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Natural product chemistry of gorgonian corals of the family Plexauridae distributed in the Indo-Pacific Ocean.
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PMID:  23203268     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The structures, names, bioactivities and references of 105 natural products obtained from gorgonian corals belonging to the family Plexauridae with an Indo-Pacific distribution are described in this review. All compounds mentioned in this review were obtained from gorgonian corals belonging to the genera Astrogorgia, Bebryce, Echinomuricea, Euplexaura and Menella.
Authors:
Li-Hsueh Wang; Jyh-Horng Sheu; Shih-Yao Kao; Jui-Hsin Su; Yung-Husan Chen; Yu-Hsin Chen; Yin-Di Su; Yu-Chia Chang; Lee-Shing Fang; Wei-Hsien Wang; Yang-Chang Wu; Ping-Jyun Sung
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review     Date:  2012-11-01
Journal Detail:
Title:  Marine drugs     Volume:  10     ISSN:  1660-3397     ISO Abbreviation:  Mar Drugs     Publication Date:  2012 Nov 
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Created Date:  2012-12-03     Completed Date:  2013-05-13     Revised Date:  2013-07-11    
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Nlm Unique ID:  101213729     Medline TA:  Mar Drugs     Country:  Switzerland    
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Languages:  eng     Pagination:  2415-34     Citation Subset:  IM    
Affiliation:
National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan.
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Animals
Anthozoa / chemistry*
Biological Agents / chemistry,  isolation & purification*,  pharmacology
Indian Ocean
Pacific Ocean
Chemical
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0/Biological Agents
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Journal ID (nlm-ta): Mar Drugs
Journal ID (iso-abbrev): Mar Drugs
Journal ID (publisher-id): marinedrugs
ISSN: 1660-3397
Publisher: MDPI
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© 2012 by the authors; licensee MDPI, Basel, Switzerland.
open-access:
Received Day: 13 Month: 9 Year: 2012
Revision Received Day: 10 Month: 10 Year: 2012
Accepted Day: 16 Month: 10 Year: 2012
Electronic publication date: Day: 01 Month: 11 Year: 2012
collection publication date: Month: 11 Year: 2012
Volume: 10 Issue: 11
First Page: 2415 Last Page: 2434
PubMed Id: 23203268
ID: 3509526
DOI: 10.3390/md10112415
Publisher Id: marinedrugs-10-02415

Natural Product Chemistry of Gorgonian Corals of the Family Plexauridae Distributed in the Indo-Pacific Ocean
Li-Hsueh Wang12
Jyh-Horng Sheu34
Shih-Yao Kao12
Jui-Hsin Su123
Yung-Husan Chen1
Yu-Hsin Chen12
Yin-Di Su13
Yu-Chia Chang14
Lee-Shing Fang5
Wei-Hsien Wang13
Yang-Chang Wu678*
Ping-Jyun Sung123*
1 National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan; Email: wanglh@nmmba.gov.tw (L.-H.W.); sweetcloud0906@gmail.com (S.-Y.K.); x2219@nmmba.gov.tw (J.-H.S.); tony_chen72001@yahoo.com.tw (Y.-H.C.); kb5634@yahoo.com.tw (Y.-H.C.); gobetter04@yahoo.com.tw (Y.-D.S.); jay0404@gmail.com (Y.-C.C.); jay0404@gmail.com (W.-H.W.)
2 Graduate Institute of Marine Biotechnology and Department of Life Science and Institute of Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan
3 Department of Marine Biotechnology and Resources and Division of Marine Biotechnology, Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804, Taiwan; Email: sheu@mail.nsysu.edu.tw
4 Doctoral Degree Program in Marine Biotechnology, National Sun Yat-sen University and Academia Sinica, Kaohsiung 804, Taiwan
5 Department of Sport, Health and Leisure, Cheng Shiu University, Kaohsiung 833, Taiwan; Email: lsfang@csu.edu.tw
6 School of Chinese Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan
7 Natural Medicinal Products Research Center, China Medical University Hospital, Taichung 404, Taiwan
8 Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan
* Authors to whom correspondence should be addressed; Email: yachwu@mail.cmu.edu.tw (Y.-C.W.); pjsung@nmmba.gov.tw (P.-J.S.); Tel.: +886-4-220-57153 (Y.-C.W.); +886-8-882-5037 (P.-J.S.); Fax: +886-4-220-60248 (Y.-C.W.); +886-8-882-5087 (P.-J.S.).

