Antimicrobial activity of glycosides from holothurians of the family Stichopodidae

Mal'tsev, I. I.; Stekhova, S. I.; Shentsova, E. B.; Anisimov, M. M.; Stonik, Valentin A.

doi:10.1007/bf00767104

Cited by 7 publications

(12 citation statements)

References 3 publications

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“…In progenin (XI), having the "rst monosaccharide unit and two monosaccharides from the upper semichain, the corresponding functional connection will be disrupted. The real antifungal activity of such progenin is actually very low (Maltsev et al, 1985). Figure 5 shows the structural}functional relationships for stichoposide B (XII), D (XIII) (stichloroside B ) (Kobayashi et al, 1991;Sharipov et al, 1981;Stonik et al, 1982b), and thelenotoside B (XIV) (Stonik et al, 1982c) from the tropical representatives of family Stichopodidae.…”

Section: Glycosides From the Sea Cucumbers Belonging To Family Stichomentioning

confidence: 97%

“…Figure 5 shows the structural}functional relationships for stichoposide B (XII), D (XIII) (stichloroside B ) (Kobayashi et al, 1991;Sharipov et al, 1981;Stonik et al, 1982b), and thelenotoside B (XIV) (Stonik et al, 1982c) from the tropical representatives of family Stichopodidae. All these glycosides have glucose instead of quinovose as a second monosaccharide unit; this signi"cantly decreases the activity (Maltsev et al, 1985). It is depicted by the corresponding negative functional connection in the scheme.…”

Section: Glycosides From the Sea Cucumbers Belonging To Family Stichomentioning

confidence: 98%

“…A linear tetrasaccharide fragment is also signi"-cant for membranotropic action (the action leading to any modi"cation of cellular membrane) (Kalinin et al, 1992;Kitagawa, 1988). Moreover, glycosides having quinovose as a second monosaccharide unit are more active (Maltsev et al, 1985). A sulfate at C-4 of the "rst xylose of nonbranched glycosides having a linear tetrasaccharide unit does not signi"cantly a!ect activity but its absence in biosides decreases their activity (Kalinin et al, 1992;Kitagawa, 1988).…”

Section: Introductionmentioning

confidence: 96%

See 2 more Smart Citations

System-theoretical (Holistic) Approach to the Modelling of Structural–Functional Relationships of Biomolecules and Their Evolution: an Example of Triterpene Glycosides from Sea Cucumbers (Echinodermata, Holothurioidea)

Kalinin

2000

Journal of Theoretical Biology

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Section: Glycosides From the Sea Cucumbers Belonging To Family Stichomentioning

confidence: 97%

Section: Glycosides From the Sea Cucumbers Belonging To Family Stichomentioning

confidence: 98%

Section: Introductionmentioning

confidence: 96%

See 1 more Smart Citation

System-theoretical (Holistic) Approach to the Modelling of Structural–Functional Relationships of Biomolecules and Their Evolution: an Example of Triterpene Glycosides from Sea Cucumbers (Echinodermata, Holothurioidea)

Kalinin

2000

Journal of Theoretical Biology

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“…In addition, Mal’tsev et al [157] stated that glycosides containing quinovose as the second monosaccharide unit exhibited more hemolytic activity than other triterpene glycosides.…”

