antibacterial and Antifungal Pigments44
Activities3 Other Bioactive Extracts 45
Anti-inflammatory Activity 14 Conclusion46
Anticancer Activity 16 Declaration of Interest 46
Antioxidant Activity 18 References47
Immunomodulatory Activity 19
Natural Products Derived From
Echinoderms Molecules Which
Have Potential Health Effects 20
INTRODUCTION
The growing numbers of drug-resistant diseases has forced a fast and continuous
growth of the pharmaceutical market [1]. Currently, about half of all new com-
mon drugs reported are of natural origin [2]. The innovation of novel drugs is
constantly encouraged, thus academic and industry researchers are striving to dis-
cover new potentially bioactive molecules from new sources, such as the oceans.
The marine environment is promoting chemical and biological novelties [2,3].
Covering most of the Earth’s surface, the oceans are responsible for hosting
a large diversity of bioactive compounds (BCs) with interesting pharmaceutical
Studies in Natural Products Chemistry, Vol. 49. http://dx.doi.org/10.1016/B978-0-444-63601-0.00001-6
Copyright © 2016 Elsevier B.V. All rights reserved. 1
2 Studies in Natural Products Chemistry
activities and potential therapeutic applications [4–6]. The marine BCs are known
to present several advantages when compared with nonnatural compounds, such
as high chemical diversity, biochemical specificity, less side effects, binding effi-
ciency, and propensity to interact with biological targets, increasing the importance
of the discovery of natural drugs [7]. Due to their broad panel of bioactivities, such
as antibacterial, antifungal, antiprotozoal, anti-inflammatory, anticoagulant, anti-
tumor, antioxidant, and antiviral activities, marine natural products (MNPs) have
been showing exceptionally interesting applications in the pharmaceutical indus-
try [3,7]. The marine environment, sheltering a vast diversity of organisms dif-
fering in their physiology and adaptation capacity, is becoming an important spot
for the identification of new medicines. Since 1990, the marine invertebrates were
described as the source of more than 11,000 new natural products [7]. In recent
years, many BCs have been continuously extracted from marine invertebrates, like
sponges, corals, jellyfish, tunicates, bryozoans, among others [3,8]. Although rela-
tively less explored, the echinoderms are an ancient group of marine invertebrates
with about 7000 living species from which various BCs with interesting pharma-
ceutical activities and a broad spectrum of biological activity have been isolated [9].
Kuznetsova et al. [10] isolated in 1982 a triterpene glycoside from 19 holothurian
species of the pacific tropical region, which exhibited cytotoxic activity against
yeast Candida albicans and sarcoma-37 cells. In 1996, Palagiano et al. [11] dem-
onstrated that 20 steroid glycosides isolated from the starfish Henricia downeyae
showed growth inhibition in bacteria Staphylococcus aureus and Micrococcus
roseus, and fungus Sordaria fimicola. Li et al. [12] found new fucosylated chon-
droitin sulfates (FucCs) from sea cucumber with anticoagulant activity in vivo, and
echinoderm FucCs may be a potential alternative to heparin for blocking metastasis
and inflammatory reactions without the undesirable side effects of anticoagulant
heparin. Later, Tapon-Bretaudiere et al. [13] described that FucCs extracted from a
sea cucumber Ludwigothurea grisea have the capacity to promote the proliferation
of blood vessels and prevent venous and arterial thrombosis in mammals, simulta-
neously. Isolated by Haug et al. [14], extracts of several tissues from sea cucumber
Cucumaria frondosa, starfish Asterias rubens, and sea urchin Strongylocentrotus
droebachiensis demonstrated antibacterial activities against Gram-negative bacte-
ria Vibrio anguillarum and Escherichia coli, and Gram-positive bacteria S. aureus
and Corynebacterium glutamicum. Various sea urchins Hemicentrotus pulcherri-
mus, Mesocentrotus nudus, and Temnopleurus toreumaticus isolated from different
regions of China also demonstrated effective against cervical lymph node tubercu-
losis, accumulation of phlegm, and sternocostal pain embolism [15]. Equally inter-
esting, was the research developed in 2001 by Aizenberg et al. [16] that discovered
single calcite crystals, which can function as lenses isolated form brittle star Ophio-
coma wendtii. These lenses have the ability to focus light on to nerve bundles that
run behind them and receive the signal to be further processed, resulting in a func-
tion similar to a digital camera that builds up the picture pixel by pixel. Currently,
the photonic industries are trying to imitate the perfect calcite lenses and their use in
signal reception [17]. Despite several interesting discoveries, the natural resources
need to be used wisely. Growing global pressures on the echinoderms by various
Echinoderms: A Review of Bioactive Compounds Chapter | 1 3
industries have put these invertebrates under threat, adding to the ongoing concern
over the worldwide depletion of marine resources. The ecological effects of over-
fishing on the structure and functioning of entire ecosystems, as well as the climate
issues, such as ocean acidification and hypoxia are also a growing concern [9].
The main goal of this chapter is to present a synthesis about the new nat-
ural compounds, with special emphasis on BC, isolated from echinoderms
over the last 5 years (2009–2014), describing their structure, distribution, and
bioactivities.
BIOLOGICAL ACTIVITIES WITH POTENTIAL BENEFIT FOR

HEALTH
Antibacterial and Antifungal Activities
An antimicrobial agent has the capacity to kill microorganisms or inhibit their
growth. They can be grouped in antibacterial and antifungal agents according to
the microorganisms which it interacts [18]. Many antibacterial agents are sold
today mainly as disinfectants, such as soaps, health and skin care products, and
household cleaners. However, the discovery, development, and clinical use of
antibacterial during last century have largely reduced mortality from bacterial
infections. A number of structurally diverse and highly effective antibacterial
agents were discovered and developed, such as Penicillium rubens the first anti-
biotic isolated and “streptomycin,” the first bactericidal antibiotic active against
tuberculosis [19,20]. Antibiotics have many mechanisms of action, including the
inhibition of cell wall synthesis; the increase of cell membrane permeability; and
the interference with protein synthesis, nucleic acid metabolism, and other meta-
bolic processes, such as folic acid synthesis [21,22]. Despite the success of new
antimicrobial agents for clinical use, their number has declined, in part due to the
huge expense of developing and testing new drugs. At the same time, an alarming
increase in resistance of bacteria, fungi, viruses, and parasites to multiple existing
agents has been reported [23]. The inevitable consequence of widespread and inju-
dicious use of antibacterial agents has been the appearance of antibiotic-resistant
pathogens resulting in a serious threat to global public health [24]. However, La
et al. [25] reported antibacterial and antifungal activity in two new sulfated alkenes
isolated from sea cucumber Apostichopus japonicus. Both molecules, (5Z)-dec-
5-en-1-yl sulfate (1) and (3E)-dec-3-en-1-yl sulfate (2) demonstrated antibacte-
rial activity against the Gram-negative bacterium E. coli, and antifungal activity
against Zymoseptoria tritici (Table 1.1) [25]. Further studies should be conducted
to verify the possible mechanism of action of these metabolites.
TABLE 1.1 New Bioactive Compounds Isolated From Echinoderms With Beneficial Health Effects
Marine Pharmacologic
Bioactivity Class Compound Name Organism Chemical Class Activity References
Antibacterial (5Z)-dec-5-en-1-yl sulfate (1) Sea cucumber Sulfated alkene Escherichia coli and [25]
substances Apostichopus Zymoseptoria tritici
(3E)-dec-3-en-1-yl sulfate (2) japonicus inhibition
Cholest-8(14)-ene- Sea urchin Saponins Trypanosoma brucei [101,102]

3β,5α,6β,7α-tetraol (9) Diadema inhibition
savignyi
Astropectenols A (87) Starfish [56,101]

Astropecten
polyacanthus
Centrocins 1 (130) and 2 Sea urchin Peptides Corynebacterium [124]

(131) Strongylocentrotus glutamicum, E. coli,
droebachiensis Listonella anguillarum,
and Staphylococcus
aureus inhibition
Antifungal Echinoside A (3) Sea cucumber Saponins Aspergillus fumigatus, [29]

substances Holothuria Candida albicans,
Holothurin A1 (4) scabra Candida pseudotropicalis,
Cryptococcus neoformans,
Fonsecaea compacta,
Microsporum gypseum,
and Trichophyton rubrum
inhibition
Marmoratoside A (14) Sea cucumber A. fumigatus, C. [73]
Bohadschia albicans, Candida krusei,
17 α-Hydroxy impatienside marmorata Candida tropicalis, Cr.
A (15) neoformans, and T.
Impatienside B (16) Sea cucumber rubrum inhibition [74]
Holothuria
(Microthele)
Echinoderms: A Review of Bioactive Compounds Chapter | 1

fuscopunctata
Cladoloside B (17) Sea cucumber A. A. fumigatus, C. [75,76]

japonicus albicans, C. tropicalis,
Cr.neoformans, M.
gypseum and T. rubrum
inhibition
Patagonicoside B (18) and C Cladosporium [77]

(19) cladosporoides
inhibition
Holotoxin D1 (20) A. fumigatus, C. [78]

albicans, C. tropicalis,
Cr. neoformans, M.
gypseum and T. rubrum
inhibition
25,26-Dihydroxy-holotoxin Cr. neoformans and A.