1. Introduction

Over the past thirty-four years, 105 natural products have been reported from gorgonian corals belonging to the genera Astrogorgia, Bebryce, Echinomuricea, Euplexaura and Menella with an Indo-Pacific distribution, all belonging to the family Plexauridae (Cnidaria: Anthozoa: Gorgonacea) [1]. This review summarizes the structures, names, bioactivities and references of all compounds in tabular form.


2. Natural Products from Gorgonian Corals Belonging to the Family Plexauridae
2.1. Genus Astrogorgia
Astrogorgia sp.

A novel 9,10-secosterol, astrogorgiadiol (1), and a new eunicellin-based diterpenoid, astrogorgin (2), along with a known eunicellin, ophirin (3), were isolated from the gorgonian Astrogorgia sp., collected at Okino-shima Island off Shikoku, Japan [2] (Table 1). The structures of new metabolites 1 and 2 were established by spectroscopic methods and by comparison of the spectral data with those of related analogs. Compounds 13 were found to display activity to inhibit cell division of the fertilized eggs of the starfish Asterina pectinifera.

Furthermore, twenty-one 9,10-secosterols, including thirteen new metabolites, astrogorgols A–M (416), along with eight known compounds, calicoferols A–C (1719), E (20), G (21), I (22), 24-exomethylenecalicoferol E (23), and astrogorgiadiol (1) and a new steroid, astrogorgol N (24), were isolated from the gorgonian Astrogorgia sp. collected from the inner coral reef in Beibuwan Bay, Guangxi province, China [3] (Table 2). The structures of new sterols 416 and 24 were determined by spectroscopic methods and by comparison of their spectral and physical data with those reported in the literature. Secosterols 1, 9, 17, 18 and 23 showed inhibitory effects against a series of protein kinases. The structures of calicoferols B (18) [3,4], C (19), E (20) [3,5] and I (22) [3,6] that are shown in reference 3 should be revised as presented in the original literature.

2.2. Genus Bebryce
2.2.1. Bebryce grandicalyx

In 1998, a new unstable sesquiterpene, bebryazulene (25), with a guaiane skeleton, was isolated from the gorgonian coral B. grandicalyx, collected at the Prevoyante Reef, Lagoon of Mayotte, Comoros Islands, Indian Ocean [7] (Table 3). The structure of guaiane 25 was assigned by spectroscopic methods. This metabolite was labile and reacted with 4-phenyl-3H-1,2,4-triazoline-3,5-dione to yield a triazolinedione adduct.

2.2.2. Bebryce indica

B. indica, a gorgonian species collected off the coast of Sanya, Hainan province, China, was found to contain a new steroidal glycoside, bebrycoside (26) [8] (Table 4). The main structure of 26 was determined by spectral data analysis, although the stereochemistry of the C-25 chiral carbon was not determined. Bebrycoside (26) is the first steroidal glycoside to be isolated from the genus Bebryce.

2.2.3. Bebryce sp.

Bebryceoid A (27), a new trihydroxysteroid, was isolated from gorgonian Bebryce sp., collected off the coast of Pingtung, southern Taiwan [9] (Table 5). The structure of steroid 27 was assigned by spectroscopic methods. Bebryceoid A (27) exhibited weak cytotoxicity toward P388D1 and DLD-1 tumor cells.

2.3. Genus Echinomuricea
Echinomuricea sp.

Two sesquiterpenoids, including new natural product (7S,10R)-(+)-10,11-epoxycurcuphenol (28) and known metabolite (+)-curcuphenol (29) [10], along with a new labdane-type diterpenoid, echinolabdane A (30), a new sterol, 6-epi-yonarasterol B (31) [11], a new clerodane-type diterpenoid, echinoclerodane A (32) [12] and a new halimane-type diterpenoid, echinohalimane A (33) [13], were isolated from the gorgonian coral Echinomuricea sp., collected off the coast of southern Taiwan (Table 6). The structures of metabolites 2833 were elucidated by spectroscopic methods. Echinolabdane A (30) possesses a novel tetracyclic skeleton with an oxepane ring joined to an α,β-unsaturated-γ-lactone ring by a hemiketal moiety [11]. Echinolabdane A (30), echinoclerodane A (32) and echinohalimane A (33) are the first labdane-, clerodane- and halimane-type diterpenoids to be obtained from marine organisms belonging to the phylum Cnidaria, respectively [11,12,13].

