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Abstract

Two new (1 and 2) and six known (3-8) compounds were isolated from the methanolic extract of the Vietnamese marine spider conch Lambis lambis Linnaeus, 1758. Based on comprehensive spectroscopic analyses, particularly HRESIMS, and 1D- and 2D-NMR spectra, their chemical structures were determined to be 25,26,27-tri-nor-cholest-5-ene-2β,3α,24-triol-2,24-disulfate (1), 25,26,27-tri-nor-cholesta-2β,3α,24-triol-3,24-disulfate (2), 25,26,27-tri-nor-cholesta-2β,3α,24-triol-2,3,24-trisulfate (solomonsterol A, 3), 1-O-arachidonoyl-3-O-stearylglycerol (4), eicosapentaenoic acid (5), adenosine (6), adenine (7), and uracil (8). This is the first report of compounds 3-8 from L. lambis.

Keywords

Strombidae sterol sulfate 25 26 24-triol-2 24-disulfate 24-triol-3

Introduction

Lambis Linnaeus, 1758, commonly known as the spider conch, is a species of large sea snail, a marine gastropod mollusk in the family Strombidae.¹ The meat of L. lambis provides many nutrients, such as minerals (macro minerals, Na, K, Ca, P; micro minerals, Fe, ZN, Cu), protein, and vitamins.² Fucoidanase was isolated from the digestive glands of Lambis sp. producing sulfated fucooligosaccharides.³ The mucus extract of L. lambis exhibited cytotoxic activity.⁴ Continuing our program of study on Vietnamese marine organisms,^5-8 we report in this paper the isolation and structural elucidation of two new sterol sulfates (1 and 2) and six known compounds (3-8) from the methanol extract of the sea spider conch L. lambis.

Results and Discussion

Compound 1 was obtained as a white amorphous solid with a molecular formula of C₂₄H₃₈O₉S₂Na_2, according to its HRESIMS ion at m/z 581.1844 [M + H]⁺ (calcd. for [C₂₄H₃₉O₉S₂Na₂]⁺: 581.1825, Δ = + 3.3 ppm) and at m/z 603.1637 [M + Na]⁺ (calcd. for [C₂₄H₃₈O₉S₂Na₃]⁺: 603.1645, Δ = −1.3 ppm). The ¹H NMR spectrum of 1 showed the presence of two methyl singlets at δ_H 0.75 and 1.19 (each 3H), one methyl doublet at δ_H 0.99 (3H, d, J = 7.0 Hz), and one olefinic proton at δ_H 5.37 (1H, dd, J = 2.5, 2.5 Hz), along with two methine carbinol groups at δ_H 4.04 and 4.46 (each, 1H, br d, J = 2.5 Hz) and one oxygenated methylene group at δ_H 3.98 (2H, td, J = 7.0, 2.5 Hz). The ¹³C NMR and HSQC spectra of 1 showed the presence of 24 carbons, including three quaternary carbons (δ_C 37.8, 43.5, 139.6), nine methylenes (δ_C 21.9, 25.3, 27.2, 29.2, 32.9, 33.2, 35.8, 39.0, 41.2), eight methines (δ_C 32.8, 36.9, 51.8, 57.5, 58.1, 69.6, 78.3, 123.5), and three methyls (δ_C 12.1, 19.1, 22.2) (Table 1). The above information suggested that 1 was a sulfated sterol compound having one double bond, three oxygenated carbons, and which was structurally similar to solomonsterol A (3) (Figure 1).^9,10 In the HSQC spectrum of 1, methyl protons at δ_H 0.75, 0.99, and 1.19 had cross peaks to carbons at δ_C 12.1, 19.1, and 22.2, respectively, while protons at δ_H 3.98, 4.40, 4.46, and 5.37 correlated with carbons at δ_C 69.7, 69.6, 78.3, and 123.5, respectively. In the ¹H-¹H COSY spectrum of 1, correlations of H-1/H-2/H-3/H-4, H-7/H-8/H-9/H-11/H-12, H-8/H-14/H-15/H-16/H-17/H-20/H-21, and of H-20/H-22/H-23/H-24 (Figure 2) were observed. This evidence suggested that the A, B, C, and D rings of 1 were similar to that of (20R)-cholesta-5,24-diene-2β,3α,21-triol-2,21-disulfate,¹¹ and the side chain was similar to that of solomonsterol.^9,10 These suggestions were confirmed by the HMBC spectrum. HMBC correlations were observed from H₃-19 (δ_H 1.19) to C-1 (δ_C 39.0)/C-5 (δ_C 139.6)/C-9 (δ_C 51.8)/C-10 (δ_C 37.8), from H₃-18 (δ_H 0.75) to C-12 (δ_C 41.2)/C-13 (δ_C 43.5)/C-14 (δ_C 58.1)/C-17 (δ_C 57.5), from H₃-21 (δ_H 0.99) to C-17/C-20 (δ_C 36.9)/C-22 (δ_C 33.2), and from H₂-24 (δ_H 3.98) to C-22 (δ_C 33.2). In addition, the lower field signals of C-2 (δ_C 78.3) and C-24 (δ_C 69.7), together with the complete match of the NMR data of the A and B rings of 1 with those of (20R)-cholesta-5,24-diene-2β,3α,21-triol 2,21-disulfate,¹¹ and of the side chain of 1 with that of solomonsterol A (3)^9,10 suggested two sulfate groups were at C-2 and C-24, and the hydroxy group was at C-3. These were further confirmed by the interpretation of ¹H NMR, ¹³C NMR, ¹H-¹H COSY, HSQC, HMBC, and NOESY spectra. The small proton coupling constants of H-3 and H₂-4 (J = 2.0∼2.5 Hz), H-2 and H₂-1 (J = 2.0∼2.5 Hz), and of H-2 and H-3 (J = 2.5 Hz) confirmed that H-3 and H-2 were β/equatorial and α/equatorial, respectively. This were further indicated from the observation of the NOE correlation of H-2 (δ_H 4.46) and H-3 (δ_H 4.04). The other key NOE correlations of 1 are shown in Figure 3 indicating that its relative configuration was similar to that of (20R)-cholesta-5,24-diene-2β,3α,21-triol 2,21-disulfate.¹¹ The CH₃-20 group was suggested as having an α-orientation due to the biosynthetic characteristics of all sterols.¹² From the above evidence, compound 1 was determine to be a new compound, 25,26,27-tri-nor-cholest-5-ene-2β,3α,24-triol-2,24-disulfate.