A1 (21) fumigatus inhibition
Holotoxin D (22) A. fumigatus, C. [76,79]

albicans, C. tropicalis,
26-Nor-25-oxo-holotoxin A1 Cr. neoformans, M. [76]
(23) gypseum and T. rubrum
Holotoxins E (24) inhibition
5
Continued
TABLE 1.1 New Bioactive Compounds Isolated From Echinoderms With Beneficial Health Effects—Cont’d

Holotoxins F (25) and G (26) C. albicans, Cr.

neoformans and M.
gypseum inhibition
Coustesides A–J (27–36) Sea cucumber C. albicans inhibition [80]

Bohadschia
cousteaui
Typicosides A1 (37), A2 (38), Sea cucumber Aspergillus niger, C. [81]

B1 (39), and C2 (40) Actinocucumis albicans, and Fusarium
typicall oxysporum inhibition
Variegatusides C–F (41–44) Sea cucumber C. albicans, Candida [82]

Stichopus parapsilosis, C.
variegates pseudotropicalis,
C. tropicalis, Cr.
neoformans, and M.
gypseum inhibition
Cucumariosides A1 (47), A6 Sea cucumber A. niger and F. [84–87]

(52), A8 (54), and A15 (61) Eupentacta oxysporum inhibition
fraudatrix
Cucumariosides A2–A5 (48– A. niger inhibition
51), A7 (53), A9–A14 (55–60),
and B2 (61)
Anti-inflammatory Astrosteriosides A (5) and D Starfish IL-12 p40, IL-6, and [38,39]
substances (6) Astropecten TNF-α inhibition
monacanthus
Astrosterioside C (7) IL-6 inhibition
Astebatheriosides B–D Starfish Asterina IL-12 inhibition [123]
(137–139) batheri
Agglutinin (149) Sea cucumber Lectin Neutrophils reduction [133]

Holothuria grisea in vivo
Comaparvin (150) Crinoid – Expression of iNOS [134]

Comanthus protein and mRNA

bennetti in LPS-stimulated
macrophage cells
inhibition
Anticancer (5Z)-dec-5-en-1-yl sulfate (1) Sea cucumber A. Sulfated alkene A549, MG63, and [25]
substances japonicus U251 cell proliferation
inhibition
(3E)-dec-3-en-1-yl sulfate (2)
Astrosteriosides C (7) Starfish A. Saponins HL-60, PC-3, and SNU- [39]

monacanthus C5 cell proliferation
inhibition
Astrosteriosides D (6) HL-60, PC-3, and SNU-

C5 cell proliferation
inhibition and apoptosis
induction
Leucospilotaside B (8) Sea cucumber HL-60, MOLT-4, A-549, [49,50]

Holothuria and BEL-7402 cell
leucospilota proliferation inhibition
Cholest-8(14)-ene- Sea urchin D. HL-60, PC-3, and SNU- [56]

3β,5α,6β,7α-tetraol (9) savignyi C5 cell proliferation
induction
7
Continued
Pentactaside I (75) and II (76) Sea cucumbers P388, A-549, MCF-7, [93]
Colochirus MKN-28, HCT-116,
Pentactaside III (77) quadrangularis and U87MG cell
proliferation inhibition
Pentactaside B (78) and C (79) P388, HCT-116, MCF-7, [94]

MKN-28, and A-549 cell
Desulfated echinoside A (80) Sea cucumber HepG2 cell proliferation [95,96]

Pearsonothuria inhibition in vivo,
graeffei NF-kB-dependent matrix
metalloproteinase-9
inhibition
Scabraside D (81) Sea cucumber H. P-388, A-549, MKN- [97]

scabra 28, HCT-116, and
Fuscocineroside C (82) MCF-7 cell proliferation
24-Dehydroechinoside A (83) inhibition
Pseudocnoside A (84) Sea cucumber A-549 and HeLa cell [98,99]

Pseudocnus proliferation inhibition
dubiosus
leoninus
Echinoside A (85) Sea cucumber PC-3 cell proliferation [100]

Holothuria inhibition
nobilis
Cholest-8-ene-3β,5α,6β,7α- Sea urchin D. HL-60, PC-3, and SNU- [56]
tetraol (86) savignyi C5 cell proliferation
induction
Astropectenol A (87) Starfish A. HL-60, PC-3, and [102]

polyacanthus SNU-C5 cell

Astropectenol C (88) HL-60 and PC-3 cell
Astropectenol D (89) HL-60 and SNU-C5 cell

Anthenoside A (95) Starfish Anthenea HL-60, MOLT-4, A-549, [107]

chinensis and BEL-7402 cell
Anthenosides E, G, H and I K-562 and BEL-7402 [108]

(96–99) cell proliferation
inhibition
Anthenosides J (100) and K K-562, BEL-7402,

(101) and U87MG cell
Astrosteriosides B (102) Starfish A. HL-60, PC-3, and SNU- [39]

monacanthus C5 cell proliferation
inhibition
Leptasteriosides A–F (103– Starfish RPMI-7951 and T-47D [110]

108) Leptasterias cell proliferation
ochotensis inhibition
9
Continued

5α-Cholesta-9(11),24-dien- Starfish Archaster MDA-MB-435 [111]

3β,6α,20β-triol-23-one typicus and Colo205 cell
3-sulfate (109) proliferation inhibition
Cariniferoside F (110) Starfish RPMI-7951 and T-47D [112]

Asteropsis cell proliferation
carinifera inhibition
Novaeguinosides A–D Starfish Culcita K-562 and BEL-7402 [113]

(111–114) novaeguineae cell proliferation
inhibition
Sodium (20R,24S)-6α-O- [114]
(4-O-sodiumsulfato-β-d-
quinovopyranosyl)-5α-cholest-
9(11)-en-3β,24-diol 3-sulfate
(115)
Sodium (20R,24S)-6α-O-[3-O-
methyl-β-d-quinovopyranosyl-
(1→2)-β-d-xylopyranosyl-
(1→3)-β-d-glucopyranosyl]-5α-
cholest-9(11)-en-3β,24-diol
3-sulfate (116)
Archasterosides A (117) and Starfish A. HeLa and JB6 P+ [115,116]

B (118) typicus Cl41 cell proliferation
inhibition
Diplasteriosides A (119) Starfish T47D, RPMI-7951, [117,118]
Diplasterias and HCT-116 cell
brucei proliferation inhibition
Diplasteriosides B (120) T47D and RPMI-7951 [117]

cell proliferation
inhibition

6α-O-[β-d-fucopyranosyl- Starfish Asterias RAW 264.7 cell [119]
(1→2)-β-d-galactopyranosyl- amurensis proliferation inhibition
(1→4)-[β-d-quinovopyranosyl-
(1→2)]-β-d-quinovopyranosyl-
(1→3)-β-d-galactopyranosyl]-
5α-chol-9(11)-en-23-one-3β-yl
sodium sulfate (121)
6α-O-[β-d-fucopyranosyl-
(1→2)-β-d-galactopyranosyl-
5α-cholesta-9(11),24-dien-23-
one-3β-yl sodium sulfate (122)
6α-O-[β-d-fucopyranosyl-
(1→2)-β-d-galactopyranosyl-
5α-cholest-9(11)-en-23-one-
3β-yl sodium sulfate (123)
11
Continued
Hippasterioside D (124) Starfish HT-29 cell proliferation [120]