In biological activity experiments, sesquiterpenoid 29 displayed a significant inhibitory effect on the release of elastase by human neutrophils. This compound also exhibited weak cytotoxicity toward DLD-1 and CCRF-CEM tumor cells [9]. Steroid 31 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils [11]. Clerodane 32 exhibited weak cytotoxicity toward MOLT-4 and HL-60 tumor cells and displayed a significant inhibitory effect on the generation of superoxide anions by human neutrophils [12]. Halimane 33 exhibited cytotoxicity toward K562, MOLT-4, HL-60, DLD-1 and LoVo tumor cells and displayed a significant inhibitory effect on the release of elastase by human neutrophils [13].

2.4. Genus Euplexaura
2.4.1. Euplexaura anastomosans

Four new steroids of the cholestane class, anastomosacetals A–D (3437), were obtained from the gorgonian coral E. anastomosans, collected off the shore of Keomun Island, South Sea Korea [14] (Table 7). The structures of steroids 3437 were determined by spectroscopic methods, and these four compounds are the first examples of marine steroids possessing an unusual hemiacetal linkage formed by oxidation of the C-21 methyl group.

In addition, seven new moritoside class farnesylhydroquinone glycosides, euplexides A–G (3844), were isolated from E. anastomosans [15,16] (Table 7). The structures of glycosides 3844, including their absolute stereochemistry, were elucidated by spectroscopic and chemical methods. Compounds 3844 exhibited moderate cytotoxicity and antioxidant activity as well as an inhibitory effect against PLA2.

2.4.2. Euplexaura erecta

A prostaglandin derivative, PGF (45), was isolated from the gorgonian coral E. erecta collected at Shimoda, Sagami Bay, Japan [17] (Table 8), and this compound was proven to be the active component in E. erecta. This finding is the first demonstration that gorgonian corals containing prostaglandins are not limited to species in the Caribbean area.

Furthermore, a bluish-violet oil, guaiazulene (46), was isolated from E. erecta collected at Enoshima Island, Kanagawa, Japan [18] (Table 8). The structure of guaiazulene (46) from E. erecta was determined by spectroscopic methods and by comparison of the spectral data with those of reported data. This is the first isolation of guaiazulene from an animal, and this compound showed mild antimicrobial activity [18].

2.4.3. Euplexaura flava

Four new unnamed fatty acid derivatives 4750, which contain a butenolide moiety, were isolated from the gorgonian coral E. flava, collected at the coral reef of Ishigaki Island, Okinawa, Japan. The structures of butenolides 4750 were elucidated by spectroscopic and chemical methods [19] (Table 9).

2.4.4. Euplexaura nuttingi

Six new tetraprenylated purine alkaloids, nuttingins A–F (5156), were isolated together with five new compounds, malonganenones D–H (5761), and three known metabolites, malonganenones A–C (6264), from the gorgonian coral E. nuttingi collected in Uvinage, Pemba Island, Tanzania. The structures of compounds 5164 were elucidated by interpretation of spectral data [20] (Table 10). Mixtures of nuttingins A and B (51 and 52), C–E (5355), malonganenones D and E (57 and 58), and F and G (59 and 60) have been found to inhibit growth of K562 and UT7 tumor cells. Nuttingins A–E (5155) and malonganenones D–H (5761) induce apoptosis in transformed mammalian cells [20].

2.4.5. Euplexaura sp.

Moritoside (65), a new hydroquinone glycoside derivative was isolated from the gorgonian Euplexaura sp., collected near Morito beach in the Gulf of Sagami, Japan. The structure of glycoside 65 was determined by spectroscopic and chemical methods [21] (Table 11). This is the first example of the occurrence of D-altrose in natural products, and this compound inhibits the first cell division of fertilized starfish (Asterina pectinifera) eggs.

2.5. Genus Menella
2.5.1. Menella spinifera

The gorgonian M. spinifera collected off the South China Sea was found to contain six known compounds, including batyl alcohol (66) [22,23], picolinic acid N-methyl betaine (67) [23,24], n-hexadecanol (68) [23], 3β-hydroxy-5α-pregnane-20-one (69) [23], 9H-purin-6-amino-N-9-dimethyl (70) [23] and thymidine (71) [23] (Table 12). The structures of compounds 6671 were elucidated by spectroscopic methods.