Section: Molecular Effect Of Saponins On Membranesmentioning

confidence: 99%

Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

Bahrami

Franco

2016

Marine Drugs

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Sea cucumbers have been valued for many centuries as a tonic and functional food, dietary delicacies and important ingredients of traditional medicine in many Asian countries. An assortment of bioactive compounds has been described in sea cucumbers. The most important and abundant secondary metabolites from sea cucumbers are triterpene glycosides (saponins). Due to the wide range of their potential biological activities, these natural compounds have gained attention and this has led to their emergence as high value compounds with extended application in nutraceutical, cosmeceutical, medicinal and pharmaceutical products. They are characterized by bearing a wide spectrum of structures, such as sulfated, non-sulfated and acetylated glycosides. Over 700 triterpene glycosides have been reported from the Holothuroidea in which more than 145 are decorated with an acetoxy group having 38 different aglycones. The majority of sea cucumber triterpene glycosides are of the holostane type containing a C18 (20) lactone group and either Δ7(8) or Δ9(11) double bond in their genins. The acetoxy group is mainly connected to the C-16, C-22, C-23 and/or C-25 of their aglycone. Apparently, the presence of an acetoxy group, particularly at C-16 of the aglycone, plays a significant role in the bioactivity; including induction of caspase, apoptosis, cytotoxicity, anticancer, antifungal and antibacterial activities of these compounds. This manuscript highlights the structure of acetylated saponins, their biological activity, and their structure-activity relationships.

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“…Inhibition of Na + /K + -ATPase activity Kalinin et al (1989a) and Gorshkova et al (1999) Psolus eximius Kitagawa et al (1976) and Maltsev et al (1984Maltsev et al ( , 1985 Holotoxin A 1 Antiprotozoal, antitumor Kitagawa et al (1976) and Anisimov et al (1983) Holotoxin A 1 , cladoloside Neurotoxic, cytotoxic Yun et al (2018) Holotoxin A 1 Cytotoxic, antiproliferative activity Ishida et al 1993 andPopov et al 1994 Holotoxins A 1 , B 1 Inhibition of Na + /K + -ATPase activity Maltsev et al (1984) and Gorshkova et al (1989) Apostichoposide C…”

Section: Psolus Fabriciimentioning

confidence: 99%

Chemical Biodiversity and Bioactivities of Saponins in Echinodermata with an Emphasis on Sea Cucumbers (Holothuroidea)

Kamyab

Kellermann

Kunzmann

et al. 2019

YOUMARES 9 - The Oceans: Our Research, Our Future

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Echinoderms are a source of a broad range of secondary metabolites with a large variety of bioactive properties. Although pigment and lipid derivatives are the major groups of bioactive compounds found in crinoids and ophiuroids, saponins represent the most abundant and diverse marine natural products (MNPs) in the phylum Echinodermata. This review is for researchers that are interested in MNPs derived from echinoderms, but with a particular focus on the structural diversity and biological function of saponins. Among the echinoderms, these steroidal compounds are mostly known for and structurally most diverse within sea cucumbers. Through compilation of extensive tables, this review provides a reference book, summarizing not only the major chemical classes of well-known secondary metabolites in the phylum Echinodermata but also further focusing on the presence of bioactive saponins in echinoderms in general and within different sea cucumber species in particular. The final compilation aims to correlate the vast structural diversity of saponins with known biological functions. The here presented data revealed that holothurians, holotoxins, cucumariosides, and echinosids are not only the most abundant saponin compounds in various genera of sea cucumbers but that these saponins can also be used as potential chemotaxonomic markers for different sea cucumber species. By studying the structure-function relationships of triterpene glycosides in echinoderms in general, or in particular within holothurians, the vast structural diversity, taxonomic distribution, and bioactivity of the molecules can be deciphered, which provides an opportunity to focus future research efforts on target species that contain MNPs with novel pharmacological activities.

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Antimicrobial activity of glycosides from holothurians of the family Stichopodidae

Cited by 7 publications

References 3 publications

System-theoretical (Holistic) Approach to the Modelling of Structural–Functional Relationships of Biomolecules and Their Evolution: an Example of Triterpene Glycosides from Sea Cucumbers (Echinodermata, Holothurioidea)

System-theoretical (Holistic) Approach to the Modelling of Structural–Functional Relationships of Biomolecules and Their Evolution: an Example of Triterpene Glycosides from Sea Cucumbers (Echinodermata, Holothurioidea)

Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

Chemical Biodiversity and Bioactivities of Saponins in Echinodermata with an Emphasis on Sea Cucumbers (Holothuroidea)

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