Hippasteria inhibition
phrygiana
Asteropsiside A (125) Starfish A. T-47D and RPMI- [121]

carinifera 7951 cell proliferation
inhibition
Lethasterioside A (126) Starfish T-47D, RPMI-795I, [122]

Lethasterias fusca and HCT-116 cell
3-(1′-Hydroxypropyl)-1,6,8- Crinoid Pigments MCF-7, SF-268, and [127]

trihydroxy-9,10-anthraquinone Colobometra H460 cell proliferation
(135) perspinosa inhibition in vitro
3-Propyl-1,6,8-trihydroxy-
9,10-anthraquinone (136)
4-Hydroxybutanoic acid (137)
Ophiodilactones A (147) Brittle star Phenylpropanoids P388 cell proliferation [132]

and B (148) Ophiocoma inhibition
scolopendrina
Antioxidant Aminopentahy- Sea urchin Pigments DPPH scavenging [65]
substances droxynaphthoquinone (10) Mesocentrotus capacity, lipid
nudus peroxidation inhibition,
and oxidative stress
protection

Acetylaminotrihy-
droxynaphthoquinone (11)
Mirabiquinone [7,5′- Sea urchin Radical-scavenging [129]

anhydroethylidene-6,6′- Scaphechinus ability
bis(2,3,7- mirabilis
trihydroxynaphthazarin)] (140)
Spinochrome monomers B Sea urchin S. [130,131]

(141), droebachiensis
and D (142)
Anhydroethylidene-6,6′- [130]
bis(2,3,7-
trihydroxynaphthazarin) (143)
and its isomer (144)
Ethylidene-6,6′-bis(2,3,7-
trihydroxynaphthazarin) (145)
Immunomodulatory Lysaketotriol (12) and Starfish Steroids Increased ROS [102]

substances lysaketodiol (13) Lysastrosoma formation by mouse
anthosticta macrophages
13
DPPh, 1,1-diphenyl-2-picrylhydrazyl; ROS, reactive oxygen species.
Despite the growing research, the development of antifungal agents has

lagged behind that of antibacterial agents [26]. This is mainly caused by the
differences in the cellular structure of the organisms involved. Bacteria are pro-
karyotic and therefore offer several structural and metabolic targets that differ
from those of the human host. In contrast, the fungi are eukaryotes, and con-
sequently most agents toxic to fungi are also toxic to the host. However, the
spectrum of activity for the licensed antifungal agents is well defined through
the results obtained in vitro and in vivo with the most common fungal pathogens
[27,28]. Isolated for the first time from sea cucumber Holothuria (Metriatyla)
scabra, echinoside A (3) and holothurin A1 (4), the two new bioactive triterpene
glycosides showed antifungal activity against C. albicans, Candida pseudotrop-
icalis, Cryptococcus neoformans, Trichophyton rubrum, Fonsecaea compacta,
Aspergillus fumigatus, and Microsporum gypseum [29].
Anti-inflammatory Activity
The inflammation process has been considered as one of responsible for the
progression of several diseases. The inflammation acts on the surface of the
body as local redness, heat, swelling, and pain. It is the basis of the body’s
healing response, bringing immune activity to a spot of injury or infection
[30,31]. Nonsteroidal anti-inflammatory drugs (NSAIDs) are a class of medi-
cines that provides anti-inflammatory effects relieving the pain, by counteract-
ing the cyclooxygenase (COX) enzyme activity [32,33]. There are two types of
COX enzymes: COX-1 and COX-2. Both enzymes synthesize prostaglandins
that promote inflammation, pain, and fever [34]. Prostaglandins are a family of
chemicals that are produced by the cells of the body and have several functions
such as to promote inflammation necessary for healing, also resulting in pain
and fever; to support the blood clotting function of platelets; and to protect the
lining of the stomach from the damaging effects of acid. NSAIDs block the
COX enzymes and reduce prostaglandins throughout the human organism. As a
consequence, ongoing inflammation, pain, and fever are reduced [31–33]. The
most common NSAIDs include aspirin, diclofenac, ibuprofen, indomethacin,

and naproxen. These drugs block both COX-1 and COX-2 enzymes [35].
Recently, new studies have been developed by IMULAN BioTherapeu-
tics, LLC. One class of peptides discovered, named immune-selective anti-
inflammatory derivatives (ImSAIDs) showed interesting biological properties
like anti-inflammatory responses. ImSAIDs function by altering the activation
and migration of inflammatory cells, which are immune cells responsible for
amplifying the inflammatory response. These peptides represent a new category
of anti-inflammatory and are unrelated to steroid hormones or nonsteroidal
anti-inflammatories [36,37]. Thao et al. [38] also found in Vietnamese starfish
Astropecten monacanthu three new asterosaponins with interesting anti-inflam-
matory activity. Astrosteriosides A (5) and D (6) exhibited anti-inflammatory
activity evaluated by measuring the production of interleukin-12 p40, IL-6, and
tumor necrosis factor alpha (TNF-α), while astrosterioside C (7) only exhibited
inhibitory effects on IL-6 production [38,39]. The cytokines have an important
role, especially in host responses to infection, immune responses, trauma, sep-
sis, cancer, and reproduction. They act directly in the inflammation process,
increasing or decreasing the inflammatory response. The cytokines modulate
the balance between humoral and cell-based immune responses, and they regu-
late the maturation, growth, and responsiveness of particular cell populations.
Cytokines like TNF-α is a potent proinflammatory cytokine and is early indica-
tor of the inflammatory process, inducing fever, apoptotic cell death, cachexia,
inhibition of viral replication, and respond to sepsis via interleukin-1 (IL-1)- and
IL-6-producing cells. Dysregulation of TNF production has been implicated in a
variety of human diseases including Alzheimer’s disease, cancer, major depres-
sion, and inflammatory bowel disease [40–42]. IL-6 also stimulates immune
response, in fighting infection, as showed in vivo against bacterium Streptococcus
pneumoniae by Van der Poll et al. [43].
Anticancer Activity
The abnormal cell growth with potential to invade and spreads throughout the
body is known as cancer or a malignant tumor. DNA damage is considered to
be one of the most worrying steps leading to cancer [44]. DNA is the source of
genetic information of each cell, being its integrity and stability essential to life.
It is subject to aggression from the environment, and any resulting damage, if
not repaired, can lead to mutation and probably cancer development. Beyond
environmental agents, DNA is also subject to oxidative damage from by-
products of metabolism, such as free radicals. The process of DNA replica-
tion during cell division also is susceptible to error. The rate at which DNA
polymerase adds incorrect nucleotides during DNA replication is a major factor
in determining the spontaneous mutation rate in an organism. Many proteins
encoded by genes tumor suppressors are involved in the prevention and repair
of genetic damage, however, some mutations survive this process [45,46]. DNA
repair processes are present in both prokaryotic and eukaryotic organisms, and
many of these proteins complexes have been highly preserved through evolu-
tion. The cells have mechanisms of action to detect and repair the various types
of damage that can occur to DNA, independently of their cause being replication
errors or external factors. During the cell cycle, checkpoint mechanisms ensure
that cell’s DNA is intact before allowing DNA replication and cell division to
occur. Failures in these checkpoints can lead to a buildup of damage, leading
to the development of mutations [47,48]. Han et al. [49] discovered a new anti-
cancer molecule with potential against several types of human tumor cell lines
(HL-60, MOLT-4, A-549, and BEL-7402). The molecule leucospilotaside B (8),
isolated from the sea cucumber Holothuria leucospilota, exhibited cytotoxicity
against leukemia, hepatocellular carcinoma, and human lung adenocarcinoma
epithelial cell lines (Table 1.1) [49,50].
Cancer is often characterized by the uncontrolled proliferation of cells with