Figure 1.

Chemical structures of compounds 1-8.

Figure 2.

Key ¹H-¹H COSY and HMBC correlations of 1 and 2.

Figure 3.

Key NOE correlations of 1 and 2.

Table 1.

NMR Spectroscopic Data for 1–3 (in CD₃OD).

Pos.	1		2		3
Pos.	δ _C	δ_H (mult, J in Hz)	δ _C	δ_H (mult, J in Hz)	δ _C	δ_H (mult, J in Hz)
1	39.0	1.60 (dd, 14.0, 2.5) 2.14 (dd, 14.0, 2.0)	41.1	1.37 (14.0, 2.5) 1.77 (14.0, 2.0)	39.3	1.44 (m), 2.09 (m)
2	78.3	4.46 (br d, 2.5)	70.0	4.09 (br d, 2.5)	76.6	4.72 (br s)
3	69.6	4.04 (br d, 2.5)	78.5	4.42 (br d, 2.5)	76.2	4.75 (br s)
4	35.8	2.82 (dt, 14.5, 2.5) 1.97 (dd, 14.5, 2.0)	30.3	1.60 (m), 1.84 (m)	30.8	1.61 (m), 1.28 (m)
5	139.6	-	40.6	1.06 (m)	40.2	1.59 (m)
6	123.5	5.37 (dd, 2.5, 2.5)	29.2	1.25 (m), 1.30 (m)	29.5	1.32 (m), 1.91 (m)
7	32.9	1.62 (m), 1.97 (m)	33.2	0.95 (m), 1.70 (m)	33.2	1.12 (m), 1.72 (m)
8	32.8	1.50 (m)	36.4	1.41 (m)	36.3	1.44 (m)
9	51.8	1.06 (m)	56.6	0.72 (m)	56.5	0.73 (m)
10	37.8	-	36.3	-	36.3	-
11	21.9	1.21 (m), 1.54 (m)	22.0	1.33 (m), 1.55 (m)	22.0	1.47 (m), 1.45 (m)
12	41.2	1.20 (m), 2.06 (m)	41.4	1.16 (m), 2.02 (m)	41.4	1.18 (m), 2.02 (m)
13	43.5	-	43.8	-	43.8	-
14	58.1	1.06 (m)	57.9	1.07 (m)	57.8	1.08 (m)
15	25.3	1.10 (m), 1.62 (m)	25.2	1.29 (m), 1.60 (m)	25.2	1.09 (m), 1.51 (m)
16	29.2	1.32 (m), 1.90 (m)	29.3	1.33 (m), 1.88 (m)	29.2	1.32 (m), 1.91 (m)
17	57.5	1.13 (m)	57.6	1.12 (m)	57.6	1.14 (m)
18	12.1	0.75 (s)	12.5	0.71 (s)	12.5	0.71 (s)
19	22.2	1.19 (s)	14.6	1.02 (s)	14.1	0.99 (s)
20	36.9	1.47 (m)	36.8	1.46 (m)	36.8	1.44 (m)
21	19.1	0.99 (s)	19.1	0.97 (s)	19.6	0.97 (d, 6.5)
22	33.2	1.13 (m), 1.56 (m)	33.1	1.12 (m), 1.55 (m)	33.1	0.99 (m), 1.54 (m)
23	27.2	1.55 (m), 1.76 (m)	27.2	1.57 (m), 1.77 (m)	27.2	1.09 (m), 1.51 (m)
24	69.7	3.98 (t, 7.0)	69.7	3.97 (td, 7.0, 2.5)	69.7	3.97 (m)