2.5.2. Menella verrucosa

Four new highly-oxygenated guaiane lactones, menverins A–D (7275) [25], and two new polyoxygenated steroids, menellsteroids A (76) and B (77) [26] (Table 13), were isolated from the gorgonian M. verrucosa, collected along the coast of Xiaodong Hai, Hainan province, China. The structures of metabolites 7277 were established by spectroscopic methods. In a later study, menellsteroid A (76) was found to exhibit modest anti-inflammatory inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages [27].

2.5.3. Menella sp.

Li et al., isolated four new highly-oxygenated guaiane lactones, 1-epimenverin B (78), menverin F (79), 1-deoxymenverin F (80) and menverin G (81), along with two known guaiane analogs, menverins B (73) and C (74), from the gorgonian Menella sp., collected off the Lingshui Bay, Hainan province, China [28] (Table 14). The structures of new guaianes 7881 were elucidated by spectroscopic methods and by comparison with those of known analogs.

A chemical investigation of the gorgonian Menella sp., collected off Meishan Island, Hainan province, China, resulted in a novel highly-oxygenated racemate with a C8 skeleton, menellin A (82), a new tetrahydroxysteroid, menellsteroid C (83), a new natural product, 1β,3β,5α-trihydroxy-cholestan-6-one (84) and seven known compounds, menellsteroid A (76), cholestan-3β,5α,6β-triol (85), cholestan-1β,3β,5α,6β-tetrol (86), nephalsterol (87), cholestan-3β-5-en-6-one (88) and junceellolides B (89) and D (90) [27] (Table 15). The structures of the above compounds were elucidated by spectroscopic methods and by comparison of the spectral data with those of known analogs. The structure, including the relative stereochemistry, of menellin A (82) was further confirmed by single-crystal X-ray diffraction analysis. As already reported for menellsteroid A (76), menellin A (82) exhibited modest anti-inflammatory inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages.

Seven pregnane steroids, 3α-hydroxy-5β-pregnan-20-one (91), 3β-hydroxy-5α-pregnan-20-one (92), 3β-hydroxy-pregnan-5-en-20-one (93), 5β-pregnan-3,20-dione (94), 5α-pregnan-3,20-dione (95), pregnan-4-en-3,20-dione (96) and pregnan-1,4-dien-3,20-one (97), were isolated from the gorgonian Menella sp., collected off Meishan Island, Sanya Bay, Hainan province, China [29] (Table 16). The structures of steroids 9197 were elucidated by spectroscopic methods and by comparison with those of known analogs. The NMR data of steroid 97 are reported for the first time in this study.

Eight sesquiterpenoids, including seven new compounds, (–)-hydroxylindestrenolide (98) [30], menelloides A–E (99103) [31,32,33] and (+)-chloranthalactone B (104) [31], along with a known metabolite, seco-germacrane anhydride (105) [34] (Table 17), were isolated from the Formosan gorgonian Menella sp., collected by trawling off the coast of southern Taiwan. (–)-Hydroxy-lindestrenolide (98) and (+)-chloranthalactone B (104) were proven to be enantiomers of the known sesquiterpenoids (+)-hydroxylindestrenolide and chloranthalactone B, respectively [30,31]. Menelloide A (99) was found to possess a new carbon skeleton [31]. Seco-germacrane anhydride (105) was a known metabolite and there have been no reports of seco-germacrane anhydride (105) being obtained from any marine organism previously [34]. Several of these compounds displayed inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.


3. Conclusions

The search for bioactive natural products from marine organisms has been remarkably successful, and octocorals have been proven to be rich sources of natural products with potential biomedical application [35,36,37]. In particular, the data reported in this review indicate that terpenoid and steroid derivatives represent the major chemical classes occurring in Indo-Pacific octocoral species belonging to the family Plexauridae. Among the 105 isolated metabolites, in fact, 49 compounds are terpenoid analogs (46.7%) and 45 compounds are steroid metabolites (42.9%). These compounds continue to attract attention owing to their structural novelty, complexity and interesting bioactivities.


Notes

Samples Availability: Available from the authors.