a loss of cell cycle regulation and apoptosis [51]. The apoptotic process is trig-
gered as a result of a change in the balance of anti- and proapoptotic proteins.
Dysregulation of apoptotic signaling facilitates cancer development by blocking
differentiation; promoting angiogenesis; and increasing cell motility, invasion,
and metastasis [52,53]. To date, there are two major apoptotic pathways: the
extrinsic or death receptor pathway and the intrinsic or mitochondrial pathway.
The sequence of events that define the extrinsic signaling pathway that initi-
ate apoptosis, involves transmembrane death receptors that are members of the
TNF receptor gene superfamily. Members of this receptor family bind to extrin-
sic ligands and transduce intracellular signals resulting in cell death [54,55].
The signal transduction of the extrinsic pathway involves several caspases
(caspase-3, -6, -7, and -8), which are proteases with specific cellular targets.
Since activated, the caspases affect various cellular functions as part of a mecha-
nism that results in the death of the cells [54].
The intrinsic signaling pathways leading to apoptosis involve a diverse array
of nonreceptor-mediated intracellular signals that act directly on targets within
the cell [55]. Thao et al. [56] demonstrated induction of cell death by apopto-
sis by a new steroid (cholest-8(14)-ene-3β,5α,6β,7α-tetraol (9)) isolated from
sea urchin Diadema savignyi. The induction of apoptosis was accompanied
by alterations of the apoptosis-related protein expression, such as inactivation

of extracellular signal-regulated kinase (ERK)1/2 mitogen-activated protein
kinase (MAPK) signaling, and decreased c-Myc expression [56]. Stimuli, such
as viral infections or damage to the cell by toxins, free radicals, or radiation
can induce the activation of the intrinsic pathway for programmed cell death.
These stimuli induce changes in the inner mitochondrial membrane that result
in the loss of transmembrane potential, releasing proapoptotic proteins into the
cytosol [54,55]. In the mitochondria, proapoptotic proteins activate caspases
that mediate the destruction of the cell [55,57]. The apoptosis induction is one
of the strategies to stop the proliferation of cancer cells. Radiation and chemical
agents like iodine-131, yttrium-90, tamoxifen, doxorubicin, cisplatin, among
others capable of inducing apoptosis have been used to treat hepatocellular
carcinoma, thyroid, breast, lung, stomach, and colorectal and ovaries cancer
[58–60]. Apoptosis is a complex process that involves many different signaling
pathways and results in a multitude of changes in the dying cells [51,61].
Antioxidant Activity
The oxidation is a fundamental part of aerobic life and human metabolism with
production of reactive oxygen species (ROS) either naturally or by some bio-
logical dysfunction. A balance between ROS and antioxidants is essential for a
correct physiological function [62]. ROS is a product of cell metabolism, and
the possible damage which they can cause in the human organism is minimized
by the antioxidant ability and several defense mechanisms inside of the cell
[44]. Antioxidants have the capacity to prevent degradation of human organism
by ROS, including hydroxyl radical, superoxide anion radical, oxygen singlet,
hydrogen peroxide, hypochlorite, nitric oxide radical, and peroxynitrite radical.
ROS attacks relevant macromolecules, such as DNA, proteins, carbohydrates,
and lipids, leading to cell damage and homeostatic disruption. Various repair
mechanisms are complementary to one another, acting against ROS in different
cellular compartments. To counterbalance the detrimental effects of these spe-
cies, it is important to have a balanced enzymatic system, including superoxide
dismutase (SOD), glutathione peroxidase, and catalase or nonenzymatic sub-
stances, such as vitamins E and C and provitamin A (beta-carotene) [63].
Two major contributors to oxidative stress are the superoxide and hydro-
gen peroxide. Superoxide is converted by SOD to oxygen and hydrogen per-
oxide that is less reactive than superoxide. Catalase prevents the damaging
effects of hydrogen peroxide, by converting this ROS into water and oxy-
gen, resulting in the production of benign molecules. However, this conver-
sion is not totally efficient, and residual peroxides persist in the cell [64].
Excessive amounts can cause deleterious effects, such as Parkinson’s disease,
senile, schizophrenia, and Alzheimer’s disease [62]. Application of external
source of antioxidants can assist in reduction of this oxidative stress. Thus,
further studies are urgent to find new molecules with capacity to counteract
these effects. Zhou et al. [65] discovered two new polyhydroxylated naphtho-
quinone pigments with antioxidant activity. Isolated from purple sea urchin
M. nudus, pigments identified as aminopentahydroxynaphthoquinone (10)
(C10H7NO7) and acetylaminotrihydroxynaphthoquinone (11) (C10H9NO6)
(10 and 11 structural formula not reported) exhibited antioxidant activity
measured by 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging capacity,
lipid peroxidation inhibition in rat liver, and oxidative stress protection prop-
erties also in vivo by exposure to t-BOOH [65].
It is important to mention that nutrition plays a key role in maintaining the
body’s enzymatic defenses against ROS. Some essential minerals including
selenium, copper, manganese, and zinc are involved in the structure or cata-
lytic activity of these enzymes [64]. As an antioxidant, the role of vitamin E is
strongly associated with the elimination of ROS, protecting the integrity of lip-
ids and phospholipid membranes. Other functions such as modulation of gene
expression and inflammatory responses are also related [66]. Equally strong
antioxidant is the vitamin C, working as a scavenger of ROS into the organism.
The ascorbate is effective against the superoxide radical anion, hydrogen per-
oxide, hydroxyl radical, and singlet oxygen, making it an efficient and powerful
antioxidant in human organism [63].
Immunomodulatory Activity
The development of an immune response is a multistep process and is reg-
ulated at several levels through complex mechanisms. The immune system
can be classified into an innate immune system and an acquired or adaptive
immune system (exclusively in vertebrates) [30]. The innate immune system
covers many areas of host defense against pathogenic microbes, including the
recognition of pathogen-associated molecular patterns (PAMPs). The innate
immunity is genetically programmed to detect features of invading microbes
and is usually triggered when microbes are identified by pattern recognition
receptors (PRRs), serving as a first line of defense quick and extraordinarily
effective in eliminating most invading pathogens [67]. The PAMPs activate
innate immune responses, protecting the host from infection, by identifying
some conserved nonself molecules. Bacterial lipopolysaccharide (LPS), an
endotoxin found on the Gram-negative bacterial outer membranes, signals the

presence of infection by stimulating the synthesis of chemicals and cytokines,
such as IL-1, IL-6, IL-12, and TNF involved in the acute phase response [68].
Some promising compounds which exhibited immunomodulatory activity,
increasing ROS formation by mouse macrophages are discovered by Levina
et al. [69]. Two sterol sulfates, called lysaketotriol (12), which stimulate lyso-
somal activity in mouse splenocytes, and lysaketodiol (13) were extracted
from the starfish Lysastrosoma anthosticta (Table 1.1) [69].
In contrast, the adaptive immune system, which is composed of T and B lym-

phocytes harbor unique antigen receptors that are not encoded in the germ line
but are generated de novo in each organism. Thus, adaptive immune responses
are highly specific. The adaptive immunity creates immunological memory
after an initial response to a specific pathogen, leading to an enhanced response
to subsequent encounters with that same pathogen, serving as a second line of
defense that is highly specific and able to form immunological memory [70].
The best-characterized microbial sensors are the PRRs of the innate immune
system, which detect relatively invariant molecular patterns found in most
microorganisms of a given class. The adaptive immune response is antigen-
specific and requires the recognition of specific “nonself” antigens. Antigen
specificity allows for the generation of responses that are tailored to specific
pathogens or pathogen-infected cells [71]. Disorders of the immune system can
result in autoimmune diseases, hypersensitivities, and immune deficiency [72].
NATURAL PRODUCTS DERIVED FROM ECHINODERMS

