Pachydictyols B and C: New diterpenes from dictyota dichotoma hudson

Ghada S.E. Abou-El-Wafa; Mohamed Shaaban; Khaled A. Shaaban; Mohamed E.E. El-Naggar; Armin Maier; Heinz H. Fiebig; Hartmut Laatsch

doi:10.3390/md11093109

Pachydictyols B and C: New diterpenes from dictyota dichotoma hudson

Ghada S.E. Abou-El-Wafa, Mohamed Shaaban, Khaled A. Shaaban, Mohamed E.E. El-Naggar, Armin Maier, Heinz H. Fiebig, Hartmut Laatsch

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)] decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1-6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC₅₀ = 0.6 μg mL^-1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC₅₀ of >30.0 μM.

Original language	English
Pages (from-to)	3109-3123
Number of pages	15
Journal	Marine Drugs
Volume	11
Issue number	9
DOIs	https://doi.org/10.3390/md11093109
State	Published - Sep 2013

Keywords

Bioactivity
Dictyota dichotoma
Diterpenes
Marine brown alga
Pachydictyols

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Pharmacology, Toxicology and Pharmaceutics (miscellaneous)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.3390/md11093109

Cite this

@article{e7850aae234e41869670b32249ae9db6,

title = "Pachydictyols B and C: New diterpenes from dictyota dichotoma hudson",

abstract = "Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)] decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1-6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 μg mL-1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 μM.",

keywords = "Bioactivity, Dictyota dichotoma, Diterpenes, Marine brown alga, Pachydictyols",

author = "Abou-El-Wafa, {Ghada S.E.} and Mohamed Shaaban and Shaaban, {Khaled A.} and El-Naggar, {Mohamed E.E.} and Armin Maier and Fiebig, {Heinz H.} and Hartmut Laatsch",

year = "2013",

month = sep,

doi = "10.3390/md11093109",

language = "English",

volume = "11",

pages = "3109--3123",

number = "9",

}

TY - JOUR

T1 - Pachydictyols B and C

T2 - New diterpenes from dictyota dichotoma hudson

AU - Abou-El-Wafa, Ghada S.E.

AU - Shaaban, Mohamed

AU - Shaaban, Khaled A.

AU - El-Naggar, Mohamed E.E.

AU - Maier, Armin

AU - Fiebig, Heinz H.

AU - Laatsch, Hartmut

PY - 2013/9

Y1 - 2013/9

N2 - Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)] decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1-6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 μg mL-1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 μM.

AB - Two new diterpenoids, pachydictyol B (1a/1b) and C (2), were isolated from the dichloromethane extract of the marine brown alga, Dictyota dichotoma, collected from the Red Sea coast of Egypt, along with the known metabolites, pachydictyol A (3a), dictyol E (4), cis-africanan-1α-ol (5a), fucosterol (6), tetrahydrothiophen-1,1-dioxide and poly-β-hydroxybutyric acid. GC-MS analysis of the nonpolar fractions also indicated the presence of β-bourbonene and nonanal, along with three hydrocarbons and five fatty acids or their simple derivatives, respectively. GC-MS analysis of the unsaponifiable algal petroleum ether extract revealed the presence of a further eight compounds, among them 2,2,6,7-tetramethyl-10-oxatricyclo[4.3.0.1(1,7)] decan-5-one (7), N-(4-bromo-n-butyl)-pipe ridin-2-one (8) and tert-hexadecanethiol. Structures 1-6 were assigned by 1D and 2D NMR, mass spectra (EI, CI, HREI and HRESI) and by comparison with data from related structures. The crude algal extract was potently active against the breast carcinoma tumor cell line, MCF7 (IC50 = 0.6 μg mL-1); pachydictyol B (1a) and dictyol E (4) showed weak antimicrobial properties, and the other compounds were inactive. Pachydictyols B (1a) and C (2) demonstrated a weak and unselective cytotoxicity against twelve human tumor cell lines with a mean IC50 of >30.0 μM.

KW - Bioactivity

KW - Dictyota dichotoma

KW - Diterpenes

KW - Marine brown alga

KW - Pachydictyols

UR - http://www.scopus.com/inward/record.url?scp=84885041079&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84885041079&partnerID=8YFLogxK

U2 - 10.3390/md11093109

DO - 10.3390/md11093109

M3 - Article

C2 - 23975221

AN - SCOPUS:84885041079

SN - 1660-3397

VL - 11

SP - 3109

EP - 3123

JO - Marine Drugs

JF - Marine Drugs

IS - 9

ER -

Pachydictyols B and C: New diterpenes from dictyota dichotoma hudson

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this