Acknowledgments

This work was supported by grants from the National Dong Hwa University; the National Museum of Marine Biology and Aquarium (Grant No. 10120022); the Division of Marine Biotechnology, Asia-Pacific Ocean Research Center, National Sun Yat-sen University, (Grant No. 00C-0302-05); the Department of Health, Executive Yuan, Taiwan (Grant No. DOH101-TD-C-111-002); and the National Science Council (Grant No. NSC 101-2325-B-291-001, 100-2325-B-291-001, 101-2320-B-291-001-MY3 and 98-2320-B-291-001-MY3), Taiwan, awarded to Yang-Chang Wu and Ping-Jyun Sung.


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35.. Rocha J.,Peixe L.,Gomes N.C.M.,Calado R.. Cnidarians as a source of new marine bioactive compounds—An overview of the last decade and future steps for bioprospectingMar. DrugsYear: 201191860188610.3390/md910186022073000
36.. Blunt J.W.,Copp B.R.,Keyzers R.A.,Munro M.H.G.,Prinsep M.R.. Marine natural productsNat. Prod. Rep.Year: 20122914422210.1039/c2np00090c22193773
37.. Berrue F.,Kerr R.G.. Diterpenes from gorgonian coralsNat. Prod. Rep.Year: 20092668171010.1039/b821918b19387501

Tables
[TableWrap ID: marinedrugs-10-02415-t001] pii: marinedrugs-10-02415-t001_Table 1.
Table 1 

The natural products from Astrogorgia sp.


Structure No. Name Biological Activity Ref.
1 Astrogorgiadiol Inhibited cell division of fertilized starfish (Asterina pectinifera) eggs at a concentration of 50 μg/mL. IC50 (ALK, Aurora-B, AXL, FAK, IGF1-R, MEK1 wt, MET wt, SRC, VEGF-R2) = 7.6, 25.1, 16.9, 13.2, 2.8, 48.9, 78.0, 1.9, 4.4 μM. [2,3]
2 Astrogorgin Eunicellins 2 and 3 inhibited cell division of fertilized starfish (Asterina pectinifera) eggs at a concentration of 10 μg/mL. [2]
3 Ophirin [2]

[TableWrap ID: marinedrugs-10-02415-t002] pii: marinedrugs-10-02415-t002_Table 2.
Table 2 

The natural products from Astrogorgia sp.


Structure No. Name Biological Activity Ref.
4 Astrogorgol A (R1 = H, R2 = SC1) [3]
5 Astrogorgol B (R1 = H, R2 = SC2) [3]
6 Astrogorgol C (R1 = OH, R2 = SC1) [3]
7 Astrogorgol D (R1 = OH, R2 = SC3) [3]
17 Calicoferol A (R1 = H, R2 = SC3) IC50 (ALK, AXL, FAK, [3]
IGF1-R, MET wt, SRC,
VEGF-R2) = 4.2, 14.7, 9.9, 2.4,
47.6, 2.2, 4.6 μM.
20 Calicoferol E (R1 = H, R2 = SC5) [3,5]
22 Calicoferol I (R1 = OH, R2 = SC5) [3,6]
23 24-Exomethylenecalicoferol E IC50 (ALK, AXL, FAK, [3]
(R1 = H, R2 = SC4) IGF1-R, MET wt, SRC,
VEGF-R2) = 4.4, 20.2, 10.7,
2.3, 27.5, 1.5, 4.9 μM.
8 Astrogorgol E (R1 = H, R2 = SC1, R3 = β-OH) [3]
9 Astrogorgol F (R1 = H, R2 = SC3, R3 = β-OH) IC50 (ALK, [3]
Aurora-B, AXL,
FAK, IGF1-R, MET
wt, SRC, VEGF-R2)
= 9.3, 38.1, 21.9,
16.9, 3.2, 34.0, 2.4,
5.0 μM
10 Astrogorgol G (R1 = H, R2 = SC5, R3 = β-OH) [3]
11 Astrogorgol H (R1 = H, R2 = SC3, R3 = α-OH) [3]
12 Astrogorgol I (R1 = H, R2 = SC2, R3 = α-OH) [3]
13 Astrogorgol J (R1 = H, R2 = SC6, R3 = α-OH) [3]
14 Astrogorgol K (R1 = H, R2 = SC7, R3 = α-OH) [3]
15 Astrogorgol L (R1 = OH, R2 = SC3, R3 = α-OH) [3]
16 Astrogorgol M (R1 = OH, R2 = SC4, R3 = α-OH) [3]
18 Calicoferol B (R1 = OH, R2 = SC5, R3 = α-OH) IC50 (ALK, AXL, [3,4]
FAK, IGF1-R, MET
wt, SRC, VEGF-R2)
= 4.7, 32.6, 9.6, 2.5,
71.5, 2.2, 6.0 μM.
19 Calicoferol C (R1 = H, R2 = SC4, R3 = α-OH) [3,5]
21 Calicoferol G (R1 = H, R2 = SC8, R3 = α-OH) [3]
24 Astrogorgol N (R = SC7) [3]