MOLECULES WHICH HAVE POTENTIAL HEALTH EFFECTS
Saponins
Two new triterpene glycosides, known as marmoratoside A (14) and 17 α-hydroxy
impatienside A (15), were isolated from the sea cucumber Bohadschia marmo-
rata in China South Sea and exhibited antifungal activity against six species:
A. fumigatus, Cr. neoformans, T. rubrum, C. albicans, Candida tropicalis, and
Candida krusei [73]. Collected at the same region, the sea cucumber Holothuria
(Microthele) fuscopunctata is a source of impatienside B (16) that showed anti-
fungal activity against the same six species [74]. Cladoloside B (17), extracted
from sea cucumber A. japonicus, showed growth inhibitory antifungal activity
against C. albicans, C. tropicalis, Cr. neoformans, T. rubrum, M. gypseum, and A.

fumigatus [75,76]. Sea cucumber Psolus patagonicus, yielded two new triterpene
glycoside, named patagonicoside B (18) and C (19), that exhibited antifungal
activity against the phytopathogenic fungus Cladosporium cladosporioides [77].
Two new holostan-type glycosides, named holotoxin D1 (20) and

25,26-dihydroxy-holotoxin A1 (21) isolated from the sea cucumber A.
japonicus, exhibited antifungal activity. Glycoside (20) exhibited growth
inhibitory activity against the same six species, while compound (21) only
showed antifungal activity against Cr. neoformans and A. fumigatus [78].
Reported for the first time by Yuan et al. [79], holotoxin D (22) was isolated
from the sea cucumber A. japonicus, which exhibited growth inhibitory anti-
fungal activity against C. albicans, C. tropicalis, Cr. neoformans, T. rubrum,
M. gypseum, and A. fumigatus (Table 1.1) [76,79]. A nortriterpene glyco-
side, 26-nor-25-oxo-holotoxin A1 (23): three triterpene glycosides, includ-
ing both holostane- and nonholostane-type analogs, holotoxins E-G (24–26)
(sea cucumber A. japonicus from Sea of China), showed also antifungal
activity. Compounds (23) and (24) had inhibitory activity against C. albicans,
C. tropicalis, Cr. neoformans, T. rubrum, M. gypseum, and A. fumigatus,
while (25) and (26) exhibited selective antifungal activities against C.
albicans, Cr. neoformans, and M. gypseum [76]. Ten new saponins, called
coustesides A–J (27–36), isolated from sea cucumber Bohadschia cousteaui
showed antifungal activity against C. albicans [80].
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Launcelot.—Nay, indeed, if you had your eyes, you might fail of
the knowing me: it is a wise father that knows his own child. Well, old
man, I will tell you news of your son: give me your blessing. Truth will
come to light; murder cannot be hid long,—a man’s son may; but, in
the end, truth will out.
Gobbo.—Pray you, sir, stand up: I am sure you are not Launcelot,
my boy.
Launcelot.—Pray you, let’s have no more fooling about it, but give
me your blessing: I am Launcelot, your boy that was, your son that
is, your child that shall be.
Gobbo.—I cannot think you are my son.
Launcelot.—I know not what I shall think of that: but I am
Launcelot, the Jew’s man; and I am sure Margery your wife is my
mother.
Gobbo.—Her name is Margery, indeed: I’ll be sworn, if thou be
Launcelot, thou art mine own flesh and blood. Lord, worship’d might
he be! What a beard hast thou got! thou hast got more hair on thy
chin than Dobbin, my fill-horse, has on his tail.
Launcelot.—It should seem, then, that Dobbin’s tail grows
backward: I am sure he had more hair of his tail than I have on my
face, when I last saw him.
Gobbo.—Lord, how art thou chang’d! How dost thou and thy
master agree? I have brought him a present. How ’gree you now?
Launcelot.—Well, well; but, for mine own part, as I have set up my
rest to run away, so I will not rest till I have run some ground. My
master’s a very Jew: give him a present! give him a halter: I am
famish’d in his service; you may tell every finger I have with my ribs.
Father, I am glad you are come: give me your present to one Master
Bassanio, who, indeed, gives rare new liveries: if I serve not him, I
will run as far as God has any ground.—O rare fortune! here comes
the man:—to him, father, for I am a Jew, if I serve the Jew any
longer.
—Act II, Scene II, Lines 29-104.
HAMLET’S DECLARATION OF FRIENDSHIP
Hamlet. What ho! Horatio!
Horatio. Here, sweet lord, at your service.
Hamlet. Horatio, thou art e’en as just a man

As e’er my conversation coped withal.
Horatio. O, my dear lord,—
Hamlet. Nay, do not think I flatter;

For what advancement may I hope from thee
That no revenue hast, but thy good spirits,
To feed and clothe thee? Why should the poor be flatter’d?
No, let the candied tongue lick absurd pomp,
And crook the pregnant hinges of the knee
Where thrift may follow fawning. Dost thou hear?
Since my dear soul was mistress of her choice
And could of men distinguish, her election
Hath sealed thee for herself; for thou hast been
As one, in suffering all, that suffers nothing,
A man that fortune’s buffets and rewards
Hast ta’en with equal thanks: and blest are those
Whose blood and judgment are so well commingled
That they are not a pipe for Fortune’s finger
To sound what stop she pleases. Give me that man
That is not passion’s slave, and I will wear him
In my heart’s core, ay, in my heart of hearts,
As I do thee.
—From Act III, Scene 2.
OTHELLO’S APOLOGY
[The speech calls for great dignity, ease, and power, in both speech
and manner.]
Most potent, grave, and reverend signiors,
My very noble and approved good masters,
That I have ta’en away this old man’s daughter,
It is most true; true, I have married her:
The very head and front of my offending
Hath this extent, no more. Rude am I in my speech,
And little bless’d with the soft phrase of peace;
For since these arms of mine had seven years’ pith,
Till now some nine moons wasted, they have used
Their dearest action in the tented field,
And little of this great world can I speak,
More than pertains to feats of broil and battle,
And therefore little shall I grace my cause
In speaking for myself. Yet, by your gracious patience,
I will a round unvarnish’d tale deliver
Of my whole course of love; what drugs, what charms,
What conjuration, and what mighty magic,—
For such proceeding I am charg’d withal,—
I won his daughter.
...
Her father loved me; oft invited me;
Still question’d me the story of my life,
From year to year,—the battles, sieges, fortunes,
That I have pass’d.
I ran it through, even from my boyish days,
To the very moment that he bade me tell it:
Wherein I spake of most disastrous chances,
Of moving accidents by flood and field,
Of hair-breadth scapes i’ the imminent deadly breach,
Of being taken by the insolent foe
And sold to slavery, of my redemption thence
And portance in my travels’ history:
...
This to hear
Would Desdemona seriously incline:
But still the house-affairs would draw her thence;
Which ever as she could with haste despatch,
She’d come again, and with a greedy ear
Devour up my discourse: which I observing,
Took once a pliant hour, and found good means
To draw from her a prayer of earnest heart
That I would all my pilgrimage dilate,
Whereof by parcels she had something heard,
But not intentively: I did consent,
And often did beguile her of her tears,
When I did speak of some distressful stroke
That my youth suffer’d. My story being done,
She gave me for my pains a world of sighs:
She swore, in faith, ’twas strange, ’twas passing strange,
’Twas pitiful, ’twas wondrous pitiful:
She wish’d she had not heard it, yet she wish’d
That heaven had made her such a man: she thank’d me,
And bade me, if I had a friend that loved her,
I should but teach him how to tell my story,
And that would woo her. Upon this hint I spake:
She loved me for the dangers I had pass’d;
And I lov’d her that she did pity them.
This only is the witchcraft I have used.
THE SEVEN AGES

[This is a succession of purely imaginative ideas which the voice
should touch lightly. In this speech one meets always the question of
impersonation: shall the mewling infant, the whining schoolboy, the
sighing lover and the rest be imitated by the reader? It is in better
taste not to impersonate these seven characters beyond certain
almost imperceptible hints which the gayety of Jaques’s mind might
naturally throw off.]
All the world’s a stage,