The NMR spectra of 2 were similar to those of 1 and 3 suggesting that 2 was a sterol. The double bond signals of 1 were absent from the NMR spectra of 2. In addition, the molecular formula of 2 was determine as C₂₄H₄₀O₉S₂Na₂ from the exhibition of ions at m/z 583.1977 [M + H]⁺ (calcd C₂₄H₄₁O9S₂Na₂ = 583.1982 Δ = −0.9 ppm) and m/z 605.1808 [M + Na]⁺ (calcd C₂₄H₄₀O9S₂Na₃ = 605.1801 Δ = + 1.2 ppm). The above data suggested that 2 was a disulfate sterol, similar to compounds 1 and 3.^9,10 The NMR data of 2 were elucidated based on analyzing its ¹H, ¹³C NMR, HSQC, ¹H-¹H COSY, HMBC, and NOESY spectra in comparison with the corresponding data of 1 and solomonsterol A (3), measured in the same solvent (Table 1).^9,10 In the HSQC spectrum, protons H-1 (δ_H 1.16/2.02), H-2 (δ_H 4.09), H-3 (δ_H 4.42), H-4 (δ_H 1.60/1.84) and H-5 (δ_H 1.60) correlated to carbons at δ_C 41.4, 70.0, 78.5, 30.3, and 40.6, respectively. In addition, COSY correlations of H-1/H-2/H-3/H-5/H-5 were observed. This evidence indicated two oxygenated carbons were at C-2 and C-3. The complete agreement of the NMR data of the A, B, and C rings of 2 with those of (20R)-5α-cholest-24-ene-2β,3α,21-triol-3,21-disulfate (in the same solvent, CD₃OD)¹² suggested that one sulfate moiety was at C-3 and one hydroxy group was at C-2. The NMR data of the side chain of 2 were compared to those of 1 and solomonsterol A (3) and found to match perfectly, suggesting that the other sulfate group was at C-24. The key HMBC correlations of 2 are shown in Figure 2. HMBC correlations from H-3 (δ_H 4.42) to C-5 (δ_C 40.6), from H-2 (δ_H 4.09) to C-10 (δ_C 36.3), from H₃-21 (δ_H 0.97) to C-22 (δ_C 33.1), and from H-24 (δ_H 3.97) to C-22 (δ_C 33.1)/C-23 (δ_C 27.2) further confirmed the positions of the hydroxy group at C-2 and two sulfate groups at C-3 and C-24. Similar to 1, the small proton coupling constants between H₂-1 and H-2, and H-2 and H-3, as well as the observed NOE correlation between H-2 and H-3 clearly indicated equatorial positions of both H-2 and H-3. Thus, compound 2 was elucidated as a new compound, 25,26,27-tri-nor-cholesta-2β,3α,24-triol-3,24-disulfate.