[TableWrap ID: marinedrugs-10-02415-t003] pii: marinedrugs-10-02415-t003_Table 3.
Table 3 

The natural product from B. grandicalyx.


Structure No. Name Ref.
25 Bebryazulene [7]

[TableWrap ID: marinedrugs-10-02415-t004] pii: marinedrugs-10-02415-t004_Table 4.
Table 4 

The natural product from B. indica.


Structure No. Name Ref.
26 Bebrycoside [8]

[TableWrap ID: marinedrugs-10-02415-t005] pii: marinedrugs-10-02415-t005_Table 5.
Table 5 

The natural product from Bebryce sp.


Structure No. Name Biological Activity Ref.
27 Bebryceoid A ED50 (P388D1, DLD-1, CCRF-CEM, HL-60) = 18.5, 7.2, >40, >40 μg/mL [9]

[TableWrap ID: marinedrugs-10-02415-t006] pii: marinedrugs-10-02415-t006_Table 6.
Table 6 

The natural products from Echinomuricea sp.


Structure No. Name Biological Activity Ref.
28 (7 S,10R)-(+)-10,11-Epoxycurcuphenol Showed inhibitory effects on the generation of superoxide anions (inhibition rate 35.3%) and the release of elastase (inhibition rate 38.8%) at a concentration of 10 μg/mL. [10]
29 (+)-Curcuphenol Showed inhibitory effects on the generation of superoxide anion (inhibition rate 36.9%) and the release of elastase (inhibition rate 83.6%) at a concentration of 10 μg/mL. ED50 (DLD-1, CCRF-CEM) = 12.5, 11.8 μg/mL. [10]
30 Echinolabdane A Not active in terms of inhibition of the generation of superoxide anions (inhibition rate 2.5%) or the release of elastase (inhibition rate 1.8%) at a concentration of 10 μg/mL. IC50 (HL-60) = 19.1 μg/mL. [11]
31 6- epi-Yonarasterol B Showed significant inhibitory effects on the generation of superoxide anions (IC50 = 3.0 μg/mL) and the release of elastase (IC50 = 1.1 μg/mL). [11]
32 Echinoclerodane A Showed inhibitory effects on the generation of superoxide anions (inhibition rate 68.6%) and the release of elastase (inhibition rate 35.4%) at a concentration of 10 μg/mL. IC50 (K562, MOLT-4, HL-60, DLD-1, LoVo, DU-145) = 37.1, 13.2, 14.9, 23.4, 21.7, 53.9 μg/mL. [12]
33 Echinohalimane A Showed a significant inhibitory effect on the release of elastase (IC50 = 0.4 μg/mL).IC50 (K562, MOLT-4, HL-60, DLD-1, LoVo) = 6.3, 2.1, 2.1, 1.0, 0.6 μg/mL. [13]

[TableWrap ID: marinedrugs-10-02415-t007] pii: marinedrugs-10-02415-t007_Table 7.
Table 7 

The natural products from E. anastomosans.


Structure No. Name Biological Activity Ref.
34 Anastomosacetal A Steroids 3437 were not toxic to P-388 cells or brine-shrimp larva. [14]
35 Anastomosacetal B (4,5-dihydro) [14]
36 Anastomosacetal C (1,2-dihydro) [14]
37 Anastomosacetal D (1,2,4,5-tetrahydro) [14]
38 Euplexide A (R1 = OH, R2 = R3 = OAc) Glycosides 3840, 43, 44 exhibited cytotoxicity toward K462 cells (IC50 = 2.6, 3.1, 5.2, 8.7, 11.3 μg/mL). Glycosides 3840 displayed antioxidant activity of 3.4, 3.6 and 3.5 times, respectively, that of superoxide dismutase (SOD) at a concentration of 10 μg/300 μL. Glycosides 38, 39, 43, 44 exhibited 52, 71, 47 and 58%, respectively, inhibition of PLA2 at a concentration of 50 μg/mL. [15]
39 Euplexide B (R1 = R2 = R3 = OAc) [15]
40 Euplexide C (R1 = H, R2 = R3 = OAc) [15]
43 Euplexide F (R1 = H, R2 = OH, R3 = OAc) [16]
44 Euplexide G (R1 = H, R2 = OAc, R3 = OH) [16]
41 Euplexide D IC50 (K462) = 8.1 μg/mL. [15]
42 Euplexide E IC50 (K462) = 9.4 μg/mL. Displayed antioxidant activity of 3.1 times that of superoxide dismutase (SOD) at a concentration of 10 μg/300 μL. [15]