And all the men and women merely players:
They have their exits and their entrances;
And one man in his time plays many parts,
His acts being seven ages. At first the infant,
Mewling and puking in the nurse’s arms:
And then the whining schoolboy, with his satchel
And shining morning face, creeping like snail
Unwillingly to school. And then the lover,
Sighing like furnace, with a woeful ballad
Made to his mistress’ eyebrow. Then a soldier,
Full of strange oaths and bearded like the pard,
Jealous in honor, sudden and quick in quarrel,
Seeking the bubble reputation
Even in the cannon’s mouth. And then the justice,
In fair round belly with good capon lined,
With eyes severe and beard of formal cut,
Full of wise saws and modern instances;
And so he plays his part. The sixth age shifts
Into the lean and slipper’d pantaloon,
With spectacles on nose and pouch on side;
His youthful hose, well saved, a world too wide
For his shrunk shank; and his big manly voice,
Turning again toward childish treble, pipes
And whistles in his sound. Last scene of all,
That ends this strange eventful history,
Is second childishness and mere oblivion,
Sans teeth, sans eyes, sans taste, sans everything.
—“As You Like it,” Act II, Scene 7.
SOLITUDE PREFERRED TO COURT LIFE
Duke S. Now, my co-mates and brothers in exile,

Hath not old custom made this life more sweet
Than that of painted pomp? Are not these woods
More free from peril than the envious court?
Here feel we but the penalty of Adam.
The season’s difference, as the icy fang
And churlish chiding of the winter’s wind,
Which, when it bite and blows upon my body,
Even till I shrink with cold, I smile and say
’Tis no flattery; these are counselors
That feelingly persuade me what I am.
Sweet are the uses of adversity,
Which, like the toad, ugly and venomous,
Wears yet a precious jewel in his head;
And this our life, exempt from public haunt,
Finds tongues in trees, books in the running brooks,
Sermons in stones, and good in everything.
I would not change it.
Amiens. Happy is your grace,

That can translate the stubbornness of fortune
Into so quiet and so sweet a style.
...
Duke S. Come, shall we go and kill us venison?

And yet it irks me the poor dappled fools,
Being native burghers of this desert city,
Should in their own confines with forked heads
Have their round haunches gor’d.
—“As You Like It,” Act II.
THE POTION SCENE

Scene: Juliet’s Chamber
(Enter Juliet and Nurse, who bears wedding garments.)
Juliet (looking at garments).
Ay, those attires are best; but, gentle nurse,

I pray thee, leave me to myself to-night;
For I have need of many orisons
To move the heavens to smile upon my state,
Which, well thou knowest, is cross and full of sin.
(Enter Lady Capulet.)
Lady Capulet.
What are you busy, ho? need you my help?
Juliet.
No, madam; we have cull’d such necessaries

As are behoveful for our state to-morrow:
So please you, let me now be left alone,
And let the nurse this night sit up with you;
For, I am sure, you have your hands full all,
In this so sudden business.
Lady Capulet (crossing and kissing Juliet on the forehead).
Good night;
Get thee to bed and rest, for thou hast need.
(Exit Lady Capulet with nurse.)
Juliet (looking after them).
Farewell! God knows when we shall meet again.

I have a faint cold fear thrills through my veins,
That almost freezes up the heat of life:
I’ll call them back again to comfort me. (Runs to R.)
Nurse! What should she do there?
My dismal scene I needs must act alone.
Come, vial. (Takes vial from bosom.)
What if this mixture do not work at all?
Shall I be married then to-morrow morning?
No, no! (draws dagger) this shall forbid it.
(Lays dagger on table.)
Lie you there. (To vial.)

What if it be a poison, which the friar
Subtly hath ministered to have me dead,
Lest in this marriage he should be dishonored
Because he married me before to Romeo?
I fear it is; and yet, methinks, it should not,
For he hath still been tried a holy man.
(Puts vial in bosom.)
How if, when I am laid into the tomb,

I wake before the time that Romeo
Come to redeem me? there’s a fearful point!
Shall I not then be stifled in the vault,
To whose foul mouth no healthsome air breathes in,
And there die strangled ere my Romeo comes?
Or, if I live, is it not very like,
The horrible conceit of death and night,
Together with the terror of the place,—
As in a vault, an ancient receptacle,
Where, for these many hundred years, the bones
Of all my buried ancestors are packed;
Where bloody Tybalt, yet but green in earth,
Lies festering in his shroud; where as they say,
At some hours in the night spirits resort; ...
O, if I wake, shall I not be distraught,
Environed with all these hideous fears?
And madly play with my forefathers’ joints?
And pluck the mangled Tybalt from his shroud?
And, in this rage, with some great kinsman’s bone,
As with a club, dash out my desperate brains?
O, look! methinks I see my cousin’s ghost
Seeking out Romeo, ...
Stay, Tybalt, stay!—
Romeo, I come! (Drawing out vial—then cork.)
This do I drink to thee.
(Throws away vial. She is overcome and sinks to the floor.)
—From “Romeo and Juliet,” Act IV, Scene 3.

BANISHMENT SCENE
SCENE III, A ROOM IN THE PALACE
(Enter Celia and Rosalind.)
Cel. Why, cousin; why Rosalind;—Cupid have mercy;—Not a
word?
Ros. Not one to throw to a dog.
Cel. No, thy words are too precious to be cast away upon curs,
throw some of them at me; come, lame me with reasons.
Ros. Then there were two cousins laid up; when the one should be
lamed with reasons, and the other mad without any.
Cel. But is all this for your father?
Ros. No, some of it for my father’s child: O, how full of briars is this
working-day world!
Cel. They are but burrs, cousin, thrown upon thee in holiday
foolery; if we walk not in the trodden paths, our very coats will catch
them.
Ros. I could shake them off my coat; these burrs are in my heart.
Cel. Hem them away.
Ros. I would try; if I could cry hem, and have him.
Cel. Come, come, wrestle with thy affections.
Ros. O, they take the part of a better wrestler than myself.
Cel. Is it possible, on such a sudden, you should fall into so strong
a liking with old Sir Rowland’s youngest son?
Ros. The duke my father lov’d his father dearly.
Cel. Doth it therefore ensue, that you should love his son dearly?
By this kind of chase, I should hate him, for my father hated his
father dearly; yet I hate not Orlando.
Ros. No ’faith, hate him not, for my sake.
Cel. Why should I not? Doth he not deserve well?
Ros. Let me love him for that; and do you love him, because I do:
Look, here comes the duke.
Cel. With his eyes full of anger.
(Enter Duke Frederick, with Lords.)
Duke F. Mistress, despatch you with your safest haste, and get
you from our Court.
Ros. Me, uncle?
Duke F. You, cousin, within these ten days if thou be’st found so
near our public court as twenty miles, thou diest for it.
Ros. I do beseech your grace, let me the knowledge of my fault
bear with me: if with myself I hold intelligence, or have acquaintance
with mine own desires; if that I do not dream, or be not frantic (as I
do trust I am not), then, dear uncle, never so much as in a thought
unborn, did I offend your highness.
Duke F. Thus do all traitors, if their purgation did consist in words,
they are as innocent as grace itself: let it suffice thee, that I trust thee
not.
Ros. Yet your mistrust cannot make me a traitor: tell me, whereon
the likelihood depends.
Duke F. Thou art thy father’s daughter, there’s enough.
Ros. So was I, when your highness took his dukedom; so was I,
when your highness banish’d him: treason is not inherited, my lord:
or, if we did derive it from our friends, what’s that to me? my father
was no traitor: then, good my liege, mistake me not so much, to think
my poverty is treacherous.
Cel. Dear sovereign, hear me speak.
Duke F. Aye, Celia; we stay’d here for your sake. Else had she
with her father rang’d along.
Cel. I did not then entreat to have her stay, it was your pleasure,
and your own remorse; I was too young that time to value her, but
now I know her; if she be a traitor, so am I: we still have slept
together; rose at an instant, learn’d, play’d, eat together;
And wheresoe’er we went, like Juno’s swans,

Still we went coupled, and inseparable.
Duke F. She is too subtle for thee; and her smoothness,

Her very silence, and her patience,
Speak to the people and they pity her.
Thou art a fool: she robs thee of thy name;
And thou wilt show more bright, and seem more virtuous,
When she is gone: then open not thy lips;
Firm and irrevocable is my doom
Which I have pass’d upon her; she is banish’d.
Cel. Pronounce that sentence then on me, my liege;

I cannot live out of her company.
Duke F. You are a fool:—You, niece, provide yourself;

If you outstay the time, upon my honor,
And in the greatness of my word, you die.
(Exeunt Duke Frederick and Lords.)
Cel. O my poor Rosalind: whither wilt thou go?