Compounds 3-5 were identified as 25,26,27-tri-nor-cholesta-2β,3α,24-triol-2,3,24-trisulfate (solomonsterol A, 3),^9,10 1-O-arachidonoyl-3-O-stearylglycerol (4),¹³ and eicosapentaenoic acid (5)¹⁴ by the coincidence between their NMR spectral data and those of the corresponding reported data, and further confirmed by HSQC and HMBC spectra. Compounds 6-8 were identified as adenosine (6), adenine (7), and uracil (8) ¹⁵ by analyzing their ¹H NMR data, and comparison with authentic samples by HPLC analysis. Compounds 3-8 are reported for the first time from L. lambis. The sulfated sterol solomonsterol A was isolated from a sponge for the first time. This compound has been reported to exhibit anti-inflammatory activity and attenuated systemic inflammation and immune dysfunction in a mouse model of rheumatoid arthritis.¹⁶ The isolated new compounds are its analogs and it seems to be obvious that substances 1–3 have a dietary origin from a sponge eaten by L. lambis. Hence the found substances are food markers.

The NMR spectra for compounds 1-8 are shown in Supplemental Figures S1-S31. The NMR data of 4 and 5 are shown in Tables S1 and S2.

Materials and Methods

General Experimental Procedures^17,18

Optical rotation was measured on a Jasco P-2000 polarimeter. HRESIMS were measured on an Agilent 6530 Accurate Mass Q-TOF system, and NMR spectra on a Bruker Avance III 500 MHz spectrometer. For preparative HPLC, an Agilent 1260 Infinity II system was used equipped with a YMC J′sphere ODS-H80 (20 × 250 mm, 4 µm) HPLC column. Flash column chromatography was performed using either silica gel or reversed phase (RP-18) resins as adsorbent. Thin layer chromatography was carried out on pre-coated silica gel 60 F₂₅₄ and/or RP-18 F_254S plates.

Animal Materials

The samples of Lambis Linnaeus, 1758 were collected from Truong Sa archipelago, Vietnam (8°51′53″N 112°15′27″E, 8°51′53″N 112°15′27″E, 8°38′39″N 111°55′21″E, 8°58′30″N 113°42′23″E, 10°22′30.9″N 114°28′55.4″E, 112°15′27″E, 8°51′53″N 112°15′27″E, 8°38′39″N 111°55′21″E, 8°58′30″N 113°42′23″E, 10°10′41″N 114°21′50″E, 10°01′23″N 113°51′19″E) during June 2021 and identified by Dr Nguyen Thi Bich Nga, Institute of Biotechnology, Vietnam Academy of Science and Technology. The voucher specimen (TS07-08) has been deposited at Vietnam - Russia Tropical Center, Vietnam.

Extraction and Isolation

L. lambis (2.5 kg) was defrosted, then extracted with MeOH in an ultrasonic bath (3 times × 10.0 L MeOH, 40 ^oC, 3 h). The MeOH extract (121.1 g) was suspended in distilled water (2.5 L) and extracted with CH₂Cl₂ (2.5 L) to obtained the CH₂Cl₂ extract (LL1, 10.3 g). LL1 (10.0 g) was chromatographed on a silica gel column, eluting with a gradient solvent system of CH₂Cl₂ in MeOH (100:0, 40:1, 20:1, 0:100) to obtain four fractions, LL1A-LL1D. LL1A (1.8 g) was chromatographed on a silica gel column, eluting with n-hexane/EtOAc (7/1, v/v) to obtain compounds 4 (13.5 mg) and 5 (17.1 mg). LL1B (1.2 g) was chromatographed on a RP-18 column, eluting with acetone/water (4/1, v/v) to give compound 6 (23.1 mg). LL1C (4.3 g) was chromatographed on a RP-18 column, eluting with acetone/water (3.5/1, v/v) to obtain 5 fractions, LL1C1- LL1C5. LL1C2 (736 mg) was purified by HPLC (J’sphere ODS H-80, 250 mm × 20 mm column), eluting with 35% acetonitrile (ACN) in H₂O to yield 3 (6.1 mg, t_R 37.8). LL1C3 (679 mg) was chromatographed on an HPLC (J’sphere ODS H-80, 250 mm × 20 mm column), eluting with 45% acetonitrile (ACN) in H₂O to yield 1 (5.2 mg, t_R 42.5) and 2 (4.7 mg, t_R 44.6). LL1D (2.7 g) was chromatographed on a RP-18 column, eluting with acetone/water (2/1, v/v) to give compounds 7 (6.1 mg), 8 (4.6 mg), and 9 (7.2 mg).