[TableWrap ID: marinedrugs-10-02415-t008] pii: marinedrugs-10-02415-t008_Table 8.
Table 8 

The natural products from E. erecta.


Structure No. Name Biological Activity Ref.
45 PGF Contracting activity towards isolated guinea-pig ileum strips. [17]
46 Guaiazulene Showed mild activity against fungi, gram-positive and gram-negative bacteria. [18]

[TableWrap ID: marinedrugs-10-02415-t009] pii: marinedrugs-10-02415-t009_Table 9.
Table 9 

The natural products from E. flava.


Structure No. Name Ref.
47 R = SC1 [19]
48 R = SC2 [19]
49 R = SC3 [19]
50 R = SC4 [19]

[TableWrap ID: marinedrugs-10-02415-t010] pii: marinedrugs-10-02415-t010_Table 10.
Table 10 

The natural products from E. nuttingi.


Structure No. Name Biological Activity Ref.
51 Nuttingin A (R = SC1) Compounds 5155 and 5761 induce apoptosis in transformed mammalian cells at a concentration of 1.25 μg/mL. Mixtures of compounds 51 and 52 displayed inhibitory activity on the proliferation of UT7 and K562 cell lines, although they were approximately 3-fold less potent than mixtures of compounds 5355. [20]
52 Nuttingin B (R = SC3) [20]
53 Nuttingin C (R = SC1) Mixtures of compounds 5355 induced 50% inhibition of cell growth in UT7 cells and 30% in K562 cells after 48 h of exposure at a concentration of 0.4 μg/mL. [20]
54 Nuttingin D (R = SC2) [20]
55 Nuttingin E (R = SC3) [20]
56 Nuttingin F (R = SC2) [20]
57 Malonganenone D (R = SC1) Mixtures of compounds 57 and 58 displayed inhibitory activity on the proliferation of UT7 and K562 cell lines, although they were approximately 3-fold less potent than mixtures of compounds 5355. [20]
58 Malonganenone E (R = SC2) [20]
62 Malonganenone A (R = SC3) [20]
59 Malonganenone F (R = SC1) Mixtures of compounds 59 and 60 displayed inhibitory activity on the proliferation of UT7 and K562 cell lines, although they were approximately 3-fold less potent than mixtures of compounds 5355. [20]
60 Malonganenone G (R = SC2) [20]
63 Malonganenone B (R = SC3) [20]
61 Malonganenone H (R = SC2) [20]
64 Malonganenone C (R = SC3) [20]

[TableWrap ID: marinedrugs-10-02415-t011] pii: marinedrugs-10-02415-t011_Table 11.
Table 11 

The natural product from Euplexaura sp.


Structure No. Name Biological Activity Ref.
65 Moritoside Inhibits the first cell division of fertilized starfish (Asterina pectinifera) eggs at a concentration of 1 μg/mL. [21]

[TableWrap ID: marinedrugs-10-02415-t012] pii: marinedrugs-10-02415-t012_Table 12.
Table 12 

The natural products from M. spinifera.


Structure No. Name Ref.
66 Batyl alcohol [22,23]
67 Picolinic acid N-methyl betaine [23,24]
68 n-Hexadecanol [23]
69 3β-Hydroxy-5α-pregnane-20-one [23]
70 9 H-Purin-6-amino-N-9-dimethyl [23]
71 Thymidine [23]

[TableWrap ID: marinedrugs-10-02415-t013] pii: marinedrugs-10-02415-t013_Table 13.
Table 13 

The natural products from M. verrucosa.