Wilt thou change fathers? I will give thee mine.
I charge thee, be not thou more griev’d than I am.
Ros. I have more cause.
Cel. Thou hast not, cousin,

Pr’ythee, be cheerful: know’st thou not, the duke
Hath banish’d me his daughter?
Ros. That he hath not.
Cel. No? hath not? Rosalind lacks then the love

Which teaches thee that thou and I art one:
Shall we be sunder’d? shall we part, sweet girl?
No; let my father seek another heir.
Therefore devise with me, how we may fly,
Whither to go, and what to bear with us:
And do not seek to take your charge upon you,
To bear your griefs yourself, and leave me out;
For by this heaven, now at our sorrows pale,
Say what thou can’st, I’ll go along with thee.
Ros. Why, whither shall we go?
Cel. To seek my uncle.
Ros. Alas, what danger will it be to us,

Maids as we are, to travel so far?
Beauty provoketh thieves sooner than gold.
Cel. I’ll put myself in poor and mean attire,

And with a kind of umber smirch my face;
The like do you; so shall we pass along,
And never stir assailants.
Ros. Were it not better,

Because that I am more than common tall,
That I did suit me in all points like a man?
A boar-spear in my hand; and in my heart
Lie there what hidden woman’s fear there will,
We’ll have a swashing and a martial outside;
As many other mannish cowards have,
That do outface it with their semblances.
Cel. What shall I call thee when thou art a man?
Ros. I’ll have no other worse than Jove’s own page,

And therefore, look you, call me Ganymede.
But what will you be call’d?
Cel. Something that hath a reference to my state:

No longer Celia, but Aliena.
Ros. But, cousin, what if we assayed to steal

The clownish fool out of your father’s court?
Would he not be a comfort to our travel?
Cel. He’ll go along o’er the wide world with me;

Leave me alone to woo him: Let’s away
And get our jewels and our wealth together;
Devise the fittest time, and safest way
To hide us from pursuit that will be made
After my flight: Now go we in content,
To liberty, and not to banishment.
—From “As You Like It,” Act I.
CORYDON
By Thomas Bailey Aldrich
SCENE, A ROAD-SIDE IN ARCADY
Shepherd. Good sir, have you seen pass this way

A mischief straight from market-day?
You’d know her at a glance, I think;
Her eyes are blue, her lips are pink;
She has a way of looking back
Over her shoulder, and alack!
Who gets that look one time, good sir,
Has naught to do but follow.
Pilgrim. I have not seen this maid methinks,

Though she that passed had lips like pinks.
Shepherd. Or like two strawberries made one

By some sly trick of dew and sun.
Pilgrim. A poet.
Shepherd. Nay, a simple swain
That tends his flocks on yonder plain
Naught else I swear by book and bell.
But she that passed you marked her well
Was she not smooth as any be
That dwells here—in Arcady?
Pilgrim. Her skin was the satin bark of birches.
Shepherd. Light or dark?
Pilgrim. Quite dark.
Shepherd. Then ’twas not she.
Pilgrim. The peaches side

That next the sun is not so dyed
As was her cheek. Her hair hung down
Like summer twilight falling brown;
And when the breeze swept by, I wist
Her face was in a somber twist.
Shepherd. No that is not the maid I seek;

Her hair lies gold against her cheek,
Her yellow tresses take the morn,
Like silken tassels of the corn,
And yet brown-locks are far from bad.
Pilgrim. Now I bethink me this one had

A figure like the willow tree
Which, slight and supple, wondrously
Inclines to droop with pensive grace,
And still retain its proper place.
A foot so arched and very small
The marvel was she walked at all;
Her hand in sooth, I lack for words—
Her hand, five slender snow-white birds,
Her voice, tho’ she but said “God Speed”—
Was melody blown through a reed;
The girl Pan changed into a pipe
Had not a note so full and rife.
And then her eye—my lad, her eye!
Discreet, inviting, candid, shy,
An outward ice, an inward fire,
And lashes to the heart’s desire.
Soft fringes blacker than the sloe—
Shepherd. Good sir, which way did this one go?
Pilgrim. So he is off! The silly youth

Knoweth not love in sober sooth,
He loves—thus lads at first are blind—
No woman, only womankind.
I needs must laugh, for by the mass
No maid at all did this way pass.
PART FOUR
Oratoric Reading and the Art of Public Speech
Discussion of forceful speech in making history. Value of forceful
speech. Practice selections.
HAMLET’S INSTRUCTION TO THE PLAYERS

Speak the speech, I pray you, as I pronounced it to you,—
trippingly on the tongue; but if you mouth it, as many of our players
do, I had as lief the town-crier spake my lines. Nor do not saw the air
too much with your hand, thus, but use all gently; for in the very
torrent, tempest, and, as I may say, whirlwind of your passion, you
must acquire and beget a temperance, that may give it smoothness.
Oh! it offends me to the soul to hear a robustious periwig-pated
fellow tear a passion to tatters,—to very rags,—to split the ears of
the groundlings; who, for the most part, are capable of nothing but
inexplicable dumb show and noise. I would have such a fellow
whipped for o’erdoing Termagant; it out-herods Herod. Pray you
avoid it.
—Shakespeare.
CHAPTER XIII
ORATORIC READING AND THE ART OF PUBLIC SPEECH
Upon this important subject of public speaking, and the

interpretation of the addresses made by others, great men have thus
expressed themselves: Dr. Charles W. Eliot, formerly President of
Harvard University, says: “Have we not all seen, in recent years, that
leading men of business have a great need of a highly trained power
of clear and convincing expression? Business men seem to me to
need, in speech and writing, all the Roman terseness and the French
clearness. That one attainment is sufficient reward for the whole long
course of twelve years spent in liberal study.” Abraham Lincoln
likewise said: “Extemporaneous speaking should be practiced and
cultivated. It is the lawyer’s avenue to the public. However able and
faithful he may be in other respects, people are slow to bring him
business if he can not make a speech.”
Every thinker knows what a vital part eloquence plays in national
as well as individual welfare. If at first thought effective speaking
seems a simple thing and a superficial part of education, on mature
thought and consideration it will be found to be one of the most
complex, vital and difficult problems that education has to meet. And
yet, notwithstanding this complexity of the problem, the teacher is
cheered by the delightful assurance of giving the student a
consciousness of his latent talents and the ability to reveal and make
use of them for the proper influencing of his fellow men.
There is a belief fairly commonly held that only a limited few need
study the art of public speaking. Never was there a greater error or a
more fatal mistake—especially in a republic like ours, where every
man should be vitally interested in public affairs. No single citizen
can afford not to be able to stand before his fellows and clearly,
pleasingly and convincingly present his ideas upon any subject of
local, state, or national importance. It is no more an ornamental
accomplishment than is grammar, penmanship or simple arithmetic.
It should be as universal as “the three r’s.” The hints and selections
that follow are carefully chosen to incite every good citizen to the
acquirement of this useful and practical aid for his own benefit as
well as that of his fellows. All the lessons and analyses that have
gone before in these pages will materially aid in the elucidation of
these brief lessons.
The basis for development in Effective Speaking rests upon one’s
bodily, emotional and mental agencies of expression, and a
knowledge of their respective importance and efficient use. That
which counts most for development is conscientious practice; without
which, progress is impossible.
There are three definite means of communicating thought and
feeling to others: (a) Pantomime: face, hands, body; (b) Vocal: tone
sound; (c) Verbal: words, which are conventional symbols
manifesting mental and emotional states.
The problem, then, is to obtain a harmonious coördination of these
three languages. In other words, the content of the word when
spoken should be reflected in the tone and in the body. Thus speech
becomes effective merely because it receives its just and fair
consideration.
With this general understanding let us take up and master the
successive steps which ultimately lead to a realization of the desired
end.
The first important essential of effective speaking is the Spirit of
Directness. By this is meant natural, unaffected speech. Nothing can
be more important than that the person speaking use in public
address the ordinary elements of Conversation.
Hence, the first step is practice in natural speaking. Commit to
memory Hamlet’s Instructions to the Players given on a preceding
page. Do this not line by line, but the entire selection as a whole.
First: Read it through silently three times to familiarize yourself with
the subject-matter. Second: Read it aloud at least five times. Third:
Speak it conversationally at least five times from memory. In this
practice always be intensely conscious that you are addressing an
individual and not an audience.
Now take any of the prose or poetic selections from the earlier
pages of this book, memorize them, after studying them as the
instructions require, and speak them directly and naturally, in the
ordinary conversational style.
Sufficient practice in this is the necessary preparation for the next
step, viz., the acquiring of a natural elevated conversational style,
which is merely another name for the higher type of public speaking.
Commit all, or a part, of the following selections, keeping in mind
that in speaking them you are addressing a group of people.
THE GETTYSBURG ADDRESS