3.3.1. 25,26,27-Tri-nor-cholest-5-ene-2β,3α,24-triol-2,24-disulfate (1)

White amorphous solid, : + 8.7 (c 0.1, MeOH); HRESIMS m/z 581.1844 [M + H]⁺ (calcd. for [C₂₄H₃₉O₉S₂Na₂]⁺: 581.1825, Δ = + 3.3 ppm); m/z 603.1637 [M + Na]⁺ (calcd. for [C₂₄H₃₈O₉S₂Na₃]⁺: 603.1645, Δ = −1.3 ppm). ¹H NMR (CD₃OD, 500 MHz) δ (ppm), ¹³C NMR (CD₃OD, 125 MHz) δ (ppm) data: see Table 1.

3.3.1. 25,26,27-Tri-nor-cholesta-2β,3α,24-triol-3,24-disulfate (2)

White amorphous solid, : + 12.3 (c 0.1, MeOH); HRESIMS m/z m/z 583.1977 [M + H]⁺ calcd C₂₄H₄₁O9S₂Na₂ = 583.1982 Δ = -0.9 ppm; m/z 605.1808 [M + Na]⁺ calcd C₂₄H₄₀O9S₂Na₃ = 605.1801 Δ = + 1.2 ppm. ¹H NMR (CD₃OD, 500 MHz) δ (ppm), ¹³C NMR (CD₃OD, 125 MHz) δ (ppm) data: see Table 1.

Conclusions

From the methanol extract of the Vietnamese marine spider conch Lambis Linnaeus, 1758, two new (1 and 2) and six known compounds (3-8) were isolated. Their chemical structures were elucidated as 25,26,27-tri-nor-cholest-5-ene-2β,3α,24-triol-2,24-disulfate (1), 25,26,27-tri-nor-cholesta-2β,3α,24-triol-3,24-disulfate (2), and 25,26,27-tri-nor-cholesta-2β,3α,24-triol-2,3,24-trisulfate (3), 1-O-arachidonoyl-3-O-stearylglycerol (4), eicosapentaenoic acid (5), adenosine (6), adenine (7), and uracil (8) based on extensive spectroscopic methods, including HRESIMS, 1D- and 2D-NMR spectra. Compounds 3-8 are reported herein from L. lambis for the first time.

Supplemental Material

sj-docx-1-npx-10.1177_1934578X221113184 - Supplemental material for Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Supplemental material, sj-docx-1-npx-10.1177_1934578X221113184 for Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758 by Nguyen Trong Dan, Le Thi Giang, Cu Nguyen Dinh, Truong Ba Hai, Nguyen Dang Hoi, Vu Thi Loan, Dan Thi Thuy Hang, Nguyen Xuan Nhiem, Bui Huu Tai and Phan Van Kiem in Natural Product Communications

Footnotes

List of Abbreviations

NMR, Nuclear Magnetic Resonance

COSY, Correlation Spectroscopy

HRESIMS, High-resolution electrospray ionization mass spectrometry

HMBC, Heteronuclear Multiple Bond Correlation

HSQC, Heteronuclear Single Quantum Coherence

Author Contribution

Research idea NT Dan, NX Nhiem, PV Kiem; Isolation, DTT Hang, BH Tai, CN Dinh, ND Hoi, VT Loan; Collection of samples: NT Dan, CN Dinh; Structure elucidation and writing, BH Tai, NT Dan, NX Nhiem, PV Kiem.

Declaration of Conflicting Interests

The author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Ethical Approval

Our institution does not require ethical approval for reporting individual cases or case series.

Funding

The author(s) disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This work was supported by the Project KCB-TS-07, (grant number Project KCB-TS-07).

ORCID iD

Phan Van Kiem

Statement of Human and Animal Rights

This article does not contain any studies with human or animal subjects.

Statement of Informed Consent

There are no human subjects in this article and informed consent is not applicable.

Supplemental Material

Supplemental material for this article is available online.

References

Boncka

Ompi

Andaki

. Occurrence of the common spider shell, Lambis (L.) (Gastropoda: Strombidae) in the intertidal zone of Karatung, Sangihe, Indonesia. Phuker Mar Cent Spec Publ. 1994;13:159-161.

Amin

Hamza

Moharram

. Chemical composition, nutritional value, safety, and acceptability of Egyption red sea coast fresh and dried spider concho (Lambis lambis) meats. Egypt J Aquat Biol Fish. 2020;24(6):153-165.

Silchenko

Kusaykin

Zakharenko

, et al. Endo-1,4-fucoidanase from Vietnamese marine mollusk Lambis sp. which producing sulphated fucooligosaccharides. J Mol Cat B: Enzym. 2014;102(4):154-160.