Structure No. Name Biological Activity Ref.
72 Menverin A (R1 = α-H, R2 = β-OH, R3 = α-methyl) [25]
73 Menverin B (R1 = α-H, R2 = β-methyl, R3 = α-OH) [25]
74 Menverin C (R1 = α-OH, R2 = β-OH, R3 = α-methyl) [25]
75 Menverin D (R1 = R2 = β-OH, R3 = α-methyl) [25]
76 Menellsteroid A (22,23-dihydro) Exhibited a modest inhibitory effect with an IC50 of 33.9 μM compared to the positive control aminoguanidine, with an IC50 = 25.0 μM. [26,27]
77 Menellsteroid B [26]

[TableWrap ID: marinedrugs-10-02415-t014] pii: marinedrugs-10-02415-t014_Table 14.
Table 14 

The natural products from Menella sp.


Structure No. Name Ref.
78 1-Epimenverin B [28]
79 Menverin F (R = α-OH) [28]
80 1-Deoxymenverin F (R = α-H) [28]
81 Menverin G [28]

[TableWrap ID: marinedrugs-10-02415-t015] pii: marinedrugs-10-02415-t015_Table 15.
Table 15 

The natural products from Menella sp.


Structure No. Name Biological Activity Ref.
82 Menellin A Exhibited a modest inhibitory effect (IC50 = 71.3 μM) compared to the positive control aminoguanidine (IC50 = 25.0 μM). There were no obvious scavenging effects for compounds 76 and 8290 on the antioxidant capacity in a radical DPPH free-radical assay. [27]
83 Menellsteroid C (R1 = H, R2 = OH) [27]
85 Cholestan-3β,5α,6β-triol (R1 = R2 = H) [27]
86 Cholestan-1β,3β,5α,6β-tetrol (R1 = OH, R2 = H) [27]
84 Menellsteroid D (1β,3β,5α-trihydroxycholestan-6-one) [27]
87 Nephalsterol [27]
88 Cholestan-3β-5-en-6-one [27]
89 Junceellolide B [27]
90 Junceellolide D [27]

[TableWrap ID: marinedrugs-10-02415-t016] pii: marinedrugs-10-02415-t016_Table 16.
Table 16 

The natural products from Menella sp.


Structure No. Name Ref.
91 3α-Hydroxy-5β-pregnan-20-one (R1 = α-OH, R2 = β-H) [29]
92 3β-Hydroxy-5α-pregnan-20-one (R1 = β-OH, R2 = α-H) [29]
93 3β-Hydroxy-pregnan-5-en-20-one [29]
94 5β-Pregnan-3,20-dione (R = β-H) [29]
95 5α-Pregnan-3,20-dione (R = α-H) [29]
96 Pregnan-4-en-3,20-dione (1,2-dihydro) [29]
97 Pregnan-1,4-dien-3,20-dione [29]

[TableWrap ID: marinedrugs-10-02415-t017] pii: marinedrugs-10-02415-t017_Table 17.
Table 17 

The natural products from Menella sp.


Structure No. Name Biological Activity Ref.
98 (–)-Hydroxylindestrenolide Displayed a weak inhibitory effect on the generation of superoxide anions (inhibition rate 13.4%) at a concentration of 10 μg/mL. [30]
99 Menelloide A Displayed a weak inhibitory effect on the generation of superoxide anions (27.6%) at a concentration of 10 μg/mL. [31]
100 Menelloide B Not active in terms of inhibition of the generation of superoxide anions (inhibition rate 2.9%) and the release of elastase (inhibition rate 0.7%) at a concentration of 10 μg/mL. [31]
101 Menelloide C [32]
102 Menelloide D Displayed a weak inhibitory effect on the release of elastase (inhibition rate 10.5%) at a concentration of 10 μg/mL. [32]
103 Menelloide E Displayed weak inhibitory effects on the generation of superoxide anions (inhibition rate 19.9%) and the release of elastase (inhibition rate 27.0%) at a concentration of 10 μg/mL. [33]
104 (+)-Chloranthalactone B Displayed a weak inhibitory effect on the generation of superoxide anions (inhibition rate 16.5%), but was not active in terms of inhibition of the release of elastase (inhibition rate 6.6%) at a concentration of 10 μg/mL. [31]
105 Seco-germacrane anhydride [34]


Article Categories:
  • Review

Keywords: Plexauridae, gorgonian, Astrogorgia, Bebryce, Echinomuricea, Euplexaura, Menella.

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