By Abraham Lincoln
Fourscore and seven years ago our fathers brought forth upon this
continent a new nation, conceived in liberty, and dedicated to the
proposition that all men are created equal. Now we are engaged in a
great Civil War, testing whether that nation, or any nation, so
conceived and so dedicated, can long endure. We are met on a
great battlefield of that war. We are met to dedicate a portion of it as
the final resting place of those who here gave their lives that that
nation might live.
It is altogether fitting and proper that we should do this. But in a
larger sense we cannot dedicate, we cannot consecrate, we cannot
hallow this ground. The brave men, living and dead, who struggled
here, have consecrated it far above our power to add or detract. The
world will little note, nor long remember, what we say here, but it can
never forget what they did here.
It is for us, the living, rather to be dedicated here to the unfinished
work they have thus far so nobly carried on. It is rather for us to be
here dedicated to the great task remaining before us, that from these
honored dead we take increased devotion to the cause for which
they gave their last full measure of devotion; that we here highly
resolve that these dead shall not have died in vain, that the Union
shall, under God, have a new birth of freedom, and that the
government of the people, by the people, and for the people, shall
not perish from the earth.
By this time you should have mastered Ordinary Conversational

Style; Elevated Conversational Style; and Abandon and Flexibility of
Speech. The next consideration is the importance of Clearness.
Clearness in speech means making prominent central words and
subordinating unimportant words, or phrases. In other words, the
logical sequence of thought must be clearly shown. This is brought
about by a variety of inflections, changes of pitch, pause, etc.
Clearness in speech is dependent upon clearness of Thinking.
It is important now to give full consideration to the subject of
Emphasis. There are more ways than one of emphasizing your
thought. The most common way is by merely increasing the stress of
voice upon a word. This, however, is the most undignified form of
emphasis. It is common to ranters and “soap-box” orators and is one
mark of an undisciplined and uncultured man. Remember that
loudness is a purely physical element, and does not manifest
thought. Such emphasis is an appeal to the brute instinct, and is only
expressive of the lower emotions. But Inflection, Changes of Pitch,
Pause, Movement and Tone-Color—as have been fully explained in
preceding pages—all appeal to the exalted nature of man.
In proportion to the nobleness of an emotion or thought, we find a
tendency to accentuate these above-named elements. Such
methods of emphasis are appropriate to the most disciplined and
cultured man. More than that, they are the surest evidence of a great
personality.
Commit, then make clear to the hearer, the vital thought in the
following:
He have arbitrary power! My lords, the East India Company

have not arbitrary power to give him; the King has no arbitrary
power to give him; your Lordships have not; nor the
Commons; nor the whole legislature. We have no arbitrary
power to give, because arbitrary power is a thing which

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Studies in Natural Products Chemistry

49 1st Edition Atta-Ur-Rahman (Eds.)

Studies in Natural Products Chemistry Volume 51 Atta-

Studies in Natural Products Chemistry Volume 52 Atta-

Studies in Natural Products Chemistry Volume 53 Atta-

Studies in Natural Products Chemistry Volume 44 1st

Studies in Natural Products Chemistry Volume 41 1st

Bioactive Natural Products 1st Edition Atta-Ur-Rahman

Studies in Natural Products Chemistry Volume 46 1st

Studies in Natural Products Chemistry Volume 47 1st

AMSTERDAM • BOSTON • HEIDELBERG • LONDON

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Dmitry L. Aminin (55), G.B. Elyakov Pacific Institute of Bioorganic Chemistry,

deubiquitinases; and the proteasome. A number of natural product inhibitors of

BIOLOGICAL ACTIVITIES WITH POTENTIAL BENEFIT FOR

Cholest-8(14)-ene- Sea urchin Saponins Trypanosoma brucei [101,102]

Astropectenols A (87) Starfish [56,101]

Centrocins 1 (130) and 2 Sea urchin Peptides Corynebacterium [124]

Antifungal Echinoside A (3) Sea cucumber Saponins Aspergillus fumigatus, [29]

Echinoderms: A Review of Bioactive Compounds Chapter | 1

Cladoloside B (17) Sea cucumber A. A. fumigatus, C. [75,76]

Patagonicoside B (18) and C Cladosporium [77]

Holotoxin D1 (20) A. fumigatus, C. [78]

25,26-Dihydroxy-holotoxin Cr. neoformans and A.

Holotoxin D (22) A. fumigatus, C. [76,79]

6 Studies in Natural Products Chemistry

Holotoxins F (25) and G (26) C. albicans, Cr.

Coustesides A–J (27–36) Sea cucumber C. albicans inhibition [80]

Typicosides A1 (37), A2 (38), Sea cucumber Aspergillus niger, C. [81]

Variegatusides C–F (41–44) Sea cucumber C. albicans, Candida [82]

Cucumariosides A1 (47), A6 Sea cucumber A. niger and F. [84–87]

Agglutinin (149) Sea cucumber Lectin Neutrophils reduction [133]

Comaparvin (150) Crinoid – Expression of iNOS [134]

Echinoderms: A Review of Bioactive Compounds Chapter | 1

Astrosteriosides C (7) Starfish A. Saponins HL-60, PC-3, and SNU- [39]

Astrosteriosides D (6) HL-60, PC-3, and SNU-

Leucospilotaside B (8) Sea cucumber HL-60, MOLT-4, A-549, [49,50]

Cholest-8(14)-ene- Sea urchin D. HL-60, PC-3, and SNU- [56]

Pentactaside B (78) and C (79) P388, HCT-116, MCF-7, [94]

Desulfated echinoside A (80) Sea cucumber HepG2 cell proliferation [95,96]

Scabraside D (81) Sea cucumber H. P-388, A-549, MKN- [97]

Pseudocnoside A (84) Sea cucumber A-549 and HeLa cell [98,99]

Echinoside A (85) Sea cucumber PC-3 cell proliferation [100]

Astropectenol A (87) Starfish A. HL-60, PC-3, and [102]

Echinoderms: A Review of Bioactive Compounds Chapter | 1

Astropectenol D (89) HL-60 and SNU-C5 cell

Anthenoside A (95) Starfish Anthenea HL-60, MOLT-4, A-549, [107]

Anthenosides E, G, H and I K-562 and BEL-7402 [108]

Anthenosides J (100) and K K-562, BEL-7402,

Astrosteriosides B (102) Starfish A. HL-60, PC-3, and SNU- [39]

Leptasteriosides A–F (103– Starfish RPMI-7951 and T-47D [110]

10 Studies in Natural Products Chemistry

5α-Cholesta-9(11),24-dien- Starfish Archaster MDA-MB-435 [111]

Cariniferoside F (110) Starfish RPMI-7951 and T-47D [112]

Novaeguinosides A–D Starfish Culcita K-562 and BEL-7402 [113]

Archasterosides A (117) and Starfish A. HeLa and JB6 P+ [115,116]

Diplasteriosides B (120) T47D and RPMI-7951 [117]

Echinoderms: A Review of Bioactive Compounds Chapter | 1

Hippasterioside D (124) Starfish HT-29 cell proliferation [120]