Gerard

LLS

Yolanda

Florencio

VAJ

Anthony

. Cytotoxic and genotoxic studies on the mucus of Indian volute Melo broderipii (Gmelin 1758) and spider conch Lambis (Linn 1758). J Pharmacogn Nat Prod. 2016;2(3):1000120. doi: 10.4172/2472-0992.1000120

Kiem

Minh

Nhiem

, et al. The chemical constituents and biological activity of some sponges in northern Vietnam: a review. Vietnam J Chem. 2019;57(3):261-271. doi: 10.1002/vjch.201900041

Trang

Dung

Nhiem

, et al. New tetracyclic and pentacyclic isomalabaricanes from the marine sponge Rhabdatrella globostella (Carter, 1883). Tetrahedron Lett. 2022;89:153607. doi: 10.1016/j.tetlet.2021.153607

Tai

Hang

DTT

Trang

, et al. Conjugated polyene ketones from the marine sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and their cytotoxic activity. Nat Prod Commun. 2021;16(9):1-7. doi: 10.1177/1934578X211043732

Trang

Hang

DTT

Dung

, et al. Rhabdastrenones A-D from the sponge Rhabdastrella globostellata. RSC Adv. 2022;12(17):10646-10652. doi: 10.1039/d2ra01674e

Sepe

Ummarino

D’Auria

, et al. Modification in the side chain of solomonsterol A: discovery of cholestane disulfate as a potent pregnane-X-receptor agonist. Org Biomol Chem. 2012;10(31):6350-6362. doi: 10.1039/c2ob25800e

10.

Festa

Marino

D’Auria

, et al. Solomonsterols A and B from Theonella swinhoei. The first example of C-24 and C-23 sulfated sterols from a marine source endowed with a PXR agonistic activity. J Med Chem. 2011;54(1):401-405. doi: 10.1021/jm100968b

11.

Roccatagliata

Maier

Seldes

. New sulfated polyhydroxysteroids from the antarctic ophiuroid Astrotoma agassizii. J Nat Prod. 1998;61(3):370-374.

12.

Goad

Akihisa

. Nomenclature and biosynthesis of sterols and related compounds . In: Analysis of Sterols. Springer; 1997:1-42. doi: 10.1007/978-94-009-1447-6_1.

13.

Rahelivao

Gruner

Lubken

, et al. Chemical constituents of the soft corals Sinularia vanderlandi and Sinularia gravis from the coast of Madagascar. Org Biomol Chem. 2016;14(3):989-1001.

14.

Alexandri

Ahmed

Siddiqui

, et al. High resolution NMR spectroscopy as a structural and analytical tool for unsaturated lipids in solution. Molecules. 2017;22:1663. doi: 10.3390/molecules22101663

15.

Ciuffreda

Casati

Manzocchi

. Spectral assignments and reference data. Complete ¹H and ¹³C NMR spectral assignment of α- and β-adenosine, 2,-deoxyadenosine and their acetate derivatives. Magn Reson Chem. 2007;45(9):781-784. doi: 10.1002/mrc.2036

16.

Mencarelli

D’Amore

Renga

, et al. Solomonsterol A, a marine pregnane-X-receptor agonist, attenuates inflammation and immune dysfunction in a mouse model of arthritis. Mar Drugs. 2014;12(1):36-53. doi: 10.3390/md12010036

17.

Hang

Trang

Dung

, et al. Guaianolide sesquiterpenes and benzoate esters from the aerial parts of Siegesbeckia orientalis L. and their xanthine oxidase inhibitory activity. Phytochemistry. 2021;190:112889. doi: 10.1016/j.phytochem.2021.112889

18.

Yen

DTH

Yen

Hop

, et al. Charantoside L, a new cucurbitane-type glycoside from Momordica charantia L. with α-glucosidase inhibitory activities. Nat Prod Commun. 2022;17(1):1-5. doi: 10.1177/1934578X211068924

Supplementary Material

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Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus,1758

Abstract

Keywords

Introduction

Results and Discussion

Materials and Methods

General Experimental Procedures17,18

Animal Materials

Extraction and Isolation

Conclusions

Supplemental Material

sj-docx-1-npx-10.1177_1934578X221113184 - Supplemental material for Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Footnotes

List of Abbreviations

Author Contribution

Declaration of Conflicting Interests

Ethical Approval

Funding

ORCID iD

Statement of Human and Animal Rights

Statement of Informed Consent

Supplemental Material

References

Supplementary Material

General Experimental Procedures^17,18